Watching The Night Manager right now and that young one is definitely growing on me. 
OT: That is one seriously tall cast, well, other than Tom Hollander.
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In general I’d keep one or at most two pairs of khakis in the closet. Sandstone or cream have the most universal appeal. As with polos, tan khakis are hard to pull off well, and even then they’re so vastly overused that they’ve become a cliche like Ikea or Starbucks. I would advise at least one pair of khakis, one pair of basic black slacks (without cuffs are more universal, pleats are an abomination, permanent creases always add a touch of class), one pair of dark navy slacks, one pair of black jeans, one pair of dark blue jeans, one pair of light blue jeans (optional).
When you’re ready, go to a Men’s Warehouse or Jos. A Banks or Brooks Brothers Factory Outlet and get two pair of good fitting wool pants (light if you’re in a warmer climate). Get one black and one gray. While you’re there, pick up three or four off-the-rack dress shirts on sale, one white and the others a pattern or color you feel compliments your skin tone (this will help you with that How to Choose Your Best Clothing Colors: Simple Guide). They’ll have a lot of fits, and each designer/company fits differently, so give yourself time to find the fit that works best for your body shape. While you’re there, pick up one suit. I don’t know about Men’s Warehouse or Jos. A Banks, but I know Brooks Brothers still only sells all-wool suits at reasonable prices. You want to avoid wool/synthetic blends; they breath poorly, don’t drape as naturally and usually won’t last as long.
You could use the shop’s in-house tailor to get it fitted to you, but I’d avoid this, most especially if you find yourself in department stores. Even if all you need are shirts and slacks and you never care to put on a suit, finding a local tailor you trust will be the most long-impacting and important part of your style journey. A good tailor will get to know you and what you like, helping you look good while also still being yourself. Take one of the off-the-rack shirts and go find a tailor to help you fit it to yourself. This is the best litmus test. You can get a single button down collared shirt darted for $15 to $20, get a read on the tailor and it’s an alteration almost impossible to screw up, so you’re not risking threads. That good shirt will cost you about $40 to $50 on sale, but will last far longer than some piece-of-shirt from a department store.
That’s a place to start. Someday maybe you’ll be crafting your own cuff-links and sipping Scotch while a Edinburgher measures your for a bespoke Harris tweed jacket. But even if your never take it that far, you’ll already be light-years ahead of 99.9% of your peers.
My most prized piece in my wardrobe is a Langlitz Leather jacket. Leather is timeless. You can wear it with almost anything and look good.
While I disagree with @japhroaig that double-breasted suits are an abomination, someone new to style really should avoid them. If you’re going to go pinstripes, I recommend a light pinstripe so the pants can be worn without the jacket if desired.
What it boils down to is finding a style that expresses your own aesthetic. Dress for yourself and you won’t be a snob. Snobs dress to impress other people. Style is something you craft over years, as inspiration hits you. As long as you’re willing to try new things and step outside your habits, you’ll find a look you feel at home wearing.
And don’t believe you have to spend a lot of money. Half my wardrobe came from vintage shops and eBay. Don’t get caught up in fashion.
Here are a couple of forums that would be well worth your time exploring.
For the most part, the natives there are friendly and helpful.
“Don’t be a snob about the way you dress. Snobbery is only a point in time. Be tolerant and helpful to the other fellow — he is yourself yesterday.” ~ Cary Grant
ETA: Oh, and get one good black belt (or if you wear brown shoes more, get a good brown belt, eventually you’ll want at least one of each) from Allen Edmonds or a comparable quality manufacturer. Eventually you might end up with 18 like me, but for now, dropping $60 to $100 on a good quality leather belt is an investment as important as a good pair of semi-dress shoes. That surface-dyed stuffing-filled bonded-leather belt you can find in a hundred iterations at the department store will not hold up nearly as well. If you wear jeans a lot, you might also want to invest in a Saddleback Leather belt that really will outlive you. Also, get some Kelly’s Leather Lotion and gently rub in a small amount on your belts every six months or so. One bottle will last pretty much forever, and prevent cracking of the leather.
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Riding boots are bad-ass. Hipsters just be jealous.
These are my faves…
And I love my Danner Fort Lewis boots, but they’re not so good for riding.
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I’d like to subscribe to your newsletter 
Pleated
Pleated pants are an abomination.
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Shudders
Shivers
But that said, here is Idris Elba looking snappy in a double-breasted suit…
Since none of us are Idris Elba, I think we can all agree to avoid even trying that at home.
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@japhroaig No, pleated pants have their place. If a man is… Generous in the mid section, pleats can help the pants hang properly. Best with a suit, in that way.
My suits all have two sets of pants, and I have one cut a bit fuller with pleats, and the other a bit more trim with flat fronts. Cuffs on everything, because I have a weird thing about having cuffs on my pants.
Pleated khakis are an abomination. We don’t speak of pleated jeans.
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True, but pleated suit pants are extremely idiosyncratic. They look good on a fairly small percentage of the male population, IMHO. I saw a fit stockily built gentleman with a generous behind wearing a tailored gray two-piece with pleated pants and they looked great on him. It’s really down to hip and butt shape/size. That said, as you yourself alluded, the same accommodation can be reached with tailored or bespoke flat-front suit pants, so pleats are never truly necessary.
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Shoes.
I loooove beatle boots. The pair I have are knockoffs, but they look great. This is what I aspire to.
Some day I want to get a pair of cowboy boots, but I have size 15 feet. So theyd likely cost half a grand.
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At least, but ay dios mio will you love wearing them. If you ever make it to Austin, I’ll take you to Heritage Boots. I bought these Firebirds without the patent finish for country western dancing and they’ve aged beautifully.
[Trying hard not to turn @nimelennar’s thread into a boot porn gallery]
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I hardly think anyone here would mind if it was boot porn.
Anyone? Bueller?
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Another thought, although we’re going into summer and I don’t know where you live (however, air conditioning may nullify my concern)…
Wearing a dress shirt with a good quality knit (wool, cotton, or silk) vest and tie can put you up a half-notch or so. Not as much as a sport coat, but it doesn’t sound like that would make sense at your job anyway.
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Fashion, eh?
(sharp-eyed observers of sartorial elegance will note the stylish paperclip adorning my hoodie’s busted zipper)
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Wow, thanks everybody for the suggestions, this is great. I’ll have to spend a weekend going clothes shopping.
On an tangential note, I am seriously regretting this thread title, as every time my email points me about a new reply, I get Smash Mouth stuck in my head. Again.
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My Adidas
As a note to anyone who is considering buying GSG9-2s, they can be a bit narrow so either try em on before purchasing or consider ordering a half size above your usual size.
Edit: the tops of these boots lace tight so don’t expect to blouse your pants legs into them. Better to roll or ruck.
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Yup, and well-matched vest can also be a great substitute for a jacket in the evening in warmer climates. There’s this guy I dance with regularly who has a dazzling array of vests. It’s something he’s made his own.
A quick word on ties to our thread host. I absolutely love wearing ties, but don’t get overly dependent on them. When wearing them to work, take the extra two minutes to tie a full Windsor knot instead of a half WIndsor (learning time, 5 minutes)…
Attention to details often make a world of difference.
When wearing a tie out on the town, consider giving yourself a extra two to three minutes to do a more complicated knot. This dandy fellow will teach you, among other things, to tie the Eldredge knot (learning time, 20 to 30 minutes, but entirely worth it). [I liked it before Hugo Strange made it cool on Gotham 
]
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Holy shit that’s a cool knot! I’m 6’3" so finding ties that I can reasonably do a full Windsor is tough (a full Windsor takes a lot more tie for the knot, so tall gents usually have to half it out of necessity). And yes, I can tell a half from a full at least twenty feet away.
…
Gawd, I’m gonna go out and buy ties this weekend, aren’t i.
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I ended up buying a couple of pairs of Cydwoq boots after Cory went on about them a few times here. Really an unforgivable indulgence. Way too expensive and I don’t wear them often. But I do love them.
One of these days I’ll get around to getting some double monk shoes.
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Some men have beefier necks, some have longer bodies, so why don’t ties come in different lengths?
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