My Perfect Transitional Piece? A Pair of Great Socks

I can’t quite pinpoint when I first started wearing socks with a fashionable intent, but I know it’s been a while. I remember a photo of myself in second grade, dressed up in a “fancy dress” with white, foldover ruffle socks, black patent Mary Janes, and a flowy, floral dress. I also had scrunched-up cotton Wigwams paired with double-laced Keds (known as “bow-bows” in my elementary school), worn with bike shorts and an oversized T-shirt. Damn, the '90s really knew how to do socks well.

But I don’t think I truly embraced the quirky sock wardrobe until Alessandro Michele’s Gucci revival of the loafer. From that moment on, I’ve never looked back. Living in New England, there’s a specific summer marker for me: the day I can go barefoot in my home again. For nine months out of the year, I stay pretty socked up. Wearing socks actually helps prolong the life of footwear by creating a barrier against the general unappealing nature of feet. There are some shoes I’ve never worn barefoot, intending to keep them for a long time. Besides their practical purpose, socks also serve as a transitional layer, helping to extend the shorter silhouettes of warm weather before boot season begins. Plus, they add a touch of playfulness and childlike nostalgia.

My sock choices often lean toward a girly, bookish vibe or camping-inspired styles. I’m excited to show you how I embrace these looks for cooler weather.

Block It Out

An easy way to extend the jean shorts season is by simply adding a sock. But please, not just any sock. I love adding a solid pop of color with socks to almost anything, especially to some unexpected colorblocking. Mixing bold colors always looks stylish. Even if it’s outside your comfort zone, adding just a splash of color with a sock feels like a low-risk way to try something new. These Colorful Standard socks are reasonably priced, made with organic cotton and environmentally friendly dyes that hold up really well over time: the ones shown here are over two years old. They are slim enough to fit into a vibrant ballet flat—a pairing I adore. Finding super bright ballet flats can be tricky, but I encourage you to keep an eye out—it’s much more fun to choose a color over a neutral. I paired it with a two-toned rugby shirt and a wicker box bag for a look that’s a little unexpected.

Pattern and Texture

A cozy camp sock is a great alternative to a technical athletic sock, immediately adding a more rugged and nostalgic feel to your look. My favorites are from Maggie’s Organic, and I wear these almost year-round. When styling them in a more fashionable way, I drew inspiration from the marled brown and white colorway and ran with it. I chose to focus heavily on texture and pattern for this look, pairing fuzzy flats over the socks with a plaid skirt I usually wear with boots, a tan striped tee, and a pop of color in my bag and sweater because I’m still me and I love color.

When Stripes Become a Neutral

A striped sock is almost as versatile as a pop of color, and versatility is key to sock styling. You don’t want anyone thinking you’re a one-trick pony! I see a stripe as a neutral that looks great even with a monochromatic outfit or something simple like a navy sweater and jeans. But this is not a tube sock—it’s an all-over striped sock that feels a little less sporty and more preppy. I played into that look by adding a layered shirt dress with quirky boat shoes. I’m so glad they’ve made a comeback because this has been an underrated shoe for me as a non-sailor: it’s a bit more polished than a sneaker and not as fussy as a loafer. I also added a mesh grocery tote to keep this vibe super low-key.