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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