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Fashion Challenge: Try Winter Shorts


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!

Posted on on November 25, 2010 / Filed Under: Fashion Tips / Tags: , , , , , , ,

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21 Responses to “Fashion Challenge: Try Winter Shorts”

  1. 1
    November 25th, 2010 at 11:26 am

    Outfits two and three are perfection! Great work on this one, Chelsea. :)

  2. 2
    November 25th, 2010 at 11:52 am

    South Florida is warm enough today to wear shorts without tights and no jacket at all. But the tights look really cute, so I might try to wear something like that for the night time. I actually think it is a great look for Florida’s colder days that will hopefully come the next few months.

  3. 3
    November 25th, 2010 at 11:55 am

    I love the idea of shorts with tights during winter!
    I wear them all the time usually paired with boots. I love the third outfit! Might wear something similar for uni next week :))

  4. 4
    November 25th, 2010 at 12:35 pm

    I love this trend! I’ve been wearing fall/winter shorts since September. I’ll definitely be submitting my photos soon. :)

  5. 5
    November 25th, 2010 at 1:38 pm

    How about we call these fall shorts? A lightweight look like this should be reserved for the nice days of autumn. The majority of places during winter (in the US at least) get cold, too cold for shorts and tights. In that case, function wins over fashion- the look is cute, but jeans, thermals, and boots have to come out to keep warm.

    I mean, if you want to be bold and try it out when it’s mad-cold outside, sure, but don’t be surprised is if someone asks you if you’re lost your mind.

  6. 6
    November 25th, 2010 at 1:40 pm

    Wow. I really love the second and third outfits. I’m wearing shorts and thights almost everyday right now although it is already snowing where I live. But I normally wear a nice, long shirt or pullover, that is longer than the shorts and therefore covers it. I just love it.!
    The first outfit is nice too, but not really my style. Good job.!

  7. 7
    November 25th, 2010 at 4:23 pm

    It’s pretty cold here in Connecticut but on one of out warmer days I threw on a pair of shorts with cream colored wool thigh highs (& boots). Worked out great! Wasn’t too cold! Perfect winter trend!!!

  8. 8
    November 25th, 2010 at 5:33 pm

    I love these looks, but it’s tooooooo cold here for them! SIGH. I wear shorts + tights all autumn long, but once I pull out my wool coats they just look silly, haha.

  9. 9
    November 25th, 2010 at 10:03 pm

    Love the idea of winter shorts :) though im wearing my summer laced shorts today, im wearing them over tights and with boots so its nice and warm :) thinking of buying tweed shorts like the one in outfit one

  10. 10
    November 25th, 2010 at 10:19 pm

    I love this. I wear shorts and tights allll year long!!
    It’s getting pretty cold here in Minnesota but I have been wearing shorts and knee socks but then I progressed to tights!!
    I did a style challenge on my blog a few weeks ago where I wore the same pair of shorts every day for a week :]]] That was definitely a challenge, but it showed how versatile one pair of shorts can be!!
    I love all of these outfits. I bought a pair of sequin shorts like the second outfit for my friend’s Glam Rock birthday but I definitely want to get them out again after seeing this!!
    The third outfit is amazing. Well done, Chelsea- I always love your posts!!

    Charlotte xxx

  11. 11
    November 25th, 2010 at 10:28 pm

    Unfortunately, Canada is much too cold a place to try a trend like this in the winter time. Maybe early/mid spring though, before it warms up too much! :)

  12. 12
    November 25th, 2010 at 11:17 pm

    These might actually be a practical look for a party, when you’re outside for mere moments, but its blazing hot inside. I really like the looks you featured, even though they would be too cold for campus.

  13. 13
    November 25th, 2010 at 11:38 pm

    I’m not sure what part of Canada you are in Deanne, but I will be wearing this (as I did last year) in the winter! As long as you pile on lots of top layers and warm boots it works! love this look :)

  14. 14
    November 25th, 2010 at 11:39 pm

    I’m in Newfoundland, Canada, by the way :)

  15. 15
    November 26th, 2010 at 1:15 am

    i like this look but not be entirely functional in really cold areas.

    for christmas had on my black tuxedo shorts and patterned black tights with black booties, and a light grey long sleeve shirt with black detailing but i was told by several people that wearing shorts in the winter looks/looked rediculous.

  16. 16
    November 26th, 2010 at 1:18 pm

    I actually found this really cute outfit in a magazine and the girl was wearing shorts and stuff for the winter (can’t tell you all the deeds. Don’t wanna spill the outfit lol. I’ll post it on my website). Anyways I will definitely try that style when I get the right kind of shorts. I still got three months!

  17. 17
    November 26th, 2010 at 3:13 pm

    Wearing tights with my shorts outside is a must in the winter, but they’re often warmer than a skirt.
    Last year I really liked to contrast my dark shorts with my bright tights, but this year I’m definitely opting to keep it more muted.

  18. 18
    December 28th, 2010 at 8:20 pm

    love the sequin shorts

  19. 19
    November 12th, 2012 at 7:06 pm

    Wearing shorts and pantyhose for winter fashions? Why not do it !!!!

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