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
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.
SHOP THE LOOK
This feels like a very 2023 take on the cargo pant.
These block heels look comfy enough to wear all day.
When you're not wearing with wide-leg trousers, toss on a floral maxi dress and let these peek out from the bottom.
Arket brings these back every year, and for good reason.
2. CHUNKY LOAFERS
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.
SHOP THE LOOK
It's worth investing in a great pair of black trousers.
A modern classic.
Mango's AW23 shoe collection is seriously impressive.
The gold hardware instantly elevates these.
3. POINTED-TOE SHOES
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.
SHOP THE LOOK
One of our all-time favourite pairs of wide-leg trousers.
Slingbacks always feel so elegant.
This mink shade is a nice change from black and brown pairs, but just as versatile.
It's looking like the mesh footwear trend will continue into early autumn.
4. COWBOY BOOTS
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.
SHOP THE LOOK
I own these trousers in other colours and get so much wear out of them.
Ganni makes the coolest cowboy boots around.
A subtler version that can easily be slotted into all your autumn looks.
These will also look so chic with longline dresses and skirts.
5. RETRO TRAINERS
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.
SHOP THE LOOK
Arket's trousers never disappoint—I'd style this pair with one of the brand's oversized blazers.
This colour palette is so easy to style.
The ultimate autumn trainer.
I'm picturing these with black trousers and a relaxed charcoal jumper.
6. FLAT ANKLE BOOTS
Style Notes: Opt for a slight crop, and you can still make use out of your beloved chunky flat ankle boots.
SHOP THE LOOK
I adore the styling here. Well done, COS.
The Row's sell-out Zipped boots are back for another year, and we couldn't be happier about it.
You can also pick these up in black.
I always turn to Other Stories for designer-looking footwear.
This story was published at an earlier time and has since been updated.
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