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 it’s too big, it will drape and sag like a pillowcase and be unflattering. Too tight and you’ll look like a stuffed sausage — a look that can read as some combination of narcissistic, flamboyant, and/or douchey. If you’re in shape, and have a good build, you can lean towards tighter over looser. If you’re carrying extra weight, leans towards a looser fit — but don’t go too far, as too much extra fabric will only make you look larger rather than smaller.

Shoulder seams. The seams where the sleeves attach to the body should ideally exactly align with where your shoulder ends rather than lower on your arm or towards your neck.

Sleeves. A tee’s sleeves should hit about halfway up your upper arm. Sleeves that extend a little farther down can look proportional if you’re very tall.

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. Any shorter and you’re heading into midriff terriotry, and run the risk of showing your back/butt crack/belly when you bend over. Longer than that and the shirt starts trending into a nightgown.

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.

A well-fitting tee that hits all these metrics can be hard to find but is worth looking for. And while it may mean $25 instead of that $5 touristy tee, you’ll notice the difference and won’t go back.

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.

The crew collar. This is the most classic option, and offers a timeless look. It best suits men who have a slight build and frame, as the collar draws the viewer’s eye out, broadening the neckline and creating the appearance of squarer shoulders. The crew collar is also a good choice for men with longer necks and narrower faces, as it balances and adds proportion to these features.

The v-neck. A v-neck has a slightly less formal feel than the crew collar, and adds a little more visual interest and style to the standard tee. It’s well-suited for the shorter man, as it makes one appear less boxy and adds a bit of height to the appearance. It complements men with rounder and/or wider faces as well. I would not recommend a v-neck for those larger in size, however, as the v tends to draw the eye down to the belly.

There are other types of tee necklines out there — like the scoop or boat neck — but these are rarely a good look for men.

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.

There isn’t necessarily a correlation between the thickness of a t-shirt’s fabric and its quality; pima and Egyptian cotton, for example, are made with longer fibers and are lighter than regular cotton but also softer and more durable. In general, however, thicker tees look more substantial and put-together. Thinner, gauzier tees tend to look cheaper and sloppier, and can cling to your belly/love handles in an unflattering way.

Thinner tees in a neutral color also tend to look more like undershirts than t-shirts. The main difference between the two garments is fabric weight; undershirts are thinner, and also fit more tightly in order to soak up perspiration.

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:

• White — with its origins in the undershirts of sailors and soldiers, is the granddaddy of them all. When paired with jeans, it still evokes echoes of the “rebels without a cause” who turned the garment into outwear in the post-war period.
• Navy — almost always sharp-looking.
• Gray — a flattering color, but easily shows armpit sweat.
• Black — is hardest to pull off, as it looks a little starker and harder (though that may be what you’re going for).

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.

(By the way, if you have a bunch of graphic tees from high school or college that are no longer really wearable, but you can’t get rid of for sentimental reasons, a good solution is to have them turned into a quilt.)

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. If you’re going to put a tee under a sport coat, the jacket needs to be an especially casual one — think texture, soft draping, and natural fabric. Even then, it’s going to be a better look if you swap the tee for a casual button-down.

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.

Don’t tuck your tees in. It’s almost always going to come off as nerdy.

Conclusion

T-shirts have become a simple go-to staple of most men’s casual wardrobes. But that doesn’t mean you should grab and wear them without any thought. By paying attention to things like fit, color, and style, you can elevate the humble tee into a versatile, classic piece of clothing that feels great and looks sharp.

Article Credit: http://www.artofmanliness.com/2015/07/14/the-best-damn-guide-to-mens-t-shirts-on-the-internet/