Let me start by talking about suiting in general.
Guys, please, I beseech you, buy a suit that actually fits.
I know that most guys don't want to bother - basically if they can put the jacket on and button it closed, then it's good to go.
Most won't care if it's blue, grey, black, striped, plaid, etc.
Most won't care if the sleeves come past their wrist.
Most won't care if the lapels are narrow, or if it's double-vented.
For most guys, comfort is the most important quality that is sought after...and that's why you will look like most guys if you feel the same way. Shlubby.
So - let's start caring.
Quick guide to looking good in a suit:
#1 Rule - Get thee to a tailor - get your suit made to measure - please spend that extra $100-120. That's it, no more rules...because unless you are built exactly like the mannequins used to develop mass market suits, you will most definitely need to get the suit altered to your body.
It will do you a world of sartorial good, as well as make your girl take a breath when she sees you in your suit (that last part may be something of a fantasy).
Some buying guidelines:
1) Before trying on the jacket, make sure you are wearing a button down shirt.
Try on the jacket, if it fits roomily, try on a size smaller - see if you can button the suit closed. If you can't, go back to the larger size.
2) Pants must be flat front (no pleats).
3) Colors - grey (light and dark) and blue (no black).
4) Patterns - no multi colored stripes, no multi colored windowpane, just a simple blue, grey, or blue/grey pinstripe. Unless you want to look like a pimp.
5) Jacket length - shorter is better, it should just cover your butt.
Some styling guidelines:
1) Lapels - thinner than wider please.
2) Buttons - 2 is what I prefer, 3 if you must, you go beyond that - you've entered the pimp zone.
3) Pants - if you got short legs, no cuffs (they make your legs look shorter).
4) Fit - try to get a slim fitting suit, you will look more youthful and modern.
So that's it, my thoughts on suiting - if you don't want to spend the dough for a Tom Ford suit, you don't have to - I own a Lands End suit (wrinkle-free) for business travel which I had altered and I love it - especially since I paid less than $ 300 for it. You can alter any suit, even $100 ones from H&M - after being tailored, you will look like you had it custom made.
Here's one that I like a lot - not bespoke pricing, but definitely a good investment if you're willing...
(photo: courtesy of JCrew.com)
This is the Ludlow suit from J.Crew. It's made from Loro Piana wool, it comes in grey and blue (and black if you want) - jacket and pants can be ordered separately (total cost is $ 540). Ludlow is their slim fit offering, the Aldridge style is roomier.
I took a look at this suit in person - and I have to say, it's gorgeous and quite the nice price too.
It's available on their site (www.jcrew.com) - please note, this is exactly the way your suit should fit - if you get to a tailor (see my #1 Rule above) - the pants are flat front, leg opening is slim, jacket is closed but hugs the torso (tailored), about 1/4 - 1/2" of shirt cuff should show (tailored), and the jacket fits around the neck (tailored). You could throw caution to the wind, and try to work the tie bar and pocket square - but let's not live too dangerously (fashionably) - baby steps guys....