What To Wear With Flare Leggings

Flare leggings a.k.a. yoga pants have made a comeback along with so many early 2000s trends. The current version is high-waisted, slim through the thighs, and slightly flared from the knees to your heels. Compared to skinny leggings which end at your ankles, flare leggings give you the illusion of longer legs. The flared shape balances your hips (whereas skinny leggings emphasize the difference between your hips and ankles). Ready to try them? Here’s what to wear with your flare leggings…

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Cropped Sweatshirt And Sneakers

For an effortlessly casual and chic look, wear your flare leggings with a cropped sweatshirt. I’m wearing the Magic Rinse™ Relaxed Crewneck Sweatshirt from J.Crew. It’s really lightweight, almost like a t-shirt.

My leggings are the Restore Soft High Waist Pocket flare leggings which I wear a lot! They hardly ever make it into my closet as I usually grab them right out of the laundry basket. I’ve washed them many times and they have kept their shape, color, and feel. I also love that the pockets are deep enough for my cell phone.

My sneakers are Allbirds Tree Runners which are now available at Nordstrom. If you haven’t heard of Allbirds, I wrote about them in this post (spoiler: they’re really comfortable sustainable sneakers).

Cropped T-Shirt And Jacket

In the 90s we saw flare leggings with body-hugging baby tees and flip-flops. For an updated look wear a cropped relaxed t-shirt with your flare leggings.

My navy t-shirt is J.Crew’s Broken-In Jersey T-shirt in XS. This style is currently on sale with an extra 50% off if you use the code SHOPNOW. (Note that it is final sale). I like that it has a lot of stretch and a relaxed fit (ideal for a mid-life belly!)

If you like extra coverage, then add a structured jacket or open front cardigan.

My Puff Sleeve Denim Jacket is currently on sale and available in regular, tall, and petite sizes. I’m wearing it with my Zella Studio Twist Back T-shirt. My boots are the Miller Water-Resistant Chelsea Boots which are c currently available in black leather or olive suede at Nordstrom.

My camouflage t-shirt is the Organic Daily Relaxed T-shirt in XSP (as Athleta styles are usually longer than other brands). And my open front cardigan is the Pranayama Wrap also from Athleta.

Turtle Neck Or Half-Zip Fleece

If you like that Aprés Ski look try a turtle neck top or half-zip fleece. My turtleneck top is the Perfect Fit Ribbed Turtleneck from J.Crew. I sized up to a Small but it’s still a snug fit on me so I probably will wear it under a puffer jacket or vest.

If you’re looking for a cute and affordable half-zip fleece, take a look at this Dynamic Fleece Half-Zip Sweatshirt

Other Options For Your Flare Legging Outfits

Can you wear your flare leggings with an oversized top? Absolutely. Try this Vintage Soft Mockneck Split-Hem Sweatshirt. An oversized top with loose pants (joggers, sweatpants, wide leg pants) can look a bit frumpy or sloppy. But because flare leggings are fitted around the thighs, they work nicely with an oversized CYA top.

How about with a sweater? Sure! I love this striped Felted Merino Half-Zip which has a casual but cool vibe.

A blazer? Yes, but I would recommend a casual sweater blazer rather than a classic one. I have seen some office-wear looks with flare leggings, but in my option, they don’t belong in a traditional workplace.

What about shoes? Sneakers, fitted boots, and loafers (especially chunky ones if you want to embrace that 90s look) all work!

Your turn! Which of these looks is your favorite? Do you own any flare leggings? Let me know below…

P.S. Join me on Instagram to see lots of outfit options in a Reel.