How to Winterize Summer Clothes: 4 Fun Strategies

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

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Learn how to winterize summer clothes so you can take advantage of off-season apparel sales (and also get more use out of your warm-weather wears).

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 winterize summer clothes — shift dresses, crop tops, light maxi skirts and dresses — and wear them 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.

Winterize summer clothes 4 ways

1. Crop top over a maxi dress

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. Because 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 the one I’m wearing above, stick with a simple, solid-colored dress. Or, pair a solid crop with a patterned dress. Have fun with this!

2. Crop top over a maxi skirt with leggings

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.

If you’re inspired to try these looks, here are some crop tops on sale as of September, 2023:

• Madewell long-sleeve turtleneck crop top at Nordstrom Rack ($19)
• Calvin Klein cotton crew long-sleeved crop on sale for Macy’s VIP sale ($33)
• Dusty rose crop top on final sale at Lulus ($19)

3. Short dress as a tunic

Any short dress you have hanging around can live a double-life as a tunic in the colder months. Pair it with jeans, skinny pants or leggings. If you need more structure, add a short blazer or moto jacket.

My lace-up shift dress wears easily over dark denim jeans and combat boots. The addition of the white top underneath adds contrast and puts more emphasis on the dress’s lace-up front. There’s another benefit of this under-layer — I don’t have to worry about the laces loosening up and showing off my bra.

Here are a few summer dresses on sale that would work as tunics in the colder months:

• Button-front shift dress by J. Crew ($75)
• Puff-sleeve mini dress by Gap ($75+50% off at checkout)
• Tassel shift mini dress by Forever 21 ($17)

4. Sweater under a shift dress

Here’s a simple tip that may blow your mind. A sweater often looks better under another garment than over it. Try it and see! Slip on sleek sweater underneath a dress that isn’t too tight. Shift dresses work well for this tactic, because they won’t show the extra bulk of your sweater.

Here, I’ve paired this adorable peach shift dress with a cream-colored, ruffle-sleeved sweater. Those long sleeves extend this little dress’s life span right into fall. And, since the dress falls well above the knee, you could also add leggings or skinny pants for even more warmth.

5. Sweater, crop top, and dress

So, sweaters can go under dresses and crop tops can go over dresses. And here’s what happens when you do both.

Crop tops are fun, right? And you don’t even have to show any skin

Get creative to winterize summer clothes

Adding warmth to your summer pieces can take some creativity, mostly so you don’t end up shapeless and over-layered. But you can have fun with it. Dig into your closet and pull out garments that seem like unlikely partners. You may be surprised at the combos you already have on hand.

Do you have any tricks for styling your summer wardrobe for fall? Share in the comments!