Do you want a made to measure suit, tailored to your body? Or do you want a bespoke suit (mostly the same, but tailored entirely by hand).

If you're in America and you'd like an entry level "luxury" made to measure suit, Brooks Brothers is nice at $1500/suit or so. You can also try for other luxury brands, up to and including Tom Ford, at $40,000/suit (or more).

For a bespoke suit you can spend anywhere from $2000 (cheap) to mid five figures. Saville Row in London is "the place" to go for these, but if you're in America there are many small shops in New York City across all sorts of price ranges.

In general a bespoke suit is better than a merely made to measure suit (at least financially it has a better cost justification and there is an "experience" factor), and a brand name is commonly thought of as less desirable than an independent tailor.

Beyond that it's harder to give a good answer without more detail on what you want, how much you can spend and where you are. Personally I'd never get a suit at Men's Wearhouse, I have found the attention to detail and patronage there is lacking. At the absolute bottom in terms of price, mysuit.com is nice for bang for your buck factor.

My personal recommendation is to spend the money on a bespoke suit, all things being equal. An experienced tailor making a bespoke suit will cost more, but will more easily achieve an attractive and comfortable fit than a machine will. You also have much greater choice.

In my opinion, paying for a made to measure suit is only slightly better than buying off the rack. Bespoke suits are usually offered by independent tailors, not larger brand names. This means that bespoke suits are usually expensive due to the skilled labor costs associated with making a fitted suit by hand. But a made to measure suit is usually just a higher offering than an off the rack suit at a brand name luxury store (Brooks Brothers, Emporio Armani, Canali, Brioni, Zegna, etc.). In other words, you pay for some tailoring skill and a lot of brand name. I'd rather spend $5000 on a bespoke suit from an obscure but skilled tailor on Saville Row than $5000 on a made to measure Canali.

I encourage everyone who can to purchase bespoke or made to measure suits, however. I find tailored suits so comfortable that I enjoy wearing them. The signaling effect is also nice. You can clearly tell the difference between a suit off the rack and a suit that has been tailored to a custom fit. If you spring for higher quality materials you can vastly improve the durability and comfort as well.

If you'd like a few exact brands to check out, indiscriminate of price:

• Bespoke suits - Huntsman, Gieves & Hawkes

• Made to measure suits - Brooks Brothers, Canali

• Tailored shirts - Thomas Pink, Turnbull & Asser

• Ties - Hermes, Drake's of London

• Shoes - John Lobb, Stefanelli, Bemer

Hope this helps you out.

EDIT: petewailes also has good advice in this subthread