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Wow, some great insight here - thanks for the input.
I happen to love the black suit, and it is surprisingly common to see a black suit in court, that said, I will not buy another one. I think charcoal is more useful.
As for budget - I am a new attorney so Jos. A. Bank (GASP!) is comfortable on the wallet, although I know I will be replacing them in 2-3 years.
I am redefining with staples to start (white, light blue shirt oxford shirts, conservative ties [hard to ditch my Garcia ties though :(], etc)
As for shoes, I do see the value there first, so I will try to improve that area first.
Keep it coming and thanks again!
For shirts, I recommend Charles Tyrwhitt over anything from JAB. You can check out the Charles Tyrwhitt thread for thoughts on fits and sizing, but these shirts are much better than what JAB sells IMO. If you buy on the UK website, they are having their 4 for 100GBP semi-perpetual "sale," which translates to 4 for $160 or so plus shipping ($40 per shirt).
I don't think 4 items is too much if the store allows for returns and you happen to know what size you are.
I mean, a 15.5/34 (as an example) isn't going to vary widely from one maker to the other and there are certainly enough CT posts on this forum if the OTR fit is a question.
+1. The biggest issue is getting the correct fit (regular / slim / extra slim) and the sizing guide is helpful here. It's doubtful returns would be necessary but if they are CT's returns policy is great.
Edit: whether or not Charles Tyrwhitt quietly has such a policy, some retailers penalize customers who return a high rate of purchases, which adds an extra risk to buying a batch of items as like-or-return.
FWIW, I've also never had any issues returning items to Charles Tyrwhitt. I don't see OP being penalized even if he does need to make returns.
Why assume he has no wearable dress shirts or needs everything fast? Anyway, there will be sales at other reputable menswear stores, including Brooks Brothers. For shirts, Paul Fredrick and Jos. A. Bank are passable and often on sale (PF has a new customer dress shirt offer).
BB even on sale tends to be more expensive than the CT offer and he's on a budget. OP said that he was looking for help building a wardrobe / starting out, which I took to mean he doesn't have too much other than what he told us about. If he's working, he'll need a decent amount of dress shirts. If he doesn't need shirts right now, he has some more time (though adding a few from CT, if he does not already have shirts from there, would reduce "duplication").
+1. We're also talking about $40 shirts, not some $300 luxury shirt.
Proceed at your own risk with online MTM. If you get everything right, it can be wonderful but we see a lot of disasters on here as well. If you are going to try online MTM, I would only do one shirt at a time until you get your pattern right and be sure you are not getting shitty cloth.
Ok, I think I got it.
First things first - I am going to a tailor on saturday to alter a suit I bought online so I will get him to take all my measurements.
I am going to try a Modern Tailor shirt, to see the quality and hopefully get a feel for "proper fit" - all my clothing now is OTR, but the JAB suits were measured and seem to fit really well.
I think my next suit will be my "upgraded suit" as archibald suggested - depending on how my MTM experience goes, it may be Black Lapel, but OTR Brooks Bros will be a close #2.
I've been soaking up the site a little bit and see references to black tie rigs, i'm not there yet, but can you really eff that up? Isn't a tux "in style" for a while if you go the trad route?
And my last noob question - anyone with opinions on tie bar ties for the conservative tie game?