(edited on 12/10/13 to include the recommendations of other members)
I went from knowing absolutely nothing about men's fashion 6 months ago to having a solid basic understanding today, largely thanks to this forum and others. Sometimes the amount of detail can be overwhelming, so I thought it'd be helpful to give an extremely simple (deliberately oversimplified) guide. The goal is to have a half page that a recent college grad can look at and very quickly put together a wardrobe.
Color: Black is the most formal, followed by Burgundy and Brown.
Style: Oxford Balmoral captoe or plain toe are the most formal, followed by Bluchers and more ornate styled oxfords.
$80-$170: Ecco and Clark make attractive and comfortable shoes, but these are too casual for some formal business environments.
$130-$250: Cole Haan and Johnston & Murphy are the place to look.
$250-$500: Allen Edmond and Alden make fantastic shoes and you'll need never go to a price point beyond here for business purposes.
Color: White and light blue are the most conservative. Next you can go with a light yellow, light pink, narrow stripe, or microcheck pattern.
Style: In the US, french cuffs are considered very formal, and generally inappropriate for most work environments if you're under 30. Try to avoid the "blousey" look and get a slim fit if you need it. Get a french placard and a good default is the semi-spread collar.
$40-$80: Lots of good options. You can try a package deal from an online shirt maker like Indochino, Neiman Marcus sells quality shirts discounted in this range on "Last Call", or a package discount deal from Brooks Brothers.
$80+: You can buy off the rack and get your shirts tailored. Once you have a bit of knowledge, consider getting MTM from an online retailer like Blank Label, Indochino, or your local tailor. It's more important to have a well fitting shirt than the finest fabric.
Pants: No pleats, cuffs are optional. Get dark gray or navy. Calvin Klein and Ralph Lauren offer solid options for $60 a pair.
Color: Your first suit should be navy, your second charcoal. Avoid patterns until you're on suit #4.
Style: In the US, you can't go wrong with a 2-button single breasted notch lapel suit with side vents.
$300-$700: Buy something off the rack (on sale) and get it tailored.
$700+: Off the rack with tailoring remains an option but you can also consider a MTM suit from a local tailor or trying MTM from an online retailer like indochino once you have gained some knowledge.
Style: Keep it understated and simple, with a leather band. It's not necessary, but ideally your watch color should match your belt (silver or gold). It's not a bad idea to have one inexpensive watch in each color.
Tiers: Watches are best thought of in terms of tiers. Any watch listed is fine for all business purposes (until you're above executive director at a bulge bracket bank.) The A tiers are the most expensive, and I haven't listed any "outrageously" expensive watches.
C tier: Citizens, Tissot, Oris
B tier: Omega, Tag, Breitling
A tier: Breguet, JLC, Rolex
Ties, belts and socks:
Ties: Solid or simple patterns, 100% silk. You can find decent ties for $30, over $80 and you won't see much difference.
Belts: Simple or slight perforation. Belts should match your shoes. No need to spend more than $60 per belt.
Socks: Merino wool or cotton blend. Socks should match your pants, and most traditional is a shade between your pants and shoes. For the most formal environments wear a solid color, but for most occasions, and understated argyle or other simple pattern is fine.
Care for your clothing:
Dress shirts and pants should generally be laundered (not dry cleaned) but check the care instructions on the item. Shirts should generally be laundered after each use, pants after 3 to 6 wearings. Hang everything on thicker hangers (not the wire hangers dry cleaners give you) to avoid wrinkles. Suits should be dry cleaned two to four times a year. Shoes should be shined frequently (from 2 to 8 times a month depending on frequency of wear). Keep your shoes in good shape with cedar shoe trees and by rotating the shoe you wear. Many people like laundering and ironing their own clothes and it'll save you more than $1,000 a year, but your time has value too.
Putting it all together:
Navy suit, white shirt, solid red tie, burgundy oxfords, navy socks, and a burgundy belt.
Charcoal suit, light blue shirt, silver and blue tie, gray socks, and black belt.
In your closet: 3 suits (navy, charcoal, light gray or pinstripe), 10 dress shirts (4 white, 3 light blue, 1 light pink, 1 light yellow, 1 bengali striped), 2 pairs of shoes (one black, one burgundy), 3 belts (2 black, 1 burgundy), 5 ties (assuming you don't have to wear a tie daily, otherwise 12 ties), 2 watches (1 silver, 1 gold), 10 pairs of dress socks (4 navy, 6 gray/black)
At the entry level prices listed, this wardrobe will cost about $3,500 and should comfortably last you 5 years (budgeting an extra $400 a year to replace things that become damaged.)
Edited by CalabaiLion - 12/10/13 at 9:04pm