Original Message From JWD:
preliminary q: are you ok with me posting this response in the "Men's Fashion Thread"? it occurs to me that other people might want to take a look/comment.
okay, here are my thoughts. as long as you do not anticipate any more significant changes in your body type, you should spend your $2000 on a handful of high-quality versatile staple items that you will enjoy wearing and can count on looking good both casually and at work (so, e.g., 1 belt is perfectly fine). as you get a feel for what you like and what your wardrobe lacks, you can think about buying more clothes.
I'm sure it's possible, but tbh I've found it very difficult to make smart purchases when setting out to "buy new clothes" en masse. so I think it's great that your budget is right around what will allow you to get some basic items in your closet. if your experience is anything like mine, you will be surprised at how much use you can get out of a few staples — if you mix up, say, only your shirt, tie, and pocket square and wear the same shoes, belt, jacket, and pants every day, you can look good and fool a hell of a lot of people into thinking you have a normal-sized wardrobe (the average person seems to associate "dressing well" with "having a lot of clothes").
if your only requirement at work is that you wear a tie, I think you should go with trousers/jacket combo rather than a suit. this is slightly more casual, but will make your $2000 go much further. a good suit could wipe out that $2000 itself, and would be much less versatile.
also note that I'm going to leave outerwear out of this, because it is not a priority on a $2000 budget. outerwear is not necessary for much of the year and you may be able to make do with what you already have (side thought: I recommend making much use of a local tailor to save what nicely-made clothes you already own. massive alterations are possible, especially to simpler clothes like pants).
finally, many of the brands I will recommend you are American and may have more accessible Japanese alternatives. I encourage you to make good use of
http://styleforum.com and...uhh...google, I guess, to find similar options in Japan. I don't know anything about buying clothes there, but can tell you that Japan is viewed as a hub of men's style to rival the UK/Italy.
to be safe, I assume that you know what I knew before I started reading anything about clothes (basically nothing). apologies if I mention stuff you're already aware of.
oh, and one more thing: this is all imo, obviously. I try to adhere to established, classic/traditional rules of dressing, so I don't think anything I recommend will be out of the norm for stylish men. but mine is just one opinion, and this is just one way of looking at dressing well. given that I can only give good advice that's consistent with my sense of style and within my area of knowledge, the best way I could think of to approach your question is to explain almost exactly what I'd buy in your situation. hopefully you can extract from this very particular explanation bits and pieces of advice that you think are worth following.
shoes (~$300): I think you should start with the advice that I gave on shoes in my most recent blog post.
pants (~$550): given how often you will be in work clothes, I would put off buying denim and instead focus on 2-4 pairs of nice trousers. I'm thinking 1 winter (wool/flannel/tweed in navy, dark grey, or dark brown), 2 all-year (khaki/chino/twill in navy, khaki, grey, or olive), and 1 summer (linen/tropical wool in a pastel). higher-end brands I would look at are Unis, Incotex, and Epaulet. lower-end are J.Crew (I like the "Urban Slim Fit" alright — fear not the stupid name), Dockers, and Rugby. beware going too casual (especially when looking for "chinos"); I would not buy any material that you can't get a crisp crease down the leg of. in general, keep in mind that it is infinitely easier to dress a clothing item down than it is to dress it up.
jacket (~$500): start with one medium-weight navy wool blazer. you can wear this jacket on almost any day. the key to looking good is just to make sure that the jacket fits properly. here is a general guide:
http://putthison.com/post/9394551419/three-basic-points-of-fit-waist-shoulder . and here is a dude that I think is a fantastic model for how clothes should fit:
http://mostexerent.tumblr.com/tagged/WWIW (lately he has been wearing casual clothes; page through for some suits). the three most common pitfalls are: (1) too-long sleeves (your sleeves should leave about 3/8 inch of shirt sleeve peeking out — no shirt sleeve visible = sleeve is too long); (2) too much room around the waist; and (3) improper jacket length (it should cover your ass, and end somewhere along your thumb in the front).
brands are not so important here because all of the work is in the fit. just look for something that is 2-button and good quality wool (beware under ~$350 retail, and do not buy a jacket without real buttons/buttonholes on the sleeves). a high-end department store is your best bet imo, since I'm not sure what brands will be available and this is definitely an item you want to try on before buying. when you are fitting the jacket off the rack, keep in mind that, though the waist is easy to take in and the sleeves may be shortened or lengthened a little bit (can be tricky, though, with buttons), the overall length of the jacket and the shoulders/chest are basically impossible to change.
after you have your navy blazer game right, the next two jackets to think about are (1) a tweed jacket for fall/winter and (2) a linen jacket for summer.
shirts (~$250): this is a tough category because imo there is nothing worth buying in between a high-quality made-to-measure or bespoke shirt ($300-$400, research your local options) and a cheap off-the-rack oxford cloth button-down ($30-$60 on sale at Brooks Brothers or Rugby). it's also tough because it's the one area where I think there is a true dichotomy between appropriate work wear and appropriate casual wear: imo with a suit or jacket and tie you really want to wear buttonless spread or cutaway collars, but without a tie and without a tie+jacket you want to wear Oxford cloth button-downs (OCBDs). in my experience it is hard to find an off-the-rack OCBD with a collar that will
"stand up" properly enough to wear with a jacket (or a jacket+tie).
starting out and with a reasonable budget I think your best bet is to go with cheap OCBDs that have the most jacket+tie-worthy collars you can find (here Rugby is terrible). check Brooks Brothers and whatever other brands are at your local department store (beware shitty fabrics though; look for something that feels nice and has
the right weave). keep in mind that you can easily have shirts taken in around the waist (darting, costs like $5-$10/shirt and takes a day at the tailor's) but it will not be worth it to have a tailor perform any other alterations to a cheap shirt. so get shirts that fit you around the neck and shoulders and have a proper sleeve length. this may take some tinkering.
the reason OCBDs are advantageous is that you can wear them in any weather and both with a jacket+tie and casually without. I'd shoot for 5 shirts (1 for each day of the workweek). 2 white, 2 blue
now let me digress a bit on the issue of short-sleeved shirts and wearing a tie without a jacket. any stylish man I know would hate to be caught wearing a tie without a jacket. the tie developed (and still exists, imo) as an accessory to a jacket. ties look even more out of place with a short-sleeved shirt (there's a reason clowns and Dwight Schrute are dressed this way). in general short-sleeved shirts are extremely casual and imo they have no place in a workplace where a tie is standard. plus, they are much less versatile than long-sleeved shirts (e.g. OCBDs) and so are really hard to justify spending money on given any budget.
how to deal with these constraints, especially when it's hot?
(1) when in the zone at work (not in public), like in an office or classroom, it's probably acceptable to take off your jacket and wear your shirt and tie around. this is kind of like kicking off a pair of shoes. don the jacket when you need to go out.
(2) in casual settings (no tie), roll up your sleeves or leave them unbuttoned
(3)
above all: choose fabrics carefully. in the Western world there is this funny idea that it is always cooler to wear less clothing. in truth, summer-weight fabrics (here linen is king, but even lightweight cotton can work) can make you feel cooler than wearing nothing at all, by keeping sun off your skin and wicking away sweat. (how else could people in the fucking hottest places in the world wear
shit like this every day?). for this reason I think the ultimate solution to dressing well in high heat is just to wear a linen shirt and jacket. in my experience OCBDs will work well enough, though.
on super hot days, you can also pull tricks like carrying your tie and jacket in to work and then putting them on when you're inside AC. the real point is just never to be caught with a tie but no jacket option.
(ofc, your tolerance for heat may be different than mine. just keep in mind the above tips.)
ties (~$200): on a $2000 budget, I'd shoot for 4 ties (counting on the fact that a navy knit is unobtrusive enough to wear twice a week — more on that in a couple sentences). stick to conservative patterns (solids, small geometric patterns, stripes) in basic colors. I think, given your work environment — it sounds like "wear a tie" is the
floor for formality — you would do well to buy 2 sold knit ties (1 navy, 1 another color).
the knottery has a bunch in good colors at ridiculous prices, but I'm not sure whether they'll ship to you. J.Press and Drakes London are the gold standards (higher quality, like lifetime quality). in general, you might just check a department store/men's clothing store for ties.
anyway: the reason I recommend solid knits is that they are appropriate with any but the most formal getup (certainly appropriate with any jacket+trousers combo), people seem to fucking love them (#1 most complimented item of clothing in my wardrobe is my navy knit), they stand out without being loud, and imo they're much easier to get away with wearing loosely (with top shirt button unbuttoned — an occasional luxury) than a regular silk tie.
pocket squares (~$150): don't neglect these. the advice I always think of is (I read this somewhere): "pocket squares are the reason that your jacket has a breast pocket". it's true, and the main reason I now feel funny wearing a jacket without a PS.
plus, PS are a cheap way to vary what you're wearing. no, you do not need to look like a poof with some obnoxiously bloused-out colorful silk pocket square. I fold mine flat and just let them peek out of my breast pocket.
to start I'd invest in 1 or 2 plain white linen squares and maybe 2 other linen/cotton/silk that you think will match your shirt and tie combos. I try to keep PS and ties real simple, because otherwise they would overpower the rest of my (simple, staple-based, beginner) wardrobe. I'm not really an expert on pocket squares or pattern matching with them, so the only tip I have here is that I've got tons of use out of
this J.Press square. the blue edge seems to make it go with everything (plain white square + blue shirt is a bit too much contrast imo, even though I think it is generally accepted that plain white PS can be worn with almost anything).
like shoes, ties and pocket squares are a good opportunity to save $ by buying used (eBay probably your best bet). no big sizing issues, no stink issues, and you can pretty much tell what you're getting from a photo.
belt (~$50): something leather (ok, duhhhh, I know). try to get the buckle to match any metal on your watch/glasses/jewelry and the leather to match your shoes.
a "final purchase" type belt (something top quality that you can use forever) will obviously cost you way more than $50, but, like with the OCBDs, I figure here is a chance to save $ for worthwhile purchases elsewhere by just getting something passable "for now". skimping on PS or ties doesn't make sense because they're relatively cheap and you can literally use a high-quality tie or PS for your entire life. skimping on shoes and jacket doesn't make sense because these are the most crucial pieces of your wardrobe and they're going to be pretty big purchases no matter what.
I'm also including a list that I've started working on, of all the things I'd like to have in my closet in, say, 10 years. it's incomplete (no trousers, e.g.) but maybe it will help give you some idea of clothing items to consider.
+ Show Spoiler [list] +============================= FOOTWEAR =============================
x dress socks, black
X dress socks, navy
x dress socks, khaki
X dress socks, charcoal
X dress socks, grey
o wool socks
X dressy-leaning brown leather shoe (crispy polished)
X casual-leaning brown leather shoe (beat to shit)
X black dress shoe
X navy bucks
casual-leaning black leather shoe (for e.g. clubs; at night comme Sinatra
http://refinedcoast.tumblr.com/post/11572640944/theres-no-excuse-for-brown-shoes-past-sundown)x white canvas sneakers
white bucks
x spring/summer suede chukka
espadrilles
X galoshes
X deep snow-fit boots
brown dress boots
============================ OUTERWEAR ============================
baseball jacket
fallish quilted jacket
x military jacket
X peacoat
x dressy winter jacket, charcoal
X trenchcoat
x casual+lightweight rain jacket, with hood
============================ SUITING/JACKETS ======================
X tweed jacket
X navy wool blazer, single-breasted
navy wool blazer, double-breasted
x navy linen blazer
x grey suit, year-round wool/wool blend
x navy suit, year-round wool/wool blend
charcoal suit, winter-leaning wool
air force blue suit, summer-leaning fabric
tuxedo
============================= SHIRTING ============================
x 2x blue OCBD
x 2x white OCBD
x 1x pink OCBD
x 1x bengal stripe OCBD
x chambray work shirt
x 1x blue dress shirt, cutaway collar
1x blue dress shirt, spread collar
x 3x white dress shirt, spread collar
1x white dress shirt, cutaway collar
=========================== ACCESSORIES ===========================
X navy knit tie
chocolate knit tie
X green knit
deep red knit
purple knit
X various patterned silk ties
black bowtie
x white linen pocket squares
o various colored/patterned pocket squares
4x lapel flower
x brown leather belt
x black leather belt
x blue ribbon belt
white ribbon belt
X brown casual belt
x umbrella
X dress watch, silver/brown
dress watch, silver/black
x casual watch
o NATO straps
X multiple-wrap leather bracelet
braided leather bracelet
nice collar stays
pen
x brown leather briefcase
black briefcase
X brown leather messenger bag
x brown leather weekending duffel
2x tote bags (groceries; beach trips)
canvas rucksack
X large bag
garment bag, business trip satisfactory
brown leather gloves
black leather gloves
x warm winter gloves
X cutoffs
x winter beanie
X casual scarf
dress scarf (dark)
=========================== PANTS AND SHORTS =======================
x swim trunks
x seersucker short
x khaki short
x selvage denim
X white jeans
============================= LAYERING =============================
heavier light denim shirt
x nautical stripe button neck sweater
patterned white knit crew neck sweater
X various other sweaters
X layerable flannel shirt
x rugby