Are jeans tucked into boots over?

Let’s call this the second installment of panicked texts from a client that turns into a blog post. The first in this series was “Is it ok to wear pantyhose?” and that post has turned into my all-time #1 most popular and most googled post.

So needless to say when this text came in a few weeks ago I knew it was a blog post in the making.

“I have a very important question… Are jeans tucked into boots done? I feel like they don’t look current anymore.”

“Well, yes aaaand no. It’s not a cut-and-dry answer…”

“Don’t you know I need a cut-and-dry answer?!?”

“LOL! The short answer is, it’s not totally done but some combos can feel very dated. To update it, you have to play with the proportions. Like, make the boot taller (OTK boots) or the top longer (more tunic type top).”

“So, are you saying I need to buy over the knee boots?”

“No, I’m saying I feel a blog post coming on…”

DON’T wear them this way…

How NOT TO wear boots tucked into jeans:

AKA the old way…There is too much space between the bottom of the shirt and the top of the boot. That is why it’s feeling outdated.

Image result for jeans tucked into boots women


Image result for jeans tucked into boots women

And just as a side note – ripped jeans and tall boots are always a no-no. It visually interrupts the long lean lines.

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DO wear them this way…

And HOW TO tuck jeans into boots and look current:

With an OTK (Over The Knee) Boot – see how the proportions between the boots and the tops have changed? It’s that change that makes it look/feel 2010 vs. 2019

Image result for jeans tucked into otk boots street style

Model Lily Aldridge looks effortlessly chic in this easy-to-replicate look. She wore over-the-knee boots with a tee, a black coat and a wide-brim hat.

How to still wear your tall boots from past seasons

If over-the-knee boots are just not your thing. Or if you want to wear your tall boots that aren’t all that tall, you just need to change the length of your top so not that much leg is showing – that’s the proportion play, the amount of leg that is between the sweater or shirt your wearing and the top of the boots.

Pair a longer sweater with a boot that hits under the knee (probably a type of boot you already have in your closet) to make them feel fresh.

Grey Tunic + Jegging + Tall Black Boots

To take this whole boot thing even a step further, I was asked to help WKYC, Channel 3 news anchor Sara Shookman with her new segment “Love Your Look”. We talked all about the 3 boot styles every woman needs to make it thru the snowy winters in style. It aired at 11 pm and 6 am last week but here’s the in-depth segment (that runs about 10 minutes) that visually explains how all of this proportion stuff works (and more).

Here are links for all the items we are wearing in the segment.

And here are some more budget-friendly versions with the same great looks.

Sock Booties

Utilitarian Boots

OTK Boots

So, to any of you out there struggling with a  style or fashion question. PLEASE ask us! Write something in the comments below or shoot us an email. We truly, sincerely WANT TO KNOW! And, if you have the question, chances are someone else does too. Team TWC can answer it for everyone AND create more useful blog content at the same time.

As 2018 comes to an end, we want to thank you all for your continued interest and support. Truly, without you, this could never happen.  Wishing you a year filled with peace, love, and laughter.

2019 Bring. It. On!!




Photos via 1 // 2 // 3 // 4 // 5 // 6 // 7

Photo: Molly Nook

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Post updated 3/1/21


Cleveland-based personal stylist and fashion blogger.


  1. Helen Marie Collins Reply

    Want to know is there a age limit
    on when one can can wear Camo pants? If not
    how to wear over age 60?

    • Hallie Abrams Reply

      Hi Helen, Thanks for the question – I LOVE READER QUESTIONS!!!
      There is not an age limit on camo pants per se, I think it has more to do with HOW you wear them. If paired with a silk top and pointy toe pumps or a black turtleneck and booties camo pants can feel grown up and sophisticated. Or try a camo sweater or scarf and wear it with jeans. Have a great day! xo

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