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.
Reformation
Abalonia Chunky Maryjane
Tory Burch
Violet T-Strap Flat
Sézane
Monique High Mary Janes
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.
SALOMON
Speedcross 3 Rubber and Mesh-Trimmed Ripstop Sneakers
SALOMON
Xt-6 Rubber-Trimmed Mesh Sneakers
Nike
Zoom Vomero 5 Sneaker
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.
Toteme
The Wedge Leather Pumps
Mango
Patent Leather-Effect Heeled Shoes
Nine West
Propper Pointed Toe Kitten Heel Pump
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.
Tory Burch
Eddie 2.0 Ballet Flat
Jeffrey Campbell
Aurora Flats
Mango
Leather Ballet Flats With Bow
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.
Gola
Gola Race Leather Sneakers
Adidas Originals
SL 72 Og Sneakers
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.
Reformation
Agathea Chunky Loafer
G.H. Bass
Marion Buckle Weejuns Loafers
J.Crew
Maison Ruched Loafers in Leather
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.
Reformation
Maddox Slingback Heels
Zara
Faux Patent Leather Slingback Shoes
Proenza Schouler
Trap Slingback Pumps
Black Sneakers
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.
SALOMON
Acs Pro Advanced Rubber-Trimmed Mesh Sneakers
Jeffrey Campbell
Aleta Sneaker
Adidas Originals
Samba MN Suede-Trimmed Leather Sneakers
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.
Mansur Gavriel
Everyday Mules
Veronica Beard
Fern 2 Genuine Shearling Clog
Zara
Animal Print Leather Mules