That’s a tough one but here are some of my favorites in categories because this is how much I think about clothes. Also i might be a little biased towards some Self Edge brands since I work and shop there:
Jeans: Strike Gold makes some of the most interesting fabrics and their cuts work well for me. Just picked up a pair of 5105 jeans. I’m also a huge fan of Norman Porter based in Philly. They make everything in house and the details are top notch. 3sixteen is also a long time favorite.
Shirting: Flat Head is hands down my favorite for shirts. I nerd out about the fabric they use and the fits on their button downs and tshirts usually fit me well. Rogue Territory makes my favorite shirts domestically. Taylor Stitch tshirts are a good basic too.
Outerwear: I don’t have one of their jackets yet but one of these days, I’m going to own a Real Mccoys leather jacket. Also, same with Mother Freedom from Massachusetts.
Shoes: Bootwise, i can’t get enough of Viberg especially their service boots on a 110 last. Sneaker wise, i’m fairly simple and keep to PF Flyers.
Leather Goods: Tanner Goods has always worked well for me. I’ve recently been liking what Black Acre has been doing as well. Ewing Dry Goods is also one of my favorites.
Headwear: Ebbets Field and Norse Projects hats fill up my closet. I also wear a fair amount of beanies and my favorites are made by Buzz Rickson and John Lofgren.
They’re almost certainly from different years, but generally they both fall in the late 70s-80s. I suspect the cordovan pair are a little newer, but worn harder, because the scotch grain pair has the original leather soles and a v-cleat, while the cordovan pair has been resoled at some point and given a rubber heel. Theoretically, they should be more similar, or at least the sizes should be more consistent because the Imperial line was based off of the same silhouette for about thirty years. Florsheim still makes this model but uses corrected grain and sends it offshore to be produced.
I am also more drawn to the cordovan, but they don’t fit as well. I’m thinking I could wear the scotch grain more Thom Browne style to make them more interesting.