Here is a cross-post of mine from another thread, but I hope that it can help you guys looking into this level of shoe. It took me a while to put together, so i figured that i would post it around. There is a part on Awl and Sundry further down.
There really are quite a few brands of good to very good quality shoes that are available for under $500, but as a few of the regulars on here have stated, the fit is going to be a big factor. It doesn't matter how good a shoe is if the last doesn't fit your foot shape.
The next part is between the entry level of good shoes or the close to $500 shoes. the difference is mainly the last shapes and attention to details like finer stitching and nicer polish jobs on the leathers before getting the pair.
You also have to think about where the shoe is shipping from and where you are living. Allen Edmonds ($250-400) is a great option for people in the US just going into quality shoes because they have all the needed qualities for a good shoe with reasonable prices, especially if on sale or from the Shoebank ($130-300) for factory seconds (slight cosmetic imperfections). They have a ton of different last shapes an a huge variety of sizes to accommodate just about everyone.
Alden is a very sturdy shoe that many people love for causal shoes and boots, but they are generally above $500 now. I love them and they make a huge variety of sizes and widths, but are difficult to find besides online since there are very few retailers who carry them. They are bulky to many people but very comfortable and can last decades if taken care of.
Another factor is how sturdy and hardy of a shoe you want. AE and Alden are big shoes that can last a long time and really take a beating. There are some great Blake stitched shoes out there to look more elegant if you don't mind the compromise on durability. I'm not a big fan of the styles but Mezlan and Magnanni are made in Spain in mainly Blake stitch constructions but are still an entry to higher quality shoes and can be bought for big sales (usually $250-350). I have seen them for $100 for certain styles in Nordstrom.
Here are some extra notes on a few brands of shoes that I was able to get my hands on to try out in my size range. There are limited brands, but I hope that they help:
If you want a nice pair of shoes that are designed by an American who also writes a major mens fashion blog (The Fine Young Gentleman), here is a great way to get good shoes at a great price by Jay Butler. They are made in Mexico, where nicer shoes have been made for an extremely long period of time. He only has loafers being made at the moment ($145 range), but they are a very light and sturdy Blake construction. The insole has a very nice cushion under the leather and it is thicker in the arch to give a nice arch support instead of the normal flat insole for loafers: (sorry for any poor quality pictures throughout the post, but I took them quickly with my iPhone.)
If you are into more european shoes made in Goodyear welt construction, Shoepassion.com is another source. They are designed in Germany and made in Spain. They have a huge variety of styles and sizes. They are very durable but have a feel much more like Crockett and Jones of England (usually more than $500 from the US) but these shoes are more in the $200-300 range. They are nice people who run the company and the shoes are quite good for the price. I consult and review shoes for various shoe companies around the world and here are some pictures of a pair that they sent me to evaluate for them. I made some recommendations of things to work on (as I do to all companies I help out), but I think that they are worth considering as an entry pair if you find a style that you like or as a reasonably priced extra pair depending on your financial situation:
You just need to speak to them about sizing because they have a variety of lasts and sizes are not the same as US either. I'm a US 14 or so and I got a 12.5 in this model on this last since this one runs so long and is in UK sizing. They also come with a pair of rubber sole covers that can be applied, extra laces, and shoe bags. The leather insole has a bit of a cushion under it as well.
Another great option is Scarosso. They are another German company but they produce shoes in Italy. They offer a large variety of sizing as well as styles in ready to wear (RTW). They also offer a full Made To Order (MTO) service that is online. They have a variety of styles here and let you choose details to change as well as leather type, color, sole type/color, lining, etc. They have an even larger variety of sizing with MTO than RTW. Here is a pair that I designed as something different for them to send to me. I wanted to try their online MTO process as well as evaluate their shoes. The RTW shoes are in the mid $200 range and the MTO are in the low to mid $300 range depending on details that you choose. Their shoes are Blake stitch but you can also request Blake Rapid in the MTO, which is what I did, since I like a more substantial construction. I ordered a deerskin chelsea boot with a leather sole in Blake rapid construction:
They also have their own sizing system that is not US or UK sizing. It is a modified european. This is a 48 but according to them is a US 15 which is normally a 49.5 or 50 depending on the brand for me. These also came with a nice shoe bag and a shoe horn. The insole is very smooth leather and there is a small heel cushion under the half sock liner.
For a little bit more ($350) Awl and Sundry is a company based out of New York City that makes hand welted shoes that you can design to an even higher level of detail right from your computer. These are not goodyear welted, but really by constructing the main parts of the shoe by hand. I discussed this at length with the owner to make sure that this term was not being used incorrectly.
The brand has multiple last shapes that you can choose from as well as many basic styles of shoes to modify. You can even add in multi tone of different leathers, suede, grain leather, etc. You even can choose the stitching color for the leather upper. This price also comes with a nice pair of wooden shoe trees, shoe horn, and a pair of shoe bags.
The soles are only available in a reddish burgundy at this time instead of more traditional browns or black, but they are very nice and do stand out a bit. They are a very solid constructed shoe, even more than Shoepassion or Scarosso, but have a different type of aesthetic from them as well. They are getting close to the solid feel of Alden but are not as bulky as Alden by any means. They have a wide variety of sizes available as well and are working on even carrying widths right now.
I wanted to try a pair of double monks but in the spectator style with both leather and suede:
As you can see, I really controlled a lot of the details of the leather vs suede combinations and wanted it to be asymmetrical. This is also another brand that you should ask about sizing advice just to make sure. They are in US sizing but your size in these may not be the same as normal. I went down here too. The insole on these is a leather covered foam cushion, so they are very comfortable after a much shorter time than most welted shoes.
I know that there are quite a few other newer brands who are giving great shoes for the price and here are just a few:
J Fitzpatrick (by Justin "The Shoe Snob) Fitzpatrick) $400-450
Meerman (good entry level that offer multiple quality levels) $175-250 for regular line and $290 - 350 for hand welted.
Carmina (top notch service and great quality goodyear welted shoes that rival great British shoe brands like Crockett and Jones) $350-600 depending on where you get them. I recommend Skoaktiebolaget in Sweden who has phenomenal staff and service plus the lowest prices that I have seen for Carmina.
Jack Erwin (designed in the USA and made in Portugal of either Blake or Goodyear construction depending on the line) $200
Paul Evans (designed in NYC and made in Italy by Blake construction) $350-400
Cobbler Union (designed in the USA and made in Spain by Goodyear construction but with higher finishing details like beveled waist, quilted leather insole, etc.) ($400-500)
I know that this isn't everything (didn't include any of the many new French shoe brands due to lack of availability in many areas), but I hope that this is a great start to help you new guys out as well as for many guys who want to try something different without completely breaking the bank. For some of you guys on the high end of shoes, it could be worth trying one or two of these out for casual shoes or to take a shot at designing something new. You EG, GG, Lobb, etc. guys could even get a pair to just beat up for poor weather, heavy walking, etc.
Feel free to add things to this and to ask questions or even cross-post this to some other threads to help it be more seen. You have my permission!