So, I met some friends at a local bar recently. I wore navy Mabitex houndstooth pants, a white Oxford, a blue blazer (no tie), and bluchers. Yes, I was dressed better than anyone in this casual sports bar. A good friend, female 32, said I was dressing like an old man. (This is not some tacky Jersey Shore type either, but an educated professional) For example, she could not get over the padded shoulders that protrude a bit when propping your elbows up on a bar stool. To be clear, I am not trying to dress like a 20-something. In fact, I dove into the SF realm in order to age gracefully. However, I am NOT trying to age myself prematurely either! The next day, I gave this some thought. I think there is merit to this. There is a very fine line b/w dressing like an old man and looking "GQ/Esquire" sharp (for lack of a better term). As you know, one subtle item can swing the entire vibe of an outfit. So, what is the tipping point? For one, I think a light blazer vs. dark blazer is a huge differentiator. Rarely do I see young 20s "GQ" models wearing loud checked "vintage golf pant" blazers. (Evidenced by Uniqlo, H&M, etc) It's always dark jeans, white oxford (or T), and dark blazer. To that end, I think I'll avoid any blazer that is not grey or navy. Even tweed I have given away or stopped wearing. If there is a pattern, it has to be DARK and SUBTLE. I have been doing this from the start, but now it's "official". Next, I also think choice of pants is a huge determinant. Wearing dress slacks (even if slim fit) gives off a very different vibe than dark jeans. Stiff and formal vs. hip and casual. 40s vs 20s? For now, I love wearing slacks, but also realize it's best to sport jeans if I am on a date with a 20-something female. Choice of tie. First, I rarely ties in social settings, as much as I'd like to (overdressed, trying to hard, out of place, etc) It's just too over the top, and only at certain venues would it fly (fundraiser vs. local happy hour) But, if I do wear a tie, it is something with texture or character (Drake's Shatung, square knits, grenadines, purples, etc) ie: I'm avoiding generic "corporate drone" ties. These are 3 measures I have decided to take. Has anyone else in their 20s and 30s also struggled with this fine line?