Ask CF: How Do I Wear Sneakers in a Fashionable Way?

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Converse All Stars sneakers

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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?

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 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!



Outfit #1

ask cf-fashionable sneakers-scarf outfit

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

Ask CF-Sneakers-Dress Outfit

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

Ask CF-Sneakers-Shorts Outfit

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

Ask CF-Sneakers-Skirt Outfit

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.

Do you have a fashion question? Send it our way!

Is there something in your closet that you can’t seem to figure out how to wear? Do you have an event coming up and need an outfit idea? Do you have a specific fashion conundrum you need help with?

If you have a question you want to see answered in this column, just send it on over via email to askcf @ and one day you might see your question answered right here on the site!

Please note: We get A LOT of email and unfortunately we will not be able to respond to every single question. However, we will read through each question and then decide which ones will be most helpful to the largest number of readers. Thanks for understanding!

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!

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