Be very careful with that black blazer. Wear it with grey trousers or jeans or something, but never with black trousers unless they match EXACTLY (same maker bought at the same time as a suit or suit separates). NEVER EVER EVER wear almost-matching separates! You'll look like you want to wear a suit but don't know what one is.

I second the idea of more shirts. You can wear a nice collared shirt with any kind of sport coat over jeans and pass muster everywhere except a formal office. Don't be afraid of color or patterns; nothing says "dude who has no idea" like sticking with boring shirts exclusively. On the other hand, you don't want to go insane, with skulls painted down the side Ed Hardy-style. Robert Graham shirts are over the top for me, too -- I love flowered shirts but not four different floral patterns and stripes all together.

One thing you can do is go to a couple of department stores and check on brands that appeal, like Thomas Pink or Ben Sherman, and then look on Ebay. One of the advantages of being a man is that pretty much every sized dress shirt (i.e., with separate neck and sleeve sizes, 16/35 or whatever) is going to fit the same, unless you are carrying a little bit of gut and trying to fit into a tapered or "athletic fit" shirt.

One absolute essential, which should be much higher on your list than bespoke tailoring (which is awesome, don't get me wrong), is GOOD SHOES. Nothing you wear is more telling. A good pair of classic men's dress shoes is maybe more money than you're used to spending but they will last forever and never go out of style. Skip the funky trendy stuff with big square toes or sharp pointy toes or whatever and go for the classics (this is true of all categories, actually): I like Allen Edmonds, but Florsheim Imperial, Bostonian, Mezlan, Johnston and Murphy, etc. Go with SHOE companies and not general men's designers with a shoe line (like Kenneth Cole).

Get a suit. Get a bunch of suits, eventually, but start with a basic suit in some sort of grey pattern like a glen plaid or a subtle check or something. A great place to go for suits if your budget is limited is Nordstrom Rack. You'll have to have patience, but you'll find something. But before you start going there, go to someplace good where the sales clerk can FIT YOU PROPERLY. For starters, don't look at your sleeves; look at your shoulders. A professional will guide you through this process, and from then you'll know your size and won't have to hunt around for it -- you'll just go straight to the 42 regulars or whatever you are.

A really good place to get this treatment is Nordstrom, where they understand suit fitting. Macy's used to, back when they were the Bon, but the guy waiting on you now will likely be an ignorant creep (not always). The best place is Brooks Brothers, but you need money. Barney's is even better but you need a suitcase full of money.

You should also get an everyday sport coat, which unfortunately isn't going to be your black or blue blazer, though those have their place. You want something in a tweed or subtle check.

Neckties are a fun way to break out a little, and every store has a nice lady working in the tie department who will love helping you pick out some ties to go with your new shirts. She will flirt with you a little. She will be in her 50s or or 60s. Listen to her!

Your first suit should be a navy suit or a charcoal suit in a 3-season weight. Don't get one on the cutting edge, fashion-wise, so skip the narrow lapels and short jackets, and your suit will be stylish for years, and style (not fashion) is what makes you look good. Make sure the suit is canvassed, and not fused. Canvassed is more expensive, but is worth it.

Your second suit should be whatever color you didn't buy for your first suit. Unless you have a hard-to-fit body type, bespoke or even made-to-measure might not be necessary, as long as you take your off-the-rack suits for some tailoring. You'll save quite a bit, and will have something very close to bespoke. If you're harder to fit (body builder, very short/slim, etc.), then bespoke might be easier. Try on lots of different suits, because suit brands vary widely. The most important thing is the shoulders - they shouldn't be any wider than your natural shoulders, and that's one thing a tailor can't really fix.

Don't bother with a black suit ever; even for a funeral, a charcoal or navy suit will be appropriate if paired with a white shirt and solid dark tie.

Get good shoes. Allen Edmonds Park Avenues are an excellent starter shoe. Get them in a darkish brown, and you'll be able to wear them with pretty much everything except that black suit that you didn't buy. Get shoe trees for your shoes, and don't wear the same pair two days in a row. If you do that, your Allen Edmonds will last you 10 years, at which time you send them back for refurbishment, and then they last you another 10 years. That works out to less than $20 a year, compared to the $80 kenneth cole crap that will disintegrate in one season.

Solid grenadine ties always look fantastic. Start with a navy one, then a brown or dark red one.

For slightly more casual, look for some oxford cotton button-down shirts (button-down means that the collars button down) in white and light blue. Brooks Brothers make the classic OCBD, but you can find nice ones elsewhere.

My advice to you would be to go slowly on getting custom clothing made. It's easy to jump in with a tailor to make you a bunch of clothes all at once, but you may realize that you got them made in a way that you don't really care for after a year of learning more about fashion and men's clothing.

People have hastily blown lots of money when they realize they don't care for their wardrobe.

Spend a year picking up a piece here and there as you learn what you like and what matters to you.

Small world... :)

I second the suggestion about getting good shoes, and I'll also suggest looking at how much the bespoke outfits are going to cost here, versus elsewhere. I had some stuff made while we were visiting Thailand, and based on the reactions I've seen since I got back, they look great and cost a lot less than some people assumed. Two suits + a blazer + four shirts + 3 ties came to $1500, if I remember correctly, and they made everything to the exact the specs I wanted.

If the cost for bespoke here is going to be close to the cost of bespoke there + air fair, it's time to start thinking about a trip abroad!

If that does sound intriguing, let me know and I can send you the info for my guy in Thailand. His shop is 1,000 miles away from the "$100 suit" crap in a lot of Bangkok; he's established, high-quality, and very very professional.

Neck ties and pocket squares!!!

I love to wear an ascot for casual occasions and a Full Windsor knotted neck tie when I am feeling fancy.

A colorful pocket square in your sport coat will help pull your look together and won't you feel gallant when you offer it to a lady (or gentleman) in need?