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Fashion Challenge: Pair Boots with Shorts


Celebs wearing denim shorts and boots
Photo Credit

It’s no secret that here at CF, we’re crazy about our boots! From over-the-knee boots to cowboy boots, we love finding new ways to wear these closet staples. And although this might not be a novel idea to most of you, pairing boots with shorts can be both fun and unexpected. It’s a good way to get some use out of your favorite boots in the summer months, and is an easy way to make a plain outfit look super stylish.

Since it’s finally starting to warm up across the country, now is the perfect time to debut your favorite pair of shorts for the season! Pick out your favorite pair of boots and get ready to rock the challenge!

Tips and Tricks for Wearing Boots with Shorts

  • Consider boot height. I love the look of over-the-knee boots, knee-high boots, and ankle boots with a pair of shorts – to figure out which look you like best, try on different pairs with your shorts and compare. When deciding what shorts to pair with your boots, think about how dressy your shorts are and where the hem hits your thigh.
  • Another important thing to think about is how tall of a heel your boots have. A sky-high pair of over-the-knee boots with a pair of short-shorts might looks reminiscent of Julia Roberts in Pretty Woman. A safe rule to stick to is the shorter the shorts are, the lower your heels should be.
  • Earthy, beat-up leather boots look great with denim shorts! That combination will give any outfit a bohemian flair.
  • Dressy shorts made from tweed, lace, silk, leather, or sequins look awesome with ankle boots and a pair of tights.
  • Try pairing shorts with combat boots. Your outfit will look daring and grunge-inspired.
  • A structured top, like a blazer or military jacket, contrasts nicely with the rebel vibe that wearing boots and shorts together gives off.
  • Fringe-y moccasin boots look cool with shorts as well!
  • We don’t usually talk “fashion don’ts” here, but this is one big exception: DO NOT WEAR UGGS OR SNOW BOOTS WITH SHORTS. I’m sure you guys probably wouldn’t do this anyway, but I just had to mention it. This look is pretty much never cute (not to mention that it makes no sense).
  • Wear accessories and rock a lot of confidence. Your attitude can really make or break an outfit. If you constantly ask your friend if you look okay or hide in the corner of a party, people will question what you’re wearing. If you smile and hold your head high, people will think you look like a rock star!

Outfit Inspiration

How to wear shorts and boots - springtime outfit
Boots, Jacket, Shirt, Ring, Shorts

This outfit is perfect for springtime, because it has a bright pop of color but will still keep you warm. Since these over-the-knee boots are pretty much flat, you can get away with wearing short-shorts with them without looking too scandalous. Next, a plain white t-shirt won’t steal attention away from a salmon-colored military jacket. Finish with a edgy snake ring.

How to wear shorts and boots - dressy outfit
Top, Shorts, Earrings, Blazer, Ankle Boots

This outfit is dressy enough for a nice dinner or a date! Tailored khaki shorts provide a neutral foundation to work with, while a ruffled blouse like this one will look awesome under a structured blazer. Finish with ankle boots and a simple pair of stud earrings.

How to wear shorts and boots - rocker chic outfit
Shorts, Combat Boots, Ring, Shirt, Jacket

If you’re feeling a bit rock and roll, try pairing some fierce shorts with combat boots! These faux leather shorts look tough but not too over the top – they’re also a great trendy piece right now, so you can wear them everywhere. Red Dr. Martens are bold, but are wearable with a little dose of confidence. Finish the lo0k with a band t-shirt, denim jacket, and double-finger ring.

Took the Challenge? Send us Photos!

Did you wear your favorite pair of boots with a pair of shorts this week? Take a few snapshots and send them 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 feature pictures here to inspire other CF readers.

Can’t wait to see what your girls come up with!


Do your ever wear shorts with boots? Do you think this looks good, or should boots only be worn in the winter? What are you thoughts on heels with shorts? Let us know what you think my leaving a comment!

Posted on on March 17, 2011 / Filed Under: Fashion Tips / Tags: , , , , ,

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19 Responses to “Fashion Challenge: Pair Boots with Shorts”

  1. 1
    March 17th, 2011 at 11:27 am

    LOVE those brown boots in the second picture (the peep toes). Know where I can find them in the states, or something similar?

  2. 2
    March 17th, 2011 at 12:21 pm

    These outfits are super cute! I want them so bad, haha.

    Oh and thanks a million for saying that uggs with shorts do not count. I’ve seen so many fashion disasters doing this, and you’re right, it makes no sense.

  3. 3
    March 17th, 2011 at 1:12 pm

    I love this look! I actually had saved that picture of Alexa Chung a while back because I loved the look so much!

  4. 4
    March 17th, 2011 at 1:29 pm

    LOVE this! I haven’t tried doing boots with shorts yet, but have always thought it was cute. when it gets a littleeee warmer I want to try it! and I also agree with the no shorts/uggs combo, that would not be cute haha

  5. 5
    March 17th, 2011 at 2:50 pm

    it’s a cute look! i’m a bit iffy on it for myself when there are no black tights involved. It’s still winter where I am, so we’ll see when it gets warmer. :)

  6. 6
    March 17th, 2011 at 3:18 pm

    I love pairing boots with shorts. I’ve been doing it for the past two summers, in fact. I can’t wait until it’s warm enough where I am to pull the shorts back out!

  7. 7
    March 17th, 2011 at 3:39 pm

    I just tried out this trend for the first time last week! I wore high-waisted black shorts with black tights and knee-high black suede boots with a cozy cashmere v-neck sweater. Shorts and tights is definitely becoming a major trend at my school, so I thought this would be a fun way to wear it. It took a little bit of confidence, but I liked it!

  8. 8
    March 17th, 2011 at 3:41 pm

    To each her own, but I only wear boots when I really have no choice about it (aka in winter) and even then I usually keep wearing regular shoes until there’s snow on the ground and it’s below freezing. I put away my boots with delight as soon as possible and take them out reluctantly in late November or December.

    So I just can’t imagine ever wanting to wear boots in the summer when I have the option of wearing pretty shoes.

  9. 9
    March 17th, 2011 at 5:19 pm

    I love all those outfits you’ve created, I’d love to try the second look! I’ve never thought to try pairing them with shorts. Great ideas :)

  10. 10
    March 17th, 2011 at 8:36 pm

    I’d like to point out that dr.martens do not have to be worn in a grunge-y way.

  11. 11
    March 18th, 2011 at 2:30 pm

    Ankle boots with a pair of neat tailored shorts are pretty nice, but black high boots with denim shorts just scream Ke$ha.

  12. 12
    March 19th, 2011 at 3:09 pm

    I love this combo! <3

  13. 13
    March 20th, 2011 at 6:51 pm

    I would love to try this out, but the weather never works for it! Either it’s too cold for bear thighs or it’s too warm for wearing the boots. So if I do this look, I would have to inklude tights under the shorts.

  14. 14
    February 15th, 2012 at 9:59 am

    This combination is soo cute, and I’m glad someone thinks it’s appropriate! I always feel self conscious when I do wear it because my parents don’t think it’s appropriate- But now I can tell them its fashionable!

  15. 15
    April 21st, 2012 at 8:02 pm

    I disagree with the shorts/UGGs comment. I wear my UGG sweater boots with jean shorts all the time and it looks super cute!

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