The Best Jeans for Women in Every Style and Shape

September 21, 2020September 21, 2020 by Megan Kristel

Let’s talk about finding the perfect pair of jeans.

I promise you, they exist, but finding your best pair can be frustrating and a little discouraging. I’ve been there, literally breathless in a dressing room, or my closet, trying to get a pair of jeans over various parts of my body.

Happily, over the years, I’ve discovered truly great pairs for myself, clients and my readers.

So, today, I’m hoping to make your search a little easier by rounding up my picks for the very best jeans for women in every style and size.

I’m including regular or missy, petite and plus sizes for skinny, straight and bootcut styles.

The Best Jeans for Women in Every Style and Shape

Jeans: Joe’s Curvy Skinny (on sale) | Tee: $9.50 | Boots: $100

The Three Most Popular Style of Jeans

For today’s post, I’m focusing on a classic five pocket design, in a dark or medium wash in skinny, straight and bootcut styles.

I picked two or three of my favorites at different price points, so within each category you’ll have a high, medium and low price (or what I call splurge, spend and save).

Currently, my favorite pair of jeans are these Joe’s Curvy Skinny jeans I scored on sale at Off 5th (above). When I was a stylist, Joes Jeans were a client favorite. Their Curvy Bootcut make your legs look a mile long and their Petite Provocateur Bootcut jeans have a cult like following.

We feature a lot of skinny jeans in our posts. Mostly because they are the abundantly available. They are also more flattering than you may think, if you find the right pair.

Universally speaking, a straight leg works well on most body types. You still want them to be narrow, but this cut will give you the current silhouette of a slim cut bottom without having to deal with fabric clinging to your legs.

The bootcut style has come and gone over the years. Recently, bootcuts have gone back to their original glory, as a better version of their late 90s predecessors. The flare on most current styles is just enough to cover your shoe. Its slim cut helps bring some much-needed balance if you have wider hips and broad shoulders.

The Fit of Jeans

Jeans are the kind of garment you just have to try on and see what happens. There are no blanketed rules telling us what style works for what body type. It all comes down to how the jean fits you as an individual and how you feel in them.

I’ve had a plus sized client fall in love with a skin-tight pair of skinnies and look phenomenal in them; and a petite client, who swore up and down that a bootcut would overwhelm her, walk out with two pairs that helped show off her curves. There is no science to it.

Generally speaking, the more stretch in a jean, the more they will stretch out, so consider sizing down when ordering. You want a new pair of jeans to almost feel too small, because after wearing them for just a few hours, they’ll start to conform to your body.

Also, if you run into the very common issue of your the waistband either feeling too loose or gapping, have them fitted by a tailor at the waist. It’s an easy fix so you can get them over your hips and sit comfortably at your waist. I did it all the time for clients.

Scroll down to find your size and preferred cut.

The Best Straight Leg Jeans for Women

One, $178 | Two, $89 | Three, $27

One – DL 1961 Jeans are my favorite. They are expensive, but the quality and fit are out of this world. There is just enough stretch, great for travel, perfect for the office, and easy to wear on the weekend. Available in sizes up to a 34 which is about a 16.

Two – KUT from Kloth is a well priced, quality brand with nice fit and style. Available in sizes 0 – 16.

Three – Old Navy won’t last you more than a season or two, but are a fantastic price and fit well. Available in regular, petite and tall, in up to a size 20 with short, regular and long lengths.

The Best Skinny Jeans for Women

One, $179 | Two, $37 | Three, $32

One – Paige Denim are like the gold standard of skinny jeans. They have classic style, awesome fit and last for a good long time. These have a mid-rise available in up to a 34 or a size 16.

Two – Article of Society are a great deal at their regular price, but on sale they’re a no brainer. I’m a big fan of their fit and styling. They will stretch out faster then premium denim so you may consider sizing down. Limited sizes include 22 – 34.

Three – Old Navy’s Mid-Rise Rockstar one of my all time favorites. They look like designer denim for a fraction of the price. Again, these will stretch out quickly so you’ll get one season at the most out of them. Available in regular, petite and tall, in up to a size 20 with short, regular and long lengths.

The Best Bootcut Jeans for Women

One, $110 | Two, $90 | Three, $68

One – Joe’s boot cut jeans are my favorite. They have impeccable fit and a classic dark wash. Also, note the length in the picture above, this where you want them to hit, just slightly puddling on top of your shoe. These have a high rise and go up to size 34, which, for Joe’s is a 14/16.

Two – KUT from Koth has nice stretch in a dark, go with everything wash. These run large so size down, available up to a size 14.

Three– Wit & Wisdom is another well priced option at under $70. They are more casual, ideal for the weekend and run big so size down when ordering. Available in regular and petite sizes, up to a 18 or 14W.

The Best Petite Straight Leg Jeans for Women

One, $109 | Two, $84 | Three, $68

One– NYDJ makes fantastic jeans in all sizes. Their petite straight leg was a go-to for clients. Available in three colors up to a size 18P.

Two– We don’t see a lot of Jag Jeans anymore but they also make a sold jean for under $100. There pull on style (above) give you the slim look of a skinny jean with more comfort and room. Available in regular and petite up to a size 12.

Three– Wit & Wisdom have what they call an “Ab-solution” which is basically mesh panels that hold you in (yes, please). These run big so size down. Available in regular and petite sizes, up to a 18 or 14W.

The Best Petite Skinny Leg Jeans for Women

One, $238 | Two, $139 | Three, $59

One – Citizen of Humanity are not specifically a petite jean, but I’ve had luck with them for petite clients. Worth trying if you want a premium denim. Available in sizes up to a 12, runs small.

Two – Another NDJ in a super dark wash. Nice for those of you that like a high waistband that sits above your belly button. Available in regular, plus and petite up to a size 24.

Three – Liverpool has comfortable, under $60 jean in a dark designer wash. These are pull on so they will feel like a legging and feel comfortable at your natural waist. Available in up to a size 12P.

The Best Petite Bootcut Jeans for Women

One, $185 | Two, $68 | Three, $35

One – Joes makes by far the BEST pair of petite boot cut jeans, especially if you are a little curvy. Available in up to a size 32, runs small, high waisted.

Two – Wit & Wisdom has enough stretch and a waistband that sits right at your natural waist. Also available in regular up to a size 18.

Three – These Old Navy jeans are just a solid option, in a classic dark wash for under $0. Also available in regular, and tall up to a size 20.

The Best Plus Straight Leg Jeans for Women

One, $144 | Two, $44

One – NYDJ makes the best plus size jeans in all styles. They consistently have great fit and proper pocket placement. Available in sizes 14 – 28W, with a high rise. Order one size down.

Two – These Old Navy have an incredibly reasonable price tag and classic fit. Available in sizes 16 – 30, in regular, short or long lengths.

The Best Plus Skinny Leg Jeans for Women

One, $144 | Two, $28

One – I say show off your curves. Wear these James Jeans skinny’s with a killer heel and your favorite going out top. Available in sizes 12 – 28.

Two– If you don’t want to spend, Target has you covered with their brand Ava & Viv. Just remember they are a one, maybe two season wear, but are under $30. Available in sizes 14 – 30.

The Best Plus Bootcut Jeans for Women

One, $109 | Two, $98 | Three

One – From NYDJ these are like a trouser jean, great for the office on a casual day paired with a one or two button blazer. Available in sizes 14 – 28.

Two – These jeans from KUT are the most casual, they could be your go to weekend jean, but are still polished. Available in sizes 14 – 24.

Three – A slim boot cut is ideal to bring balance to your shape without creating more volume and these Seven7 jeans are just that at a fantastic sale price.

Tall Sizes

Let’s talk about tall sizes. Many of the options above include tall sizing and are noted. Old Navy in particular offers all kind of sizes from traditional tall cuts to just longer inseams (depending on what you need).

Banana Republic and J.Crew also offer a solid tall selection and Talbots has long as an option within their sizes.

I am 5’10, but don’t wear specifically tall cuts. Instead I’ve had luck with premium denim offering longer inseams – something to consider as well.

Our Content is Inspired by Our Readers

Our readership inspires all of our posts and is not sponsored or paid for by brands or retailers.

Recommendations are based on my experience as a personal stylist View Postand wardrobe consultant for over a decade. I worked with busy, down-to-earth women who wanted to look chic and feel confident but were often confused by so much of retail.

Some links are affiliate links, which means if you purchase via our site, we receive a small commission.

If you enjoy our content and would like to help us grow, please consider following on Instagram and join our Private Facebook Group to access more advice and exclusive in-depth conversations with other like-minded women.

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A Zoom Perfect Piece for Under $40

September 16, 2020September 16, 2020 by Megan Kristel

J.Crew Factory Button-collar pullover sweatshirt in green, pink, and ivory

Here on the East Coast, right outside of Philadelphia, it feels like we skipped over a lingering summer and jumped headfirst into Fall. The leaves are already turning orange, and it’s cold enough in the mornings that my kids voluntarily wear a hoodie to the bus stop.

Our big girls are back to school (in person!), the baby is turning two and has two speeds: running and asleep, and our calendars are as overscheduled as they were in the pre-COVID good old days.

I’ve never been more grateful for all the things on our plates. Whenever I want to complain about the busyness, I remind myself that the alternative is a disaster.

Now that we are in full swing with the Fall season, I need to spend some time organizing my closet, and pulling my wardrobe together, so getting dressed for the day is easier. It’s no surprise that after this last six months, my closet needs some TLC.

To start with, I need a few casual tops, that are cozy and chic, like this button top sweatshirt I found at J.Crew Factory. I’m always looking for a basic with a twist and this checks all the boxes.

J Crew Factory Button Top Sweatshirt

Sweatshirt: $44.50 (plus 20% with Code: COMFY) NOW $35

I picked it up in white and green (head over to my Instagram to see how I’m wearing it today). You can wear it on it’s own, or layer over a long sleeve tee or collared shirt with your favorite jeans.

Right now, it’s on sale for $35, in all sizes including a 3X. It’s just the thing if you are looking to add some casual yet polished options to your early fall wardrobe.

And! Don’t forget! Our Fall 2020 Wardrobe Challenge starts THIS FRIDAY! This is the BEST time of year to participate, whether you are new to The Well Dressed Life, or have participated in the past, you will walk away with insights, clarity and a perfectly organized closet.

Our Content is Inspired by Our Readers

Our readership inspires all of our posts and is not sponsored or paid for by brands or retailers.

Recommendations are based on my experience as a personal stylist and wardrobe consultant for over a decade. I worked with busy, down-to-earth women who wanted to look chic and feel confident but were often confused by so much of retail.

Some links are affiliate links, which means if you purchase via our site, we receive a small commission.

How to Dress While Losing Weight

September 15, 2020September 15, 2020 by Megan Kristel

Losing weight is a challenge. For women, especially as we age, we battle everything from shifts in our hormones to demands on our time, and the level of disciple required to make even the slightest bit of progress is exhausting. You wouldn’t think figuring out how to dress while losing weight would be difficult, but it is.

Having a plan and some guidance can make all the difference.

Over the years, I’ve spoke with hundreds of women, all in the middle of a weight loss journey. Without exception, they all struggled to figure out what and when to spend on new clothes and how to dress their changing body.

So today, I’m sharing my best tips to make this small but essential part of the weight loss a little bit easier.

How to Dress While Losing Weight

A Quick Note

Here at The Well Dressed Life, it is important for me to maintain a space that encourages size inclusivity and body positive messaging. Women are inundated with unrealistic, photoshopped images all day long. As a woman and mother of three girls, I find it incredibly frustrating that society is still trying to sell an impossible standard of beauty to us.

So, I don’t want to talk about weight loss in a way that contributes to our insane diet culture. Rather, this is about being healthy, having energy and feeling strong. It’s important for us to love ourselves at any size.

If you are currently losing weight, I encourage you to ignore your instinct to wear oversized sweatshirts and leggings all day long. Feeling good while you are losing weight is a major motivator to help you reach your goals.

And we all know that looking good and feeling good go hand in hand.

Best Tips for Getting Dressed While Losing Weight

#1 Edit Your Current Wardrobe

To make this easy, QUICKLY go through your closet and select only the pieces that fit you well right now, and put them on a rolling rack. I did this after my last baby was born (two years ago in December) and it made life so much easier.

I essentially created a small capsule that allowed me to get up, get dressed and go about my day without feeling like a total hot mess. I filled in the gaps with inexpensive pieces from Old Navy and Amazon. Every few weeks I paired down the rack, retiring pieces that got too big, and bringing in affordable wash and wear options.

This not only made getting dressed fast and easy, it helped my mental health stay strong and kept me focused on my goal.

For now, simply isolate what works from everything else. Don’t worry about getting rid of anything. Once you either reach your goal, or lost a significant amount of weight, you can properly edit your wardrobe.

#2 Be Realistic

Despite our deepest wishes, weight doesn’t just fall off. If you are following a healthy plan, you’ll lose 1 – 2 pounds a week. That gives you several weeks, or even a few months to see and feel a difference in your clothes. At first, the clothes you have may start to fit better. In time, you may need a waistband taken in, etc.

Pay attention to what is fitting well, what could use an alteration, and what needs to be replaced. If you have to buy something new, buy your current size. You’ll likely be able to wear it for at least a season.

#3. Understand Dress Sizes

This is my most important tip. A weight loss of about 10 pounds translates to going down one American dress size. You could lose up to 15 pounds and your clothes may fit better – so try everything on frequently. Most basics can be altered down two dress sizes before you compromise the garments integrity.

That’s good news! It means you don’t have to replace your entire wardrobe, and you can still have clothes that fit well during the process. You just need to watch how your body changes and how your clothes fit. Taking garments that are a little big to your local dry cleaner or seamstress to be fitted is key.

#4. Ask a Friend

I remember working with clients who had lost a significant amount of weight, and they had a hard time seeing the changes in their bodies. Often, they would insist on bringing larger sizes into the dressing room. And even after putting them on, would overlook the size discrepancies. Items would still be oversized and ill-fitting. This is when having an objective opinion is helpful. Have a friend come over or, even better, take you shopping, to help pull you out of your comfort zone.

Now that so much of our shopping is done online, it is imperative that you take your measurements and have them in front of you when ordering. Doing so will help you order the correct size and limit the amount of returns you have to make.

#5. Know When to Replace Your Clothes

When something can no longer be altered, is starting to overwhelm you or looks worn out, buy new. And don’t feel guilty. Celebrate your accomplishment! There are many well-priced options available that have real staying power. Of course, only buy what you need, and remember, you can restart the clock on alterations. So if you go down one more size, some easy alterations are all you’ll need.

Weight Loss Capsule

I thought it would be helpful to share a sort of “Weight Loss Capsule.” To pull this together, I imagined you were my client, and you asked for a list pieces you can buy now that will see you through a good portion of your journey. Some of these are one season wears, others, are year round that can be alter, all or wardrobe builders that will give you lots of options with the pieces you already have in your closet.

Weight Loss Capsule Shopping List:

Perfect Black Pants, $128: These pants are worth every penny. They fit great, are slimming, and are easy to alter.

Ruched Top, $59: Look for simple tops with side ruching. This does two things. First, it shows off your shape by pulling you in at the waist. Second, the extra detail gives the top depth, so you don’t need to add much to it to create interest.

Jeans, $78: While losing weight, you can get away with a slightly oversized top or dress, but your jeans and pants need to fit well all the time. Wit & Wisdom make my favorite under $100 jeans. The fit is fantastic, with just the right amount of stretch.

T-Shirt Dress, $30: Casual dresses are a great alternative to leggings and sweats during weight loss. They are more polished, but just as comfortable and offer more flexibility with sizing. I’m featuring tee shirt dresses here, but you can replace them with a midi, or maxi dress, in solid colors or play with pattern.

Tee Dress, $25: Another slimming tee shirt dress option, so easy to throw on. Add a denim jacket and sneakers.

Blazer, $128: Include a few structured pieces into your weight loss wardrobe. These will help you look professional at work and create a shape for your outfits. This specific blazer from Everlane will carry you through formal and casual looks.

Shell, $39: These layering tanks at Nordstrom are fantastic for everyone and affordable enough to stock up on what you need at your current size.

Cardigan, $63: Finally, knits are the one category you can’t alter, so look to update yours seasonally, as needed. Pick neutral colors in classic cuts to get the most wear out of them as possible.

Have a Question about How to Get Dressed While Losing Weight?

Add it in the comment section below and I’ll answer it!

Our readership inspires all of our posts and is not sponsored or paid for by brands or retailers.

Some links are affiliate links, which means if you purchase via our site, we receive a small commission.

How to Wear White Jeans in the Fall

September 10, 2020September 10, 2020 by Megan Kristel

On the East Coast, the leaves are just starting to change, and you can smell fall in the air. Which means it’s time to begin to transition into our cooler weather wardrobe. But before you go and pack away some of your summer staples, there are a few you should keep on hand, like your white jeans. Today, we’ll break down how to wear white jeans in the fall, with inspiration using pieces you probably already have hanging in your closet.

How to Wear White Jeans for Fall

I came up with three looks you can easily recreate, with items that are key pieces for a fall wardrobe. You’ll see me repeat these throughout the next few months.

To build your look, wear whatever jean works best for your body type: skinny, straight, or subtle bootcut. As much as I love a distressed jean, save them for the warmer weather. Skip styles that have rips and tears, frayed hems, and other embellishments.

For today’s post, I’m using these best selling white skinny jeans from NYDJ.

Outfit One: Camel and White

Blazer, $228, Tee, $35, Bag, $230, Flats, $124

Pairing tan and white together is such a gorgeous combination. Here, I took a simple white tee from Loft and used it to create a column of color. The tee is a little oversized, providing a relaxed vibe.

To layer on top, this go-to blazer from J.Crew in camel is divine. It’s almost always available online, in petite, missy, and tall sizes up to 24. Right now, it’s 40% off with the code ADDTOBAG making it under $140.

Then, play with neutrals to pull the look together. Add some texture with a tonal, embossed flat, and a top handle bag by Marc Jacobs on a fantastic sale at Off Fifth give structure and style.

Outfit Two: Black and White

Headband, $23, Earrings, $48, Sweater, $37, Flats, $59

Next, the easiest look to recreate: black and white. Simply grab your favorite black sweater like this reader favorite from Banana Republic. It’s a silk and cashmere blend, with a relaxed fit in sizes XXS – XXL and it’s under $40.

Then, black suede loafers like these from Nine West, under $50 studs and a tortoise headband from J.Crew.

Outfit Three: Olive and White

Jacket, $109, Bootie, $130Tee, $30, Crossbody, $65

This look is my favorite, using items I’ve featured for years.

Take a striped tee, you can use any neutral color combination, here I used gray and white. Then, layer an olive green jacket, like this timeless staple from LL Bean. Add our go-to Sam Edelman tan suede booties and a black crossbody bag from Sole Society.

Our Content is Inspired by Our Readers

Our readership inspires all of our posts and is not sponsored or paid for by brands or retailers.

Some links are affiliate links, which means if you purchase via our site, we receive a small commission.

How to Wear Spanx Perfect Black Skinny Pants to Work

September 9, 2020September 9, 2020 by Megan Kristel

The Spanx “Perfect” Black Skinny Pants are among the most popular items we featured during the Nordstrom Sale. With all the comfort of a legging, these better basics can take you anywhere.

Good thing because we’re not only transitioning from the summer to the fall, but also from staying home to getting back out into the world. So whether you are working from home or are in the office, you will get a ton of use out of these pants.

How to wear the Spanx “Perfect” Black Skinny Pants

Spanx The Perfect Black Pant, $128

First, let’s talking about the pants, available in an XS – 3X.

The comfort is next level. As someone who goes from sitting on the floor with my toddler, to working at my desk, to dropping my big girls off at sports practices, these pants let you move while looking polished.

And now that we are inching closer to sweater weather – their flat front and pull on style are ideal.

Look One: Work from Home

Sweater, $69, Scarf, $51, Mules, $70, Yeti Mug, $29

To work from home on a chilly day, add a cozy sweater. Chelsea28, available at Nordstrom, makes lovely, affordable knits. This particular sweater is supposed to be oversized. The shoulder is relaxed (or “dropped”) and the sleeves are extra long, so you can scrunch them up or pull them over your hands.

I happen to love a turtleneck. So here, I would pull my hair up in a messy ponytail and tie it with a scarf, like this one on sale at Wolf & Badger.

Then, instead of a real shoe, this hybrid of a slipper and mule by Ugg. I wear my Uggs all the time. They keep your feet toasty warm, but you can walk around in them to grab the mail or drive to the car line for school pick up. And of course, a mug to keep the never ending stream of coffee warm.

Look Two: Back in the Office

Blazer, $109, Shell, $39, Earrings, $91, Bag, $328, Shoes, $69

I’ve been hearing from readers who are back in the office and looking to find balance in dressing for a more relaxed environment, but still wanting to look professional.

Grab these pants, and add a few simple workwear basics, starting with this plaid blazer by Liverpool (available at Bloomingdale’s). It’s a beautiful piece that adds some casual structure to an outfit. It’s available in sizes up to XXL, with a little bit of stretch that will match the pants’ comfort.

Next, you need a layer, which is often hard to find. This one, by Halogen, is under $40. Scoop it up in ivory (above) and black if you need to refresh your core work wardrobe. There are also six other prints to choose from, including a classic leopard print you can layer under a black blazer or cardigan. Available in petite and missy.

Then, a comfortable but professional shoe. I found these suede slingbacks with a block heel on sale for under $70. For jewelry, you have so many options. You could add a long necklace to create a lovely layered look under the jacket’s neckline or a bold earring, like these black onyx drops that mix classic and modern design.

Finally, a splurge-worthy quilted bag by Michael Kors to show how adding textural elements can elevate an outfit. You can see, by matching your hardware and metal tones, you can create a cohesive look easily.

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Our Content is Inspired by Our Readers

Our readership inspires all of our posts and is not sponsored or paid for by brands or retailers.

Some links are affiliate links, which means if you purchase via our site, we receive a small commission.

Buy Now, Wear Now and Later: J. Crew Polka Dot Top

August 14, 2020August 14, 2020 by Megan Kristel

Well Dressed - How to wear a polka dot top two ways

Buy Now, Wear Now and Later posts are some of my favorites to create.

The idea behind this series is to help you maximize your wardrobe, in between seasons.

Today, I’m working with this lovely polka dot peplum top, available in sizes 00 – 16 for under $80. (Currently 25% off with code EPIC)

As we move into fall, I’m going to start talking more about specific body types and how pieces I’m featuring can work to hence your shape. So going forward, on posts like this one, I’ll highlight how and why it will work for certain body types.

But before I dive into it below, please remember these are just guidelines. Nothing in fashion is set in stone.

Key Piece: J.Crew Polka Dot Peplum Top

Top, $79.50

Take 25% off with code EPIC

A peplum top looks best on lean or straight up and down, sometimes called “boy” shape body types because it adds curves and dimension.

It will add the same benefit for some rectangles.

If you are an inverted triangle it will bring balance to your shoulders.

For an hourglass, it will highlight your curves, so go for it!

Avoid a peplum if you are a traditional triangle, or an apple shape.

How to Wear in the Summer

Summer: Top, $79.50 | Jeans, $68 | Earrings, $33 | Slides, $77 | Bag, $38

Shop Summer Look

How gorgeous is this look, made with items you may already have and under $100 if you want to pick up something new.

What’s important here are the jeans. If you wear a peplum top you MUST wear a slim bottom, either straight or skinny, depending on what looks best on you.

I’m using these Wit & Wisdom jeans because I know many of you already have them. It’s nice that they hit right at the ankles, this creates an airiness to the outfit. For a other white jean options in all sizes check out our series Basics Building: The Best White Jeans.

Now, the accessories. There is a lot going on in the top, so while we want to keep the rest fairly simply, it’s nice to also draw attention to your face. These these affordable earrings are stunning. They add texture, movement and are just incredibly chic.

Then, this stunning bag, that was originally $177 is now only $48. WHAT? Yes. Total year end steal.

Finally, since this is for the warm weather, these slides are perfection. They are part of the Nordstrom sale and 40% off. Scoop them up now, wear for the next month or so and have them at the ready next spring.

How to Wear in the Fall

Shop Fall Look

Now let’s take this pretty piece into the fall. I have no idea where we’re going, but let’s pretend we’re finally go out and about with friends. Like brunch! Remember brunch?

I use another Wit & Wisdom jean, this time in black, but wear your favorite.

As a much needed layer I added this long cardigan by Halogen , also part of the Nordstrom sale, fully stocked and under $40 and comes in regular and petite. I went with a tan instead of an ivory because it’s not as sever of a contrast. The tan makes it feel monochromatic and seasonally appropriate.

For shoes, swap out your sandals for a bootie, like this pair by Vince Camuto on sale for under $100 at DSW. They get rave reviews and will become an instant go-to in your fall wardrobe.

Then, for a little more movement a pair of hoops (gold tone will work best with the colors in this outfit).

Finally, another cognac bag option. You don’t need both, either work in each outfit. This one by Sole Society is made of vegan leather for $60.

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Our Content is Inspired by Our Readers

Our readership inspires all of our posts and is not sponsored or paid for by brands or retailers.

Some links are affiliate links, which means if you purchase via our site, we receive a small commission.

How To Find Your Style

August 13, 2020August 13, 2020 by Megan Kristel

Today we’re talking about how to find your style.

Discovering your personal style seems easy enough, but start to dive into it and you’ll quickly realize it can be confusing and a little overwhelming.

Have you ever sat down and thought about what kind of clothes and looks you like?

Probably not, because as busy women… who has the time?

For many, myself included, there comes a point in life when we end up with less of a style and more a closet full of clothes we accumulated over the years.

How to Find Your Style

The decades since I graduated from college are a hodgepodge of personal style trial and error.

I fully embraced late nineties style with my low rise jeans and mid drift tops, not so much a style as it was required uniform for frat parties and college life.

After graduating I remember so clearly trying to look like a “grown-up” or what I thought I grown up looked like. Thankfully, that was a quick phase and I spent most of my twenties and early thirties experimenting with different styles, all while having babies, and building a business.

While I’ve always understood the fundamentals of dressing, like proportion and fit, it’s very different to navigate personally. As we age and watch our bodies change, it took me a minute to understand that what worked in my 20’s and 30’s doesn’t work on my body at 40 after three pregnancies – no matter how much I work out.

At my core, regardless of my age or size, I’ve always loved classic American Style. As a young girl, I worshiped Oscar de la Renta and Carolina Herrara. I was mesmerized by their shows, models, and dreamed of growing up to exude their effortless elegance.

But it wasn’t until my late 30s and now at 40 when I felt like who I am as a woman and my personal style match. Like they are finally meeting at the same point.

Because for years, I convinced myself that that was too boring. So I bought things because:

I thought I should like it.
It was on sale.
I was just happy it fit.
Or all of the above.

Maybe that’s the beauty of aging, the confidence you get in being able to say, this is who I am.

How to Find Your Style

So how do you create a style that feels authentic?

What are you supposed to do when you like everything?

And where should you start if you have no idea?

Today, we’ll talk about how you can find your personal style, based on what worked for me, and the strategies we used to help clients over the years.

How to Find Your Style in 6 Easy Steps

When I worked with clients, the first step in our process was to figure out her style.

I created a client questionnaire, which included a section that asked them to think about women with a style they admire. It could be anyone, but it always ended up being celebrities from Jackie Kennedy and Grace Kelly, Laura Hutton, or more current famous women like Jen Anniston or fictional characters such as Olivia Pope.

It was an easy first step to get a sense of what the client liked.

To start this process, ask yourself, who do I think always looks great?

This is like a brain dump; it can be anyone with any style. THEN, take that list and narrow it down to who you want to dress like.

For example. I love Diane Keaton and Helena Bonham Carter. I so appreciate their bold, wild, and unique style. But do I want to dress like them? No.

Readers often tell me they get stuck here because they like everything. And I get that!

It’s a lot like when you’re in the process of decorating your home. You can enjoy all kinds of style, but what do you want to live in?

Can you want to live in more than one? Sure!

And that’s what makes your style unique. It’s how you combine those elements in your own unique way.

I narrowed my list down to three:

Gwyneth Paltrow
Oliva Palermo
Carolina Herrera

What do they have in common? They all share a classic American style with some modern elements that feel relaxed and casual.

Who’s on your list?

Of course, we don’t have the resources (budget, stylist, make up artist, etc.) to dress like a celebrity every day. So we want to create a visual to help guide us in a practical way.

This step is by far my best, most well received tip. We go through this process in detail in our free Wardrobe Challenge (coming back in September!).

It’s the most effective way to break down the difference between styles you like and styles you want to live in, AND it helps you build a wardrobe you love quickly and easily.

Spend some time on Pinterest. Create a personal style board, and “pin” all the looks you like. Then, and this is important, go through them and edit down to only the ones you love.

You may have pinned all different styles. But remember, there is a difference between having an appreciation of a style and wanting to live in it. The pins you keep should only be the ones you want to live in.

After you gather a few dozen pictures look for cohesive elements.

Do you prefer:

Pants or skirts?
Silver or gold?
Mixing prints and patterns or monochromatic?
Romantic or tailored pieces?
What colors show up over and again?

You’ll quickly discover there is a thread of commonality within the looks you keep.

Having clarity around your preferences is the first step in understanding your style and making better choices going forward.

Once you’re board is together, use it as a guide while shopping. Before you make a purchase, ask yourself if that piece will help you create the look you are going for.

Armed with your Pinterest board, do a quick edit purging everything in your current wardrobe that doesn’t get you to your ultimate style goal.

Quite literally, stand in your closet with your Pinterest board open and see if your current wardrobe is a reflection of it.

Don’t be discouraged if it doesn’t. That’s generally the takeaway.

Follow our tips on how to organize your closet in 60 minutes.

Be ruthless. You’ll feel lighter when you get rid of items you don’t like, need, or use.

As you look at your favorite styles, look for what pieces keep showing up.

For me, my signature pieces ended up being dark skinny jeans, an animal print flat or bag, a crisp button-down, white tee shirts, a tan boot, and better jewelry and for work, sleek dresses and neutral-to-me pumps.

These pieces work as an anchor for your style. They are the items you can always count on to ensure your outfit “looks like you.”

One of the reasons our wardrobes and style goes off the rails is because we don’t put the proper time and strategy into shopping. We need to be intentional about what we bring into our closet.

As simple tip to follow when building your wardrobe is to only buy something you can wear three different ways.

The pieces that meet this criterion are what should be your core wardrobe pieces. These will help define your personal style and make it easier to get dressed.

Of course, you’ll buy items that you can’t wear three ways, but they should be few and far between.

As you move through the process of discovering your style, you’ll start to feel more confident in your choices. It’s important to trust your instincts.

Don’t talk yourself into a purchase you’re not thrilled to make.

Stop wear something because someone told you to.

Avoid buying something just because it’s on sale.

The process of building a wardrobe takes time. Try not to feel overwhelmed by everything you might need. Write a list of what you could use to pull some outfits together, and only purchase from that list.

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