After about 9 years working for a large hedge fund, I quit my job last year to start something of my own. I had to sit out a year for some legal reasons (with my former employer) and that year is due to end in a couple months (I'll be able to start work in Apr).
I am looking to create a "consistent" dressing format for me. At my previous place, my consistent clothing was dark wool slacks and a white (Banana Republic Tailored Slim Fit, size M - fit me very well except perhaps the sleeves could be 0.25-0.5 in shorter than they were). It worked for me and I did not have time to spend on choosing clothes - so I would simply go online and buy a bunch of shirts or slacks at a time, wear them till they would start losing the "new" feel and then repeat.
Right now I have time to think - I won't once I start working again. So I am thinking of changing over to wearing a suit every day. My preferences are:
0. Once I am wearing what I am wearing, I need it to recede in the background. When I am working I do not want to be adjusting my suspender/belt, worrying about whether my shirt is slipping out or not, whether I am sitting on my pants right or not - nothing of the sort. I prefer not wearing a tie. I own a few Ascot ties that I have worn (inside open collars) on occasion with suits. I find closed collars uncomfortable, but maybe I just have been doing something wrong.
1. I need to be able to dress for work without thinking too much about what I am wearing. Whatever I go with, I will plan to set up a rotation and follow it blindly (unless there are special occasions).
2. It needs to look good - it needs to fit me well. I will much prefer sticking to slacks-and-shirt that work well rather than an ill-fitting suit. I don't care for branding at all, I do care for quality.
3. It should be good value for money. The fact that I can afford fairly high end stuff doesn't translate to me actually spending on it. I am not brand conscious at all.
I am 5ft10in, and I weigh in at 180lbs. I have muscular shoulders, and a bit of belly/love-handle fat (usually choose a size 30 to 32 in trousers, but I realize that my actual waistsize in inches is perhaps higher because of the way trousers are marked) that I am working to get rid of. I usually fit in a 38R suit. I stand and sit tall, and I tend to move fairly actively (even though my day involves a lot of work on the computer, I walk around and move a lot - I do a fair bit of my work standing).
1. Three piece suits. Primarily to (1) avoid having to worry about the shirt coming slightly untucked at the waist (2) hide suspenders out of view (see below). But also to look a bit different and dressier than usual. I am happy to abandon this idea (and stick to more conventional two piece suits) if my assumptions are incorrect.
2. Suspenders rather than belts - again with a view to not have the shirt pinched in at the waist.
3. 5 suits to start with and depending on what works buy 5-10 more over the year. I own 3 suits right now - two from Zegna and one from Hugo Boss. They were all bought on heavy discount from either Saks Fifth Ave or Bloomingdales. I don't think any of them was more than USD2k, all in price. None of them get much use. I like the fit of the Zegna suits much better than the Hugo Boss suit, and so the latter has perhaps been work exactly once. I am not going to count these suits - for that reason.
4. I don't want to spend more than around USD1.5K per suit - including perhaps an extra pair of trousers. I need to know that I am getting good value for my money.
I request your suggestions!
1. What are your thoughts about my plan above? Does it sound insane to the extent that I should simply stick to my usual slacks-and-shirt? Indeed that is what most people in the industry wear.
2. In case the plan makes sense, does my budget make sense? What is a reasonable budget for an everyday suit?
3. Where should I get the initial 5 suits from? I am lucky in that I live in NYC - practically everyone has a shop here that I can easily visit. I have spent the last day researching various varieties of bespoke/made-to-measure/etc. options on the internet and the short summary of what I have been able to learn is that it is a competitive and dirty industry (and the fact that the work starts only after you give up the money doesn't bode well for the experience, in my view). On the one hand everyone touts Martin Greenfield - they seem to run an assembly line operation and still charge fairly expensive prices. I am happy to buy off-the-rack suits if they have long-term quality and fit well. I tend to think I am a very conventional body type and fit easily, but I might be completely off about how the suits I have already really fit.
I would much prefer a no-BS small no-name shop - OTR or tailor - that fits me well than a more highbrow concern where I would worry about being ripped off.