A few weeks ago, I mentioned to a friend that there should be a guide for wearing cowboy boots. His response: “Is there ever a time you should wear cowboy boots?”

I paused for a moment, picturing my outfit from the previous weekend – a short, tight, strapless white dress, a wide tan belt and … tan cowboy boots.

“Yes, there is always a time for cowboy boots.”

And in my defense, not only did I think my outfit was cute, but I’ve seen Jessica Simpson, Sienna Miller, Rachel Bilson, Jessica Alba and Ashley Olsen looking pretty cute in their cowboy boots too.

It’s true, even if you don’t call Tulsa your hometown, you can still rock cowboy boots. And even better? You can wear them in a way that makes hillbilly look chic. (If that’s possible.)

Distressed denim skirts and halter-tops are a cute way to wear cowboy boots at country concerts in the summertime, but for fall, boots should be paired with dresses or jeans.

You want to keep the length above the knee and avoid fancy fabrics like satin (cowboy boots don’t pair well with evening gowns – even in Oklahoma), but these boots can work with almost any short cocktail dress – from floral prints to black mini dresses.

When matching your boots to dresses, remember that your new cowgirl boots are fun and flirty so your style should mirror that. Don’t forget to add a long cardigan with your dress and boots to take your outfit into the evening.

Cowboy boots are also perfect tucked into skinny or straight leg jeans and paired with a longer shirt and a cropped, structured jacket.

With the right outfit you can even wear leggings tucked into cowboy boots. Try a black (short) cotton dress with a ruffled hem, belted at the waist, with black leggings and your new cowboy boots.

It’s important to avoid brighter colors and flashy pieces. You also might want to make the boots the only country piece in your ensemble. Don’t pair your boots with short denim shorts, a plaid button up shirt, a dusty cowboy hat and pigtails – unless it’s your Halloween costume.

All the rules aside, it’s time to find your dream cowboy boots and hit up a hoedown near you. Yee haw!

Tags: Ashley Olson, black mini dresses, cowboy boots, distessed denim skirts, ensemble, Jessica Alba, Jessica Simpson, leggings tucked into cowboy boots, Rachel Bilson, ruffled hem, short cocktail dress, Sienna Miller, straight leg jeans, strapless white dress, structured jacket, wide tan belt

This entry was posted on Tuesday, September 29th, 2009 at 7:00 pm and is filed under Fashion Addict. You can follow any responses to this entry through the RSS 2.0 feed. You can leave a response, or trackback from your own site.