So, starting a new job in Feb. where it's suit and tie almost everyday except Friday. I believe sportscoat and trousers are acceptable, but from what I saw after three rounds of interviews, I only saw guys suited up. Anyhow, for the past 12 years, I worked from home (Chicago) working for a Boston based business. So, my business clothes mostly consisted of PJ's, jeans, and t-shirts. Being in sales, I do own many business casual outfits, but only 1 formal black suit. In my industry, blazer and trousers is the norm, but mostly nice slacks and a button and maybe the occasional sweater. So, I am looking to build my wardrobe, but it's been such a long time I have shopped for this kind of stuff, I needed some help. This website has been great in educating me on many things. I thought I had a decent fashion sense, but am now dated. First things first, I need to add two suits, solid Navy and Charcoal are my first buys. Budget for 2 suits, (1) pair of brown shoes, 3 white dress shirts (I have plenty in different light blues and many other non trad colors/designs), 4 ties is $1,500. I know, not a lot for most on SF, but I am not going to drop a ton right now. I am gonna get a sense of what the office is like and after 6 months, want to add navy pinstripe and med gray suit. My biggest decision right now is to either bye OTR at Off 5th Saks, they are currently running BOGO on their suits. I know, the Hugo Boss and Ermenegildo Zegna offered here are not the higher caliber suits offered at flagship Saks, but at ~$800 for two suits, I believe offer good value for a decent suit, even though it is most likely fused. However, after reading here about Suitsupply, for $1K, I can get two decent half canvassed suits. I tried on the suits at off 5th the other day and I believe they fit great in the shoulders. I have a pretty ave body, 42R 34"waist so in the past, buying jackets have been pretty easy OTR. However, if spending $350 more can get me that much better quality, I would easily move budget that way. Figure, if I went with the Off 5th option, I would have about $700 left. - $350 for a pair of brown AE shoes, some kind of wingtip (already have Black AE Park Ave) - $350 for three white shirts and ties (probably gonna go cheap on ties, tiebar.com, and probably BB oxfords) If I went with SuitSupply, I can sacrifice quality and get shirts at Land's End and maybe Cole Haan shoes. Not too worried about paying for tailoring, my Mom is a Tailor and can get the suits just fine. However, I believe SuitSupply includes fitting? Maybe I am wrong, but if I order online and ship to store, they will include tailoring? Any help here from you guys would be great. Thanks!