I’d like to suggest a middle path: t-shirts as a classic, versatile piece of clothing appropriate to wear on some occasions, but not others. Allow me also to suggest that even if t-shirts constitute a simple staple of one’s wardrobe, there are ways to wear them better, and worse.
When to Wear a T-Shirt
How active will you be? Tees were made for labor, sports, and generally getting things done. The more you’ll be moving and sweating, the more appropriate wearing a t-shirt will be.
How old are you? T-shirts are better suited for young men, than those in their post-college years.
What’s your build? Nearly all clothes look better on a fit physique, but this is especially true of t-shirts. If you’re overweight or thin, the tee will either cling to and emphasize your belly, or drape lifelessly over your skinny frame. So too, the contrast between the sleeve and your skin will draw attention to your alternately pudgy or bony arms. Thus thin and overweight men always look better in garments like dress shirts and sports jackets that add some structure to their frame, build out their shoulders, take in their waist, and form a more masculine v-shape. Even casual tops like short-sleeved henleys and polos are more flattering for large men, as they include details around the neckline that draw attention towards the face and away from the belly. These options are just as easy and comfortable as t-shirts, and are nearly always a better choice for most men, even those who are fit and can more readily get away with wearing tees.
How to Choose a T-Shirt
Tees
Things like fit, material, and design can all have a big effect on how a t-shirt looks.
Fit
Fit is the cornerstone of good style. But while we often think of this dimension in regards to garments like the suit and dress shirt, it’s important to get a good fit in your t-shirts, too.
Size/Tightness.
A t-shirt should be neither too baggy nor too tight. If you’re in shape, and have a good build, you can lean towards tighter over looser.
Length.
The bottom hem of tee should hit no higher than your hips, at least cover your waistband, and ideally extend a few inches below it.
Shape.
Avoid boxy tees that wear like a sandwich board with sleeves. You want the tee to be cut so it follows the shape of your body a little.
Collar/Neckline
T-shirts come with two main types of necklines: the crew and the v-neck. Each works best according to the look one is going for, as well as the proportions of your face and body.
Material
In general, choosing t-shirts made from 100% cotton is the way to go. Natural, soft, cool, and static-resistant, cotton looks and feels great. A 50/50 blend of polyester is a decent option as well; the synthetic fiber is less breathable, pills more easily from wear, and increases static, but makes the shirt less moisture absorbent and prone to wrinkling and shrinking. Tees made entirely from special synthetic fabrics may wick away perspiration better, but are only appropriate for workout wear, and unless you’re working up a big sweat, feel a lot less comfortable than pure cotton.
Color/Pattern/Design
T-shirts can be broken into two broad categories: classic and graphic.
Classic Tees
The most classic looking tees are those that come in traditional solid colors: whte, navy, gray, black. Other colors from reds to greens to purples can work fine too, depending on your skin tone.
Graphic Tees
Graphic tees came on the scene later than their solid-colored counterparts, and thus have a more modern, and younger, feel to them. They’re also more casual. And the bolder/bigger the graphic gets, the more casual it becomes. Thus, graphic tees of all kinds are best reserved for things like going to the gym, running errands, and laid-back get-togethers. Tees from your alma mater or your favorite sports team work well for watching the game at home with friends, or at the stadium, but not for dinner parties.
Choose graphic tees that sport interesting and tasteful designs; avoid giant, screaming logos, metallics, funny gags, and ironic images, all of which read as lowbrow and rather juvenile.
Tips for Wearing a Tee With Style
Pair solid-colored white or gray tees with dark denim or khakis. An incredibly classic look that’s hard to do wrong. Crewnecks look especially smart with khakis.
Pair navy/blue tees with khakis. Lighter pants with a darker shirt generally looks better than blue-on-blue.
If the dominating color of a graphic tee is dark, pair with a lighter bottom. And vice versa.
Layer with care. While some modern dudes have adopted the sport jacket/blazer + t-shirt look, many style experts aren’t big fans of it. The relative formality of the jacket jars with the casualness of the tee.
On the other hand, a t-shirt tee can look fantastic underneath a leather jacket or a blouson (à la Dean above), or even a cardigan sweater.
