Fashion Challenge: Try Winter Shorts

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Winter shorts

Photo Credits: 1, 2, 3, 4

Winter shorts have been popping up everywhere, worn by everyone from style bloggers to celebrities. This is the perfect week to try out a pair! They can be really dressy and festive when styled correctly, and are a great alternative to the usual jeans or leggings for this time of year.

This holiday weekend is sure to bring plenty of reasons to celebrate, so pick up a pair of winter shorts this Black Friday and read on for tips on how to make this challenge work for you!

Tips & Tricks for Rocking Shorts in the Winter

  • Take inventory before you shop. You might already own a pair of shorts that will work just fine in the winter time. Look for styles made of a heavy fabric, or a dark or muted color. You can also go in the opposite direction, like Olivia Palermo does above, and rock light shorts with a dark ensemble.
  • Try wearing tights underneath. Tights will make shorts more season-appropriate, without the bulk of leggings.
  • If you're feeling bold, try shorts with thigh-high socks or boots. As long and the thinnest part of your thigh is the part that's exposed, you will look chic and proportional.
  • Leather or sequined shorts are more versatile that you think. Dress them up with ankle boots, a blazer, or a cardigan, or dress them down with a t-shirt, denim jacket, and flat boots.

Outfit Inspiration

Outfit 1: Daytime Casual

shorts outfit 1

Shorts, Boots, Tank, Cardigan, Earrings, Headband

This outfit is a little bit preppy and a whole lot of fun! It's perfect for a daytime event or class when you want yourself to stand out. Tweed shorts are perfect for any afternoon, and when paired with high boots, they become fashion-forward. You can also add tights for a more conservative look. Now all that's left to do is pull on a classic cardigan, and finish with pearl studs and a girly headband.

Outfit 2: Dressy Night Look

shorts outfit 2

Shorts, T-Shirt, Blazer, Tights, Necklace, Ankle Booties

This outfit is perfect for a party or a night on the town. Tone down the sparkle of the sequined shorts with a plain white t-shirt, a black boyfriend blazer, and matte black tights. Finish the look with a fun necklace and sexy ankle boots.

Outfit 3: Edgy and Urban-Chic

shorts outfit 3

Shorts, Combat Boots, Tights, Necklace, Top, Fedora

Sometimes, wearing something a little edgy and "model off duty"-esque is just what you need to break out of a style rut. Style bloggers have been rocking leather (or faux leather) shorts lately, and they look great with a shredded sweater and combat boots. Finish off the outfit with patterned tights, a chain necklace, and fedora.

Rocked the Challenge? Be our Cover Girl!

Did you wear a pair of winter shorts this week?? Send in a photo of you wearing a pair of these bad boys to fashionchallenge AT along with your name, school, a description of what you're wearing, and the URL of your blog if you have one. We'll post the pictures here to inspire other CF readers!

Can't wait to see what you girls come up with!


Have you tried wearing shorts in the winter before? Is it too cold to try this challenge where you live, or is it still warm in your college town? What would you do to dress up or dress down a pair of shorts? Let us know with a comment!

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