Does this season's jeans & boots have you confused?

/ Melanie Lippman /

Jeans and boots are a classic go to uniform for the winter… Today’s version of the look has gotten super chic and a little challenging to decode. Jeans are cropped, flared, embellished, or straight and boots are short, chunky, funky, or flat this season. 

Wear your jeans over your boots

I’ve been suggesting that straight leg jeans are more flattering than skinny jeans, but the questions always comes up…. what does do I wear with them? I suggest styling their jeans over your boots, with hemlines ranging from grazing just over the top of the boot to hanging down several inches.  My favorite way to wear them is a little cropped giving attention to your awesome boots! Here are a few of my favorite boots to wear inside your jeans.

boots shopping long island

Tuck Your Jeans In Your Boots

This one is the trickiest of all in my opinion.

  • Do tuck your denim when it is very skinny at the ankle and will not bunch. It also has to be long enough to tuck.

  • Do tuck your denim when your boots have a wider opening at the top.

  • Don’t try to tuck your denim when your boots are very short (i.e. hit at your ankle), only when they are a bit taller.

Here are a few fab boots to tuck your jeans into.

boots image personal shopper

Cropped Denim

This is perhaps the easiest way because your jeans do all the work for you. If you are wearing a cropped pair of jeans, they are already not going to conflict with your booties.

  • Do let your denim hit above your booties

  • Don’t let there be too much skin between the bottom of your jeans and the top of your booties. This may mean (depending on how cropped your jeans are) that you need a taller ankle bootie (one that hits above your ankle bone) or you can go for a more relaxed look with a little fold.

Here are some great booties to pair with a cropped jean.

BOOTIES image personal shopper
image shopping

Happy to help!

If you are still having trouble in front of the mirror, contact me for an in-person or virtual consultation on how to polish your style and dress your best. Our first half-hour together is complimentary. I look forward to helping you!
xo,
Melanie