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

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

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

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

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

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

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

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

(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

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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