It's been over 15 years and probably closer to 20 since I had to purchase a lot of suits but I always went to Manny's. I'd pick out three suits some shirts and ties there was a big shoe store around the corner so I'd head over there pick out three or 4 pairs of shoesm, go grab a burger and a beer and I'd come back and pick up my altered suits. Manny was or still is a big Notre Dame fan who knew the South Bend Elkhart area quite well so it was real easy to get to know him. One time Ray Meyer and his wife called in and said they were on their way over and Manny and his wife shoed the patrons to one side and cleared an area for "coach" and his wife. Manny was nice enough to give me a personal intoduction and I got to spend about 10 minutes talking to him, he had a real and genuine love for both Notre Dame and Digger. A love that stopped with his son Joey who I think was always a little bitter of Diggers and Rays relationship.
1) The ideal is to have a suit wardrobe such that you only wear the suit once every week. Wearing them more frequently than that will make them wear out faster than they should. (If you want to go to aspirational levels, one can say that the best would be to wear a suit only once a week, and to have separate sets of suits for spring/summer and winter/fall.) For someone who wears a suit every day, this generally works out to six suits (five for workdays, plus one spare/to cover things on the weekend).
2) Your best bet for reasonable price may actually be ebay. Run a search in your size based on well-made brands, such as Samuelsohn, Oxxford, Southwick, and Ralph Lauren. You can even set the search up as an RSS feed.
2a) Barring that, there are lots of places to look for some good suits. Locally (I assume you're in Chicago from your handle) Brooks Brothers, Nordstrom, and Neiman Marcus come to mind as places to buy a good suit. Online, you can expand to J. Press and O'Connell's. Jos. A. Bank can be a good price, but 1) their suits have very boxy shoulders that may not flatter or appeal to you and 2) only buy from one of their "Signature" or the "Joseph" lines; the lower-tier stuff is not great. The made-to-measure suggestion lower in the thread is a great one: that's often the best value if you can make the initial investment (which might not be more than regular price at some of the above). If you want to be a bit indulgent, the Chicago Paul Stuart is lots of fun.
2b) More important than going to one particular place is getting a good, well-fitting suit. Look for something that's fully or at least half-canvassed, with a "super" number no higher than 120s (a lot of suits are made now with thread counts as high as 150s, but the thread is thinner, weaker, and less durable). Make sure it fits through the shoulders and doesn't pull or gap in the front. Get your pants cuffed with "slight break." Finally, watch out for "fashionable" suits: a lot of stuff on the rack right now is actually cut too short for the tagged size. You'll look very "with it" right now, but a wool suit should last a long time, and the my-suit-is-too-short look probably won't.
2c) Last thing: make good color choices. Navy, charcoal, medium gray, then some stripes, windowpanes, and glenn plaids. Don't buy a black suit unless you're going to a lot of funerals or your new job is "undertaker."
They do custom suits that are of higher quality than anything you will get Jos A Bank, and for less money. I want to say you can do a 3 suit deal, plus 5 shirts and 5 ties for something like $2000. And not only will it be good quality, but everything will actually fit. You will be astonished at how much better you look in a suit built for your body.
They did my wedding tux and grey suit, and I am very pleased with both.
About ten years ago I was travelling regularly to Hong Kong and had a suit made for me there. Still have it (and most gloriously), it still fits and looks great.
If you can swing the bespoke suit, or at least custom tailored you will look great.
I guarantee it.
Wait, that's not my line.
that will even come to your office and shower you with praise and compliments. Of course, they will also call you 10 times per week to see if you want to order any more stuff.
It's worth it. I almost proposed to my sales rep. And I may or may not have left my pants off when she stepped out and asked me to try on my suit.
I would suggest a minimum of five suits - one for each work day - as a start.
I ended up with 10 suits - wearing them about twice a month. I still have suits that I wear that I bought 15 years ago.
You can make three suits work with a combination or coordinating shirts and ties.
And you need at least two pairs of decent shoes.
The number one way to kill a good pair of dress shoes before its time is to wear it every day. Keep trees shoed and don't wear them without letting them rest for a day.
The person who gets thrice daily "sale" emails from Banana Republic/Gap/Athleta, Eddie Bauer, L.L. Bean and Ann Taylor Loft among others
I have NEVER seen an ass on a mannequin like the one displaying their yoga pants. It took all my willpower not to take a picture with my phone.
in a shop window near South Beach. I mean, it was almost a joke, except that this appeared to be a pretty high-end shop. My 12-year-old son took note and giggled.
or the Men's Wearhouse, you are a sucker.
Not sure how they hold up, but a bought two at a brooks brothers outlet. I do not wear them everyday, but the price was good and my tailor thought they were decent suits.