5 Ways to Rock a Denim Shirt and Look Like a Boss

It’s time to trash your old baggy frat t-shirts. Yeah, your girlfriend might like to sleep in them, but seriously… you’re 30 now and it’s time to move on.  Let’s upgrade you into 2017 with a little denim. Denim is something that will never go out of style, so investing in a few fitted button down shirts is a great idea if you’re looking for something comfortable, but still fashionable.

Here’s our guide on how to pull off denim and look like an absolute boss.

Wear something under the dang shirt.

Trim denim shirt

If you’re not exactly David Beckham, which most of us aren’t, you’re gonna want to wear an undershirt.

First of all, you can still totally nip out through a denim shirt. Yikes. Secondly, layering is always a great idea and keeps things trendy. I would know, since I once wore two popped collars at once.

Okay, that’s a bad example, but our model in the picture above is a great example. Try one of Trim’s fitted t-shirts underneath our new upcoming line of denim shirts for the complete look.

Do not wear a baggy shirt underneath your new shirt. I’m being so serious right now. Pairing a frumpy shirt with a cool guy denim shirt is seriously only something celebrities can do. You might be hot, but do you honestly want people thinking you are the shape of a square? I know I don’t.

Also, it doesn’t have to be a ultra deep V-neck, but there needs to be a little bit of “V” going on in order to prevent you like looking like a total dad.  Even if you are a dad, be a cool one. For God’s sake. 

If you’re going to Canadian Tuxedo it, mix it up a bit.


Look, I’ve been guilty of wearing a Canadian tuxedo myself and you know what? I was totally called out on it. You can’t just go waltzing around in a full on matching denim outfit and not expect to get some sh*t for it.

Switch it up a bit and don’t go too crazy with being a human blue jean. This model has the right mix of still looking professional, yet business appropriate. Who says that you can’t wear denim to work? It’s called business casual. If you dress like this, your boss isn’t going to call you out for looking like Neil Young.

I recommend never wearing the same denim color when it comes to shirts and pants. Light blue denim with black jeans or stone washed dark denim totally matches. It actually matches way better than the Olsen Twin get up that you thought about leaving the house in.

Do not wear a denim shirt if your significant other is also wearing one.

InTouch Weekly

The year was 2001.

It’s an infamous day that will forever go down in history. This is one of the most tragic fashion incidents that the modern world has ever seen. I’m talking about the Justin Timberlake’s and Britney Spears’s jean on jean disaster. Not only was Britney wearing a full-scale evening gown made out of jeans, she made her boyfriend dress up in a jean blazer, featuring loose fitting jeans and a DENIM HAT.

I want to punch both of them in the face for this.

Don’t be this couple. I don’t care how much you are #couplegoals to the people around you, the humiliation that you’ll incur will be unbearable in the years to come.

If your partner comes over in a jean shirt, immediately take yours off and set it on fire. 

Style yourself or you’ll look gross.


Look, this goes with any kind of fashion advice I could give you: style yourself. Get a great haircut, trim your beard, and put some thought into the clothes you wear.

I know some men don’t really do this, but all it takes is a few great pieces of clothes and nice barber day once a month to really get you going. Then you don’t have to think about it. Buy five fitted t-shirts, a denim button down, a solid pair of dark wash jeans, some cool shoes, and you’re golden.

Take a day to go shopping and start building a small, but reliable source of clothes. Get rid of the crap you never wear by donating it or selling it and then replace your closet with clothes that you’ll wear consistently.

Style doesn’t have to be hard.

Don’t be afraid to spend a little money to make it looked fitted.


I hate to break it to you, but pretty much nothing great in life is cheap. Especially clothing. You pay for the quality you get. Sure, you could buy a broken down shirt from some generic place, but put it through the wash one time and watch your $17.00 go down the drain.

For instance: I could’ve bought a really crappy quality leather jacket from Forever 21. It might’ve cost me $30.00. Within six months, it would be out of style, looking cheap as hell, and tearing apart. Instead, I opted to buy a Calvin Klein leather jacket that cost me $230.00, but I wear it almost every single day and it won’t go out of style. It’s one of those staple pieces that shows people my fashion sense and I get a ton of compliments on it. I’ll be wearing it for years to come, too.

If you’re on a budget, save up and then pick out the pieces that you can wear over and over again in different ways. With a denim shirt, you can style it countless ways. Wear it with a t-shirt, wear it as a button down, wear it as a jacket, etc.

Spend money on something that won’t go out of style immediately and that fits your body type. There’s a reason that your $15.00 button down looks like crap. If you’re cheap, you’re going to look cheap.