What to Wear with Flare Leggings, As Told by Someone Who Lives in Them (2024)

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This year I had a birthday party where the guests had one requirement: come dressed like me. Before you ask, yes, I’m an Aries and if you’re in need of a party theme idea this one is seriously hilarious, as it was a joy to watch guests make up an interpretation and wear something a little out of their comfort zone. So how did my friends come dressed as me? About 60 percent of them arrived in flared leggings.

Once I discovered my first pair from Aerie, I was absolutely in love. I mean, first of all, I’m 5’9 and they make sizes in extra long. Second of all, they have what they call “extreme flare” options which I find so flattering to balance out my measurements (I’m two sizes larger on my bottom half than my top half). Ever since, I’ve been a devoted fan of flared leggings, and I’m seriously miserable right now in the summer because it’s too hot to wear them.

I’ve been styling these babies for about two years now, so I have tons of tips and tricks to share with you if you’ve ever wondered what to wear with flare leggings. These tips span the seasons because unless it’s snowing, I’m still wearing my flared leggings throughout the winter. Here’s how to style these tried and true bottoms.

First of all, let’s get into a few flared leggings options so you can shop for your base if you don’t already own a pair.

Women’s High-Waisted Slim Fit Flare Leggings

This pair from Target also comes in olive green and is available in sizes XXS through 4X for $20.

Aerie Real Me High Waisted Crossover Super Flare Legging

I’m wearing the crossover super flares in size large, long length, in the photo above. I’m a 29-inch waist, 42-inch hip size and they fit perfectly. Snag these now because they’re on sale for 55 percent off!

What to Wear with Flare Leggings:

Now let’s get into the styling tips. You may have already noticed from these pics, but I’m also crop-top obsessed. If the weather is warmer I love wearing halter tops, tank tops and anything else that lets my arms breathe. The best part about styling flared leggings is that it’s super easy to dress them up or down. In the photo above my “Howdy” tank top is from Urban Outfitters in a size medium and you can still find it on sale there for $29. But any tank top will do. I love the $5 options from Target. You can easily dress up the white ribbed tank with some gold jewelry and channel your inner Hailey Bieber.

Crop Tops

Women’s Tiny Tank Top

This tank comes in six different colors in sizes XXS through 4X.

T-Shirts

Okay, I’m aware that this is still a crop top, but wearing a fitted t-shirt or a big, baggy t-shirt is perfect for the flared leggings style. When I style flared leggings with a t-shirt, I like wearing a cropped baggy t-shirt. You can cut any t-shirt yourself to your desired length, or pick one up like this one from Free People.

We The Free CC Tee

This slouchy tee is perfect for running errands. Fun fact: I used to work at Free People when I first moved to NYC. This tee also comes in three different colors.

Women’s Short Sleeve Slim Fit 90’s T-Shirt

A simple, fitted tee does the trick as well with flared leggings. You can shop this ’90s fit in a few different colors.

Basic Jersey Cat Relaxed T-shirt

I’m also obsessed with any t-shirt Ganni makes. Graphic prints look great with flared leggings.

Long Sleeves

Alo Yoga Vixen Fleece 1/4 Zip

This sweatshirt is so similar to the one I’m wearing in the first photo. I love an all fitted look with the leggings plus this cozy sweatshirt top.

Women’s Cropped Hoodie

This cropped hoodie option is also super cute and comes in two different shades for just $20.

Shoes & Accessories

Reebok Classic Leather Sneakers

Probably the main reason that I adopted flared leggings as my year-long uniform is thanks to the fact that they look great with sneakers. As someone who lives in NYC, I can’t get around at all unless I’m in comfortable footwear. I’m wearing these in the majority of my pics and the classic white is so comfy and cute no matter how I style the leggings.

UGG Women’s Fluff Yeah Slide Checks Slipper

In the photo above I’m wearing these super cute Ugg slippers that have a rubber sole on the bottom, so you can wear them out of the house to run errands, pick up groceries, etc. I love wearing these with my flares; they’re such a funky, cute way to show pops of color in your outfit.

Round Flat Snake Chain Necklace

If you’ve read any of my other fashion articles, you know I’m always hyping up gold jewelry to instantly elevate any outfit. Having a stackable chain like this on-hand is a simple way to accessorize when your outfit needs some final finishing touches.