This is what I recommend: Suits
As someone said earlier, I would go MTM or bespoke only if you have 'non-standard' body proportions or want to achieve a look not available off the rack. So from what I can infer from your posts, RTW is the way to go. Designers: I would avoid Canali if you prefer fitted garments -- the pants are extremely baggy. I would also stay away from EBay (poor selection). There might be some value there, but you're willing to invest a good chunk of money on yourself so you might as well get the best suit that you can afford. Try Boss (Flynn or Rosselini (sp?) style), Z by Zegna, Abboud, Smith or Sander. Cost: about $800 to $1100 per suit, so for 3 suits let's estimate $2700 (negotiate if you buy them all at one place). Shirts
A regular dress shirt adds 7" x 2 to the body, while a slim-fit shirts adds 5" x 2. Here's an example of a baggy fit
and here's a proper looking fit shirt
(note that it's not a dress shirt). I like my dress shirts to fit like the latter and because I am shorter I have to go bespoke (3.5" x 2). I suggest to try shirts from Boss, Zegna, Thomas Pink, Banana Republic, Etro, Ike Behar, etc. Colors: I would get all patterned shirts (offers more combination with your suits and ties). Definitely get one with some pink in it and one with burgundy. Cost: These shirts go from $80 to $250, let's say you buy 5 shirts for a total of $800, but I'm sure you can find good deals and bring it down more. Ties
Obviously they should match your shirt or suit. I love Canali ties, but the same can't be said for their suits and shirts. Boss, Zegna and Armani are others designer ties that I own. I would avoid Bluefly, the ties there are on clearance for a reason -- they're ugly. Cost: About $80 to $120, but I would definitely wait for end-of-season sales. Get 8 power ties for say $600 and maybe less with some smart shopping. Shoes
I don't recommend any particular brands. They should be comfortable first, then durable and finally look good. Get a black oxford, a black dressy slip-on and a brown dress shoe. Cost: I would wait for sales and you could get away with 3 great shoes for about $600 Belt
Very simple -- one black and one brown belt to match your shoes. I favor Boss belts. Dolce & Gabbana, Hermes and Gucci belts are way too conspicuous for my taste. Cost: 2 x $100 for a total of $200 ------------- That said, you can spend $1000 less than what I suggested with lower-priced brand and still come away looking good. The key is to be confident about the colors you wear and to match your garments tastefully. Happy Shopping. ps: I hope you have good watches to go with all this.