Fashion Challenge: Sneakers with a Skirt or Dress
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:
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:
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!)
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Posted on on July 8, 2010 / Filed Under: Fashion Tips / Tags: Celebs, Fashion Challenge, Featured, Leighton Meester, Miley Cyrus, Rihanna, Shoes, skirts, Sneakers
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Laura
Yeah!!! I could rock that! Already do :D
Katha
LOVE the article :)
How did you create the outfits ( like which internet site)
would be great to know!
xoxo
ELLEN
maybe with skirt (like Leighton) but i don’t thk sneaker with dress looks nice..
Kelsey
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!
Kenzie
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. (:
Jojo
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
Valeria
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
Monica
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. ;)
Anaf.
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.
Charlotte
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 polyvore.com:]] but i warn you- it’s addictive!!
Charlotte xxx
Emmy
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!
Kate
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.
Books, Sweat, and Trends
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!
Emily
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.
Arielle
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.
Renee
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(:
Faith
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.)
Taylor
Love, love, love the first outfit!! Very cute!
jen
I love the first dress. It reminds me of something Sookie would wear from True Blood. And I just love what she wears :)
Leslie
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.
Ilaria
I already rock the Chuck+skirt/dress combination: a pair of black Converse gives an edgy look to every outfit!
Karissa - Elms College
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! :]
Gracey
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
Liz
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!
Yvonne
I love sneaks! I’m loving Leighton’s look!
Lindsey
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
Vicki
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. :)
Milana
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 :)
Jade
I don’t like Converse. I wear skirts with fashion high-top sneakers because I like them.
A
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.
Alycia - University of Windsor
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!!
Hannah M
aw, I love this. Miley’s outfit is soo cute!
ManicPixieDreamGirl
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!
Julie
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!!
SupaWaifu
I LOVE my chucks. I don’t wear them with dresses/skirts much, but I do love the look.
dreamer
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: http://emmarobertsstyle.com/style/movies/39.php
Shanise M
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…..
Chelsea - University of Oklahoma
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 :)
Katha
thanks charlotte! and yes, it definitely looks like something i’ll become addicted to in the next few minutes…
xoxo
Lexie
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!
Blake
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!
Blake
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!
Lalalina
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.
aish
its a cute look
tee
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. :)
callado
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!!
Kalsee voshal
Hoenstly, there is nothing fashionable about this look and I feel it’s lazy and very unflattering.
TranTran
omg Love those Nike’s!!
Eva
Mary-Janes are really cute with skirts and dresses :)
chantel
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!
Ominous_RoXX
Anybody: Would High-Top Hot P!nk Converse Look Right With A Short Denim Skirt? If So, What Kinda Shirt Should I Wear??
Smiley_Girl
soo in love with this look!!!!
but lil mamma loa mess… smh
caroline
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!
Maxine
Yes, i already rock this trend. I’d rather wear sneaks and boots with dresses any day.
Shantal D
I love it, but u gottah b able to rock it, ima b doing that 4christmas, so hatters u can kill ur selves!!!
Shantal D
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.
NJ
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.
LizaW
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
Jamie
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…
Surii
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 (:?
Kenadie
I love love love the first outfit, since I have a similar dress and a Jean jacket!
heath
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!