HOW TO WEAR Archives - The Well Dressed Life

How to Wear Boyfriend Jeans

September 15, 2020January 21, 2020 by Megan Kristel

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 Jeans Modern 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

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.)

Classic White Sneakers for Women that Go with Everything

May 17, 2019May 17, 2019 by Megan Kristel

Classic White Sneakers That Go With Anything

If you’re paying attention to trends you may have noticed that classic white sneakers are popping up all over the place. Today, you can wear them with just about anything and I am here for it.

Remember Melanie Griffith in Working Girl, taking the ferry into the city, with her white sneakers, socks, and pantyhose? That’s not what we’re talking about, but, gosh I love that movie. I wanted to be the nice version of Sigourney Weaver, and marry Harrison Ford, or someone like him.

Anyway, this new way of incorporating sneakers into everyday looks is less a trend and more a movement. It wasn’t so long ago that corporate dress codes demanded women wear stocking and heels. Sneakers becoming prevalent on the weekends at work, and beyond is not only a byproduct of a more casual environment but also a reflection of more women in leadership both at the helm of retail and at large.

Don’t get me wrong, I happily wear a good heel. It’s just nice to see that it can be a choice and not a requirement. And that we don’t have to literally walk around in pain to do our jobs. Personally, I love the look of taking a sporty sneaker, and wearing it with a more formal piece. It feels fun and approachable.

The Best Classic White Sneakers for Women

One of the lesser talked about sides of the fashion industry that I enjoy is trend tracking. Part of my job is to notice the emergence of a trend and be able to predict what will have longevity and what will come and go.

With icons like Serena Williams wearing sneakers under her gown to both the most recent royal wedding and the Met Ball early this month, and sneakers showing up in high fashion street style, you can tell blending comfort and style is going to continue to trickle down to the mainstream.

Tips for Wearing White Sneakers

Recently a popular LA-based blog I follow did a round up of classic white sneakers for women, and their recommendations were ridiculous. Do you have $495 for a pair of kicks? I sure don’t. And if I did, I still wouldn’t spend $500 on sneakers.

Prices that are outrageous for the sake of being outrageous bothers me. There are some shoes that if you do spend $500 on, are gorgeous, high-quality and will last you years so your price per wear will be reasonable. But after a certain price point, expensive sneakers are expensive purely for vanity purposes. Frankly it’s just a dumb way to spend your money.

The post did, however, inspire me to create my own version for people who live in the real world. Before we start, a few things to remember:

Consider these “dress” sneakers. Do not take them to the gym and do not try to wear your gym sneakers in their place.
You want them to be all white. Avoid bright logos and accents. The whiter the more fresh and crisp they will look.
Pair them with any bottom except bootcut jeans or pants. For bootcuts to look their best, they need some kind of heel to help elongate your leg. If you wear a bootcut jean with a sneaker of any kind you’ll look frumpy and dated.
They look especially polished with skirts and dresses, you can wear them with jeans, a tee and a blazer, and depending on your personal style and industry, I’ve seen them worn with a colorful suit and look incredibly chic.
Keep them as simple as possible. You want a slim and low profile. They should feel light when you wear them and they should also feel lightweight within your outfit. Anything too clunky won’t work.

You can see here how we worked an updated pair of sneakers with an inexpensive Old Navy dress last week.

Classic White Sneakers for Women All Under $150

I set our budget at $150, most of these are well under. Within that price range there are lots of options. Below are my top picks:

If you are sporty:

For a classic, sporty style for under $60 Nike makes a canvas sneaker that will work with leggings, ankle length jeans or casual dresses. They are ideal for weekends, or busy casual days.

If you like being on trend:

Veja makes a leather low top for $150. They are super polished and will go with anything. These are especially nice with jeans and a blazer. The contrast between the formal feeling blazer and the athletic inspired sneakers looks so cool. I like these for traveling, especially if you have an overseas trip with a lot of walking on the agenda, and you want to be comfortable but still chic.

If you are classic:

Superga became famous when Kate Middleton starting wearing them. They are cute, comfortable, and under $70. (Royals – there just like us!) Much like the Duchess, I like them with dark skinny jeans and a striped boatneck top. They’re just a great everyday sneaker.

If you are modern but traditional:

For a classic spring and summer shoe, these Keds are on sale at Nordstrom Rack. They have a navy detail to them, so not exactly all white, they are sweet if you are a jeans and tee shirt kind of girl. I like this all white verson in a more current style than a traditional Ked. They are $55 and the best value of the bunch.

If you just want to give them a try:

Finally, ASOS has a simple, clean, pretty much perfect pair for $30. They also go with anything. For the price, you’re not going to get super comfort and longtime wear (go for the Keds instead) but they’ll serve their purpose for the season if you are on the fence about the look.

Wear to Work: Hot Pink Blazer

January 20, 2020March 6, 2019 by Megan Kristel

If you’re starting to feel “blah” about your current work wardrobe situation, now is a good time to shake it up a bit. Sometimes an update is as simple adding one new, cool piece — something that adds a twist to the pieces you already own.

I call these “novelty pieces.” A novelty piece is the opposite of a basic, but just as important. They add interest, help you look modern, and add a stylish element. They offer loads of impact, especially if most of your wardrobe is composed of simple basics.

Today we’re using a bold pink double-breasted blazer. I’m crazy about this outfit, like, I would wear it today if I had to go any place more interesting than my home office.

All the pieces we’re featuring today have loads of mix and match potential. Think of this as a mini capsule. This is one way to wear these pieces, but you can get some dangerous life out of every piece.

I started with a double-breasted blazer in a gorgeous hot pink. This one by Topshop is all sorts of cool. If you like this one be aware of their sizing. It runs a full size small, so if you wear a 10, pick up a 12.

It’s on sale for $57. Generally, you don’t want to invest much in novelty pieces. This one happens to look more sophisticated than it’s price tag.

Other options to consider: Banana Republic did a classic one button blazer in an equally pretty hue (all sizes available).

You can pair it with any slimmer lined black pants you already own. Make sure you use a slim pant to balance the volume of the blazer, otherwise your outfit will look oversized.

If you opt for the BR option, you could wear an updated bootcut like the Talbots “barely bootcut” we featured last month.

Related: Wear to Work: Classic Bootcut Pants

Or you can up the style factor even more and use a “dressy” pair of joggers. These are different than the sweatpant version we worked with last week. They are made of a ponte stretch knit, so they are equally comfortable, but have a better, more office appropriate hand.

I wear a version of these frequently, with various blouses and blazers. Every time I put them on, I feel like I know what I’m doing. For under $60 you can build out your outfit options. They work with everything you would wear with a classic black trouser.

When I discover a layering piece worth sharing, I shout it from the rooftop. Why is it so hard to find a simple, basic well made shell or tank to wear under blazers and cardigans that aren’t $400?

Buy this Gibson tank at Nordstrom immediately if you need a base layer for under suits and separate jackets. It’s $59 and comes in 11 different colors and patterns. Easy-peasy.

For shoes, this look is screaming for an airy pump, so a slingback and ankle strap would work well. I went with these Pour La Victoire slingbacks in black velvet on sale for $112. They are a classic style with a wearable heel. Definitely a piece you’ll use a lot.

This, a tailored satchel from Ann Taylor will neatly fit all of your daily must haves and probably work with most pieces you already own.

Finally, I used a more expensive earring. I’m trying to offer a variety of price points throughout this series. Personally, I’d rather have one cool pair of earrings I wear often than a drawer full of cheap options. I love the modern feel of these gold and opal backward huggers. They are subtle and add a little edge.

Weekend Inspiration: Loafers

September 7, 2018 by Megan Kristel

We love receiving questions from readers and old clients, so when one of my favorite former clients sent an email asking about loafers, it was like she was reading my mind. This time of year, as we dip in and out of warm and then chilly days, we need a shoe to help with the transition. Ballet flats can feel too light depending on the weight of your separates, but boots can be too heavy. Loafers can be just the answer to your in-between season shoe needs.

So how can you incorporate loafers into your outfit? Often, the weight and style of a loafer can feel clunky and throw off balance. The answer, then, is to bring balance with other pieces that add equal weight.

Loafers, $110 | Jeans, $89 | Shirt, $50 | Bag, $30 | Earrings, $10

The Loafers

I love everything about this look for early fall. The loafers are classic, and the color is a perfect “cognac.” If you pick up something similar, skip any style with extra details or hardware. They make it too hard to blend the shoe with the rest of your outfit.

Hobo

Your handbag is essential when working with a loafer (sounds so dramatic). You want something of equal weight. Here, we picked an affordable hobo by Sole Society. If you wear something too delicate, your shoe will look bulkier than they are.

Jeans

Everything else in the look is casual, and ideal for a fall weekend. These jeans by KUT are a nice break from skinny jeans. The loafers work well because the jeans have a significant cuff at the bottom and require a shoe to “stand up” to them. KUT is an awesome brand of under $100 jeans (remember when all jeans were “under $100”?). Their fit is excellent and they are available in a wide size scale.

The Shirt

I’m crazy for this shirt. Long time readers know my love of stripped shirts. This one by J.Crew feels fresh and seasonally appropriate. You can wear it on it’s on now, and as the weather changes add a quilted vest and scarf. We included these $10 CZ studs because I wear a version of them just about every day and am always asked about them. They serve as a place holder until I can afford the real deal 😉

Have a question? Pop them in the comment section or send us an email and we’ll answer it in an upcoming post. Our site is fueled by the needs of our readers!

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Wear to Work: One Pant Three Ways

September 5, 2018 by Megan Kristel

I don’t feature a lot of prints, especially in pants. But when I stumbled on these black and white windowpane printed pants, I thought they would be an excellent way to break up all the basics we feature. I discovered Liverpool pants last winter when a pair of their pants showed up in my Stitch Fix delivery. I almost sent them back without trying them on, but at the last minute I grabbed them and am so happy I did. The fit is fantastic, and they are so so SO comfortable.

Key Piece: Pant, $89

With any print, but especially with printed pants, you want to balance the look with updated basics. Keep in mind, when you’re buying a bold piece, be sure you can wear it at least three ways. This will prevent you from having random pieces in your closet you don’t know how to wear.

Option one

Key Piece: Pant, $89 | Top, $225 | Belt, $40 | Pump, $99

This look is perfect for early fall, when it’s still warm out, but wearing summer specific pieces feels awkward. I went with a white peplum sleeveless top. This one by Theory is on the expensive side, but use it as inspiration. A good peplum should fit at your natural waist and the peplum should just fall over your midsection. For this look, I added a black belt to create the feeling of a layer, and kitten heel slingbacks.

Option Two

Key Piece: Pant, $89 | Sweater, $68 | Loafer, $60 | Bracelet, $128

We tend to pair black with black and white, which is always chic but don’t discount mixing it with other neutrals for an extra sophisticated look. Here, we used an oatmeal crew neck sweater. The combination is relaxed and casual but still entirely appropriate for the office. Keeping with the laid-back look, we used a loafer to ground the outfit. Then, add your everyday jewelry and an interesting bracelet like this gold-tone wrap bracelet from Henri Bendel.

Option Three

Key Piece: Pant, $89 | Blazer, $74 | Tank, $17 | Pump, $120 | Necklace, $80

Headed to a meeting? If you’re a creative or can be casual, but still want to look pulled together, add a boyfriend blazer, and you’re set. I love this blazer from Mural; the shape works well with a slim cut ankle pant. You can layer it over our favorite J. Crew Factory drapey tank. The length of the tank and blazer work well together. Add a long necklace, like this one we’ve featured a zillion time by Kendra Scott and our go-to Sam Edelman black pumps.

Can I Wear Bootcut Jeans?

March 9, 2019August 31, 2018 by Megan Kristel

Ladies, the heavens have opened, the angels are singing, and it’s a new day. Bootcut jeans are not only back in style but readily available for the fall season.

I know so many of you are ready for an alternative to the “skinny” silhouette, and for years, wide leg jeans were almost impossible to find with any variety.

Bootcut jeans are flattering for all body types. The leg shape balances out your hips and shoulders, creating a curvy, hourglass shape. Remember, every time a style comes back there are subtle changes that make a big difference in executing a look.

This means the bootcut jeans you held onto sitting on a shelf in your closet might not translate.

The updated cut is much slimmer. It will narrow around your thigh and softly open to the hem. The leg opening has a mild flare, rather than an exaggerated one.

For today’s post we worked with a classic 5-pocket cut from Wit & Wisdom. These fit so well, have great stretch. They do run big, so size down at least one, and if you’re ordering online, bring in one and two sizes down. (Sizes include petite, 00 – 18.)

I seriously love this look. It’s a great example of simple pieces, in rich neutral colors, combined in a sophisticated way. There is nothing fussy about it, but it’s elegant. We mentioned these ankle boots on Monday’s Ten List, and already so many of you ordered them. I own these in putty (color above) and wear them all the time. They are also available in “saddal”.

The sweater, featured in oatmeal, is divine and comes in 14 equally gorgeous colors. It’s just a chic and comfortable piece to throw on with your jeans and be out the door looking polished in minutes. I added the belt to create a layer and some interest. When you wear a belt with a sweater, make sure the sweater is lightweight and slightly tuck it into the front side of your jeans to show off the belt.

Accessories are essential when you are dealing with basic pieces. You don’t want to over do it, or be too sparse. When done well you can elevate a basic sweater and jeans combo to something extra.

I geek out when I discover the perfect accessory that makes a look cohesive. I found this scarf and based the rest of the accessories around it. The scarf is $20 and has all the colors of fall. If you like scarves, pick it up before it sells out.

To pull out the color in the scarf and general feel of the outfit, I used a hobo by Dooney and Bourke in a rich burgundy. Don’t overlook burgundy as a neutral, it’s a modern, go with everything color that never fails. Want a different color? The same bag is available in over a dozen colors.

Lastly, a gold button earring with a metal swirl detail and an open gold-tone cuff bracelet complements the hardware on the hobo and is just enough to finish the look.

Fall is right around the corner, and I can’t wait! We are finalizing our editorial calendar for the season. Be sure to ask any questions or make any requests in the comments of each post, and we’ll continue to use them as inspiration for upcoming content.

Enjoy the long weekend!

Wear to Work Now and Later: Floral Skirt

August 29, 2018August 29, 2018 by Megan Kristel

Think about some of the pieces you already have hanging in your closet. You know the ones, we all have them. The random skirt (dress, pant, or blouse) usually in a print, that we found on sale, or bought on a whim because “this is what everyone is wearing.” I do it all the time, and I write about fashion “rules” for a living. It’s hard not to be lured by the $24.99 price tag hanging on a sale rack. Sometimes, when paired with better basics, these bargains can be great additions to your wardrobe. So let’s try to work with some of those pieces you already own before you put them in the donate pile.

For today’s wear to work post, imagine that random piece and start to think about how you can put it into your office outfit rotation. As an example, I’m using this floral pencil skirt from Macy’s. It’s on sale and available in a variety of prints and patterns. (Also in plus and petite.) The pattern is bold but still chic and sophisticated. It reminds me of all the years when I worked with clients. I would stand in their closet and have them show me an item they like, but couldn’t figure out how to wear. Most of the time, the solution was super simple.

Skirt, $41 | Shoe, $99 | Wear now with: Shirt, $58 | Necklace, $35 | Later swap shirt for: Sweater, $98

When working with a separate in a bold print, you want to balance it with basics. I would call this skirt a novelty piece. It stands out, but when you’re creating a look, you don’t want one element to walk in before everything else. You want a cohesive, balanced look. Pairing a novelty piece with basics is how you create that balance, but basics don’t have to be boring.

The Shirt

My first thought was to pair the skirt with a white button down, my typical go-to. Instead, I went with the light blue option. It’s creates a subtle difference. Just by swapping out the color you create a more modern look. Of course, if white shirts are your thing, or that’s what you already have, keep it white. Brooks Brothers still makes the most affordable, comfortable, and best quality button down.

Tuck the shirt into the skirt since it has a beautiful waistline. I like a tucked in shirt. So many women think they can’t pull it off, but almost everyone can. Why hide your curves?

The Shoe

For shoes, I did an ankle strap pump because they are wear now and later. (If you have a classic black pump, that works too!)

When wearing an ankle strap it’s important to understand that the shoe will cut off the line of your leg so be sure that the skirt hits at the proper part of your leg. We’re trying to show as much of your leg as possible to create a flattering proportion for your height. Usually, for a shape like this skirt, have the hem stop at the very top of your knee. If you’re petite, you can go a little shorter, but not much. Any longer and it will weight you down. Louise et Cie (they are owned by Vince Camuto) makes a gorgeous, well-made shoe. I have a few of their flats and pumps and have been very happy with the comfort level and how nicely they polish up after a quick end of season visit to the shoemaker.

The Necklace

The trend now with jewelry is layers of light and delicate pieces. But it’s a trend, so you can still wear some of your statement necklaces. I wouldn’t go too oversized, just something that fits into the neckline of the shirt. By incorporating stone and metals, you give life to a look. It’ keeps it from feeling too flat, and also works as a layer in the warmer weather. This particular necklace pulls out the neutral colors of the skirt, and that helps the look feel on purpose without being matchy-matchy.

The Sweater

Bringing this outfit into the fall is easy peasy. You have two options, depending on your comfort level. You could layer a simple sweater over the shirt. Maybe it’s my 12 years of Catholic school uniforms, but I still love the look. You’re creating layers, without having to use a cardigan or blazer. Blazers are awesome, but they can feel redundant after a long winter.

I know though, for as much as I’m down with the combo, some women can’t stand the feeling of “all those layers.” In that case, wear the sweater on its own and keep the necklace. The combination of the texture of the shirt, with the elements in the necklace and the pattern of the skirt all, work happily together. I could live in this J.Crew sweater (it comes in a rainbow of colors), all fall, and winter. It’s that perfect, Jackie O style sweater that you can wear on its own for a simple and chic look or add a necklace or scarf. It’s lightweight enough to even wear under a blazer when it’s super cold outside.

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