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

3 / 8
Make sure the t-shirt has a "tailored" appearance, meaning it fits well--not overly baggy--but isn't skin tight.

4 / 8
Similarly, make sure your trousers aren't painted on. A well-tailored trouser with pleats will add an air of elegance to a very casual and chic look.

5 / 8
Accessorize well.

6 / 8
For a chilly summer night, a suede jacket is a great option.

7 / 8
This is the Valstar Valstarino in sand suede.

8 / 8
Cool and confident.

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.

t-shirt formal 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.

t-shirt formal pants

| 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.

t-shirt formal pants

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.

t-shirt formal pants

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.

t-shirt formal pants

Thanks, as always, for reading.

Stylishly Yours,

Brian Sacawa
He Spoke Style

Chime In

  • What’s wrong with Don Johnson?

    • http://hespokestyle.com/ Brian Sacawa

      Touche! Just to be clear, we’re talking about Miami Vice Don Johnson. If you’re of a certain generation, yes, Don Johnson was awesome in the 1980s, but that look could be considered tacky nowadays. Particularly the colorful t-shirt and light-colored suit. But the reference was mostly tongue-in-cheek.

  • I realize you weren’t really disparaging Don Johnson, and you’re right, the Miami Vice look of the 80s can be tacky. That being said, I live in San Diego where daytime temps routinely hit the high 90s and I have effectively used a few style cues from that show to remain both stylish and cool. Cool as in temperature, not Don Johnson “cool.”

  • http://gentlemanwithin.com Khoi | Gentleman Within

    Hm, I hadn’t considered this, but I think you really pulled it off. T-shirt and trousers can project an image of timeless elegance. High-low at it’s finest. Well done! Love the suede jacket, btw.

  • RJ Giddings

    One of the things I noticed about pleats – they come and go. They were popular for a bit in the early 90’s…then it faded away for maybe 20 years…and is now coming round again. Since I’m now in my late 40’s I still try to avoid pleats as I somehow always look like I just inhaled a double cheeseburger. The t-shirt works in these couple of photos as classy. Look at Marlon Brando in A Streetcar Named Desire ( 1951) and you’ll see it.

  • ana sousa

    Hi, I think you pulled it off
    I have been seeing shoes and found this startup, they make shoes that seem to me to be very good and are colorful and I would like to know your opinion, if you like them, and how you would wear them. They are beautiful but they seem a bit eccentric and so sometimes they can be a bit more difficult to use, what do you think?

    https://www.indiegogo.com/projects/khepry-portuguese-footwear-with-d-q-e/x/18540156#/

  • Simon

    You’re fucking 40?