Fashion / Celebrity Style

The Top 10 Shoe Trends To Style With Socks This Autumn

When it feels like the classic items in my wardrobe have taken over and my outfits are getting a bit predictable, a little injection of quirky styling is usually the fix. It’s never anything too dramatic, just something small and unexpected that effs up a perfectly fine look—like a way-too-fancy vintage brooch, a belt that feels a bit wrong, maybe an off-season handbag that doesn’t quite make sense.

This kind of effortless quirk is synonymous with Gen Z styling, which I love for all the irony and messy individuality it brings to fashion that can feel dominated by wardrobe staples and investment-worthy neutrals. It’s the kind of fun, covetable styling I associate with writer and stylist Michelle Li, who may have just missed out on technically being Gen Z, but whose delightfully unpredictable sense of style defines the genre. As I dove into her feed for some autumn footwear inspiration, I couldn’t help but notice the easy styling trick she uses to layer in a tiny bit of extra personality to her looks. Here’s Li wearing 10 of this season’s most on-trend shoe styles, that she’s proving look even better with socks.

T-Bars

Fashion influencer and stylist Michelle Li wearing chic fall footwear with socks.

T-bar styles are popping up all over the place this autumn, with a preppy school-uniform vibe that lends itself perfectly to being paired with socks. From Tory Burch and Reformation’s easy-to-wear flats to Sézane’s mock croc heels, these are perfect if you’re a Mary Jane devotee who’s looking for what’s next.

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Technical Sneakers

Fashion influencer and stylist Michelle Li wearing chic fall footwear with socks.

Ultra-sporty and technical sneakers are here to add a little weirdness to our outfits, particularly bright neon pairs that seem designed with a potential search and rescue operation in mind. For something a little more subtle but with the same energy, look for more subdued colours with mixed textures, particularly Gortex and mesh. Pair them with dress socks to keep things quirky.

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Kitten-Heeled Pumps

Fashion influencer and stylist Michelle Li wearing chic fall footwear with socks.

I love a sticky trend. Case in point? Kitten-heeled pumps, which aren’t going anywhere. Creamy white styles are carrying over from summer, classic black pairs remain worthy of your investment, and this particularly on-trend burgundy option from Nine West gets bonus points for its suede-like finish.

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Classic Ballet Flats

Fashion influencer and stylist Michelle Li wearing chic fall footwear with socks.

Classic black ballet flats are somehow still managing to be both a wardrobe staple and an autumn trend. Keep them feeling fresh by taking a cue from Li and mixing textures, juxtaposing your go-to pair with socks that are just a little fluffier and chunkier than you’d expect.

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Retro Sneakers

Fashion influencer and stylist Michelle Li wearing chic fall footwear with socks.

Low-rise sneakers with a vintage vibe continue to dominate the space below the ankles of fashion people everywhere. A special mention to the brighter hues that fashion people are loving, which feel extra punchy when paired with fresh white socks. Ditch those no-show socks and go for something fun that feels intentional.

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Loafers

Fashion influencer and stylist Michelle Li wearing chic fall footwear with socks.

As an aging millennial, I’d say that loafers and socks go together like Summer and Seth: a little bit wrong, but oh-so-right. Lean into white socks with black loafers for some extra ’90s Julia Roberts energy.

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Square-Toe Slingbacks

Fashion influencer and stylist Michelle Li wearing chic fall footwear with socks.

Slingbacks have had a big year, and I’m personally thrilled to see some more square-toe styles are here to give our toes a little break. In terms of adding socks, I’ll just say that is styling perhaps better suited to nights when you’re getting a car right to dinner versus taking the subway. Try it out around the house first.

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Black Sneakers

Fashion influencer and stylist Michelle Li wearing chic fall footwear with socks.

(Image credit: @himichelleli)

Black sneakers are having a little moment. I love the sporty style juxtaposed with Michelle Li’s sheer silver skirt. The grey socks create a tonal look with a mix of textures.

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Clogs

Fashion influencer and stylist Michelle Li wearing chic fall footwear with socks.

Whether you’re wearing them out to the letterbox while working from home or to dinner on a Friday night, clogs deserve a little place in your autumn wardrobe. Flat styles with socks will scratch that normcore itch, while heeled mules with sheer stockings feel very downtown cool.

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