How to Wear Denim on Denim and Not Look Like a Cowboy

I will preface this post with if you want to take a more country look with a denim on denim outfit, I am not one to stop you. But I also feel like you know what you are doing, you know? This post is for those of us who want to wear denim on denim but don’t want to be asked if we have a horse. It is a niche crowd, but more populated than you’d think.

And also before you say, could you not have bothered to make your bed? I thought the light one side quilt toss would do the trick. Cue the narrator: *it in fact did NOT ‘do the trick’*

Chambray Options

Accesorize Lightly

First off, I don’t know if this needs to be said but better safe than sorry: don’t add a cowboy hat. That’s the first rule of not looking like a cowboy; simply don’t add a hat. Not just a cowboy hat but a wide brimmed hat will bring about a more cowboy-forward look. I come from a long line of cowboys, so you can trust me and the formula is this: cowboy hat, cowboy boots and a horse. If you want to wear denim on denim and you don’t want to look like you are cosplaying a generic cowboy, please leave those three out of your outfit equation. Spurs, too, but at this point if you have 4 out of 4 of those items, I must say you are most definitely a cowboy.

Jokes aside, leave the hat. For shoes, I find going with a round toe boot or a clog is going to be your best bet as well. This look would also work with a pointed toe nude flat or a trending sneaker, as well. Technically, I went with a more ‘country’ look with my cognac boots and the suede bag, but my keeping the rest of my outfit simple, it all complements each other nicely.

I like to keep my jewelry standard and simple. Light gold hoops, a light necklace, etc. Nothing too heavy or forward, I let the denims do the talking.

Cue the Hues

I personally feel like there are two ways to do denim on denim and here they are: you can either pair similar denim hues on the top and the bottom, like my outfit today OR you can pair a darker denim on the bottom and a lighter hue than the bottom chambray on top. For instance:

To me there are no other ways. If you go with the darker denim on top and lighter jeans option, it’s just not as of a cohesive look. (Not talking about white denim, which one could argue isn’t really denim on denim. Plus it’s a classic millennial look and I’m not touching that.)

With the similar hue denim on denim look, you end up creating a nice, almost monotone look which gives a chic, classic vibe. I could have easily swapped out my brown for black boots / purse for an even more elevated look. Filing that one for later.

Side note — I am team no-belt on this look because I like the streamlined look of the monochrome denim’s. 

Cut The Bootcut

For the leg of the denim, I prefer to stay away from bootcut jeans. I mean in general, honestly because the last time I wore those I also had a locker. Instead I go for a wide leg straight or a high rise wide leg flare. Flare meaning it goes from the knee all the way down past your ankle, where as boot cut will start to flare out a bit more at mid calf. This pair I’m wearing today is my favorite from Madewell, the Perfect Vintage Wide Leg Straight Jeans. (I’m in the 30, TTS!) I like that the break is right at the top of my boot as well, so it shows the boot but not too much and the hem doesn’t drag the ground.

I also think you can do a straight leg or a mom jean with this look as well, super cute options depending on your favorite silhouette of jeans.

Just as a side note: J.Crew is 25% off and some of these tops are from there! Use code SHOPNOW. The exact chambray I am wearing is on sale with an extra 50% off. Find it here (I’m in the 10)