Flare jeans look like they might come with a rule book. Thankfully, they’re easier to pull off than you think. Here’s the thing: the wide leg does most of the heavy lifting for your outfit, which means the rest can stay simple. Just pair them with the right shoes, and you’re good to go!

Alright, let’s clear things up! Bootcut jeans? Think fitted through the thighs, with just a little flare starting at the knee and kicking out at the hem. Now, flares? They’re basically bootcut’s extra-dramatic cousin—snug through the hips and thighs but really letting loose from the knee down, with leg openings that can stretch wider than 20 inches. If bootcut jeans are a gentle breeze, flares are a full-blown fashion gust. 💨
Both styles come in all shapes and sizes—cropped, ankle, full-length, you name it. They’re like the Swiss Army knife of denim; whatever vibe you’re going for, they’ve got your back (and legs).
For this post, though, we’re treating bootcut and flares as one and the same because, honestly, who’s got time to split hairs? Or hems? And between us, I’ve noticed even the experts can’t seem to tell them apart—so if they can’t, we’re definitely allowed to wing it when it comes to pairing them with shoes.
What Shoes To Wear With Flares?
Wearing flare jeans can actually be super fun and flattering once you get the hang of styling them. The key is finding the right balance with your top and shoes. Since flares have a dramatic shape from the knee down, you want to keep things a little more fitted or streamlined on top to balance out the look.
As for shoes, flares love a little height. Think chunky boots, platform sneakers, or even heeled sandals. These will keep the hem from dragging and make your legs look endless. Plus, flares can totally work for casual days or dressy nights, depending on how you style them. So, no, it’s not hard—just a little styling magic and you’re good to go! ✨
1. Chunky Ankle Boots
- Why: The slight bulk balances out the wide-leg silhouette of flares.
- How to Style: Opt for boots with a pointed or square toe to elongate your legs. A neutral leather or suede pair will match most fall outfits.
2. Platform Sneakers
- Why: Platforms add height while keeping things casual and comfortable.
- How to Style: Choose white or beige sneakers for a retro-inspired look, perfect for running errands or casual brunch outings.
3. Heeled Mules
- Why: Mules with block heels complement the flared hem and create a chic, polished vibe.
- How to Style: Pair with cropped flares or tuck your pants slightly over the top of the mules for an elevated fall outfit.
4. Clogs
- Why: Clogs add an on-trend, vintage flair that pairs beautifully with the boho vibe of flares.
- How to Style: Wear with flares and a cozy knit sweater for a relaxed fall aesthetic.
5. Loafers with a Heel or Platform
- Why: Loafers add sophistication and structure, perfect for work or more formal outings.
- How to Style: Pair heeled loafers with high-waisted flares and a tucked-in blouse for a chic fall ensemble.
6. Pointed-Toe Boots
- Why: The sleek toe elongates your legs and creates a seamless look under the flared hem.
- How to Style: Style with long flares that slightly graze the ground for an elegant touch.
7. Chelsea Boots
- Why: The snug fit at the ankle complements the wide flare, creating a nice contrast.
- How to Style: Go for classic black or brown Chelsea boots with high-rise flares and a tucked-in turtleneck for a trendy fall look.