How I’m Styling Wide-Leg Jeans: 3 Outfit Ideas

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Move over, skinny jeans! After trying on 13 pairs of wide-leg jeans, I’m completely won over.

Wide-leg jeans are here to stay in my closet, and no one is more shocked by this development than I am. They’re pretty much all I’m wearing this winter.

3 Cute Winter Outfits, Ft. The Best Wide-Leg Jeans For Curves

I found the wide-leg styles I tried on much more curve-friendly than I had supposed, and I’m happy to report that my denim collection is a little bit more on-trend now. I discovered three favorites during my roundup of wide-leg jeans, and below I’m sharing how I’m styling these jeans for winter.

Outfit 1: Silk Shirt + Black Wide-Leg Jeans + Houndstooth Coat

I love the combination of black denim with the wide-leg style, and these Madewell jeans are just the ticket. The inseam length is perfect for me without going to the trouble of hemming (I’m 5’5” for reference). The cut of the jeans also skims over my curves to create a clean silhouette.

Most important, these jeans are part of Madewell’s Curvy line, meaning that the hips and booty are cut more generously, but the waist is smaller.

These black wide-leg jeans are part of Madewell’s Curvy line, meaning that the hips + booty are cut more generously, but the waist is smaller.

similar silk shirtjeans | sneakers

To me, these black jeans almost look like trousers, just a little bit more casual. Paired with a silk shirt that can go from day to night, the overall effect lands somewhere between casual and dressed up, which is exactly where I want to be.

There are so many gorgeous silk shirts available now from brands like Quince and Everlane, and this silk shirt from & Other Stories. I picked up this shirt when I was still putting on a blazer and heels for marketing events pre-pandemic, and now I’m still wearing the same shirt, just with jeans and sneakers. & Other Stories has some beautiful colors currently available, but I also love my silk shirt from Everlane because it’s washable.

Paired w/ a silk shirt, black wide-leg jeans are somewhere between casual + dressed up, which is exactly where I want to be.

similar silk shirtjeans | sneakers 

The black-and-white houndstooth coat from Abercrombie is a perfect top layer. Midweight and midcalf, this is not a coat for the depths of winter, but it’s a versatile addition to my outerwear wardrobe for those winter days that don’t veer into Arctic-temperature territory.

I grabbed this coat as part of my Abercrombie try-on and decided it was a keeper. Although the black-and-white option is low in sizes, the coat comes in other patterns, like a classic brown plaid and solid cream color, both of which would work with this outfit formula just as well.

Midweight + midcalf, this wool-blend Abercrombie coat is not for the depths of winter, but it's a versatile addition to my outerwear.

similar silk shirtjeans | sneakers | coat 

For shoes, I kept it simple with the classic Nike Air Force Ones because I was on my way out the door for a day of bookstore and bakery-hopping in Boulder, and I knew I was going to be putting a lot of miles on my feet. Now that I’ve broken in these sneaks a little bit, they’re my most-worn shoe. Add a red lip, and I’m ready to go.


Outfit 2: Cropped Puffer Vest + Long-Sleeve Shirt + Baggy Jeans

The Good American Good Skate jeans are just fun. They’re almost true skater jeans — except, thank goodness, they aren’t because then they wouldn’t fit me. What I mean is that Good American takes curves in to account, so although the legs of the jeans are ultra-baggy, they aren’t loose in the booty or the waist.

Bonus: These jeans are soft, baby. No rigid denim here. You can lounge in these jeans like they’re sweatpants all day long.

Good American takes curves in to account, so although the legs of the Good Skate jeans are ultra-baggy, they aren’t loose in the booty or the waist.

cropped puffer vest | long-sleeve shirt | jeans | boots

Now, onto the cropped puffer vest. I may or may not have seen this vest in a TikTok post somewhere between the hours of 1 and 3 a.m. during a night of restless sleep. Every other year, I get the itch to buy a puffer vest. Every time, I think to myself: “That’s such a classic piece. I should have one in my closet.” Then, I take it home and put it on, and…wow…no. I just can’t make puffer vests look chic on me.

But then I saw the cropped version, and I was inspired to try once again. Mainly because I saw some women around my size wearing them, and I think the cropped length is more flattering than the full length because the crop shows my waist and doesn’t cover my booty. Also, I love the coffee color — I’m obsessed with a coffee-and-cream color palette this year, but tons of other colors are available.

This cropped puffer vest from Amazon is more flattering than a full-length version because it shows my waist + doesn't cover my booty.

cropped puffer vest | long-sleeve shirt | jeans | boots

Layer any lightweight, long-sleeved sweater or shirt underneath the vest. Here, I’m wearing a long-sleeve performance shirt I picked up off Amazon. I love the light stretch, the thick material, and the close-to-body fit. I will mention the shirt looks an awful lot like a certain name-brand performance shirt you can find at over twice the price.

I love the light stretch, thick material + close-to-body fit of this long-sleeve performance shirt/lightweight base layer from Amazon.

cropped puffer vest | long-sleeve shirt | jeans | boots

To keep the hem of these super-baggy jeans from dragging, I wear these with any shoe that gives me a little extra height. I’ve already updated my look with the wide-leg style and cropped vest, so I’m bringing it back to my ‘90s roots with classic Doc Martens boots.


Outfit 3: Cozy Neutral Cardigan + Cropped Wide-Leg Jeans + White Sneakers

OK, am I breaking new fashion ground here? No, I’m not. But if I’m being honest, I’ve been wearing this outfit pretty frequently. This soft cardigan (from Amazon again!) is comfy, neutral, and pairs with all of the different colors of camisoles I have hanging in my closet. I love cardigans because I don’t really like having fabric on my shoulders if at all possible, but I also have to cover up the tattoo on my shoulder for client-facing Zoom meetings during my workweek.

Hence, a cardigan that I throw on and off as I enter and exit meetings all day long.

This soft sweater (from Amazon again!) is comfy, neutral, & pairs with all of the different colors of camisoles I have hanging in my closet.

sweater | camisolejeans | sneakers | earrings | similar necklace

This particular sweater has just a little bit of a lantern sleeve and is ever-so-slightly cropped. It’s also budget-friendly and comes in a bunch of different colors. For the price, the weave of the sweater is surprisingly tight, and I expect the sweater to wash well.

sweater | camisolejeans | sneakers | earrings | similar necklace

Madewell truly hits it out of the park with jeans for me because of the variety of styles, length and — yes, once again — its curve line. These cropped wide-leg jeans are shorter than the black Madewell jeans above and have a raw hem, which I think draws attention to whatever shoes you want to show off. The high waist of the jeans also adds length to my legs (something I’m always happy about) if I give my camisole a little French tuck.

Madewell truly hits it out of the park with wide-leg jeans for me because of the variety of styles, length & its curve line.

sweater | camisolejeans | sneakers | earrings | similar necklace

Keep the outfit just a little bit playful by adding your favorite jewelry. I’m wearing little multicolored mushroom huggie earrings by Kurt Geiger and a crescent-moon necklace (this one’s similar).


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What are your go-to denim outfits this season? Are you embracing wide-leg and baggy styles?

Xo,

Anne

Pinners, you’re gonna love this!

Move over, skinnies! These wide-leg jeans (think: Good American + Madewell) have completely won me over. Here's 3 ways they're starring in my winter outfits.
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