The Top 10 Shoe Trends To Style With Socks This Fall

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 fall 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 fall, 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.

Technical Sneakers

Ultra-sporty and technical sneakers are here to add a little weird 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 colors with mixed textured, particularly Gortex and mesh—then pair with a dress sock, to keep things quirky.

I love a sticky trend, and I especially love that kitten-heeled pumps aren’t going anywhere. Creamy 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.

Classic Ballet Flats

The classic black ballet flat is somehow still managing to be both a wardrobe staple and a fall trend. Keep them feeling fresh by taking a cue from Li and mixing textures, juxtaposing your go-to pair with a socks that’s just a little fluffier and chunkier than you’d expect.

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 sockettes, go for something fun that feels intentional.

Kitten Heels

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.

Square-Toe Slingbacks

Slingbacks have had a big year, and I’m personally thrilled to see some more square-toed 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 you’re getting a car right to dinner versus taking the subway. Try it out around the house first.

Black Sneakers

(Image credit: @himichelleli)

Black sneakers are having themselves a little moment under the radar, a micro-trend if you will. I love the sporty style juxtaposed with Michelle Li’s sheer silver skirt, with grey socks that create a tonal look with a mix of textures.

Clogs

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