Thanks for the great replies! :)
My recommendation is to spend just enough for quality construction ($300+), and a couple extra bucks ($100+) for a tailor to make sure everything fits well.
That was about the level I felt comfortable at, so I'm glad that level is also requisite of quality construction.
Regarding shoes, I recommend buying the best quality shoes you can afford. I started out buying low-cost shoes and replacing them every 6-12 months. Finally, I realized that quality will last much longer, and look better as well. I have a pair of shoes now that originally cost me $250, which have been re-soled twice, and still look and feel great seven years after I bought them. A simple pair of brown or black (this is a personal choice) lace-up oxfords will be appropriate with either of the suits mentioned above.
Well, I can afford any price point necessary to acquire something of quality. What do you look for in a shoe that tells apart one that will last from one that won't (i.e. an inexpensive but quality shoe from an expensive cheap shoe)?
The key to building a Mustachian friendly wardrobe is knowing what you want and being patient enough to wait for it at the right price. For your suits, go to a department store and try on different suits to see what you like. Try different brands, cuts, and sizes until you get a good idea of what looks good on you. Then wait for a retailer to have a sale (about every other week), and buy exactly what you know you want if they have it. Don't be swayed by the salesperson in the two sizes too big suit trying to sell you anything he can. The same applies for shoes.
That's the problem: I have patience, but no idea what I want. Hence my solicitation of advice
before going into a store and becoming a salesperon's dream customer.
Your location will influence the availability of finding great items at a decent cost. Some great places to start your search are: Nordstrom Rack (larger metro areas), Suit Supply (NYC-my personal favorite), J.Crew, Banana Republic (hit or miss depending on your size/shape, but frequent sales), and your local Macy's (large selection).
The only one of those we have around here is Macy's. There's also a local place called American Outfitters, a Brooks Brother's in the mall (which I haven't been to), and a Men's Warehouse.
I've had the same, JCPenny bought suit for about 6 years now and have yet to worry about it falling apart. Could it maybe be tailored better to me? Perhaps, but the construction quality has never hindered me in any performance or interview that I've needed it for.
As for shoes, if you can happen to find a Goodwill store in a nice area you can pick up great shoes for next to nothing. My old dress shoes finally wore out after 6 years of fairly heavy use, and I immediately found a great used pair at Goodwill for next to nothing. The caveat is that this Goodwill was just a stones throw away from some of the fanciest neighborhoods around here, so it did have unusually nice things just laying around.
I've actually looked at the JCPenny suits, as there's one very close to here. There didn't seem to be anything wrong with them from what I could tell, but after trying on a few I just didn't particularly like them. I didn't like the way they sat on my frame.
As for shoes, I've taken a look at a few of the thrift and consignment shops around here. I live between two of the nicer areas of town, but all of the nearby thrift stores were pretty disappointing. The consignment shops had a decent selection, but prices were outrageous. If I knew what to look for, I could probably find bargains there. But without knowing anything particular to keep an eye out for, I could just as easily waste my money.
http://thriftygent.com/
That's a great site, thanks! :)
For shoes, double-check your size and go on ebay.
I've never had luck buying shoes online. My size is right in-between a 9 and a 10, and the size that fits the best seems to fluctuate with brands. Plus, my feet run on the wide side. I'm not sure if that'd be a particular problem with dress shoes, as they seem to run wider than sneakers anyway.
Men's Warehouse has BOGO sales that can be quite good.
I noticed they're running one right now, actually! I may go check out the Men's Warehouse here this weekend.