5 Ways To Wear Shorts in Cold Weather (Yes, It’s Possible)

Meghan Blalock

One of the most annoying things about the weather turning cold is the steady pile of shorts that we seemingly can’t wear, which serves only to mock us and remind us of the fleeting days of spring and summer. And yet—there remains a glimmer of hope that we might be able to figure out a stylish and creative way to wear the warm weather frocks now that it’s turned brisk.

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But help has now arrived! While it’s a long-debated tactic to wear tights with shorts—some people love it, some hate it—but we’re here to share no less than five ways to wear shorts in the colder months while looking chic and staying warm all at the same time. The two keys here: fabric (stay away from super-summery textures like eyelet, and linen, and instead opt for denim, wool, thick cotton, or silk) and tights.

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Read on for our thoughts!

long coat shorts chictopia

Photo via Chictopia

1. Wear a longer pair of denim shorts rolled at the bottom.

By and large, denim shorts can be awkward in the cooler months, if for no other reason than they tend to have a very “summer” vibe to them: they’re shorter, and tend to be cutoff, and those dangling hemlines just scream a day at the park or beach. But for a more sophisticated look for Fall and Winter, try a longer pair with rolls at the bottom over a dark-colored tight. We love the look here with a long, sleek jacket.

2. Wear a pleated chino short.

To really ramp up the dressy factor of any pair of shorts, go with a more conservative fabric like a chino or silk blend. We love the idea of turning a pair of beige pleated shorts into a winter wardrobe staple by pairing them with black accessories and a solid leather jacket. Also note the cute use of a belt here!

shorts and tights 1

Photo via Southern PiPhi

3. Reach for the tweed.

Tweed is one of those fabrics that only really makes sense in cooler weather, and it almost doesn’t matter how the fabric is even cut; if it’s a tweed piece, it makes sense to wear it when it’s cold. Therefore, a pair of tweed shorts bridges the gap perfectly from warm to cool weather. We love them with tights and a dressy button-up.

shorts and tights car venus

Photo via Car Venus

 4. Try a pair of sheer tights.

In keeping with the tweed theme, another way to instantly dress up your cold-weather looks is to wear sheer tights with your shorts. Admittedly, they might not be as warm as a pair of wool ones, but they are a bit dressier. We love them as they’re styled here, with a pair of low, pointy-toed booties with gold accents.

shorts tights leather park jimin

Photo by Park Kimin

5. When in doubt, add leather.

If you’re really determined to wear your favorite denim shorts this Winter (or any fabric, for that matter), a clear-cut way to dress them up and make them seasonally appropriate is to reach for leather. Whether in the form of a chic leather jacket, a leather handbag, a leather T-shirt, or really anything with leather accents, the stocky fabric is a great way to keep warm and look stylishly appopriate.