A seasonally-appropriate tweed sport coat.
Fall and tweed go hand-in-hand, making a tweed sport coat an absolute necessity.
You don't have to go for a classic brown or tan, either. This smart gray blazer from J Crew is perfect for a night on the town when you need an extra layer.
A denim jacket will become your weekend go-to.
For the early days of fall, a casual-cool denim jacket is all you need. Later on it will be an essential layering piece for tons of outfits.
The Levi's Denim Trucker Jacket is the indisputable icon in this segment.
A puffer jacket for days when both the leaves and the mercury fall.
Puffer jackets are that perfect transitional layer for gray mornings. The heavy down insulation keeps you warm without adding the bulk of a full parka or winter coat.
Patagonia's down-filled, quilted shell jacket is a great option that comes in a variety of colors.
A patterned sweater adds personality.
This Fair Isle pattern by Polo Ralph Lauren is fantastic, but if it's not up your alley, find one that speaks to you.
Go anywhere with a chunky wool sweater.
A chunky cardigan will be your best friend this winter. It's versatile and, as an outer layer, it keeps you warm well into November.
This chunky knit cardigan from Everlane perfectly fits the bill.
Give your denim a rest and give a brighter color blue a chance.
Just because the days are getting shorter doesn't mean your wardrobe needs to go dark, too. Sure, denim is great in the fall, but even your most trusted pair needs a rest once in a while.
Enter alternative blues — like these J. Crew pants in Montclair Navy.
A workman's denim shirt adds a masculine vibe.
There's no better time to show off your work-inspired wardrobe than the fall.
This Club Monaco denim shirt is the perfect candidate; it mixes well with black denim, spicy pumpkin drinks, and colorful foliage.
A warm and cozy flannel will be the most comfortable item in your closet.
If you think flannels are just for lumberjacks, you might want to think again.
This Oliver Spencer flannel is beautiful and minimalist. It goes equally well under a blazer or a denim jacket.
A dependable wool suit that fits like a glove.
We probably don't need to tell you this, but you should have at least one suit you feel amazing in for fall/winter.
This Ludlow suit in Italian wool by J. Crew is a winner by our standards, but suit shopping is a personal thing, so find a brand or tailor that fits with your style and body type.
An on-trend but not ostentatious knit tie.
Though more casual than a traditional tie, knit kneckwear is now a cold weather staple.
The Tie Bar makes a great knit tie for a reasonable $25. Get one in every color.
A chukka-style boot for your weekend wardrobe.
Loafers and moccasins are great, but eventually you're going to want to cover your ankles.
These Clark's Desert Boots strike the perfect balance: they're relatively thin and not too clunky or heavy. The slippery soles won't work in winter, but until the snow falls they'll serve you well.
Brogues for the modern gentleman.
Something about perforated leather and the crunch of freshly fallen leaves just screams autumn.
This model, the Hubert by Jack Erwin, is a longwing blucher that puts a modern spin on the classic brogue.
Colorful wool socks just for fun.
We're big fans of wool, but for fall, you don't have to think that warm yet.
This geometric Fair Isle design from Brooks Brothers is a great choice. But like we said about the patterned sweater, it's all about personal style here.
A solid-colored wool scarf goes with everything.
This is the accessory everyone forgets about — until they need it. Keep your neck warm this winter with an oversize wool scarf.
Don't forget the getaway bag.
Wherever this fall takes you, be sure you're prepared with an appropriate bag.
Everlane makes a nice size Weekender for short getaways.