I'm Obsessed With Wide-Leg Trousers—6 Autumn Shoes I'm Wearing With Them

I don’t know about you, but in the last year or two, I’ve become completely and totally obsessed with wearing wide-leg trousers to the point where I now can’t imagine what I wore before them. Whatever it was, the skinny-trouser era is well and truly over for me, and as I take on my 30s, smarter, looser trousers have been there to welcome me with open arms. I promise it’s not just because they’re a huge trend right now—although, that helps given there’s now a lot more choice on the market. Mostly, it’s because they’re comfy and cool and make me feel incredibly polished every time I wear them. They work for work, for the pub, for date nights, for relaxed weekend brunches—you name it, and I’ll wear wide-leg trousers for it. 

The only downfall with discovering a whole new trouser shape that you love is having to then figure out what shoes to wear with them. It reminds me of when skinny jeans kicked bootcuts out in my late teens, and I had to adopt Stan Smiths and ballet flats, sharpish. Wide-leg trousers, though, are luckily a little more versatile. Although, they might at first seem like a difficult trouser to pair the right shoes with, as long as you have the number for a good tailor (or you’re taller than my petite 5’2”), you’ve actually got a wealth of options to choose from—especially as we head into a new autumn season. 

In my expert opinion (and handily demonstrated by the stylish influencers below), wide-leg trousers look great with loafers (chunky or classic), boots (lots of them), heels (especially pointed-toe styles) and even trainers—all classic autumnal shoe styles. So if you’ve been struggling with finding loose-trouser outfit ideas and knowing what footwear to wear with them, keep scrolling to see and shop the six best autumn shoes that always go well with wide-legs.

1. HEELED ANKLE BOOTS

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(Image credit: @aniyahmorinia)

Style Notes: If in doubt, opt for heeled ankle boots. That's my motto. Low or high, block or stiletto, any extra height will always help wide-leg trousers look good. And the comfort and versatility of this pairing will astound you. 

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2. CHUNKY LOAFERS

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(Image credit: @symphonyofsilk)

Style Notes: In the same tailoring family, it's hardly a surprise that loafers go with wide-leg trousers. I personally prefer these smart shoes paired with a slightly cropped wide-leg and a flash of ankle. But I've seen plenty of fashion-industry insiders nailing the more androgynous full-length "puddle-pant" and loafer combo too. 

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3. POINTED-TOE SHOES

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(Image credit: @thecarolinelin)

Style Notes: If you're after a more elevated look with your wide-leg trouser outfit, I can recommend opting for a pointed-shoe silhouette. Whether it's a stiletto ankle boot or kitten-heel slingback, it's the toe you're really showing off.

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4. COWBOY BOOTS

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(Image credit: The Style Stalker)

Style Notes: Cowboy boots are set to be huge this autumn, and I particularly love them as a comfortable option to wear under wide-legs that still offers a little height. 

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5. RETRO TRAINERS

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(Image credit: @louisahatt)

Style Notes: Trainers look best with wide trouser styles that just brush the top of the shoe rather than drag on the floor in a puddle. Chunky pairs were the influencers' trainer of choice last year, but for 2023, I feel a bit of a more refined, retro revival coming. 

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6. FLAT ANKLE BOOTS

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(Image credit: @modedamour)

Style Notes: Opt for a slight crop, and you can still make use out of your beloved chunky flat ankle boots. 

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This story was published at an earlier time and has since been updated.

Up Next: 25 Expensive-Looking Autumn Shoes You Can Find on the High Street Right Now

Opening Image: @thecarolinelin