Most men hate having to think too much about clothes. Questions pop up instantly: What actually fits well? Does fit even matter? How much is this going to cost? Do I really need to go shopping? I’ve asked all of these myself—and I know most guys have too. The good news is, it doesn’t have to be complicated. As we step out of summer and into fall, you can still get away with a T-shirt and jeans well into October in much of the U.S. (honestly, in more than half the states). It’s classic, it’s practical, and it always looks good. Best of all, you don’t need to spend a fortune to pull it off. Take jeans, for example. These Wrangler Regular Fit Jeans run about $35, and they’re durable, comfortable, and cut in a way that works on almost anyone. For shirts, you can’t go wrong with a basic cotton pack like these Gildan tees - five shirts for around $20. They’re simple, breathable, and versatile. Just remember they shrink a little in the wash, so I’d recommend buying one size up. With those two pieces alone, you’ve got a complete outfit that works nearly everywhere: casual Friday at work, a night out with friends, running errands, or even a date if paired with the right shoes and a clean watch. The beauty of the T-shirt and jeans combo is that it has been a staple for decades. From James Dean in the 1950s, to Clint Eastwood in the 1970s, to Brad Pitt in the 1990s, countless icons have leaned on it because it never really goes out of style. It’s hard to look wrong in it. Of course, there are endless variations. You can go with slim fit or relaxed jeans, tuck in the shirt for a sharper look, or throw on a casual jacket when the weather turns. Footwear shifts the tone instantly—sneakers keep it relaxed, boots give it edge, and loafers make it a little dressier. But at the core, the appeal is the same: simple, timeless, affordable, and reliable. If you want an outfit that always works without draining your wallet or your energy, T-shirt and jeans will never let you down.