Ultimate Shoe Guide.
Since there are so many questions about shoes on this forum, I figured I'd write a quick guide on how to maximize the shoe you're getting for the dollar and which brands to avoid/buy. This is meant as a very fast shoe guide for anyone in finance. If you want to learn more about shoe making then there are tons of better guides floating around online.
Buying cheap dress shoes and expensive shoes you see from most trendy fashion designers are generally not worth it. You're basically burning money. I'd really recommend saving up and buying a nicer pair that will actually last. The nice thing about business wear is that trend won't change much so you can literally buy shoes for life without them going out of fashion.
The most important factor that will determine how long your shoe will last is the type of welt used. The welt is what attaches the shoe's upper to the outsole. You basically have three types which I'll describe below but if you want the TL;DR - you want shoes with a goodyear welt if paying $$$ and for anything else blake is fine. Avoid cemented shoes.
Cementing. Complete trash. Cementing means you'll never be able to get the shoe repaired properly so you get to buy another pair of shoes instead of an easy/quick repair.
Blake welting. Allows for a shoe to be resoled easily. I don't have a problem with blake stitching but would not expect to see it on top tier shoes. Always done with a machine.
Goodyear. This is the gold standard. Super easy to repair and any competent cobbler can assist. This is what you will see on shoes across a variety of price points (other than super cheap), not all shoes with a goodyear welt are created equal.
Easiest way at the lowest price is to set up alerts on Lyst.com (searches stores for sales) and eBay new without tags or new without box. The Lyst method is pretty awesome because you can catch some retailers with their pants down.
Brands/Price Points. Only going to bother with two price points here. One for the hardcore enthusiast who has a strange love of shoes and the other for everyone else working in finance with a good size budget.
Enthusiast/More Money Than Sense
John Lobb, Edward Green, Gaziano & Girling, St. Crispins. All great brands and probably the most well respected in shoe making. You get more shoe for the dollar with Gaziano or Edward Green. Unless you're a hardcore shoe nerd that will appreciate perfect stitching, expertly shaped fiddleback waists, and know too much about the difference between german and british tanning pits, then you can probably avoid this category pretty safely. At the end of the day, you're paying a lot for a very incremental gain in quality. With that said, if you're a nerd and have the wallet, go for it. I'm guilty of it but hey... Also if you're sitting on a good size cash pile and just want to see what makes for an amazing quality shoe, then buy buy buy. You won't regret it.
This is the sweet spot. Carmina. Vass. Sutor. Santoni, Crockett & Jones etc... all make great shoes on the higher end of the spectrum. At the lower end in the US I'd recommend going Allen Edmonds (sort of); their quality is good for what you pay generally...although much like American suiting, I think they look a little old man-ish and boxy. If you go Allen Edmonds, check our their factory seconds website, which sells shoes that didn't quite meet QC. Often these are very mild flaws that don't compromise the structural integrity of the shoe + nobody will notice.
If you're hunting shoes via the methods I outlined earlier, you can add brands like Kiton, Isaia, Brunello Cuccinelli, Brioni, and a few of the other high end suit guys to your list. They aren't shoe makers, but they outsource/white label from good manufacturers. If you can get them cheap enough, then they are an amazing deal. I recently picked up a brand new pair of Isaia boots for $120 from YOOX this way and they would usually run ~$1000.
Loafers. I like loafers in the summer and for more casual work related events. Not appropriate for formal events or formal suits. These come in three flavors. Penny, bit, and tassel. Would definitely recommend going with a penny loafer for your first as the other two are pretty over the top/kind of tacky. If you buy gucci bit loafers I will show up at your house and burn them.
Oxford. If I was on a tight budget, this is the first and maybe only place I'd bother spending money. Specifically on a pair of whole cut Oxfords. Cap toes look great too and wingtips are acceptable but a little busy IMO. Wholecut means the shoe is made with a single piece of leather. They look incredibly sleek. I mean... cmon:
You can get away with wearing some kinds of Chelsea boots with suits. I don't recommend it, but if you want one type of boot and want maximum versatility, go with a Chelsea. They can easily be worn casually on weekends with jeans too.
Can be worn with a suit but I'd probably flesh out a collection of Oxfords before grabbing a solid Derby.
Monk Strap (double & single)
Do not wear these in a formal/work environment. I would stay way from them entirely.
Hope that helps.