I think many guys show up at medical school interviews in cheap-looking and ill-fitting suits because they don't have the money to get suits tailored or buy suits from luxury retailers which tend to have better fit. I'd love to have a suit custom made, especially given my smaller body type. However with application costs and interview expenses expected to be at least $2000, I don't see how I can afford the recommendations here. And what with the wind of fashion shifting direction constantly? Ok so it's not news but common', 3 button suits were all the rage even as recently as last year and I feel like they're so yesterday now. All of my few suits are 3 buttons and I'd be so embarrassed wearing them this year.
Two buttons have been around forever. They will be around forever. The more the buttons, the more dangerous it is.
The three button suit is still acceptable. The SUIT is such a classic that a minor detail like # of buttons won't make a huge difference (as long as it is within the 1-3 range). Being such a classic, I would focus more on the fit of the suit since that is the most important detail. I would rather wear a 3 button suit that fits properly than a 2 button suit that doesn't.
Buying fashion is a horrible investment for the sole purpose you stated. Buy the classics. Two button charcoal wool worsted ($500 max with tailoring fee), white shirt, light blue shirt, throw in some stripe shirts (the fewer the stripes, the more classic—white being the base color) ($50 per shirt, find MTM online that will fit very well), brown leather captoe made in China ($100, $50 on sale).
The minimum chest size for suits Off The Rack (OTR) start at 36 inches. If you don't have a 36 inch chest minimum, you might have to go to Made to Measure (MTM). Do some hunting and you can find some MTM suits for $600.
The grey suede wingtips at pediwear (right click it and it will go to the actual image) is $220 shipped to the US (the British pound is very weak right now, it's a steal). For two Macy's brand shoes made in China, you can have one very well made English shoe. The investment is very sound. You get "free" shoe trees (value $20), shoe polish (value $5), suede brush (value $5), and a free silk tie of your choosing (value $10). (I know because I bought a pair.)
The purpose of showing high end items is that that is the look you're going for. The interesting thing with the clothing industry is that there are no intellectual property laws pertaining to design—only trademarks are protected. Nobody owns the rights to a wingtip brogue design or a leather captoe design. You can find a cheap American company making a captoe. There are hundreds of captoes out there. You can probably make some fake Air Force Ones and omit the Nike Swoosh and you'll be okay.
To be honest with you guys, I can almost guarantee that I have fewer clothes than about 85% of you. The value is higher (maybe—I imagine there are some of you who probably go for the expensive denim and Air Force One and BAPE and Hyphe trend), but in terms of volume, I am a minimalist. About 5 years ago, I donated all my clothes to the Goodwill and started over with just the classics. No more graphic tees. No more baggy jeans or cargo pants. No more buying Gap sweaters with a single stripe across the chest (remember those god-awful things). No more artificial fiber fleece sweaters.
This is probably the best advice I can give: go minimal and stick with the classics. Fashion is not minimal. Watch old 60s movies or Mad Men. Take note of the designs and style that are still present today. Buy those items. Within an item, also go minimal. Fewer stripes, fewer colors, fewer zippers, buttons, etc. Once you go minimal, you'll find that FIT is the most important detail. Once you're comfortable with the fit of your clothes, branch out and add more details like patterns and explore the classic designs like gingham, glen plaids, prince of wales plaid, herringbone, houndstooth, etc.
In the end, you'll end up looking like an adult. In no time, you'll be yelling at the kids to get off your lawn and to turn down that racket.
Btw, Jos A Banks stock price does very well. Click the 5 year profile and the 10 year profile.
http://quote.morningstar.com/Stock/s.aspx?t=JOSB