5 Chic Ways to Wear Socks with Heels in 2024—and 1 That Just Doesn’t Work

Sharp, angular and a great choice for petites hoping to elongate the look of their legs, pointed-toe shoes are a timeless pick, whether in kitten-heel slingback form or as a higher pump. If you have a pair on hand, you can soften up their severe shape by pairing ‘em with classic white socks, scrunched or folded at the ankle, as displayed by these 2024 Fashion Week attendees from New York to Sydney. Just note that these aren’t your thick, sporty gym socks; opt instead for thinner dress socks that keep the whole line of your foot nice and sleek.

Bayonetta glasses aren’t the only way to channel TikTok’s ‘office siren’ trend, which is sure to make a comeback in the cooler months. For a sexier take on business attire (even beyond the office), slip into a pair of sheer black knee-highs, preferably paired with a hem that’s short enough to show off the tops. They’re a little bit suggestive in their nod to hosiery, but look totally chic whether styled with bold platform heels or stilettos. If you don’t want to go the knee-high route, I’m also a fan of sheer black socks that hit at the ankles or mid-calf (which I show off in the second pic, paired with Sam Edelman heeled Mary Janes).

I love an unexpected color combo, and one that kept coming up in my deep dive of street style sock looks was gray and red. More specifically, gray socks worn with bright red shoes. Given that cherry tomato has been dubbed one of fall 2024’s hottest hues by Pantone, it’s the perfect time to pick up some fiery footwear and give it a fresh update with a gray layer. You can even don a pair with metallic threads sewn in to add some fun, dressy dimension to your look.

Platform loafers and heeled Mary Janes are fall favorites, especially if you’re going for a preppy, ‘dark academia’ vibe. While they’re easily matched with those aforementioned sheer socks, I also really like the idea of contrasting their chunky shape with some feminine accents. Think: ruffled edges, pointelle knits and even bows—a cutesy, coquettish detail that even Naomi Osaka went all in on at the 2024 US Open.

When it comes to socks, things don’t have to be so black and white (or gray, for that matter). You can totally work in a fun pop of color that either complements your outfit in line with the Three-Color Rule, or serves as a contrast to an otherwise monochrome ensemble. See how these fashion-forward street stylers work in vibrant hues to amp up the visual interest of their high heels below the knee.

I’m all about trying funky new things in your OOTD, so this is absolutely a style judgment-free zone. But if there’s one sock-and-shoe combination I just can’t get behind, it’s thick socks with slinky, strappy sandals. Not only do the thin straps appear awkward and overpowered as they try to cut through the chunkier fabric, it also just seems like it would be really uncomfortable to walk around in. If you are set on wearing strappy heels with a layer underneath, it would be best to go with thinner socks or sheer nylons that won’t create any weird bunching or pulling.