To Try or Not to Try?

I literally had three separate emails come through last week inquiring how to wear the “socks with boots” trend.  I agree that this particular trend can be a little tricky.  The most important things to remember (at least for me as a thirtysomething mama) are:

1. Keep the hemline on the longer side so as to NOT look like a teenager.
2. Keep accessories to a minimum, having the sock be the focal point of your outfit.
3. Keep the look on the more casual/day side.  Think sweater dresses and wool skirts.

So to answer your question, I say “TRY”!  After all, fashion is supposed to be fun:)  Hope you find some outfit inspiration and enjoy wearing the “sock” trend this fall/winter.  Happy Shopping!

Leather Jacket Steve Madden, Sweater Dress Banana Republic, Thigh High Socks Nicole Miller, Boots Jeffrey Campbell, Necklaces Soko and gifted, Infiniti Scarf Veond

Posted by Andrea Brusuelas

38 responses to “To Try or Not to Try?”

  1. Amanda says:

    You look awesome as usual!! And I agree, keep the hem lines down. Otherwise I feel Pretty Woman’ish 😉

  2. Great tips! This is something that I have always wanted to try, but it just felt weird to me because I wasn’t sure. Heather

  3. Gorgeous as usual!
    I almost wore a very similar outfit to work today but decided last minute on pants. I’m still planning on wearing it sometimes this week. 🙂 Great tips!

  4. molliee says:

    you pulled this off perfectly! I really love this entire look!


  5. Jules says:

    You made this trend look so casual, yet chic. I like how the sock just kind of peeks out. The blue infinity scarf is also lovely.

  6. fshnonmymind says:

    You did an excellent job with the look. I would totally wear it. I bought a pair of knee-high socks last year and have been testing out looks that will make it look right.
    I am in total love with your scarf!

  7. Super tips and the socks + boots are great! I’ve been doing the sock/boot thing for a while…it’s one of my favorite looks for fall and winter. Plus I find scrunched socks help fill the gap I often have in the calf area…boots are almost always too big on me in that spot.

  8. weasel says:

    These boots look great

  9. Yeah, it can be hard to hit the balance between too young and streetwalker. 🙂 You did it perfectly. Still jealous of the boots. . .


  10. Catita says:

    thanks for the tips, love it and great dress and necklace (always!) you got there!

  11. Alleycat says:

    Great tips. I have a couple pairs of knee high socks but just haven’t gotten around to trying them on. Think my 10 year old is borrowing them so she doesn’t have to wear tights.

  12. Eleanor says:

    Love the socks and boots!
    I wore them alot last year and plan to do it this year as well!

    Looking fabulous lady!!!

  13. Hi Carly, i am such a chicken when it comes to taking risks, and I don’t think that I could pull off the socks and boots look. But you rock this, is there anything that you don’t look good in?

  14. Great tips and love the scarf especially! xo

  15. Adele says:

    Love the subtle stripes in your top xoxo

  16. Ann says:

    Yeah! LOVE LOVE LOVE! I also LOVE the scarf

  17. Love the look! It turns your knee high boots into over the knee boots. ~jen

  18. Leslie says:

    I’m so glad I found your blog. I am thirty-something and most fashion bloggers are 19 year-olds! I love your advice.

    Check out my blog when you get a chance!

  19. Kristin says:

    You executed the look perfectly! LOVE those boots!

  20. Audrey says:

    Agree with all of your tips! perfectly done 🙂

  21. Noelani says:

    Timely post!! I have been seeing this done on some, ahem, younger ladies and wondering how to interpret it for ladies of the 30 something set. I love how you’ve worked these together, perfecto!

  22. Great tips!! I agree with them all. Now I just have a craving for a new pair of boots. xo

  23. Jill says:

    I agree it’s a try. I actually like with short boots too. Loving that necklace{s)

  24. You did a great job because this is not an easy look to pull off. It’s worth a try….and I love your necklace 🙂

  25. Julieanna says:

    Outfit looks great! Love the “pop” of color by your face. Also love love fall clothes!! Hope you get a chance to check out my fashion blog!

  26. bridgette says:

    You look elegant with a sprinkle of rock n roll. 🙂 the sock and boots trend is one of my favorites this season. you can stay stylish while being warm and comfy.

  27. amy b.s. says:

    i definitely want to try this. now i just need to find some socks that will work!

  28. Your jacket and teal circle scarf =LOVE 🙂 And those boots rock too girl!


  29. You look so fabulous – love this look. You’re inspiring me to try the sock thing!

  30. Gorgeous look. With the jacket it looks very edgy but without the jacket it is stunningly elegant. The necklace is so pretty too.
    I love the socks with boots trend.

  31. Love your take on the knee sock trend, couldn’t agree more with you on it being a “try”!


  32. I love the way this looks. You did a great job styling this look. Thanks for the tips!!! 🙂

  33. L says:

    It’s finally been cold enough to wear this look here. I really enjoy this look. And an added plus? It keeps you toasty!

  34. love you boots!

    PS. enter in my giveaway if you get a chance!!

  35. That necklace…. LOVE! I say try it! And… OMG, You look amazing. I’m totally gonna steal your idea about pairing it with a sweater dress… so CUTE!

  36. Carly I completely agree with your advice about lengths. The first time I tried this look I went with a short skirt. The fashion police (my friend) kindly pointed out the disaster. Love your look here, and grey socks/black boots is better thank black on black for sure.

  37. Polly says:

    Oh Carly you look so great, but I just don’t know if this i a trend I can pull off. I guess I’ll wait and see what is doing when Autumn hits in Australia?

  38. Sarah says:

    You look very lovely! I have a very similar jacket that I got from the saba fashion online store.