I bought my first pair of flare leggings on a bit of a whim, standing in a fitting room debating whether I was too old for the trend. Spoiler: I was not. And honestly, they have become the pair of bottoms I reach for more than any other, which I did NOT see coming.
There is something about that little flare at the ankle that makes leggings feel less like gym gear and more like a proper outfit. My sister keeps borrowing mine, which is the highest compliment she gives clothing, and now she has three pairs of her own.
So if you have a pair sitting in your drawer wondering what to do with them, or you are just here for the outfit inspo (my favorite kind of afternoon).
Twenty Ways to Style Your Favorite Flares All Year Long
Black Flare Leggings With Cropped Leather Jacket
This is the outfit I default to when I want to look like I tried without actually trying. A black flare leggings outfit paired with a cropped leather jacket just works, every single time. The cropped cut sits right at the natural waist and lets that flare do its thing.
Add a simple white tee underneath and some pointed ankle boots and you are done. I wore this to a lunch date last month and got two compliments before I even sat down.
Brown Flare Leggings With Cream Knit Cardigan
Okay, a brown flare leggings outfit with a soft cream cardigan is the coziest thing I own, and I am not exaggerating. The warm brown against the cream is so easy on the eyes, sort of like a latte in outfit form.
I like to leave the cardigan a little oversized and slightly slouchy. Slouchy is doing a lot of work in my wardrobe these days.
Gray Flare Leggings With Oversized White Shirt
A gray flare leggings outfit with an oversized white button-up feels crisp and easy and a tiny bit borrowed-from-someone-else, in the best way.
Tuck just the front of the shirt in so it hits at the waist – that little half-tuck trick changes everything, I promise.
Black Flare Leggings With Fitted Blazer
When I need to look pulled together for a meeting but I refuse to wear actual trousers, this is what I do. A fitted blazer over black flares reads professional from the waist up and comfortable everywhere else.
The blazer keeps things structured while the flare adds a bit of movement. I keep a black blazer hanging by the door for exactly this reason. It is my little cheat code.
Brown Flare Leggings With Powder Blue Tank
Brown and powder blue is a color combination I did not expect to love, and now I cannot stop pairing them. The soft blue tank keeps the look fresh and warm-weather friendly, while the brown grounds the whole thing.
This is a great one for those in-between days when it is warm out but you still want the flare. Throw a light jacket over your arm just in case.
Grey Flare Leggings With Cropped Trench Coat
A grey flare leggings outfit under a cropped trench coat is the kind of look that feels very put-together with almost no effort involved. The trench adds that classic, slightly polished vibe, and the cropped length keeps the proportions right with the flare.
My friend Dana wore this on a rainy Saturday when we went antiquing and she looked like she had wandered out of a catalog. I told her so. She pretended not to be pleased but she was.
Black Flare Leggings With Ballet Flats
Ballet flats and flares. That’s the memo. Something about the flare skimming right over a delicate flat just looks so feminine and easy.
I pair mine with a simple top and call it a day. This is my errand-running uniform, honestly, and I have run a LOT of errands in it. Ballet flats forever, in fact.
Brown Flare Leggings With Suede Bomber Jacket
A suede bomber over brown flares is such a fall look, and I mean that as the highest praise.
I found my suede bomber at a little consignment shop years ago and it still gets pulled out every October like clockwork. Some pieces just earn their keep.
Gray Flare Leggings With Matching Zip Jacket
Matching sets are having a moment and I am firmly on board. A gray zip jacket with your gray flares creates a long, streamlined look, almost like a track set but somehow more wearable out in the world.
Zip it halfway, layer a tank underneath, and add sneakers. It is comfortable enough for travel days and still looks like you got dressed with purpose.
Black Flare Leggings With Striped Rugby Shirt
A striped rugby shirt with black flares gives off this sporty-preppy energy that I find completely charming. The collar and the stripes add a playful touch, while the black keeps it from feeling too costume-y.
I stole this idea from a girl I saw at the coffee shop, if I am being honest. She had a film camera around her neck and looked incredibly cool. I went home and recreated it immediately.
Brown Flare Leggings With Butter Yellow Sweatshirt
Butter yellow was everywhere this year and I fell hard for it. Paired with brown flares, that soft yellow sweatshirt is warm and cheerful and just a little unexpected.
It is the kind of outfit that makes you feel good on a gray morning, which counts for a lot. Add white sneakers and you have got a look that says weekend without trying.
Grey Flare Leggings With Black Halter Top
For an evening out, a sleek black halter top with grey flares strikes a nice balance between dressy and relaxed. The halter shows a little shoulder while the flare keeps things grounded and comfortable.
I add small gold earrings and some heeled mules for this one. It travels well from dinner to wherever the night takes you, and you never once feel squeezed into something restrictive.
Black Flare Leggings With Cinched Waist Blazer
A blazer that cinches at the waist is a small detail that makes a big difference. Over black flares, it creates this lovely defined shape without any effort on your part.
Belt it or find one that already nips in at the middle. I wore this to my niece’s recital and felt appropriately fancy while still being able to sit through two hours of tiny dancers.
Brown Flare Leggings With White Baby Tee
Simple, simple, simple. A fitted white baby tee tucked into brown flares is about as easy as an outfit gets, and yet it looks so intentional. The contrast of the crisp white against the warm brown is just right.
This is my go-to base when I do not have brainpower to spare. Add whatever shoes are closest to the door and layer on some jewelry if you are feeling it.
Gray Flare Leggings With Burgundy Track Jacket
A burgundy track jacket over gray flares gives me a very late-90s sporty feeling, and I mean that fondly. The deep burgundy adds a pop of color against the neutral gray, and the track jacket keeps things casual and relaxed.
Zip it up, add chunky sneakers, and you are ready for a walk, a coffee run, or pretending you are about to work out when you are really just going to the grocery store.
Black Flare Leggings With Cropped Cardigan
A cropped cardigan buttoned up over black flares can double as a top, which is exactly the kind of two-for-one situation I appreciate. It hits right at the waist and lets the flare shine below.
Leave a button or two undone at the top. This is such a sweet, slightly retro look, and it works for so many settings. I have worn mine to brunch and to a school pickup, no changes required.
Brown Flare Leggings With Matching Sports Top
For a workout set that actually looks nice enough to grab a smoothie in afterward, match your brown flares with a coordinating sports top. The monochrome brown reads sleek and intentional even when you are dripping sweat.
I like a supportive top that I can move in without thinking about it. Throw an oversized zip jacket over the top on your way out the door and nobody needs to know you skipped the gym.
Grey Flare Leggings With Chocolate Brown Jacket
Gray and chocolate brown together is such an underrated pairing. The rich brown jacket warms up the cool gray flares and the whole combination feels expensive somehow, even when none of it was.
I threw this on for a fall drive with my husband, the kind where we pull over every ten minutes to look at the leaves, and I was cozy the entire time. It photographs beautifully too, not that I am fishing for photos.
Black Flare Leggings With Oversized Denim Jacket
An oversized denim jacket over black flares is the outfit equivalent of a deep breath. So easy, so comfortable, so hard to get wrong. The denim adds a laidback edge and the black flares keep it from feeling too casual.
Push the sleeves up and add white sneakers or ankle boots depending on the weather. I have owned my denim jacket for so many years I cannot remember buying it, and it still gets worn constantly.
Brown Flare Leggings With Retro Sneakers
Ending on a fun one. Brown flares with a pair of retro sneakers, the low-profile kind with the colorful stripes, feels sporty and a little nostalgic all at once. The sneakers add personality and keep the whole look grounded and walkable.
This is what I reach for on the busiest days, when I need to be comfortable and covered in walking but still want to feel like myself. And it does exactly that.
