my 2 cents: go for Boss or Canali!
Hey there, thought I'd join in since I love a nice suit & tie.
If dropping $2000 is a little steep, then go for Boss. You can find some Boss suits at places like Harry Rosen for around $800.
If you go to Seattle, check out Nordstrom Rack. They are like the Winners for Nordstrom dept stores. The best 2 are Downtown and the new Southcentre one by SeaTac. Last year Southcentre had a few Boss suits for $400 US! But it's hit&miss with selection & sizes. I bought a Boss shirt for $49 and Seven jeans for $89 or 99.
For Zegna, they have a slightly less expensive line called Zegna Z. (Um, that's less expensive for Zegna—they're still a grand!) The Z line can vary in appearance. Some look more rough/casual. I lucked out and found a Z suit that was more on the dressy side and it was 25% off at the time!
Frankly if you're going over a grand, check out Canali. They aren't as well known as Zegna, but i prefer them. I've never coughed up the $1500-2000 for a Canali suit, but I have several shirts & ties. The shirts are around the Zegna price of $225-280, but their ties are a better value: Canali 125-140, Zegna 180-250!!! And the Canali shirts and ties are both better made in my opinion.
Zegna & Canali shirts are both tailored to a slim to average build. If you're a little bigger try the french brand Faconnable for shirts.
With suits, think about how you'll wear it. Always with a tie: buy a 2-button so it shows a little more shirt & tie. Sometimes/always NO tie: Buy a 3-button.
If you're slim to average, flat front pants are more stylish. If you have a little pudge, you may want to find a suit with pleated pants, but more than a single pleat will date you.
For the jacket, you can 1, 2, or no vents at the back. I prefer the very Italian look of flat front pants, with a 2-button jacket with the side vents (ie 2 vents).
Hey it's all about personal taste! Notice the little details and don't regret spending the most you can afford on a great designer suit.
PS The suits at Moore's are absolute crap. Most are wrinkles waiting to happen if not perma-wrinkled already. And the shape is simply not as nice as a designer suit! If you can't afford a nice suit, wear a just a nice dress shirt & dress pants until you can!
The upside of buying from a place like Harry Rosen—free tailoring for life. Seriously.
PPS 2 fashion tips when wearing a suit. #1 Don't pull out the shirt too much! Just enough so you don't look like Pee-Wee Herman. #2 Learn how to tie a tie! Harry Rosen's website has a printable step-by-step. I go for the Windsor because I like a bigger knot.
PPPS No I don't work for Harry Rosen or any other store!
Wow, I can't believe I just wrote this much!