25 Items Men Over 25 Should NEVER Wear

March 13, 2024
With the evolution of style, teens are trying to figure out how to dress. So you’ll get a pass if you’re under 21, as some of the style choices that you’re making are questionable. But once you reach 25, you should make better stylistic choices. That being said, I will review some items that a man should never wear over 25.

When you’re evolving your style, eliminate these ASAP

  1. Business boy uniform. This is what I call khaki pants, button-up shirts, and ties being classified as ‘dressed up.’ As you evolve, you’ll have more events to dress up for, such as weddings, award ceremonies, and hot dates. By 25 you should be wearing your own suit.
  2. Cheap, unfitted suit. Your suit can be inexpensive, but spend a little cash on tailoring it properly. It should not be big and roomy, the length of the sleeves should expose about a half to a full inch of the cuff when your arm is down, and the pants should be cropped or hemmed. The pants should also be tapered.
  3. Long pants. If your pants puddle around your ankle, they’ll make you look short. If your pants are long in the crotch, your legs will look short. 
  4. Wide and baggy pants. This will also make you look short.
  5. Saggy pants. You don’t want your pants to be sagging off of your butt, either. Pull them up and wear a belt. Make sure your belt buckle is not flashy or big. Your belt also should not be a counterfeit designer belt. Choose something like an Anson Belt.
  6. Too many rings. You look stupid if you have more than one ring on your hand.
  7. Apple watches. Sure, they’re functional, but they’re not grown up. Upgrade your watch. There are a lot of fantastic badass watches under $100.
  8. Fake leather jackets. Some jackets are more timeless and classic than others. Opt for a bomber jacket with a simple zip-up and collar. You could also go for a racer jacket without a collar that is age-appropriate for anyone. Biker jackets with all the zippers are definitely more stylized, and if you’re a bit older, in your 40s, this may look funky.
  9. Fake leather shoes. These look funky, and you should never wear them. Leather is higher quality, not much more expensive, will last you longer, and will look better. You’ll be more confident wearing it. Spend the money and upgrade.
  10. Beat up belts. Too many belts have holes, dings, and lines. Upgrade your belt to an Anson Belt with a track system. It’s clean and sexy.
  11. Unmatched belts. Match leathers to look stylish. You can add a pop of color and express yourself stylistically.
  12. Dumb sunglasses. When you’re young and stupid, you may be wearing stupid sunglasses. Upgrade your eyewear because it’s a fantastic accessory. Look for styles such as the Wayfarer, Aviator, or Clubmaster. These styles are clean, classic, and mature.
  13. Big, bulky boots. Don’t even think about it.
  14. Running shoes. Only wear them when you’re running.
  15. Dirty shoes. Any dirty shoes are horrible and are not acceptable.
  16. Crotch-covering shirts. One of the big style mistakes guys make with button-ups is wearing them untucked. Guys think they can wear an untucked dress shirt when they can’t. Button-up casual shirts are designed to be worn untucked specifically. If your shirt covers your crotch, you will look super short.
  17. Graphic t-shirts. An occasional graphic t-shirt is fine, but one that is outlandish or offensive is not cute.
  18. Big-brimmed hats. Be careful with this choice.
  19. Baseball hats. When you wear them backward, you look youthful. If you wear them to the side, you look stupid. Wearing a baseball hat to the front is fine, but don’t tuck your ears in. That’s a big, huge no. I also make sure your baseball hat fits you correctly.
  20. Little boy backpacks. Upgrade your bag when you’re 25 years old and not living at your mom’s house. Elevate your aesthetic to a more refined look.
  21. Tight t-shirts. No, you don’t look jacked. You look like a sausage and are trying too hard.
  22. T-shirt with too long sleeves. If your t-shirt covers your entire arm, it will look smaller. Lift up those sleeves to make your arms look a lot bigger.
  23. Oversized t-shirts. This trend looks okay on younger dudes trying to express themselves and keep up with trends, but as a grown-ass man, wear a t-shirt that fits your body.
  24. Pit stains. If you have pit stains on your white shirts, toss them.
  25. Items you don’t love. Go through your wardrobe and toss or donate anything that you don’t enjoy wearing. Don’t keep it just because you have it. Make sure what you have in your wardrobe fits your body and makes you feel sexy and confident.

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