Things A Man Should Never Wear

My social media footprint represents a very solid demographic - mostly 18-40, educated, affluent, and aspirational. So I wanted to experiment with crowd-sourcing some fashion advice: what are things that a man should never wear?

I'll skip over the obvious, like socks with sandals or tank tops. And while there might be some disagreement, the general problem with men and fashion is typically that guys try too hard or not at all. As I see it, it’s a function of risk/reward; guys need to excel within their comfort zone. (Most men look terrible in double-breasted suits or turtlenecks.)

So here are 40 things a man should never wear:

1. Cargo shorts. And any shorts longer than the knees.

2. Turtlenecks. Circumcise that sweater.

3. Flamboyant pocket squares. All it says is you pay $1,200 a month for a car you can’t afford.

4. The guilt of your ancestors’ sins.

5. A pro sports jersey with another man’s name on the back of it.

6. Facial hair that doesn’t look intentional.

7. Jewelry. The only thing more disappointing for a woman than seeing a desirable man with a wedding band on, is seeing a ring on any other finger. (Obvious exception for watches and cufflinks.)

8. Backwards or flat brim baseball caps. Or any hat inside.

9. Pleated or cuffed pants.

10. Sneakers with a suit. It’s a good look… for 1% of men, and you’re not David Beckham.

11. Fashion watches. Chanel, Hermes, Gucci, and even Cartier.

12. Double-breasted suits. The vast majority of men can’t pull it off. 

13. Skinny or ripped jeans.

14. Vineyard Vines. Here’s why.

15. Country club logo golf shirts where you’re not a member. I don’t care if you played Pebble once. It’s a conversation-starter for losers.

16. Short-sleeve button-down shirts.

17. Identifiably designer belts.

18. Hoodies after the age of 40, unless the weather requires it.

19. Flips flops unless you’re near a pool or beach.

20. Dirty sneakers in the office. Even with a relaxed dress code, you should take care of sneakers in the same manner as dress shoes.

21. Oxford collars.

22. A backpack. Just get an adult bag.

23. Tevas, Crocs, Birkenstocks, or Uggs.

24. Bowties without a tuxedo.

25. Monk straps, tassels, or square-toed shoes.

26. Deep V-neck t-shirts.

27. A fake watch.

28. Statement socks. They don’t give you personality or style.

29. Dress shirts with a pocket.

30. Baggy clothes. Get the essentials tailored. 

31. Anything with big logos.

32. FinMeme merch. You never worked at Lehman Brothers and the “FTX Risk Management” t-shirt is just stupid.

33. Your heart on your sleeve.

34. Sports sunglasses. Quality shades serve an important function.

35. Noticeable cologne. Men generally have a weak sense of smell and get desensitized to their own scent, so it’s worse than you realize.

36. Graphic t-shirts.

37. Pajama pants in public.

38. Windsor tie knots.

39. A “going out” shirt.

40. Nike Sports bras.

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John LeFevre is the creator of @GSElevator and the author of the New York Times bestselling book, Amazon Book of the Month, and TIME Book of the summer, Straight To Hell: True Tales of Deviance, Debauchery, And Billion-Dollar Deals.