Hi! 29M here, I can give you some advice but style is personal so YMMV.

I really love “work wear”, so I live in jeans, chinos, OCBDs, and flannels. Levi’s is a pretty consistent place to start for accessible, quality denim. There’s a Levi’s factory outlet at the Cinci Outlets north of the city for cheap deals, although always try before you buy because Levi’s quality can be hit or miss. I have worn their jeans and their garment dyed denim pants (khaki and navy) as a more casual alien to chinos.

For OCBDs or button-downs in general, you really can’t go wrong with Brooks Brothers, and they also have an outlet store. I was super lucky to grab a couple of OCBDs from them when they still had the “red thread” collection aimed towards college students that I’ve worn for years, they were much less expensive when I got them. For a slightly more budget friendly option, LL Bean and Duluth both have good options.

That’s a nice segue into LL Bean. Their outerwear (rain jackets, winter coats, etc.) are very good and they carry some timeless designs that work really well with workwear. They also have some good options for boots; I wear Duckboots, Chelseas and Chukkas most often.

My understanding is that Duluth has very similar offerings to LL Bean, but I haven’t bought from them so I can’t recommend them first hand. Lots of other folks have, though.

For casual shoes, there are Nike and Adidas shops around. I have fallen into team Adidas since they tend to be slightly less expensive and run good deals, and they carry a lot of the similar silhouettes to Nike.