If Your Winter Outfits Feel Basic, You’re Probably Wearing Your Sweaters Wrong

Winter has a way of flattening even the most imaginative dresser. By mid-January, creativity freezes over, and suddenly everyone is wearing the same uniform: a serviceable warm sweater, familiar jeans, and sensible boots. There isn’t anything wrong with that, but it’s...unimaginative. And it can also make winter feel sadder and drearier than it needs to be; winter is long, cold, and relentless, yes, but it’s also the season that really rewards intention. If summer is about ease, winter is about craft.

So, let's get crafty and make Winter 2026 fun—starting with knitwear. Keep scrolling to discover my favorite sweater styling tips that help make my cold-weather outfits feel inspired, fresh, and full of energy.

While the urge to pile on every warm thing in your closet is a relatable one—and still a possible option—do it in a way that provides contrast and tension. For instance, start with a turtleneck, winter’s underrated hero, and layer it over the crisp white shirt you thought was retired until spring. Throw on a gorgeous pendant necklace, and you’ve created a luxe look that is winter-appropriate and quietly chic.

Or, what about your solid grey cashmere crewneck sweater? It’s lovely alone, but under a slightly different-toned grey cashmere polo-neck sweater creates more interest while doubling the warmth. The neckline stacks just so, and the sleeves peek out with purpose.

Winter is also the time to play with varying textures. Silks with thick wool plaid; sea grass with lucite; zebra stripes with florals—mixing textures is a balancing act of hard and soft, modern and antique, light reflection and absorption. And it’s in the unexpected combos that we find more delight—think about a chunky knit slung over a beaded dress; the sweater's weight grounds the shine, making the sparkle feel wearable and effortless.

And of course, a red sweater—whether tied around your waist, double layered like a sweater set, wrapped around your neck, or even your coat—provides that pop of red that every It girl swears by. In other seasons, it might be a red bag, a red shoe, or just red nail polish, but winter allows for a bolder and bigger display. Even the most color-averse dresser can join in on the fun with a rich ruby crewneck or fire-engine cardigan.

Lastly, don’t forget that while scarves usually do the job of keeping our necks warm and bundled up, sweaters are just as adept—and often offer more color and texture options. At midday, you can also knot that same scarf-sweater around your waist or tie it around your bag, both of which are nice options for when you're bundled up for 10-degree weather but in a store with the heat blazing.

My message to you is this: winter doesn’t have to be endured. When you stop dressing for survival and start dressing with intention, the cold becomes the backdrop, not the problem. Happy wintering!