Alright, let’s talk about these flare leggings. For ages, I was strictly a skinny-jeans-or-straight-leggings kind of person. The whole flare thing? Reminded me too much of my awkward teenage years, you know? But then, I kept seeing them pop up everywhere. My curiosity got the better of me, or maybe I was just bored with my usual stuff. So, I caved. I bought a pair. Black, of course. Gotta start safe.

First Impressions & Early Mistakes
When they arrived, I pulled them on. Comfy, gotta admit. But then came the big question: what on earth do I wear with these without looking like I stepped out of a time machine? My first few attempts were, frankly, a bit of a mess. I tried an old band t-shirt – nope, made me look shapeless. Then a super tight top – also a miss, felt unbalanced. I was about ready to chuck them in the back of the closet.
The Experimentation Phase: Digging Through My Wardrobe
But I’m stubborn. I’d spent money, so I was determined to make them work. I decided to dedicate an afternoon to just trying stuff on. Pulled out half my wardrobe, I swear. Here’s what I started noticing:
- Tops really matter: Oversized sweaters? Surprisingly good, especially with a little front tuck. Gave it that relaxed but put-together vibe. Fitted turtlenecks? Yes! Created a nice silhouette. Crop tops? If you’re feeling brave, they actually look pretty cool, especially with high-waisted flares.
- Shoes can make or break it: This was a big one. My regular running sneakers? Made the flares look kinda frumpy. But chunky sneakers or platform ones? Much better. Ankle boots with a bit of a heel? Now we’re talking! Really elongates the leg.
- Layering is your friend: A simple tank top with an open button-down shirt over it? Chef’s kiss. Or a denim jacket. Adds some interest.
My Go-To Flare Legging Outfits Now
So, after all that playing dress-up, I’ve landed on a few combinations that I actually love and wear all the time. No more guesswork.
1. The Comfy Casual:
- Black flare leggings (obviously)
- An oversized knit sweater (cream or a muted color)
- Chunky white sneakers
- Simple tote bag
This is my go-to for running errands or just chilling. Super comfortable but doesn’t look sloppy.

2. A Bit More Put-Together:
- Dark wash denim-look flare leggings (yes, they exist and are amazing)
- A fitted black turtleneck or a sleek bodysuit
- Black heeled ankle boots
- A longish trench coat or a smart blazer
This one I’ve even worn for a casual dinner out. The key is the fitted top and the boots really elevating the look.
3. Sporty Spice (but make it modern):
- Athletic-style flare leggings (maybe with a stripe down the side)
- A cropped hoodie or a fitted athletic zip-up
- Cool, retro-style trainers
- A baseball cap
Perfect for a walk or when I just want that athleisure vibe without looking like I actually just left the gym.
Final Thoughts
Honestly, I’m a convert. It took some effort, not gonna lie. You can’t just throw them on with anything like you might with regular leggings. But once I figured out the proportions and what works for my style, they’ve become a real staple. They’re way more versatile than I initially gave them credit for. So, if you’ve been on the fence, maybe just grab a pair and have a little closet adventure. You might be surprised!
