Ask Lori: How Do I Wear Cowboy Boots?

A mere five years ago, I was obsessed with cowboy boots.  I walked the streets of NYC searching for the perfect pair, which I finally found in some random boutique on Lafeyette in Soho.  They were the last pair left, on sale for just under 100 dollars.  All my friends laughed at me and I said…just wait…cowboy boots are cool.  When everyones wearing them in a couple years, y´all will be JEALOUS!  My obsession still lies in my cowboy boots and I wear them all time, I have to say that they are one of my most prized possessions!

And here we are five years later, my cowboys worn in but still trending!  My bff Claire recently bought a pair and asked me what she should wear them with.   First, I will share pictures below of her boots (the darker brown ones) and my lighter brown boots so you can get an idea of what we are working with.



1.  Cowboy boots are cool but the idea isn´t to actually LOOK like a cowboy.  Try not to wear these with cowboy hats, with collared shirts, denim unless you are hitting up the rodeo, in that case, bring it on!

2.  Unless you want to roll Dukes of Hazzard style, don´t wear cutoff denim shorts with them.


1. DO wear them with a cute summer sundress.

Rachel Bilson looks sassy in these red boots and LBD

They look great with this simple blue summer dress from Sfera

2.  DO wear them with tailored, classic shorts.

I couldn´t even FIND a picture on the internet of anyone wearing this correctly, so below I will put the shorts, and then picture them with either mine or Claire´s cowboy boots….perfect!

This outfit created by Avenue 7 would look perfect with Claire´s dark brown cowboy boots.

These high waisted This Next shorts would be perfect with my lighter boots.

These are just a few options….my best advice is to simply put your outfit on with the boots, look in the mirror and ponder.  Your outfit shouldn´t make you look like a cowgirl, it should have just a ´twang´ of cowgirl!


One response to “Ask Lori: How Do I Wear Cowboy Boots?

  1. thank you soo much! love love love! xo

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