1. Get Layered
Cool weather means coats, jackets, and sweaters — some of the time!
Temperatures are going to be spiking and dipping for a month or two, so plan on a layered look that puts thicker top layers over light, breathable underlayers.
This is both practical and stylish. Showing multiple visible layers makes you visually “busy” — and therefore eye-catching — and it also gives you a way to regulate you temperature, by adding or shedding layers.
Stock your closet with a good mix of short- and long-sleeved T-shirts, lightweight collared shirts, heavier fleeces and flannels, sweaters of varying thickness, and of course the time-honored sports jacket.
2. Think Solid Colors
Hand in hand with that layered look comes the time of year for muted, solid colors.
It’s not an absolute rule. But fall looks tend to be heavy on solid earth tones, dark shades of colors like green and orange, and other simple, solid schemes.
Part of that’s seasonal — fall makes us think of the outdoors, changing leaves, harvest vegetables, and so forth. Another part is practical — if you’re going to be showing several layers at once, it’s better that they be simple.
So keep the colors varied, but keep them mostly solid. Once you’re wearing three or four pieces at once, the overlap between them creates plenty of pattern on its own.
3. Wear Textured Fabrics
A good way to keep your look interesting but easy on the eyes: wear solid colors in textured fabrics.
Corduroy, tweed, woolen knits, and even velvet or suede all give you a nice, autumnal feel. They work well in dark solids or in lighter grays and other muted shades.
As an added bonus, most of the most common fabrics with a visible texture to them are on the thicker side of things. You can expect them to keep you warm on a cool day without having to throw an overcoat on top of everything.
4. Sweaters & Sports Jackets
If we were picking out iconic autumn garments, these would be two of the champions.
The traditional sports jacket doesn’t need updating here — stick to a classic, earth-tone tweed or corduroy with big flap pockets and even elbow patches if you want them, and you’ll look right at home on any leaf-lined boulevard you choose.
Lightweight sweaters give you a more casual look, and can be layered with sports jackets or blazers for the coolest fall days. If you’ve got two or three each of good sweaters and good sports jackets, you’re in good shape for the fall.
5. Break Out the Boots
Trade in summer sandals and light lace-ups for sturdy boots. Light boots like chukkas or brogue dress boots are an excellent meeting-place between style and practicality, especially on days when the weather turns wet.
You’ll want slightly higher socks to go with any high-ankled boots, so make sure you’ve got a couple pairs. Wool/synthetic blends in plain, dark tones work well — try to match them to your trousers when you can, though the boots will probably hide them if you can’t quite manage it.
6. Expand Your Light Coat Selection
The winter parka will come out eventually, but until you see the snow falling, keep to lighter coats.
A good jean or corduroy jacket, a peacoat, or a plaid “lumberjack” coat are all good medium-weight options for when a sweater on its own isn’t enough, but a heavy overcoat would be too much.
For most of the fall you won’t need a coat with your suits and sturdy sports jackets — those should be warm enough on their own. But once it starts getting chilly, or if you’re going to all-day outdoor events in your nice suits, a longer wool overcoat will be a worthwhile addition as well.
A classic Chesterfield or polo coat are both warm and stylish, or for the more aggressively informal there’s always the trusty trenchcoat. Just make sure whatever you select is longer than the hem of any jackets you wear it over. A suit jacket poking out from under a coat at the bottom hem looks silly.
7. Trade Cotton Slacks for Wool
The upper body is easy to layer as much as you need, but there’s a limited amount you can do to warm your legs.
One way to keep the lower body comfy in the cooler months is to switch to wool slacks. Even a lightweight wool will hold some head, and stouter weaves are like a sweater for your lower body.
As an added bonus, wool slacks often come in both the muted dark colors and the textured weaves we’ve already recommended, making them natural fits for your fall wardrobe overall.
8. Upgrade Your Underwear
Some men save their heavy-duty underclothes for the deepest part of winter. But breaking them out early can let you keep lighter clothing options in rotation for longer.
If you’ve got a pair of very light, breathable wool slacks that you’re fond of, for example, slip a pair of insulated long johns underneath when the weather gets cold. You’ll be able to keep wearing the pants, and you’ll get the warmth of both the outer layer of wool and the insulating underlayer protecting you from wind and cold air.
Sporting goods and farm supply stores tend to have a better selection of insulated undergarments than most department stores — don’t be ashamed to shop at a Cabella’s or a Farm & Fleet when you want a nice underlayer. No one’s going to be seeing it, and it’ll help you keep the pretty, lightweight layers that you do want people to see in service for more of the year.
9. Own at Least One Nice Cardigan
Doesn’t matter how old you are; doesn’t matter what you’ve heard about them.
Have one big, thick, slightly oversized cardigan that you can just bury yourself into when you want. That’s your go-to piece for nights by the bonfire, tailgating parties, and anywhere else you’re going to be sitting still in cold weather for a long period of time.
Go big, soft, and thick on this one. Either buttons or a zipper are fine. Make sure the fit is right in the shoulders (the top of the seam where the sleeve meets the shoulder shouldn’t be drooping down your bicep), but don’t worry if it’s a little loose in the torso. You’ll be wearing it over other clothes anyway.
It’s like having a blanket that you wear, but you look like a stylish gent instead of the guy off the Snuggies box. And yeah, plenty of macho men have worn them, from Steve McQueen to John Wayne to Daniel Craig.