TransGuys

The vast majority of men don't wear tailored clothing often enough to warrant a large wardrobe. Thus, if you're interested in tailored clothing, the easiest way to avoid looking bad is to stick to very simple things: — One "serious" suit in navy, mid-gray, or dark gray worsted wool. This should be single-breasted with notch lapels. You can wear this to weddings, funerals, religious events, and such. — One solid-colored navy sport coat made from navy wool, likely hopsack or an open weave such as Mock Leno. This should again be single-breasted with notch lapels. This is the most versatile sport coat. It's the sort of thing you wear on Mother's Day. — One or two other sport coats, likely mid- to dark brown. Make these from seasonal fabrics suited to your climate: wool-silk-linen if you live in a warm climate; tweed if you live in a colder climate. The fabrics can be patterned, but ask yourself when shopping — is this pattern something that a used car dealer or ESPN host would wear? If so, do not buy the jacket. These again should be single-breasted with notch lapels. Wear this when you want tailoring, but a suit looks out of place. — One semi-spread collar dress shirt made from a smooth white cotton fabric, such as poplin or broadcloth. Avoid cutaway collars; they are gauche. — A small stack of light-blue dress shirts — some solid-blue, some blue-white striped. If you're American and have any sense of pride in your country, get Oxford cloth button-downs where the collar points are long enough to give a full roll. If you're not American, or if you're a traitor to the United States, they can be semi-spread collars cut from smooth, pure cotton, such as broadcloth. Although I think end-on-end lends a bit of visual interest. — A matte silk rep striped tie that's not too visually busy. Get this in a basic, sober color like navy, brown, or forest green. Always tie this with a four-in-hand. Never wear a full Windsor knot or anything too complicated (those weird knots that get lots of upvotes on Reddit). — Trousers made in a classic cut (high-rise, not too slim). These should be light gray, mid gray, or tan, and then cut from seasonal materials that make sense for your climate — tropical wool for warmer seasons; wool flannel, cavalry twill, or whipcord for cooler seasons. You can get them with flat fronts or a single reverse pleat. Do not ask "are pleats stylish?" In fact, stop asking how to look stylish, young, or fashionable altogether. — Two pairs of Goodyear-welted, full-grain leather dress shoes in mid or dark brown. These can be derbies or penny loafers, since you'll likely wear sport coats, not suits. (Do not wear oxford shoes with sport coats). Never touch tan leather shoes. Or any dress shoes with a sneaker bottom. — A leather dress belt that's about 1.25" wide. The color should be close to the color of your shoes — dark brown with dark brown, mid-brown with mid-brown. — Solid navy over-the-calf dress socks. These can be thin cotton if you live in a warm climate. Otherwise, choose thin wool. Do not try to get creative. Even sticking with this formula will be creative enough, as no one knows how to wear tailored clothing anymore. Thus, you will look elegant in a sea of bad made-to-measure tailoring, Italian checked fabrics, skinny pants, tan dress shoes, black dress shirts, ugly ties, and the like.