Over the past few years, flares have transitioned from a ‘dated’ fashion relic to a chic and contemporary style staple. Kick-flare jeans, flared leggings and tailored black versions crop up constantly in the trendiest corners of Instagram and TikTok, proving the endless versatility of this rediscovered classic.
But if you're not used to wearing flared trousers, they can be difficult to style the first time around. Especially where footwear is concerned. The wide silhouette of flares can make choosing the right shoes a challenge; you're working with a different proportions, and the wrong choice could throw off the balance of your outfit. Luckily, though, some of our favourite influencers have mastered styling this 2025 essential, so we looked to them for guidance on which shoes to wear with flared trousers.
From laid-back, sporty options to dressy shoe pairings perfect for night outs, discover our favourite shoe-and-flared-trouser formulas for the season ahead.
See the Best Shoes to Wear With Flares:
1. Platforms
Style Notes: The proportions of a thick, platform sole work in perfect harmony with a flared leg—they rocked this look in the ’70s for a reason. Choose a Mary Jane style for extra trend points or stick to a chunky heeled boot.
Shop the look:
These are as comfortable as they are stylish.
Charles & Keith's new collection is full of gems like these.
For that price, how can you resist?
2. Loafers
Style Notes: Loafers are the chicest choice if you're wearing your flares day-to-day. They're comfortable, practical, and they lend a sophisticated air to every look.
Shop the look:
These also come in black and grey marl.
Two-tone loafers are set to be everywhere this year. Watch this space.
Classic penny loafers are incredibly versatile.
3. Pointed-Toe Shoes
Style Notes: If you're going out-out and seeking shoes that will elevate your flares, a pointed-toe kitten heel is the clear winner. You can also wear this combination during the day with a flat iteration.
Shop the look:
I love how dramatic the flare on this pair is.
The ultimate dancing shoes.
So on-trend.
4. Chunky Boots
Style Notes: When in doubt, add a chunky boot. This option works especially well with a slouchy jumper on top to balance things out.
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H&M has really delivered on the flared trouser front this season.
Once you break these in, they'll be your comfiest boots.
Tap into the khaki footwear trend that's circulating right now.
5. Trainers
Style Notes: Admittedly, there are few trouser styles a pair of trainers won't work with, but this pairing is perfect for a low-key weekend when you've got little on your to-do list and want a low-effort look to match.
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How cosy do these look?
You can't go wrong with New Balance trainers.
A fun pop of colour to cheer up your cold-weather outfits.
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