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Fashion Challenge: Wear Thigh-High Socks


Celebs wearing over-the-knee socks

As chilly weather breezes in, we’re approaching that awkward time of year where getting dressed for the day can be tricky. It’s too warm out for your winter coat but too cold to go bare-legged – so what’s a stylish girl to do?

This week’s fashion challenge is to try out a pair of thigh-high socks! More fashionable than a pair of leggings, and more practical than ankle socks, they provide extra coverage and warmth when paired with a dress or skirt in Fall. These babies are perfect for adding a bit of pizazz to any outfit. And they’re way more wearable than you think.

Think you’re ready to tackle the challenge? Read on for tips and outfit ideas, then scroll on down to send us YOUR look!

Tips & Tricks for Wearing Thigh-High Socks

  • It’s all about the shoes. Thigh-high socks look great with mary-janes, oxford heels, and most pumps or ballet flats. If in doubt, consult your roommate or BFF for her opinion.
  • Pair them with boots. This is the easiest and most up-to-date way to rock thigh-high socks.
  • Wear them instead of leggings. Tall socks are perfect for pairing with a sweater dress or a winter-y skirt for an updated take on leggings.
  • Make faux over-the-knee boots. If you’re craving the look of popular over-the-knee boots but don’t have the budget to buy a pair, substitute a pair of long socks underneath matching boots for a similar look.

How to Wear Thigh-High Socks: Outfit Inspiration

Outfit 1 – Thigh-High Socks, a Dress, and Boots

How to wear over-the-knee socks - outfit 1

Boots, Socks, Dress, Jacket, Earrings

Over-the-knee socks are the perfect way to transition your favorite summer dresses into fall and winter. Just pair a simple dress with a stylish jacket, like this military-inspired one. Next, slip on a pair of thigh-high socks and pull them up so they peek out from under a chic pair of boots. Finish with simple jewelry.

Outfit 2 – Thigh-High Socks, a Dress, and Heels

How to wear the thigh high socks fashion trend

Dress, Shoes, Hat, Socks, Necklace

Turn a plain-Jane black sweater dress into a fierce “model off duty”-inspired outfit with a simple pair of socks. These purple thigh-high socks go perfectly with these peep-toe mary janes — just be sure to tuck each sock’s seam under your toes to keep it hidden. Finish with a slouchy beanie and heart pendant necklace.

Outfit 3 – Thigh-High Socks, Boots, and Shorts

Thigh high socks trend

Boots, Socks, Jacket, Shorts, Belt, Earrings

Another fearless way to rock this trend is with a pair of boots and plenty of attitude. I love my Chinese Laundry Tripin Boots (pictured above) – they’re the perfect length to allow a cute pair of embellished socks to peek out over the top. Add a pair of cuffed denim shorts, a belt, and a stylish jacket or shirt, and you’re set.

Rocked the challenge? Send in your pictures to be featured here!

Did you try a pair of thigh-high socks? Fill in the information below and give us a glimpse of your fierce style! Send us a picture of you wearing this look and we’ll feature you here (see past examples) to help inspire other CF readers!

To get featured here, send your outfit photo via email to fashionchallenge AT, and include your name, school, a description of your outfit, and your blog URL (if you have one). Can’t wait to see what you come up with!


Will you be trying out this challenge? How do you think socks look underneath a pair of boots? What shoes do you think look best with a pair of thigh-high socks? What challenges would you like to see in the future? Let us know what you think with a comment!

Posted on on October 14, 2010 / Filed Under: Fashion Tips / Tags: , , , , ,

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39 Responses to “Fashion Challenge: Wear Thigh-High Socks”

  1. 1
    October 14th, 2010 at 11:37 am

    Very cute! I really love the outfits you put together!

  2. 2
    October 14th, 2010 at 11:37 am

    i already tried this look 2 weeks ago and pulled it off perfectly! :D ill upload the pic when i can

  3. 3
    October 14th, 2010 at 11:57 am

    I LOVE this look! …And the outfits you’ve put together. I’ve done it several times now, and I think it works great.

  4. 4
    October 14th, 2010 at 12:21 pm

    Thank you so much! I was just looking for this cause i buy a pair last week and i love how it looks, love college fashion always <3

  5. 5
    October 14th, 2010 at 12:31 pm

    I really love the outfits you put together- they’re all so different but still very wearable! However, I don’t think I’m able to pull this off- I don’t have the legs or the edge for it. I’ll stick to knee-high socks for now :)

  6. 6
    October 14th, 2010 at 12:37 pm

    I love thigh high socks for fall and winter! I wear them to school when I don’t have any tights or anything clean :)

  7. 7
    October 14th, 2010 at 12:41 pm

    Very nice, I love the second outfit and the third is cute too. Very well done. Thank you!

  8. 8
    October 14th, 2010 at 1:09 pm

    i love thigh high socks- I have braved them several times!!
    they’re perfect for keeping your legs warm here in minnesota!!
    i love these outfits :]]]
    great fashion challenge- yet again!!

    Charlotte xxx

  9. 9
    October 14th, 2010 at 3:45 pm

    Love your outfits, Chelsea! I have a pair of grey thigh highs that I’ve yet to wear and this gave me some great ideas.

    &&Charlotte–I didn’t know you were in Minnesota!! Me too!CF-intern meet-up?!? :)

  10. 10
    October 14th, 2010 at 3:55 pm

    i’m in california, it’s so hot here right now, and i’m STILL wearing high socks. i love them so much, and i’m wearing them with my flat oxfords! thank you for posting this article.

  11. 11
    October 14th, 2010 at 4:18 pm

    Totally digging the style (and crushing on the black pair of Trippin boots, my gray ones are amazing).

    Anyone know of a place to buy the over-the-knee socks in person?

  12. 12
    October 14th, 2010 at 4:36 pm

    I have the Chinese Laundry Trippin over the knee boots too and I absolutely love pairing them with even higher socks! Great post.

  13. 13
    October 14th, 2010 at 5:23 pm

    love it

  14. 14
    October 14th, 2010 at 6:26 pm

    I love love love thigh highs, but I always have trouble making them stay up and not slip down…does anyone have this problem/solution to this?

  15. 15
    October 14th, 2010 at 6:27 pm

    I’m trying to find a store that sells them. I can’t find them except for online, but I want to be able to see the size before I buy them.

  16. 16
    October 14th, 2010 at 8:01 pm

    love this trend. especially with the oxford shoe! =]

  17. 17
    October 14th, 2010 at 8:48 pm

    OMG I have been waiting sooo long for someone to do one of these. I have a few pairs and always get funny looks when I wear them. But I love them to death and think they are super cute! Totally been rocking this for 2 years, and ready to keep it going!

  18. 18
    October 14th, 2010 at 8:48 pm

    I think it looks adorable but so many girls with curvy legs simply cannot pull this off because of the dreaded “muffin top” that’s caused by thigh-highs being so tiny!

    Super cute, but no way on earth would I try it.

  19. 19
    October 14th, 2010 at 8:58 pm

    I’m iffy on them with shorts, but the dresses look great.

  20. 20
    October 14th, 2010 at 9:31 pm

    I love all these looks! Definitely great for staying warm this fall :)
    Where would be a good place to buy some thigh-high socks? I’m having some trouble finding them…

  21. 21
    October 15th, 2010 at 12:43 am

    I love thigh highs with heels and boots! You just can go wrong with thigh highs!

  22. 22
    October 15th, 2010 at 3:47 am

    I love this!!! I am have two pairs, a gray cable knit sweater type, and black ones. I love them with boots, heels, and plain ballet flats.

    For the person that asks where you can get them – hue makes a good pair (Belk or Dillard’s for about $15) or Target is carrying them that are VERY close to the hue socks for $5 a pair.

  23. 23
    October 15th, 2010 at 11:56 pm

    I’m not a big fan of the thigh-high socks with shorts. Maybe if it was a denim skirt or somethnig…but I ADORE the two dress pairs!

  24. 24
    October 17th, 2010 at 10:36 pm

    I love the idea, but I do think it looks a little like Cher in Clueless…ya know?

  25. 25
    October 19th, 2010 at 5:47 pm

    I have curvy thighs and I wore thigh-high socks with my knee-high boots and black shorts and I love it! One of my friends told me that it was not acceptable, but she had no personal style. My other friends told me they loved it!

  26. 26
    October 22nd, 2010 at 12:31 pm

    I love all outfits except for the 3rd one. I’m not a big fan of thigh high socks for myself, but other girls looking very nice in them.

  27. 27
    November 9th, 2010 at 12:06 pm

    i might try wearing this thigh high socks, looks pretty =)

  28. 28
    August 3rd, 2014 at 11:45 am

    I love totally the thigh high and over the knee socks + boots style. The must have outfits for a lot of combination of looks ! My favorite in Fall to spring and rainy days in summer with rubber boots :)

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