Winterize Your Wardrobe: Creative Ways to Style Summer Clothes for Fall & Winter

Thank you to TOBI for collaborating on this post. All opinions are my own.

Three outfits of summer clothes, layered for winter wearing.

The last time you went shopping, either in-store or online, did you take a spin by the clearance rack? I did, and that rack was loaded down with the cutest summer leftovers: shift dresses, crop tops, shorts, skirts, flirty maxi dresses and the like. Just the other day, I lifted a white jumpsuit out of clearance and took it home for $23 — a bargain worth bragging about, for sure.

Buying Clothes Off-Season — the Downsides

Although the deals are plentiful right now, there are a couple downsides to buying garments off-season. One, if you buy something too trendy, its useful life will be over before next spring. And two, it’s vaguely unsatisfying to buy new clothes when the weather prevents you from wearing them right away.

The solution for the first issue is easy. Stick with classic silhouettes and solid colors or stripes. Now is not the right time to invest in an off-shoulder, ruffle dress with a bold white-and-red pattern (Unless maybe you live in the South Pacific, and then—well, you’re living in paradise, so who cares what you wear?).

On the second issue, with a little creativity, you can wear those summer pieces — shift dresses, crop tops, light maxi skirts and dresses — right through the winter. And I’m not talking about simply throwing on a puffy jacket and tights on with your summer dress. I’m talking about pairing your pieces to create new, striking combos that are warm and stylish. Ready to learn how? Read on.

Styling Summer Clothes for Cooler Temps

Cropped to the Max

I actually like crop tops better in the winter than in the summer. And I know what you’re thinking: “Crop tops? I haven’t bought one since 1987!” Well, if you still have that old thing, pull it out now. Or get this one — you’ll need it to wear over your favorite maxi dress this winter.

Crop top paired with bright blue maxi dress

Top: Forever Lace Crop Top, $22, TOBI / Dress: Calvin Klein Maxi Dress, Macy’s

Crop tops look insanely fabulous over a form-fitting dress. The perfect maxi for this look will be sleek above the waist and have no sleeves. If your crop is jazzy like this one, stick with a simple, solid-colored dress. Or, pair a solid crop with a patterned dress. Have fun with this!

You can also match up your crop top with a high-waisted skirt. Add a denim jacket to this mix if you’re cold (but skip the fingerless gloves unless you’re dressing up like ’80s Madonna for Halloween). And, if the skirt is long enough, throw on a pair of leggings underneath. I won’t tell anyone if you don’t.

Tobi crop top with a white peasant skirt

Top: Forever Lace Crop Top, $22, TOBI / Skirt: White Maxi Skirt, $7.50, Kohl’s Clearance Rack

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Catherine Brock

Catherine Brock is a writer, editor and marketer who's been sharing wisdom online since 2002. She's been featured on, and ABC7 Chicago, FOX2News St. Louis and KCAL9 Los Angeles. Connect with Catherine on LinkedIn, Instagram, or Twitter. Learn more about Catherine.
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