Interesting, I love hearing about shopping options for men! There are too few options for us out there, but that's both a blessing and a curse. If you're savvy,

Interesting, I love hearing about shopping options for men! There are too few options for us out there, but that's both a blessing and a curse. If you're savvy, it can save you time. Women have more options, but they also have more to sift through. Men can be incredibly efficient by comparison, just because we have less to go through and the good stuff is easier to spot. In the last year I managed to transform my wardrobe from jeans + threadless shirts to strictly dress clothes, but without looking conventional about it or spending a lot. It took some work initially, and some courage to try things out of my comfort zone, but now I dress well by default and it feels good! First place I go is Value Village or another used clothing shop, maybe once every couple weeks. I don't spend more than 5 minutes (you learn to be efficient pretty quickly). I look at dress shirts, pants, jackets, and ties. Nothing else. I may not find anything, but I feel good when I do ($5-10/shirt, heck yes!). I've found several great shirts that would be $60+ new, and a couple really sweet blazers too. Then I hit somewhere like Winners, reasonably stylish but not so expensive. When I find something I think I like, I ask myself a couple questions: a) Does it look like a "dad" shirt/pant? b) Would a teenager wear it? Both are deal-breakers. If I'm really unsure if it's too loud, I'll try it anyway. But be strict on fit. Dress shirts that look like a garbage bag wrapped around your waist are terrible. Of course, you have to tweak to your physical size, but you can find things that flatter. If it doesn't flatter, even if it's nice, put it back (even if it's "your size"). And for the first while, have a woman come with you, but tell her what you're going for. She'll steer you away from the truly awful, but encourage you to take a chance on the brilliant too :)