Updating your summer wardrobe for winter is a smart way to make the most of off-season sales while getting more wear out of your favorite warm-weather pieces. If you’ve ever browsed a clearance rack, you’ve probably come across stylish summer finds at unbeatable prices—like a chic white jumpsuit for just $23. But buying off-season clothing comes with two challenges: trendy pieces may go out of style by next year, and it can be frustrating to buy something you can’t wear right away.
The first issue is easy to solve—stick to timeless styles, solid colors, and classic patterns instead of bold, trendy designs. As for the second, a little creativity can help you transition summer staples like shift dresses, crop tops, and maxi skirts into winter-ready outfits. And no, this doesn’t just mean throwing on a bulky coat and tights. Instead, it’s about mixing and matching pieces in fresh ways to stay warm while looking stylish.
Crop tops, for example, can be even more fun to wear in winter than in summer. Layer one over a fitted dress for a chic, modern look. If the dress is sleeveless and sleek, a bold crop top can add flair, while a solid crop top pairs well with a patterned dress. You can also wear a crop top with a high-waisted skirt, adding a denim jacket for extra warmth. If the skirt is long enough, discreetly layering leggings underneath is a great way to stay cozy.
Short dresses can easily double as tunics in colder months. Pair them with jeans, skinny pants, or leggings for a stylish layered look. Adding a structured blazer or moto jacket can provide extra warmth and polish. A lace-up shift dress, for instance, works well over dark denim and combat boots, with a contrasting top underneath to highlight the dress’s details while offering additional coverage.
Here’s a surprising trick—sometimes, a sweater looks better under a dress than over it. Try layering a fitted sweater under a shift dress to add warmth without bulk. A peach shift dress, for example, can be paired with a cream-colored, ruffle-sleeved sweater to extend its wear into fall. If the dress is on the shorter side, leggings or skinny pants can complete the outfit while keeping you warm.
By experimenting with layering, you can transform summer pieces into stylish winter outfits without looking bulky or shapeless. Dig through your closet and mix unexpected pieces—you might be surprised by the combinations you can create.