Fashion Challenge: Wear Thigh-High Socks

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Blake lively wearing thigh high socks
68989, NEW YORK, NEW YORK – Tuesday November 1, 2011. Blake Lively steps out of her trailer and onto the set of “Gossip Girl”, shooting on location in Harlem, New York City. It is being reported that Lively recently introduced her boyfriend, fellow actor Ryan Reynolds, to her parents. Photograph: © **FEE MUST BE AGREED PRIOR TO USAGE** **E-TABLET/IPAD & MOBILE PHONE APP PUBLISHING REQUIRES ADDITIONAL FEES**Ã?LOS ANGELES OFFICE: 1 310 822 0419Ã?Ã?LONDON OFFICE OFFICE: +44 208 090 4079,Image: 527396691, License: Rights-managed, Restrictions: WORLD RIGHTS, DIRECT SALES ONLY UNLESS STATED OTHERWISE IN CAPTION – Fee Payable Upon Reproduction – For queries contact – [email protected] London: +44 (0) 20 7421 6000 Los Angeles: +1 (310) 822 0419 Berlin: +49 (0) 30 76 212 251 Madrid: +34 91 533 4289, Model Release: no, Credit line: / Avalon

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.

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 pastexamples) 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!

9 thoughts on “Fashion Challenge: Wear Thigh-High Socks”

  1. 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.

  2. 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!

  3. 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 🙂

  4. 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!

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

  6. 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?!? 🙂


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