I really love shoes, its a borderline problem, and Allen Edmonds were the gateway drug.
Let's start with the quality. AE is going to be the best quality shoe you can find in this price range, hands down. The shoes are hand made in Wisconsin (they'll give you a whole spiel about the 212 steps involved in making each pair, but the bottom line is that they take a while to make). Another thing to keep in mind is the different lasts that they use. A last is the mold a shoe is built upon and is what determines what size shoe you'll be. AE has many different lasts and many, including the iconic 65 last (park avenues, strands, 5th aves), run VERY narrow. What does this mean for you? Basically that you 100% should get fitted before you buy your first pair (or you're going to end up with shoes that either hurt or are too lose and the leather is going to crease in an ugly way).
Now say that you didn't get fitted and you just bought a pair online that doesn't fit so well. Don't stress, AE has the best return/exchange policy I've ever seen in a brand. They will ABSOLUTELY take your shoes back and exchange them for ones that fit or give you a refund, no questions asked (I've heard rumors of guys who have actually worn their AE's for a few days, didn't like the way they were breaking in and were offered an exchange - seriously the lengths they will go to keep their customers happy is incredible).
If you're looking to step up your shoe game, AE is a great place to start - and if the sticker price is a bit shocking to you*, wait for a sale (they have sales a few times a year), or invest in factory seconds (shoes that have minor defects and are about half the price). Remember, a pair of AEs that you take care of will last the life of 5 or 6 pairs of cheaper shoes, they are an investment**
_________________
*If you're a student (including grad students), you'll get 15% off instore with ID, or online.
**Make sure you're using shoe trees and conditioning your leather! read more