Pulling Off A T-Shirt With Dress Pants: It’s Possible

How to wear a t-shirt with dress pants

In the past, within these pages, we’ve discussed wearing a t-shirt with a blazer as well as how to pull off the t-shirt with a suit look without looking like Don Johnson. Today, we’re tackling another version of styling a t-shirt with tailoring–how to wear a t-shirt with dress pants.

Of the tailoring plus t-shirt looks we’ve explored on HSS, pairing a t-shirt with dress pants has perhaps the highest degree of difficulty. The biggest issue here is that you are not covering up the t-shirt with a jacket, which leaves your entire t-shirted upper body exposed. This leads to two considerations.

First–there’s no way to sugarcoat this–it’s a look that is not going to work for some guys. You have to have some degree of fitness to pull it off. Remember that one of the most important aspects of dressing well is to consider your body type.

| WEARING | Michael Andrews Bespoke pants, Goodlife t-shirt, Valstar jacket, Vintage USS sunglasses, Omega watch, Belgian Shoes NYC loafers | PHOTOGRAPHY | by Rob McIver Photo

The second consideration is the t-shirt itself, specifically how it fits. As this leans more toward the “fit bro” side of the scale, there is pretty fine line to walk between looking chic and looking like a douchebag. (N.B. I find it humorous that in each of the t-shirt articles I’ve written, I’ve used some form of the word ‘douche’.) Muscle bros love to wear tight t-shirts to show off how jacked they are. Even if you are that guy, don’t do it. A little modesty goes a long way and says a lot about your character.

Choose a t-shirt that has a “tailored” fit, but that is not form-fitting. Avoid an overly baggy t-shirt. If you’ve ever wondered why movie stars look so perfect in a t-shirt, one of the reasons is that they often get them tailored. I read that somewhere and it makes sense.

The trousers you choose to pair with the t-shirt are also an important consideration. A t-shirt and dress pants look can easily look too trendy depending on the fit. If everything is too tight and fitted, you’ll look like you’re chasing trends. One caveat to that is that if you’re a younger guy and you have the confidence and physique to pull a look like that off, by all means, don’t let me stop you. Live and experiment when you’re young.

However, I’m a 40 year old man. I don’t care much for trends and prefer to project an image of timeless elegance, which although it might sound odd, can still be done with a t-shirt and trousers look. For me, this is accomplished with a pair of well-tailored pants. Bonus points if they’re pleated. And as this is decidedly a summertime look, making sure you’ve got the right fabric will show the depth of your sartorialism. Fresco is light and airy and has a subtle texture, making it a great choice.

Thanks, as always, for reading.

Stylishly Yours,

Brian Sacawa
He Spoke Style