When Does a T-Shirt Look Good?

I know “well-dressed” guys aren’t supposed to wear T-shirts, but I see a lot of younger guys wearing T-shirts in pretty stylish ways. Sometimes they’re with jackets and other times just with pants and big belts. Am I just kidding myself if I try that, or can T-shirts look good?

2 Replies to “When Does a T-Shirt Look Good?”

  1. T-shirts can look good in two different ways:

    – As a shirt worn under a jacket or similar garment in a casual outfit.

    – All on their own on the beach, at the gym, or otherwise out and exercising.

    Either way has some caveats, though:

    If you’re wearing the T-shirt as part of a stylish outfit, it should be dark, close-fitted, and paired with something that covers the rest of your arms. It’s always good to have a non-functional item like a decorative belt buckle, a pocket square, or even a scarf in outfits with T-shirts, since they make it clear that you’re creating a deliberate “look” rather than just being lazy or not understanding dress standards.

    If you’re wearing a T-shirt because you’re working out or playing sports, that’s pretty much the right place for it. However, if you don’t have a great build or you’ve got a baggy T-shirt, consider swapping it for a tighter-fit jersey or long-sleeved T-shirt, just so you don’t get that awkward look of skinny arms and flapping cloth.

  2. My take on it, with a few specific situations, from the Real Men Real Style YouTube channel:

Leave a Reply