Skip to main content

It’s here: that time of year when your closet is boring. We’re long past the days of being excited to wear coats and boots. The holidays with their velvet and sequins have come and gone. But winter drags on ahead of us: spring dresses and sandals aren’t even in sight.

Shopping is a tempting solution: stores always peddle their seasonal wares in the post-Christmas retail slump at jaw-dropping prices. Sure, you could buy five more sweaters that you don’t love but that are a great price, just to ward off sartorial boredom.

Or . . . you could make do with what you have, saving those precious pennies for when the spring lines hit the racks. I know I always regret end-of-season purchases because even if it doesn’t feel like it right now, the next season is just around the corner—at least in retail time—and you’ll soon be wishing you had more pennies in your pocket to invest in a dress you’ll wear for the next six months.

So what to do?

The first step to fixing any problem is identifying exactly what the problem is. To get the ball rolling, here are some of the major fashion ruts I know I (and I expect, you) fall into in the winter months and a few suggestions for what to wear “instead of that” that have revitalized my own winter wardrobe.

A lot of them deal with layering, because this is both a winter necessity and a great thing to play with to mix up your daily dressing. Don’t be afraid to try something you wouldn’t normally attempt: we’re all spending more time at home these days, so it’s a great time to experiment with a new look, something eccentric and eclectic, just for the fun of it. If you hate it, tomorrow is another day!

01. Instead of denim, try . . . overalls or jumpsuit + layer

Don’t get me wrong: I love my denim. And I love my sweaters. But wearing the same thing day in and day out constitutes a slump. And no matter how well the denim fits or how great the sweater is, it’s never totally outside the box. So take a leap, and move one column over to the head-to-toe pieces: overalls and jumpsuits. Wear overalls over a button-down if it’s a warmer day, or a flannel or sweater if you’re stuck in true winter. Another great option is to throw on a thin turtleneck under your favorite jumpsuit: it’s a surprisingly chic combination of nineties throwback and contemporary avant-garde. Layer on a long cardigan if you’re really needing the warmth, and enjoy the easy fit of these layers.

02. Instead of your favorite turtleneck sweater, try . . . crew or v-neck sweater + turtleneck

This nineties look is back, and I couldn’t be happier. I wear turtlenecks all winter long because I don’t like my neck being cold, which means I largely ignore my crew-neck and v-neck sweater stash. Scarves can be clunky in an indoor context, plus they always make me feel like I’m dressed for outside instead of indoor life, so I rarely make them a true “part” of my outfit. But the thin turtleneck as a layer is the perfect garment to break me out of my rut without really changing the game.

03. Instead of flannel, try . . . button down + turtleneck

I love flannel, but if you’re feeling flannel-ed out, or just looking for some brighter hues and lighter textures, grab a T-shirt weight turtleneck and your favorite button-down, and you’ve solved your problems. This look is very French-girl chic, especially if you lean into it with a blue-and-white striped button down with a borrowed-from-the-boys vibe. If you’re still a bit chilly, toss on a furry or quilted vest and you’ll be cozy.

04. Instead of black on black, try . . . winter whites

Or lights, at least! Sometimes dressing to match the world around you feels just right: drab days call for dark dressing. But dressing in somber hues day in, day out can get you down, so break out your white denim and brighten up your day with lighter hues. Whether you go full white-on-white, hit a moderate combo of neutrals, or play with color blocking of whites + brights, incorporating this feel into your dressing habits will feel fresh and new in the cold mid-winter.

05. Instead of pants, try . . . boots + dress/skirt

I always pivot away from skirts in the winter for anything other than a formal party because they’re just too open to the cold air. But there are ways to make them work and none chicer than the midi skirt + tall boots combination. If you wear thick tights or even leggings, you’ll be just as covered as in pants, and you’ll love the lady-like vibe of the look! Wearing heeled boots rather than flats adds length to combat the chunkiness of the layers. And if you’re really over your winter wardrobe, combine several of these tricks and pair a sleeveless dress with a thin turtleneck and throw on those tall boots underneath.

You may have your own style ruts. I suggest doing a self-assessment or even asking a roommate, spouse, or friend what they’ve noticed about what patterns they’ve noticed in your daily wardrobe choices. If you must buy anything to make it through this winter, my recommendation is a T-shirt weight turtleneck! But hopefully the above suggestions spark some ideas about how to innovate within the confines of what you already own.