Grey and solid black are both bad choices.
In general, I think custom-fit is the best way to go if you're buying more than 1, it looks better, fits better, you get better material and advice from a tailor who does this for a living. [not Bespoke, unless you want to spend $4-6k per suit.] Machine-cut, off-the-rack suits look terrible on most guys unless you're a perfect 40R or 42L, etc.
Your basic suits, 2 or 3-button, for light-skinned guys should go like:
navy pinstripe with a light chalk stripe, very sharp. [stripes are great for you if you're wide.]
Charcoal, or charcoal with pinstripe [better than black]
solid navy or Navy w/soft glenplaid pattern,
houndstooth looks very sharp as well, [women always comment on when I have mine on]
nice brown, or chocolate brown color - very businesslike and the right shade of brown looks great in fall.
black is okay but gets hot and not for all occasions, [& you may get mistaken for a waiter], I would get this one later, [i.e. get charcoal instead] but is fine for nighttime instead of the office.
A solid, dark olive is a nice change if you don't want to look like every other guy in the room wearing navy or white shirt/dark suit.
Avoid: I would strongly suggest you avoid gray at all costs unless you have a solid tan 100% of the time. It will make you look washed-out and overly pale. Your tailor can help with these kind of details. [colors like orange, mustard, celadon, purple, etc generally go w/o saying].
Think about if you like back vent, side vents, or no vent. Also, tailor should help you match your shirts and suits obvs, think about bringing ties along if you wear them. Spending $$ is only one step in looking good, after that you have to match what you're wearing [easy with some practice]
once you've picked out your type of suit, pleating, button, vents, colors, you still have to figure out which style/patterns you like:
solid is obvious,
so is pinstripe, altho there are different widths apart and width of striple from wide to extremely narrow
chalkstripe is a faint pinstripe, often better looking than the narrow, bold pinstripes [unless you like loud pinstriping, nttawwt]
glen plaid -
http://www.polo.com/product/index.jsp?productId=2370792
-i.e. looks like faint squares/windows
herringbone -
http://www.tmlewin.co.uk/product.asp...wearSuits!SHBN
houndstooth -
http://www.thefedoralounge.com/showt...10&t=14067
scroll down to see, 'loudness' depends on size of pattern
nail head -
http://www.execstyle.com/Sproducts_sepa.asp?pid=1758#
No man should be cursed with having only 1-3 plain, navy, solid suits.
Shirts:
There are several different great cotton fabrics in the $100 price range [or less], Sea Island, Turkish, Swiss is really good stuff - some thicker, some softer than others.
Get 2-3 white, 1-2 blue, 1-2 white with a colored stripe and you're all set with your starting lineup. Add in greens, yellows, pinks, purples, deep blue, very pale blue, windowpane as needed. [I have a lot of custom shirts...]
I like french cuffs, as the $0.05 cent plastic buttons on $100 shirts break as easily as the $10 shirts, plus cufflinks look good and mark you as more stylish than the average joe [and chicks are always fascinated by them] & you don't have to spend a lot on them - Cole, Nordstrom, etc will all have them on sale now.
Your tailor can steer you to the right kind of collar and spread, a bigger guy needs a narrower collar & vice versa. There are like 20 diff kinds, just take her advice if you can't see a difference.
Ties: to really look your best, get a few nice ties from Hermes, Versace, Ferragamo, Zegna, Barneys, etc. Wear the suit/shirt combo when you go to buy them.
Pick up a few cotton/[silk] solid/pattern pocket squares, you likely have a nice watch already, and you're all set.
As my old tailor would say, 'fashions come and go, but good style is timeless.'