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I would say you need a solid color (black or brown) cap toe oxford for business formal, wingtips/brogues/derbies for business casual, and loafers for business casual/smart casual - do not recommend boat shoes. AE is great. Would also look at Alden, Carmina, Crockett & Jones. John Lobb, Gaziano & Girling for the next level.
Good advice above but most people need a more reasonable brand choice. I’d also start with a black and brown cap or plain toe. The next would be a dressy loafer in black, wingtip brown, and fill out from there. A better J&M will do. My expensive stuff I’ve bought secondhand - work in nonprofit leadership. My oldest pair are 60 years old. I live shoes but can’t justify all I would like.
I’d say. 1) Burgundy adelaide. 2) Tassel/Penny loafer. 3) Dark brown/tan suede Chukka boot. I’d highly recommend Carmina and TLB Mallorca, as you get most for your money. If you don’t mind spending a little more I’d go for a John Lobb black cap toe oxford, Antonio Meccarillos
I’d honestly go for Myrqvist over Carmina. Swedish brand that blows them out of the park imo
AES are great for the cap toe dressy shoes or even their brogues.
At a cheaper price point I also just got my first pair of meermin suede loafers and I’m loving them. I honestly think the quality is very similar at half the AE price. They have a wide range of loafers if you’re into that.
If you’re looking for a shoe fit for summer, I can definitely recommend picking up a pair of unlined penny loafers.
Recently bought a pair from Myrqvist, and I love ‘em.