One of the most common questions I get is, “What’s wrong with a T-shirt and jeans?” The answer to that is – nothing provided you follow two rules.

1. You wear it deliberately.

2. It fits correctly.

By wear it deliberately I mean you wear it not as a default but at appropriate times. It’s the exact opposite of what a lot of men do. You see guys in a T-shirt because they don’t have a reason to dress up. But, as a well-dressed man, your default should be at minimum a polo shirt or a casual button up.

Rather than thinking that a T-shirt is the standard unless you have a reason to dress up, you should be thinking the T-shirt should be worn when you have a deliberate reason to dress down.

Could be a motorcycle ride, working out in the yard, going to a concert, or anything else really. By now you should know what is and isn’t an appropriate situation for a T-shirt. The point is that it’s not your default but you deliberately think about putting it on and wearing it that day. You don’t want to be the guy who looks uncomfortable in a T, but you also don’t want to be the guy who’s always in one. Replace it with a button up as your default and start wearing it deliberately.

Even when you do wear it deliberately, you have to make sure it fits right. The same basic rules apply to all types, crew-neck, V-neck, or scoop-neck.

Make sure the body of the shirt follows the shape of your body without constricting movement. It’s ironic that a T-shirt is the default of the fat and slovenly because – when worn appropriately – it only looks flattering on those who are in decent shape. I’m not cut by any means, but I’m built well enough to wear one. If you’re not, think of the ease with which you can see your belly through a well-fitted T as motivation to hit the gym a bit harder.

The seams where the body of the shirt meets the sleeves should line up evenly with your shoulders. This is standard procedure for any shirt and really does make the difference between a garment fitting well and looking sloppy.

The sleeves should fall just above your biceps and be tight enough that they fit your arms without constricting them.

The body of the shirt should fall just above your hips – the sweet spot is between showing any skin unless your arms are directly above your head and not covering your ass.

Lastly, make sure it’s plain. It doesn’t have to be white but if you’re doing anything in public that doesn’t involve lifting your neighbor’s heavy furniture or being covered in car grease, ditch the printed T’s. I have my favorites that I still where for those specifically dirty events, but the graphic T is the staple of the man-boy. Going with a plain color will make young men look older and more respectable and older men not look like they’re making a vain attempt to relive their glory years.