How to Dress Like Kenny Chesney

Kenny chesney in concert

Sleeves off and leather cowboy hats on! Summer is here and Kenny Chesney styles are perfect to rock during the hot months. Known for hit songs such as “Don’t Blink” and memorable duets with the likes of Time McGraw and even P!nk, Kenny Chesney is not only a legend in country music, but a style icon as well.

Stetson Men’s Apache 4X Buffalo Felt Cowboy Hat

Stetson Men’s Apache 4X Buffalo Felt Cowboy Hat

Kenny Chesney’s Style

While you may not be able to travel the world and sing famous songs, you certainly can rock the Kenny Chesney style. Known for a laid-back masculine beach look, Chesney’s style is certainly unique. At Sheplers Stampede Western Wear, we have got the complete guide on how you can dress like Kenny Chesney.

Cowboy Hat

The quintessential staple in Kenny Chesney’s wardrobe: a leather cowboy hat. It’s the first step in completing your Kenny Chesney style. He is frequently spotted rocking either a white, tan, or black coboy hat. These cowboy hats are perfect to pair with any sleeveless shirt or blue jeans.


No matter the season or the place, Kenny Chesney often wears denim blue jeans of all kinds; even on the beach. Strumming his guitar and staying cool, men’s blue jeans are a must if you are trying to dress like Kenny Chesney. Just make sure they aren’t to tight, Kenny Chesney prefers a relaxed fit compared to more form-fitting styles preferred by Tim McGraw and Luke Bryan.


Comfortable and stylish, Kenny Chesney is always seen wearing a sleeveless shirt. While his laid-back style of cut off sleeves is not suitable for everyone, Kenny Chesney frequently sports a casual T-shirt on stage. He sticks to an almost neutral color palette, choosing colors such as gray, white, and navy blue. His simple style choices make it easy to recreate and usually pairs well with just about anything you can find, just keep it casual and skip the jacket for this one though.

Last, But Not Least – Boots

Of course, the country icon’s look wouldn’t be complete without a pair of cowboy boots to tie it all together. If you are trying to dress like Kenny Chesney, go for tan and rugged style country boots to complete the look. When Kenny Chesney is not touring though, he’s just barefoot on the beach.

Kenny Chesney is a great style inspiration if you want to keep it simple, you just need to know where to get all the country and western wear. Our affordable and stylish men’s styles will have you singing and rocking tunes as if you were country legend, Kenny Chesney, himself.

© Copyright 2021 All Rights Reserved