Although I frequent thrift shops, it's not for better menswear. I "collect" interesting t-shirts. My favorite came from a thrift shop in St. Paul.
As I observe other shoppers, the age of a man seems very relevant to the types of clothes he buys in thrifts. Older men who would shop thrift in the first place are much less likely to be the class of man who dresses formally at any time.
Younger men are more likely to be looking for big savings on named brands and specifically looking to up-dress from their meager incomes, and, especially in urban markets, are looking for dressier shirts, good shoes, and some suits.
I'm very much the exception. I can certainly afford to pay retail, and have many times, but increasingly found clothes to be overpriced with ridiculous markups. Worth and price were too far apart. So, I save thousands by buying thrift, but spend the money elsewhere (landscaping, travel, dining . . .)
I love seeing both kinds of shoppers find the bargains, and recycle at the same time. It's really a great experience.
Don't you think attire is very relevant to dating, even more when it comes to sugar daddy arrangements? Most young men in the sugar daddy market tend to be clothes conscious. They are looking for the man who can free them from the thrift store circuit to go buy in the Rodeo Drive stores, or the local equivalent. They want bragging rights among their generation of status and bling.
Otherwise, the subject young partner is simply prostituting, not looking for a sugar daddy. Fuck buddies don't require the toys.
Although the OP is still fresh and way-before his "sell-by" date, I think sugar daddies are looking for someone more moldable. Maybe there's a wealthy peer available out there.
The OP is a total babe, just not twinkish in any way.
I think, especially with his degree and business experience, he has high chances of simply snagging a wealthy partner, regardless of much older or not.
But, meeting that man will likely require circulating in those social spheres.
Join a country club. Go to an upscale gym. Visit ritzy bars or clubs. Attend study groups or Meetup.com groups of the subjects that the educated prefer. Join an investing club. Join a travel club. Drive a flashy car. Dress up.
You have to spend money to make money.