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Fashion Challenge: Style a Pair of High-Top Sneakers


High top sneakers

Despite my affinity for heels and wedges, sometimes my feet need a break! Ballet flats and boat shoes certainly make great alternatives, but if you’re like me, you love making a statement (even on your laid-back days).

Once reserved for hipsters or basketball players, high-top sneakers are on their way to making a full-fledged comeback on college campuses. I was hesitant to buy a pair at first, but when I spotted the perfect pair of black, yellow, and pink Nike Dunks on sale at an outlet mall, I knew I had to have them!

It took me a little while to figure out how to style these babies — at 5’2”, shoes with no heel and thick ankles can easily make me look stumpy. But I did a bit of research and found out that my new high top sneakers can be stylish and flattering if worn correctly.

Ready to take on the challenge? Read on for secrets to pulling this look off right!

Tips and Tricks for Wearing High-Top Sneakers

  • Make a statement on your lazy days. Most people reserve sneakers for their “blah” days — I know I do! The great thing about high top sneakers is that they push boundaries just enough to make a statement without being over-the-top. Pair them with jeans and a hoodie for an extra kick.
  • To tuck or untuck? Stars like Sam Ronson like to tuck their skinny jeans into their high-top sneakers, whereas Leighton Meester prefers to wear hers with skirts. I think they look cool with a pair of untucked boot cut jeans as well!
  • Scared you’re channeling middle school emo vibes? Don’t worry. As long as you don’t pair your high-tops with neon leggings, a bandana, and Taylor Momsen-inspired makeup, all at the same time, you should be fine.

Outfit Inspiration

Outfit #1: Sporty and Casual


Jeans, Hoodie, Dunks, Bracelet, Ring

This outfit is perfect for a lazy day at class! Boot-cut or slightly flared jeans go great with high top sneakers — they’ll fall over the sides of the shoe, but leave the front on display. Next, just pull on a hoodie and simple accessories and you’re good to go!

Outfit #2: Classic and Cute


Skirt, Jacket, Tank, Converse, Headband

This outfit combines quite a few classic pieces, but is far from boring! Tuck a plain tank top into a black skirt, and throw a denim jacket on top for warmth. Lace up some high-top Converse All-Stars and finish with a cozy knit headband.

Outfit #3: Trendy and Daring


Jacket, Dress, Necklace, Jeggings, Dunks

This urban-chic outfit is a little daring, so be sure to rock it with lots of confidence! Wear a simple pair of jeggings under a black t-shirt dress, and add an on-trend military jacket. Strap on the loudest pair of sneakers you own, and accessorize with pieces that will make your shoes pop!

Rocked the Challenge? Send in Your Photos!

Now that you have some ideas, we want to see how YOU wear your favorite high-top sneakers! Send a photo of you wearing this look along with your name, school, a description of what you’re wearing, and your blog’s URL (if you have one) to fashionchallenge AT

We’ll feature your photos here to inspire other CF readers! Can’t wait to see what you come up with.

What Do You Think?

Do girls at your school wear high-top sneakers? What are your favorite things to pair them with? What do you like to wear on lazy days? What fashion challenges would you like to see in the future? Sound off with a comment!

Posted on on October 21, 2010 / Filed Under: Fashion Tips / Tags: , , , ,

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19 Responses to “Fashion Challenge: Style a Pair of High-Top Sneakers”

  1. 1
    October 21st, 2010 at 12:12 pm

    I love how MK makes sneakers look ridiculously chic (in her boho-hobo type of way).
    To be honest I’ve never before considered wearing sneakers beyond the gym, and I probably won’t start now but, I do love how they look on others.

  2. 2
    October 21st, 2010 at 12:27 pm

    omg. i just bought a brown pair of high top sneakers, i swear! lol :)

  3. 3
    October 21st, 2010 at 3:14 pm

    I never used to understand this look, but then I met one of my best friend and she consistently rocks the coolest kicks. Love her style and I love the idea but I don’t think I could pull it off!

  4. 4
    October 21st, 2010 at 4:20 pm

    Third outfit = awesome!

  5. 5
    October 21st, 2010 at 5:46 pm

    I don’t think I could rock these without being reminded of my high school, the only time I wear sneakers now is when i’m exercising.

  6. 6
    October 22nd, 2010 at 2:01 am

    I started noticing this trend as well. I think it’s a fine line if it works. Certain girls around my school wore them a lot and it just looked goofy. Others wore them once in a while and looked great. I don’t know what it was about them, but I’ll agree it definitely is hard to pull off.

  7. 7
    October 22nd, 2010 at 2:24 am

    LOL, I’ve been wearing high tops since the 6th grade. Nikes, Adidas, Puma, you name it.

    I just started getting into wearing flats/boots though. I went through this like, gangsta-hiphop-chic phase in jr. high and half way through high school. XD

    I got rid of my Forces, but I still have high top Adidas and Pumas and one RIDICULOUSLY high top pair of Nikes. I’ve only worn them twice. They’re like, super high top. They go half way up my calves, I think. They’re freaking hot. I just never know when to wear them. XD

  8. 8
    October 22nd, 2010 at 10:21 am

    I’m excited about that last one – I have a pair of really high (think short Ugg boot high) air forces that are pearl with a gold swoosh – I’ve been currently pairing them with over-the-knee lilac and pink socks and a cream dress, but I like that outfit idea as well! Anything to prevent over matching is fine by me.

  9. 9
    October 22nd, 2010 at 11:08 am

    OMG! Yay for this article. I live in a cool climate and have been thinking about getting some high tops for ankle warmth. And a couple of days ago I was wondering how I could wear them. I like the last look, but would probably do black high tops with gold or pink embelishments.

  10. 10
    October 22nd, 2010 at 11:17 am

    i actually really like this. i love the first pair you’ve featured!!
    i’m more of a low-top converse girl because I worry what high-tops will do to my already-stumpy legs, but i love the nike trainers in high tops :]]]
    i’d love to get a pair on sale :]]]

    Charlotte xxx

  11. 11
    October 22nd, 2010 at 11:56 am

    I LOVE LOVE LOVE outfit number 3. I can’t wait to try it out!

  12. 12
    October 22nd, 2010 at 12:26 pm

    yuck! no thank you lol

    although i do love outfit #2…

  13. 13
    October 22nd, 2010 at 2:48 pm

    Love the shoes(and the ring) in the first set but the 3rd set is definitely the best. I think you need to be more of a tomboy to appreciate sneakers/dunks and how to dress them properly.

  14. 14
    October 22nd, 2010 at 4:54 pm

    I’m not a fan of any high tops, except converse. Somehow, converse look neater and more polished, imo. I LOVE wearing my converse with a mini dress. I actually wore converse with my prom dress senior year, lol. It’s a bit flashback-y, but honestly, they’re just too comfortable to ditch!

  15. 15
    October 23rd, 2010 at 1:52 am

    cute looks!
    i really like all three.

  16. 16
    October 23rd, 2010 at 7:23 pm

    I’m not too big on high tops but dig sneakers (I have 3 pairs in different colors like the ones MK is wearing). However, when I saw the hoodie from outfit #1 I flipped! It’s a “poncho/cape” hoodie. It’s awesome. I ran straight to American Eagle and bought the dark gray one! LOVE IT!

  17. 17
    October 2nd, 2011 at 7:08 pm

    I just bought a navy blue high top coverse and I had no idea what I am going to wear! After seeing this I think I know what I am going to wear. By the way, Emo Styles are CUTE. They are never out of style in my opinion. I do wear clothes that are like them and you know what people need to stop worrying about them. It’s self-expression. I love hoodies. Most of all, I Love beng Lazy…I am really good at it ;)

  18. 18
    August 18th, 2012 at 2:11 pm

    How about a pink shirt tucked into skinny jean with a nice belt, and a pair of sneakers?

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