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Fashion Challenge: Sneakers with a Skirt or Dress


Celebrities like Miley Cyrus and Rihanna wearing sneakers with skirts and dresses

Hi I’m Chelsea, and I’ll be writing the Fashion Challenge articles for the next few months! Audrey certainly left big shoes for me to fill, but I’m excited to continue a column that’s so popular!

Rather than featuring a new trend, the next few fashion challenges will focus on a clothing combinations that you probably already have in your closet. I hope that the upcoming fashion challenges will help you look at your wardrobe with fresh eyes and expand your creativity when it comes to putting outfits together. As always, feel free to leave feedback and suggestions by posting a comment!

Love the breezy femininity of a skirt but not in the mood to wear heels? Sneakers are a great, comfortable option for those days when heels are too dressy. Celebrities have been rocking this look for a while now; if you haven’t already tested the waters, this week is the perfect week to start! I hope you’re ready to take the Fashion Challenge!

Tips and Tricks

  • Wearing actual running shoes might not give you the look you desire. Stick to pairing Converse, Vans, Keds, Pumas, slip-on Sketchers or retro styled sneakers with your dresses and skirts.
  • Go crazy with colors! The brighter and more unexpected, the better. Have fun with laces, too!
  • Don’t be afraid to try high-tops. They’ll give any outfit at nice retro feel.
  • Although I think this look works best as a part of a casual outfit, Kristen Stewart and Lil Mama pull it off beautifully on the red carpet in the pictures above!
  • This look is meant to break rules and is a great example of anti-fashion fashion. So do what you think looks cool, and rock this challenge with confidence!!

Get the Look

Outfit 1:

converse shoes worn with a dress

Outfit: Dress, Jacket, Necklace, Ring, Shoes

The outfit is girly and sweet, but the Chuck Taylors give it a surprising kick! Converse sneakers are classic shoes that look great with almost anything, so they’re an easy way to work this challenge. Wear a pink pair with a floral dress and denim jacket, and top off the look with a gold locket and ring.

Outfit 2:

Leighton Meester wearing sneakers with a skirt

Outfit: Tank, Skirt, Earrings, Bracelet, Sneakers

This spin on Leighton Meester’s outfit is a little more daring that the first sample outfit. Tuck a slouchy white tank top into a form-fitting black skirt, and throw on some cute black heart earrings and a charm bracelet. Pairing this outfit with some retro Nike sneakers gives it an unexpected twist bound to catch the attention of fashionistas everywhere!

What do you think?

Are you going to try this fashion challenge? Have you been rocking this look for a while now? What kind of sneakers do you think looks the best with a skirt or a dress? I can’t wait to hear all of your thoughts!!

Already work this trend? Send us pictures of you in your skirts and sneakers and we’ll feature them here!*

* Send your outfit pictures to fashionchallenge AT collegefashion DOT net! – be sure to include your name and where you go to school, as well as a description of what you’re wearing in the photo! (See examples here and here!)

Posted on on July 8, 2010 / Filed Under: Fashion Tips / Tags: , , , , , , , ,

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68 Responses to “Fashion Challenge: Sneakers with a Skirt or Dress”

  1. 1
    July 8th, 2010 at 11:46 am

    Yeah!!! I could rock that! Already do :D

  2. 2
    July 8th, 2010 at 11:53 am

    LOVE the article :)
    How did you create the outfits ( like which internet site)
    would be great to know!

  3. 3
    July 8th, 2010 at 11:55 am

    maybe with skirt (like Leighton) but i don’t thk sneaker with dress looks nice..

  4. 4
    July 8th, 2010 at 11:55 am

    Perfect timing! I was just thinking of how I was going to pull off wearing my comfortable converse in the city while still looking cute in a dress. Thanks for the tips! Love that first outfit so much!

  5. 5
    July 8th, 2010 at 12:05 pm

    At first, I must say I was particularly skeptical. All the celebrities featured at top looked way too… rough and edgy for a girl like me, who adores pink, floral, bows, and sunshine. But the first outfit? Totally my style. Good job incorporating something traditionally rebellious into something cute and sweet. (:

  6. 6
    July 8th, 2010 at 12:07 pm

    I already rock all stars and a dress!

    I have a pair of grey all stars with no laces (I think they’re mens, but w/e), and I wear them with dresses on a regular basis!

    I feel that all stars are something that everybody would benefit from wearing! lol

  7. 7
    July 8th, 2010 at 12:08 pm

    I love how it looks! Specially the way K.Stew is wearing it.
    Unfortunely my legs are too thick to rock this look. I’d look like.. I don’t know, weird
    I HATE my legs

  8. 8
    July 8th, 2010 at 12:35 pm

    I’ve been planning to buy a pair of red converse sneakers for a while to wear with a cute floral dress that I have. Now it seems the perfect time. I wish I could find one on sale. ;)

  9. 9
    July 8th, 2010 at 12:48 pm

    I LOVE wearing sneakers with dresses. I never go anywhere without Converse and it makes outfits less high-maintenance. I wore a dress with full tights then slipped on Converse and it instantly made it more casual and more appropriate for the event I went to.
    Sneakers with dresses also makes it WAY easier to dance in. All of my friends wore Converse to prom and we were the only girls still dancing with shoes on at the end of the night.

  10. 10
    July 8th, 2010 at 12:51 pm

    i have to be honest, i didn’t expect to like this post. skirts and converse was a combination i used to wear a lot in the days when i painted my nails black and wore red eyeshadow, but i love the outfits you’ve put together. the first one is especially gorgeous!!
    i’ve just got back from europe and couldn’t believe how popular converse low tops were and have come home to try and dig out a pair of my old ones!!
    i think this is tricky to pull off without looking like you’re trying too hard to be “unique” (a la Kristen Stewart- I’m not really a fan of her style), but I would definitely be tempted to try something like the first outfit- although my pink chucks are high tops!! maybe it’s worth investing in some low tops- i think they look much cooler with a dress especially in black or grey.
    loved this :]]]
    oh and sorry to butt in but Katha- the outfits were most probably made on]] but i warn you- it’s addictive!!

    Charlotte xxx

  11. 11
    July 8th, 2010 at 12:59 pm

    LOVE this! I got a pair of lavender/purple converse for my birthday.. and i have a pair of pastel nike hi-tops that i havent worn in awhile.. i’m gonna have to try both of these looks out!

  12. 12
    July 8th, 2010 at 1:03 pm

    Nice. I wore Converse with a dress to my college’s spring formal, and since I wear them just about every other day, it really worked. You’re right about the color. I wore a black dress and red low-top Chucks, plus a red scarf to pull it all together. All my friends loved it because it’s just my personality to wear stuff like that anyway.

  13. 13
    July 8th, 2010 at 1:19 pm

    I didn’t expect to like this post. But the first outfit kind of won me over. I loathe Kristen Stewart’s converse with a dress look on the red carpet. But the first look actually looks cute and summery. I’m not a fan of the second look. I would think that high tops with a dress would just make my already-short legs look even stumpier!

  14. 14
    July 8th, 2010 at 1:39 pm

    I wouldn’t want to emulate the styles of any of the girls you offered for inspiration, but I wear sneakers and skirts all the time. Good for babysitting on a hot day.

  15. 15
    July 8th, 2010 at 1:48 pm

    This look reminds me of middle school or junior high. In my opinion, wearing sneakers with a skirt or dress just ruins the point of wearing something girly. If anything, wear flats with a little athletic design if you want to wear sneakers. I cannot count the many times I saw girls, and women older than me, wear this look, making me want to shake my head in disappointment.

  16. 16
    July 8th, 2010 at 2:02 pm

    OMG I totally love this trend Im wearing it for years! Even yesterday I paired my pink vans with a high waist jean looking skirt and it looked fab! I also loved all the outfit ideas, I MUST try those high-top nike sneakers!!
    Great start Chelseaa(:

  17. 17
    July 8th, 2010 at 2:12 pm

    Wearing sneakers with skirts/dresses is the one fashion thing I absolutely refuse to do. It just rubs me the wrong way. (Granted, I hate flats in general.)

  18. 18
    July 8th, 2010 at 2:18 pm

    Love, love, love the first outfit!! Very cute!

  19. 19
    July 8th, 2010 at 2:28 pm

    I love the first dress. It reminds me of something Sookie would wear from True Blood. And I just love what she wears :)

  20. 20
    July 8th, 2010 at 2:32 pm

    Hmm…. I think it works with Miley’s outfit, and I like Outfit 2, but I think it may look better with just the classic Converse instead of a high-top sneaker.

  21. 21
    July 8th, 2010 at 3:15 pm

    I already rock the Chuck+skirt/dress combination: a pair of black Converse gives an edgy look to every outfit!

  22. 22
    July 8th, 2010 at 3:27 pm

    Great first post Chelsea! I did not think that I would like this Fashion Challenge, but the first outfit was so cute! I might just have to try this one! :]

  23. 23
    July 8th, 2010 at 3:38 pm

    Really cute outfits! I really love them, but I hate wearing sneakers of any kind. I wish I liked wearing them so I could wear these outfits haha :) great post

  24. 24
    July 8th, 2010 at 3:47 pm

    This is definitely something I want to try before I get to “old” for it! Only wish my Converse and Vans were in a bright color!

  25. 25
    July 8th, 2010 at 4:10 pm

    I love sneaks! I’m loving Leighton’s look!

  26. 26
    July 8th, 2010 at 4:23 pm

    It’s an interesting look…. and definitly a challenge. But I have to be honest, even after reading this article, I HATE this look. I feel like dresses should be worn with nicer shoes than sneakers. Not even that… just that sneakers majorly chop up the line of your leg and make you look much shorter and/or stumpier than you really are. (I would know! I’m 5’2″! lol)
    Just my personal opinion, but I think sneakers should be saved for the gym.
    A comfy casual option that I feel works best for casual dresses during the summer is a good ole pair of Rainbow flipflops. I live in mine. lol

    Just an opinion!
    Very fun read! Thanks! :)
    PS. I adore this entire website!!!! <3

  27. 27
    July 8th, 2010 at 4:24 pm

    I’ve tried this trend out a few times and it either looks really good or really bad. I think they look great with high waisted denim shorts and floaty tops tucked in. And I have that ‘love’ ring from Topshop! Unfortunately, it turned my skin green, but I love it so much that I coated it in clear nail varnish and haven’t had a problem since. :)

  28. 28
    July 8th, 2010 at 4:58 pm

    It’s a great city look! I love it, but I don’t personally wear it, because I’m 5’1 and I love my heels :)

  29. 29
    July 8th, 2010 at 5:37 pm

    I don’t like Converse. I wear skirts with fashion high-top sneakers because I like them.

  30. 30
    July 8th, 2010 at 6:00 pm

    I’d do the first dress with some jazz shoes and a nice lacy pair of socks, but then again it might be that I just can’t stand converses and hi tops.

  31. 31
    July 8th, 2010 at 7:01 pm

    Sounds like I’m not alone here when I winced at the idea of sneakers & a skirt… but now that I see it, I might just have to try it!! :-) Great post, Chelsea!!

  32. 32
    July 8th, 2010 at 9:28 pm

    aw, I love this. Miley’s outfit is soo cute!

  33. 33
    July 8th, 2010 at 10:54 pm

    I LOVE the first outfit! Maybe not so much the jean jacket, as it reminds me of my 90’s childhood, but I think I would pair it with a slouchy white cardigan. Converse don’t offer wide width either, so I think I’ll go with keds!

  34. 34
    July 8th, 2010 at 11:06 pm

    I love the second outfit inspired by leighton,
    I wasn’t expectung to love this post at all, especially because I only wear sneakers for running/going to the gym, but your outfit creations really won me over and impressed.
    great job!!

  35. 35
    July 8th, 2010 at 11:59 pm

    I LOVE my chucks. I don’t wear them with dresses/skirts much, but I do love the look.

  36. 36
    July 9th, 2010 at 2:18 am

    i hardly ever wear skirts or dresses, but i may actually try this one day (:
    has anyone seen the movie “Hotel For Dogs”? Emma Roberts wears converse with her dress and from memory she looked great!

    Here’s the link:

  37. 37
    July 9th, 2010 at 9:01 am

    I love the look on Miley and the two outfits you put together! I don’t usually like this style (mostly because i reserve my dresses for dressy occasions rather than causal wear) but now I want to try it! Though because I’m shorter and have slightly thicker legs I think it won’t work for me…..

  38. 38
    July 9th, 2010 at 9:33 am

    I’m so glad I was able to pleasantly surprise a lot of you! That’s what I want Fashion Challenges to be about–showing readers new ways to style their wardrobe!

    A few comments mentioned being self conscious about how sneakers would make their legs look–I recommend trying out this look with Keds or Vans, they’re cut low enough to show off your ankles so they’re more flattering than high-tops.

    If anyone has idea for future Fashion Challenges, I’d love to hear them :)

  39. 39
    July 9th, 2010 at 1:08 pm

    thanks charlotte! and yes, it definitely looks like something i’ll become addicted to in the next few minutes…

  40. 40
    July 9th, 2010 at 2:29 pm

    I just got some crazy bright nike 6.0s and wasn’t sure how versatile they would be, thanks for the ideas! I’m excited to try it out!

  41. 41
    July 9th, 2010 at 2:44 pm

    Love the high tops! I like wearing sperry’s with casual dresses, and some of my friends like to wear tom’s with dresses too!

  42. 42
    July 9th, 2010 at 2:46 pm

    Tom’s and Sperrys are also a good alternative for those who are concerned about how their legs may look, they show the ankle and are less bulky than sneakers!

  43. 43
    July 9th, 2010 at 10:29 pm

    I agree with Arielle, this look is very middle/high school. I just think is it not sophisticated or a good casual option for someone that is a college student or young adult.

  44. 44
    July 10th, 2010 at 7:22 pm

    its a cute look

  45. 45
    July 10th, 2010 at 8:15 pm

    Well here in the UK wearing “sneakers” with dresses and skirts have been around since last year. I even rocked a floral dress with some keds last night. love the look but it is so common atm. :)

  46. 46
    July 12th, 2010 at 4:46 pm

    i love both outfits,just discovered that i have a floral print knee length dress and high top sneakers. i can fold them to fulfil the adorable look.gosh i cant wait!!!much appreciation!!

  47. 47
    July 12th, 2010 at 10:59 pm

    Hoenstly, there is nothing fashionable about this look and I feel it’s lazy and very unflattering.

  48. 48
    July 13th, 2010 at 1:02 pm

    omg Love those Nike’s!!

  49. 49
    July 15th, 2010 at 1:21 am

    Mary-Janes are really cute with skirts and dresses :)

  50. 50
    July 17th, 2010 at 4:42 am

    rihanna and miley are really rocking the look because they have nice legs… so i think you should try it only if you have nice legs. but i don’t think i would ever try it! i prefer flats heels and sandals. i don’t even have a pair of converse.. the closest pair i have is for wushu… and only for that! also because i cannot wear them outside

    still nice looks for some ladies out there!

  51. 51
    July 20th, 2010 at 7:41 am

    Anybody: Would High-Top Hot P!nk Converse Look Right With A Short Denim Skirt? If So, What Kinda Shirt Should I Wear??

  52. 52
    July 26th, 2010 at 12:16 pm

    soo in love with this look!!!!
    but lil mamma loa mess… smh

  53. 53
    August 10th, 2010 at 10:10 am

    I love this post!
    I can no longer wear flip flops, ballet flats, or most sandals due to the fact that I had foot surgery last summer. (Surgery #2 was postponed four months ago.) My foot problems simply will not allow me to wear those styles comfortably. My podiatrist told me that I need to wear lace up shoes. My husband bought a pair of Vans for me so that I could wear them with cute summer dresses. Dresses with sneakers can be achieved with the right style shoe!

  54. 54
    October 23rd, 2010 at 11:05 pm

    Yes, i already rock this trend. I’d rather wear sneaks and boots with dresses any day.

  55. 55
    December 21st, 2010 at 3:09 pm

    I love it, but u gottah b able to rock it, ima b doing that 4christmas, so hatters u can kill ur selves!!!

  56. 56
    December 21st, 2010 at 3:14 pm

    I dont know about yall but i wana b able to dance when i go out, im a hip- hopper, i dont wana b that girl in heels standing around, while every1 is danceing, and i wana wear a dress sooooooo yeah ima do me.

  57. 57
    January 26th, 2011 at 7:32 am

    I’ve tried this way back n my teen years and I still do. And people gave me funny looks, darn it now them sleazy girly girls who’ve never worn sneakers in their life are gonna do it cuz some celeb did it.

  58. 58
    February 15th, 2011 at 9:25 pm

    Cool!! finally something about sneakers! XD I always use sneakers with skirts! and yeah people probably thought I looked awful, but now that celebs do it, they won’t anymore 8D

  59. 59
    June 13th, 2011 at 9:47 pm

    I love this post, because I can’t stand flip-flops, but I can’t wear flats! And I can’t just wear heels every time I want to wear a dress or a skirt; I can’t walk in them well. =(
    But anyway, I love the idea of Converse, my only problem is convincing my Mom to let me get a pair. She can’t stand them. And she’s one of those, ‘you’re under my roof you’ll follow my rules’ type of parent. Yeesh…

  60. 60
    June 25th, 2011 at 3:25 pm

    I already do this haha! I never wear heels, so whenever I wanna look more girly I just curl my hair and wear sneakers with a skirt! Easy haha (:?

  61. 61
    November 21st, 2011 at 10:07 am

    I love love love the first outfit, since I have a similar dress and a Jean jacket!

  62. 62
    August 13th, 2012 at 3:17 pm

    Recently, I wore a grey & Black checkered skirt, with a white tank top (that had a gey bow on it) with a pair of ankle converse in grey and almost knee length colorful socks!

    Rocked it!

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