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.
How to wear a t-shirt with dress pants
Although I’m not a huge proponent of following the rules of style to the letter, there are certain rules and/or traditions that I like to adhere to.
One of those traditions is always leaving the bottom button of your waistcoat undone.
Like always having one button unbuttoned on your jacket cuff it’s hard to trace the origins of the practice, but somehow it just looks “right”.
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.
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.
The perfect t-shirt
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.
Trousers
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.