Ask CF: How Do I Wear Sneakers in a Fashionable Way?
Welcome to the latest edition of Ask CF! Every two weeks, we select a reader fashion question and answer it here on the site. Do you have a specific fashion question for us? Scroll to the bottom of this post to learn how to send it our way!
Ask CF Question:
Dear CF,
I’ve always been a ballet flats girl, but after a year at college, doing hard walking and running between classes, I have to start admitting that perhaps my feet need more support than flat-flats. I’ve resorted to my Keds for more foot support, but do you have any suggestions for cute sneakers and suggestions on how to dress up sneakers?
Sincerely,
Painful Soles
Our Response:
Dear Painful Soles,
Thank you so much for your question! Many people find themselves in a similar predicament (me too!). Luckily, you don’t have to sacrifice comfort and support for style.
For me, the trick to wearing sneakers in a fashionable way is to pair them with other casual pieces - if you are wearing them with denim jeans or shorts, for example, you have casual covered, so you can opt to add some fun accessories or keep the whole look super casual and relaxed. This is the easy way to wear them in a fashionable way.
The challenge with wearing sneakers comes when pairing them with dressier items such as dresses and skirts. But again, all you need to do is bring another casual element into your outfit to help balance out the overall feel of the look.
Below, I have created a few looks that will help explain this idea and get your inspiration going. And like always, you can check out Lookbook.nu for more inspiration to see how stylish people all over the world are wearing them (or any other trend, for that matter). I hope you find this post helpful. Have fun sneaker shopping!
Sincerely,
Jessica
Outfit #1

Product Information: Scarf, Sweater, Pants, Shoes, Earrings, Watch
One of the most classic ways to wear sneakers is to pair skinny jeans with high tops. Here, I chose some funky suede ones that fold over. Next, try adding a maroon pull over sweater – one of fall’s must-have items. Layer on a mustard scarf to up the ante on your look. If you’re a fan of leopard like myself, you’ll love this leopard watch. Finally, accessorize with some simple blue studs.
Outfit #2

Product Information: Jacket, Dress, Sunglasses, Shoes
Some people might think wearing a dress with sneakers is difficult. However, if you add in some casual pieces, it’s not all that difficult. This outfit incorporates the gym class trend that’s popular this fall. I love this dress since the stripes give it a collegiate prep feel that’s a little casual already. A varsity jacket is another casual piece that’s super popular this season. Finish this look with some simple white sneakers and aviator sunglasses.
Outfit #3

Product Information: Bag, Tank, Jacket, Shorts, Necklace, Shoes
Denim shorts and sneakers are a classic combination. For a look that will make you stand out from the crowd, try pairing the combo with a structured blazer. A simple grey tank is an easy layering piece. Try some printed high-top sneakers to add a playful element to the look. Finally, accessorize with some red accents such as this chain necklace and cross-body bag.
Outfit #4

Product Information: Shirt, Skirt, Tank, Shoes, Bag
For this outfit I paired a bandage skirt with sneakers. While the floral skirt is quite feminine and could easily be used for a going out look, wearing it with a simple black tank layered under a chambray shirt dresses the look down. You can wear your chambray shirt open, or you can also try tying it in front for an ultra-trendy look. For shoes, I love these metallic sneakers and I think they would look great with this outfit. Finish the look with a pink bag that picks up on the pink color found in the skirt.
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What do you think?
Are you a ballet flats, sandals, or sneakers girl? Do you want to start incorporating more sneakers into your wardrobe or do you already rock sneakers daily? Did you find the outfits inspiring? Which one is your favorite? Please let us know what you think by leaving a comment below!
Posted on on September 18, 2011 / Filed Under: Fashion Tips / Tags: Ask CF, Clothing, Comfort, How To, Inspiration, Outfits, Shoes, Sneakers, Tips













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Ashley
great post!! love you guys :)
Mina
I’m a fan against anything that’s comfortable which definitely includes sneakers. Great post!
Anna
The outfits are super cute, but I also feel like you really don’t need to overthink this. At all. As long as you’re not going to a cocktail party or wedding or job interview, sneakers will look fine with all your outfits.
Christine
I have to agree with Anna, so long as you’re not pairing sneakers with something business/formal for an important event, sneakers can go with your everyday outfits. If you’re already wearing something comfy and cute with your flats, sneakers can easily substitute. I do like the shoes in the first outfit paired with the third outfit, though. :)
Lana
I love the fourth outfit! I would definitely wear something like that
linda
these are cute but what about non-converse style sneakers (like pumas, nikes, etc)?
cate
Number two is adorable.
maxine
I wear sneakers mostly like Adidas and Nike regulary because heels are killer for my feet.. I will only wear heels once a week.
Victoria
I wear my converses all the time (especially last semester when I was taking lab and had to wear closed toe shoes every monday during the fall) and they’re suprisingly versatile–like this post does a great job of showing. I feel like this is super easy to go wrong with but I like all the outfits featured!
Sally
I like this post! Ballet flats are simply not comfortable when you’re walking around a lot. Love these outfits, especially the first one!
Emily
I can’t find the first pair of shoes shown in Outfit #1 with the link given. Do you know of any other places/websites I can find similar sneakers?
Holly
great post! veru useful
Holly
great post! very useful
Cinna B.
I would love to have seen more of a twist on this article, like pairing sneakers with a cocktail dress. Still, these are cute, wearable outfits, and I’m loving Outfit #2. The model’s fierce attitude helps, too :)
Cristina
I like Hello Kitty Vans.
Rashi
i love #2 and #4!!!! great post! :)
Laura
Two is so lovely! But I like the fourth one too!! Great post. After shool i’ll do some shopping ;)
Blair
3 and 4 would make me feel self-conscious. Save the tennis for the gym. There are tons of comfortable flats out there.
Jani
I really enjoyed this post and wear my Converse All Stars almost everyday! Outfit #2 makes me smile. I do not believe I can pull off that look, but I think its very very cute especially for a girl in college.
Thanks for this great post.
Sarah
Keds? A pair of white Keds is crisp and casual.
J
if the idea is to wear something with more support than ballet flats, converse all stars is not really going to be much better
Kelsey
Love this post! After starting college sneakers have quickly become a staple in my wardrobe. Thanks for new ideas! (:
Ashley
I’m definitely a running shoe person; I was trying to wear flats, but like the Painful Shoes eventually had to give up. My feet just couldn’t take it. Plus I’m in and out of the theatre all day, closed toed, work shoes are a must. I’ve stuck to the style of shoes shown in this article and have found them to be fairly versatile. Like a couple of other readers I’m curious to see how other styles of running shoes would look with skirts, dress etc. Very cute outfits overall.
AJ
You should check out Sam’s outfit in S Darko. She wore her Keds with super cute dresses with a nice low-key way. I would love to see outfit inspiration from that movie!
Rosanne
Freaking love these outfits. I love when you guys do outfits students can wear and still look fab.
shooped
LOVEEEE<3
Samantha
I’ve never like tennis shoes on myself, even when paired with cute outfits like these :) I’ve lived in my Sperry Boat Shoes since freshman year when I realized that walking for hours a day in flip-flops was going to be the death of me. They have the support I needed, are the most comfortable shoes I’ve ever owned, and work better with my wardrobe than tennis shoes :)
Jennifer
Dear CF
For the fall and winter months I find myself wearing jeans and leggins with cardigans. So the other day I was cleaning my closet and found that I dont have too many tops to pair my jeans and leggins this year. My style is all about comfort. I dont want to wear cardigans all year with my jeans and leggins so is there any pretty sweaters that are affortable and instyle this fall and winter season that can keep me warm and instyle?
Staci
I didn’t even know how to tie sneakers when I came to college (I go to cornell, so don’t think I’m dumb, just developmentally challenged!), but my roomate is a trackie. I had always found kicking around in flats or uggs fine, but with the intense hills we have up here, nothing but sneakers will cut it! I went and got a REAL pair of running sneakers that I actually wear with grey skinny jeans & a sweater like the first outfit. And my “gym sneakers,” shiny silver converses, are now a staple to wear with everything but gold. One of my favorite outfits for going out is a black and red floral pair of GUESS? sneakers that I haven’t worn in 5 years and almost didn’t bring, but now I wear them with all my dark floral dresses to transition them to winter. I’ve learned so much from reading CF, thanks as always!
Chrissie
Outfit #4 is my favorite!
Jennifer
Love the 1st outfit and the 4th. Im a fan of sneakers and i do wear them only in the cold months like fall and winter if theres no snow. Im not a flat or heel kinda girl but they do come in handy when u need them the most. I do agree with some of you when it comes to sneakers they go with anything. These outfits are for the fashionista kinda girl. Now if u are not into fashion then some jeans and a cute t-shirt will do with any sneakers. =)
Jess
I’m a sandals girl at heart, but I live in Oregon so I’ve hard to learn how to morph into a rainboots girl come fall/winter/spring.
I’ve never had much luck with sneakers, although I’ve always wished I could be the type who can throw on any pair of sneakers and make it look natural and funky. For some reason I’ve had the worst time when it comes to how big most sneakers seem to make my feet look. It’s like they either make them look to round/wide, or way too long/pointy. (I’m a size 8 – that seems to be pretty normal, so it isn’t like I have huge feet to begin with) I size down, and suddenly I can’t feel my feet. D: It’s insane. I’ve found a couple pairs that have worked though…
And jeans always bunch up around sneakers. Never much around sandals or flats. I’m really short though, so jeans are gonna bunch until they’re tailored, haha.
(I have to say though, I LOVE those suede high tops. Yummy.)