New or vintage, cowboy boots never go out of style. I love styling them street style with denim, skirts or dresses. Effortless yet intentional.

Autumn is upon us. This is my favorite time of year. I could live forever wearing jackets and boots. It is also a chance to put my cowboy boots back into rotation.

I have two pairs of vintage cowboy boots and two pairs that are more current, purchased within the last ten years. All are different and offer countless styling options.

Vintage Cowboy Boots

I found these yellow and gold vintage cowboy boots at an indoor flea market for $25.  I didn’t have anything like this (or this color) in my shoe closet so I was excited to style them up.  The sequin jeans are from Anthropologie and the floral blouse is from Bloomingdales. 

Flea markets are an awesome source for cowboy boots. You’ll find a myriad of vintage styles at all price points.

The styling options are vast. I love cowboy boots street style; with jeans, skirts and dresses. This vintage dress is a flea market find from Brimfield Flea.

I found a green pair at a vintage shop in San Francisco for $30.  I love this color and the fact that someone broke them in for me.  Styled here with my shredded vintage Lee jeans, and a lace bomber jacket from Zara.

Vintage cowboy boots will be broken in. Buying new boots is a different animal. Here are some tips:

• Don’t go by your shoe size. It’s imperative to try them on in-store and wear socks.
• Be prepared for them to be stiff and hard to get on. You want them to be snug. They will stretch over time but it will take months to break them in.

More Current Styles

These gunmetal gray boots are from Nashville Cowboy in downtown Nashville where you can buy two for the price of one.  It’s a great way to incorporate the trend without spending a lot of money.  Not being an actual cowgirl, I was looking for affordable options.  I like to wear this dark gray pair with a very old pair of DIY vintage Levi’s that I thrifted in 1998.

This is the 2nd pair of boots that I bought at Nashville Cowboy.  I love the graphics on this pair.

I’m on the hunt for one more affordable pair of cowboy boots to cut and DIY into an ankle boot.  A red pair would be cool but until then, I’m satisfied with the gems I already own.

Let me know in the comments below how you like to style cowboy boots.

More vintage outfits on Mad Chipmunk