How to Wear Boyfriend Jeans

How to Wear Boyfriend Jeans - The Well Dressed Life
How to Wear Boyfriend Jeans - The Well Dressed Life

Today, we’re breaking down how to wear boyfriend jeans, specifically for the grown up crowd.

If you’re looking for a jean that is chic, casual and comfortable, look no further than a boyfriend jean.  Admittedly, we feature a lot of skinny jeans, especially in the winter because they pair so easily with boots.  But, maybe skinny jeans are not your favorite, or you are just ready for some variety.


Boyfriend JeansHow to Wear Boyfriend Jeans - The Well Dressed LifeModern Boyfriend Jeans, Everlane: $68

There are many options when it comes to boyfriend jeans. Generally, they will be loose fitting, and the hem will stop around your ankles.  The most flattering fits will have classic 5-pocket styling, and a relaxed yet slim leg. 

Some variations will have distressing around the knee and hem.  I happen to like that look, but I know many readers aren’t into it. 

For the purpose of today’s post, I picked these Modern Boyfriend Jeans by Everlane.  I like the quality, color of the denim and price. These are a more traditional denim, meaning there is not much stretch so keep that in mind. 

 This darker wash by Madewell are easy to wear and look great with everything. Plus size?  I like these by KUT.  Petite?  Take a look at these from NYDJ.

Shop these other options in all sizes:


You can make boyfriend jeans super casual or date night ready. They are a comfy alternative to leggings, especially if you work from home but want to feel a bit more pulled together. 

I created three different looks with a variety of items you may already have in your closet. 

Three Ways to Wear Boyfriend Jeans 

How to Wear Boyfriend Jeans - The Well Dressed Life

Let’s break down each outfit.

Outfit One

Top, $50  |  Sneaker, $65  |  Bag, $22

Boyfriend jeans are ideal for casual looks.  Here, we paired them with this updated striped top from J.Crew.  The tie at the waist puts a fun twist on an otherwise classic top. 

If you wear the tie, skip a necklace.  To keep the look modern, roll the hem of the jean and wear a pair of fresh white sneakers.  Superga is a popular and affordable option.  They have a low profile, so they complement where the hem will hit you on your calf and the width of the jean leg.

I found this red bag at Target.  It’s a sweet little pick me up for the warmer weather, also available in black and soft blush.

Outfit Two

Jacket, $98  |  Clutch, $149  |  Heel, $96

For nights out  a moto jacket is where it’s at and the boyfriend jean pairs perfectly.  There is a wonderful contrast between the sleekness of the jacket with the slouch of the jean, yet they “go” together because they are both still casual. 

I’m of the opinion that when you wear a moto jacket, the jacket is the outfit and you don’t take it off.  Keep the under piece simple, like your favorite white tee shirt, or a tank and leave the jacket unzipped to create longer line of the body.

Here’s where it gets fun. Pair your jeans with a ladylike pump. This helps elongate your leg, gives you some height and feels dressed up.  These beige Sam Edelman pumps are divine and under $100.  Because you’re going out, I added this small Clare V. pouch.

Outfit Three

 Sweater, $13  |  Heel, $70  |  Bag, $140

In our last outfit we kept the whole look cozy.  First of all, this sweater by H&M is $13, and as I write this, most of the sizes are still available. We featured the gray, but I was close to using the navy – hard choices. 

The heels are by Franco Sarto. From my experience, they are crazy comfortable. Once the weather warms up, even the tiniest bit, I would pull these out. The shoe is still substantial, even though it has an open toe and the block heel works well with the shape of the jean.

Finally, we found a wear-with-everything crossbody, in a remarkably similar color to the shoe. Not that it has to match, but when you’re going for easy and casual, it helps.

Tips on How to Wear Boyfriend Jeans

  •  You can wear any shoe from strapy stilettos to flip flops. Take your height into consideration. If you’re tall, a pointed toe flat will look lovely if you roll the hem of the jean. If you’re short, a wedge will help elongate your leg.
  • To dress up the jeans, think in terms of contrast. Add a fitted blazer, a blouse with lace detail or a pump with some embellishment. Pieces with some kind of luxe detailing elevates the look instantly.
  • Avoid capri style boyfriend jeans.  You want these to hit at or close to your ankle.  Mid calf is the least flattering place for a pant to hit on your leg. (See my unfiltered thoughts on capris here.)




How to Dress Off a Column of Color

Must Have Boucle Jacket for Under $60

There is a trick to creating an easy work “uniform” that you are likely already using without even knowing. It’s called dressing from a “column of color” and it is the easiest way to quickly pull together a professional look. 

Start by creating a column of color with your better neutral basics. You can use any combination: tank/skirt, top/pant or dress (a solid structured sheath works best) as long as it is one color like black, navy, grey, or winter white. 

This “column” creates one continuous line and acts as a base. Then, simply add a blazer, preferably with some interest or a color that complements the column. The blazer works to add contrast which creates a visual that makes your body look longer and leaner.

Below is work wear look I pulled together combining some pieces I’ve had forever, and two updated items, including this gorgeous jacket that is under $60 and stunning flats I found on sale at J.Crew

How to Dress off a Column of Color 

Must Have Boucle Jacket for Under $60

Jacket, $60  |  Pants, $265  |  Shoes, $99  | Similar Tank, $65  | Similar Bag, $298  |  Hoops, $55 

Rarely am I this impressed with a jacket, but H&M hit it out of the park. I picked this up last week for $59 (regular price). Online the sizes are limited but at the H&M in King of Prussia (PA) there was a rack full of them. 

This beauty fits true to size, I’m wearing an 8. Feels great on, it’s substantial but not too heavy and doesn’t feel bulky even though it’s tweed. And it’s lined.  Lined – for under $60. 

Any time I find something that combines black and navy, I scoop it up, because it’s a piece that will pull so many other items together. Wear it with an all black column, swap out black for navy or throw it over a white tank and dark jeans for a super chic Friday office look.  

Despite the affordable price point, this is a quality and will live in my closet for as long as it fits!

Just take a look at the details …

Must Have Boucle Jacket for Under $60

Related: Easy Red Blazer Outfit for Work 

Extra Special Touches

In the same trip I hit J.Crew for some end of year sales and walked away with more shoes than I needed. My favorites are these slingback flats with bow stud details

Must Have Boucle Jacket for Under $60

These are the kind of shoes that make my heart sing. They are flat, so I don’t feel too tall, and I can walk in them all day. But it’s the studded ribbon bow that instantly sold me.

Tip! Look for extra little details on simple styles of shoes to elevate a basic outfit. Doing so adds visual interest, which creates overall depth. 

Here, I like how the shoes balance out the busy-ness of the jacket by creating proportion. 

Related: 6 Flats to Wear When You Can’t Wear Heels 

I paired my two new purchases with some serious wardrobe workhorses I’ve had forever. Theory makes my favorite suit pants. They are expensive so I try to buy them when they go on sale so I have a few to rotate through. I’ve had the ones above for at least 5 years and wear them all the time. 

Note: Theory’s sizing is all over the place, so you might have to size up more than usual. 

My tank is from Banana Republic. I linked to a similar option here. They have great sales so if you don’t need on right away, keep an eye out for a discount code. 

Finally, I’m wearing the gorjana hoop earrings I featured on Monday. They are light and comfortable – I can’t recommend the enough. 

Related: Affordable Earrings that are Office Appropriate

This outfit is a beautiful example of how to combine higher end pieces (the Theory pants) with something more affordable (the H&M Jacket) to create a look that feels sophisticated and doesn’t scream like you shopped off the mannequin of one store.

Shop all items below:

Must Have Boucle Jacket for Under $60

Jacket, $60  |  Pants, $265  |  Shoes, $99  | Similar Tank, $65  | Similar Bag, $298  |  Hoops, $55 



Our content is not sponsored or paid for by brands or retailers in any way. Recommendations are based on personal experience and my time working with women as a stylist and wardrobe consultant for over a decade. 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 for even more free tips, and join our Private Facebook Group for access advice in-depth conversations with other like-minded women.

Waterproof Boots for the Office

Wear to Work: Waterproof Boots
Wear to Work: Waterproof Boots

When the weather is cold and rainy, it’s not the time to pull out a delicate skirt and your favorite suede heels. You need to think practically, and often that means we start to compromise on style.

But when you have the right pieces in your closet, you can still pull together a look that feels stylish without looking ridiculous or risking showing up at work with sopping wet feet (and ruined shoes). 

Today’s look is a mix of better basics, all on sale, that you can mix and match throughout your wardrobe, and wear together on days you need to stay extra dry and warm. 

Waterproof Boots for the Office

Wear to Work: Waterproof BootsBooties, $130  |  Pants, $145  |  Coat, $210  |  Sweater, $98  |  Lipstick, $28  |   Sunglasses, $80  |   Bag, $139

While these boots are far from high fashion, they are clean, classic and best of all, waterproof. They look very similar to the Sam Edelman booties we’ve featured here dozen of times, and when paired with a straight leg pant they practically disappear on your leg.  So you can wear them for your commute and all day in the office without having to switch out your shoes.

We paired them with these stretch wool straight leg pants. Lafayette 148 is typically expensive. These pants retail at almost $300, but certain colors are on deep sale right now at Off 5th. The black option is $120 – that’s 60% savings. 

Their quality is fantastic. I used to work with them regularly when I worked with private clients, especially women with executive level roles.  The fabric travels beautifully, and the styling is timeless. 

STYLE NOTE: These pants are currently available in five colors including sizes 0 – 18. You will have to have the length altered to fit you.  A tailor would typically charge between $10 – $20.

It important to pair these boots with a straight leg pant, or a slight bootcut, they are too clunky to wear with skinny pants and are not the right cut for an ankle. 

I lean towards black staples this time of year, so a vibrant pop of color adds some personality.  Many of you have this J. Crew everyday sweater. It’s a solid basic that works as a layer or on its own. Stock up on over 20 colors in sizes XXS – 3X. 

To round out the look, I found this plaid wrap coat at Boden.  It’s actually a very dark navy, not black, which still works. It would also look chic with a dark pair of jeans and a white blouse for a causal outfit option. Alternatively, it’s available in classic red. 

Finally, nothing makes me feel more confident than wearing a dark pair of sunglasses, a structured bag (on sale!) and a red lip.  The combination instantly makes whatever else you are wearing feel sophisticated.

STYLE NOTE: Not all red lipsticks are made equal. Kosas makes a nontoxic lipstick with gorgeous pigment. The color stays put without over drying your lips, and it doesn’t feather or bleed.  I wear their red regularly, and also like their “rosewater” for a neutral everyday color.


Our content is not sponsored or paid for by brands or retailers in any way. Recommendations are based on personal experience and my time working with women as a stylist and wardrobe consultant for over a decade. 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 for even more free tips, and join our Private Facebook Group for access advice in-depth conversations with other like-minded women.


Cozy Holiday Pajamas

Cozy Holiday Pajamas

I am 40 years old, and here I am, posing in my jammies. Considering I’ve only been putting myself in these posts since the Fall, embarrassment has come sooner than I imagined.

But it’s for a good reason. Pajamas are essential this time of year!

Whether you wear matching family sets for Christmas morning or, more practically, need a few pairs for visiting and staying with family, or a thoughtful last minute gift,  today’s post has you covered.

Good Old Fashioned Pajamas

Cozy Holiday Pajamas
J Crew Set, $45

Let’s start with practicality.

Pajamas are a wonderful way to help you transition from day to night. What’s better than coming home from work, taking off a pair of tights or worse, Spanx, and putting on something soft and warm? 

I have always loved sleepwear, but lately, like everything, their prices seem outrageous. I’ve seen sets for upwards of $400. I think if I had money to burn, I would burn it on so many other things. 

This year I did splurge on this bathrobe for myself, and last December, I bought these Ugg slippers that rarely leave my feet. Other than that, I keep an eye out for pretty sets at places like Target, Nordstrom Rack which is a gold mine, and J. Crew Factory always has a small but lovely selection. . 

Like this menswear-inspired set which is my current favorite. If I could wear them all the time, I would. I look forward to slipping into them after a long day of work and kids. Frankly, they make me feel like a person. 

For today, I found a handful of options perfect if you spend a day over the holidays in your jammies, if you’re heading to someone else’s home for a few nights, or maybe you still need a gift.


Cozy Holiday PajamasRed Stripe, $40  |  Heather Gray, $88  |  Light Blue, $45  | Gray Cropped Top and Bottom  |  Buffalo Check, $20  |  Navy, $128

Red Stripe, $40: Featured below! These are my “Christmas Pajamas.”

Heather Grey $88: More like a cozy indoor sweatsuit, ideal for movie watching, or to put after a long day outside in the snow. 

Light Blue, $45: Crisp, yet soft and perfectly preppy.

Grey Cropped $50: A fantastic sale for a set you can wear all day long. Top, bottom, purchased separately. 

Buffalo Check, $20: An adorable and trendy Target find, in missy and plus sizes

Navy, $128: A splurge worthy set from Barefoot Dreams. It feels like you’re wearing clouds, if you’re into that kinda thing (raises hand). 

Holiday Pajamas

Cozy Holiday Pajamas
Rachel Parcell Red Stripe Set, $35

 I have so many happy Christmas memories as a kid. One of my most favorites is our “Christmas Eve Pajamas” tradition.  Every year, my mom bought my brothers and me pajamas to wear on Christmas Eve – you couldn’t wear them before, you had to save them for the big night. They were always soft and cozy and helped make the night magical. 

My mom had a way of using clothes to celebrate events and make them even more special.  She used them to mark and evoke a memory. I still remember being little, wearing my new pajamas, and feeling special, safe and well loved

Once I had kids of my own, I could not wait to do the same for them. And I have, every year since they were born. One could argue I spend too much time trying to find the perfect ones, pouring over options, looking online AND going into stores, but I enjoy it. 

We don’t ever “match” as a family. The girls always get matching sets, and I buy Bri and me a new pair of something extra nice that we can wear all winter. It’s the only way Bri gets pajamas 😉

But this year, I couldn’t pass up this pretty set from Rachel Parcell. So I bought the red strip for Maddie and me and this red Fairisle print for Ava and Vivi

They are perfect since I have to appease a very cool preteen, and still find something sweet for our almost one year old 😉 

Shop: Woman / Kid / Baby All On Sale I’m wearing a Medium.






How to Wear a Faux Leather Skirt to Work 3 Ways

How to Wear a Faux Leather Skirt to Work

If you need an affordable wardrobe kick that is easy to incorporate into your current wardrobe today’s post is for you. Last week, while running into Target, I spotted this skirt and immediately scooped it up. 

It’s a nice quality, faux leather skirt, in a classic cut that’s perfect for work, and easy to tweak to go from a day in the office to a night out. 

The best part? It is only $25.  (Actually scratch that, as I publish this it’s $18!) 

Skirt Details: Available in sizes up to an 18, limited inventory. I love the cut, since so often leather-like skirts are obscenely short. Be sure to check at your local store if your size is not available online. 

3 Ways to Wear a Faux Leather Skirt to Work

Today, I wanted to show you how easy it is to wear this in a professional setting. It feels chic while still totally appropriate. Any time you can bring a different kind of texture into a traditional piece, like faux leather, suede, velvet, even a brushed cotton, you instantly add visual interest and that creates a more complex look that makes your outfit sophisticated. 

It’s the little details that elevate a look. 

Side note: If you’re new around here, welcome! You should know that the pictures of me below are not retouched or photoshopped in anyway and I don’t have professional hair or makeup (I wish!).

This is what I look like every day, I wear between a size 6 – 10 depending on the brand and I am 5’10. In the looks below I’m wearing a size medium or an 8. 

I purchase my wardrobe with my personal money and never do reviews or make recommendations in exchange for compensation from brands or retailers. 

When available I always list inclusive size options. 

Let’s jump in. 

 Outfit 1: Simple Basics 

How to Wear a Faux Leather Skirt to Work

My goal is to help you build out a wardrobe, rather than having to reinvent the wheel every time you get dressed. A big part of that is making sure you have your basics covered, so when you find a little gem like this skirt, you can quickly pull your look together without having to buy anything else.

For the first, incredibly easy outfit, I used this hunter green cashmere crew neck sweater (similar version here). I’ve had it for a few years and wear it quite often, especially this time of year.

The cashmere, paired with the faux leather, makes it feel lux even though the pieces themselves are a basic as you get.

To stay warm, a pair of Hue opaque tights (these wash well) and my go-to Sam Edelman Hazel Heels in black

Shop: Sweater / Skirt / Tights / Heels

Outfit 2: Neutral Layers

How to Wear a Faux Leather Skirt to Work

This look is my favorite because it plays with tonal texture and includes camel, which just makes it look so expensive even though it’s not. 

I added a simple black knit I found at H&M for $12.99 (I’m wearing the medium) and these fantastic Nine West boots (featured in my Best Buys of 2019 post on Monday). 

Then, I topped it off with this camel coat, also from H&M, I bought for under $60. 

Shop: Coat / Top / Skirt / Tights / Boots

Outfit 3: Print Blouse

How to Wear a Faux Leather Skirt to Work

Finally, I found this blouse at Nordstrom last week and absolutely love it.

Isn’t it so hard to find a blouse for work that stands on it’s on? This one will go with so many things, like the faux leather skirt, or your favorite black pants. You’ll look finished without needing an additional layer. 

The blouse is available in green print and solid black in sizes xxs – xxl (about an 18 or 16W) I’m wearing a medium. 

I kept the tights and heels the same as in the first outfit – but this look is totally different. I like it for an after work holiday party, or a festive lunch, you could even wear it for one of the upcoming holidays. 

Shop: Skirt / Blouse / Tights / Heels 

Women’s High-Rise A Line Faux Leather Skirt

Faux Leather Skirt from TargetFaux Leather Skirt, $18


Under $20 Holiday Ready Sweater

Under $20 Holiday Ready Sweater

When I host a holiday party at home, I skip the heels and party dress and opt instead for a festive sweater and comfy pants. I want to be able to move around the kitchen, chase after a kid, and curl up next to a friend.

Many of you have similar needs and requested a few options for your casual end of year entertaining. So today, I’m kicking off a series of posts that feature holiday-ready pieces at super affordable prices, starting with this pretty ivory beaded sweater

Under $20 Holiday Ready Sweater

Under $20 Holiday Ready Sweater

Sweater: $19.99 | Pants: $89 | Clutch: Old 

Let’s talk for a minute about what is going on in retail right now. I ran to the mall for the first time in forever this week and could not have been more underwhelmed.

Everything looks the same, is designed for tweens, or is frumpy. I spent most of my adult life looking forward to the day I could walk into Nordstrom and buy whatever I want, and now that I can afford a few nice things, I couldn’t find anything that looked special.

So I wandered around the mall and ended up in H&M, where I could have bought half the store.

They currently have lots of pretty neutrals, fun little details and super affordable prices – so you can try something a little outside your comfort zone without feeling like you have to make a huge commitment. 

Everything use to run small, but lately they have made strides in aligning their sizes with more standard American sizes, Additionally, they committed to becoming more sustainable and transparent with their manufacturing practices

Under $20 Holiday Ready Sweater

This sweater is $19.99 and that feels like a steal for a sweater I’ll wear a handful of times this season, and maybe next. I bought it in ivory, but you have four other color options, in XS – XL. It’s suppose to be oversized, with a drop shoulder. I’m wearing the medium. 

I’m wearing it here with a stretchy pair of black pants by Liverpool that feel like leggings but are cut like a jean. They are available in size 0 – 16 including petite. I’m wearing an 8. 

Under $20 Holiday Ready Sweater

I don’t normally wear embellishments, but the tonal look here helps it feel subtle. I like that it’s lightweight, so you can be in a warm kitchen or crowded house and not over heat. 

Have a great weekend!

Knee High Boots for the Office

Knee High Boots for the Office

You would think, considering the time of year, that knee-high boots would be easy to check off our shopping lists. But, like everything in retail right now, our options are either ridiculous-looking or perfect except for the fact that they cost the same as a mortgage payment.

What I try to present on our site is a collection of ideas and recommendations that balance practicality and function with beauty and style. I use my own life as a framework: working mom, with three kids, loves fashion, enjoys feeling stylish, but any semblance of disposable income now goes to travel sports and piano lessons. 

When I recommend items and inspiration, I think about the woman wearing it: who she is, where she’s going, and how she can stretch the pieces out into her wardrobe.

Price becomes an issue because I don’t want something so expensive that it’s unrealistic for the majority of readers, but I also don’t want something so cheap that it lacks value.

Finding that sweet spot where value, function, and style intersect is key.

That’s what we have here with these boots by Sam Edelman.

Knee High Boots for the OfficeKnee High Boots for the Office

Boots, $135  |  Dress, $138  |  Belt, $7  |  Bag, $268  |  Tights, $12  |  Earrings, $21 

Sam Edelman has become a go-to for me over the years. Their shoes aren’t overly trendy, but they look current, and their price points are approachable.

Finding knee-high boots, with clean lines, for under $200 is a dream. These are on sale right now for under $150, so scoop them up if they are on your must-have list. They are available in black, tan, and a terrible snakeskin that you should never, ever wear. 

These are classic with a twist. They are some subtle details, like interesting top stitch and a few tiny studs at the toe that elevate these just a bit. 

The tan is my favorite option. It’s a rich tone that goes with absolutely everything. Above I paired it with a simple black knit fit and flare dress (sizes 0 – 20) and tights. This is another look you can take to the office or wear outside of work.

To give the outfit some depth, I would remove the tie belt and add a leather one instead. Then I kept it classic with gold hoops (only $21) and this stunning black satchel from Lauren Ralph Lauren.

Because we are all about versatility, wear these with everything. From a skirt with tights to jeans and a sweater. You’ll be able to take these from day to night to the weekend: one boot, endless possibilities.

You may also like:

How to Wear Tights