20+ NYC Fall Outfits You'll Love to Wear on Your Next Trip

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There’s something about New York in the fall that makes getting dressed feel easy. The air snaps a little, the light goes golden, and suddenly a great sweater, straight-leg denim, and a sharp jacket do all the heavy lifting. You don’t have to overthink it – the city’s crisp sidewalks and changing trees handle half the styling for you.

I’ve always been a fall-outfits person. More layers, more texture, more excuses to wear a great coat and a scarf you “accidentally” bought in September. No heatwave chaos – just cozy, polished, and a little romantic.

These are the looks I reach for on repeat in NYC – unfussy, comfortable for long city walks, and still chic when you slide into a booth for a last-minute dinner. Effortless, slightly thrown together, and totally wearable for real life.

Here are my absolute favorite NYC Fall Outfits I’m loving right now. I have a feeling you’ll be into them too.

25+ NYC Fall Outfits You’ll Love

Brown Wool Poncho Coat + Straight-Leg Jeans + Black Longsleeve + Ankle Boots

Peak October energy: a wool poncho you can cocoon into on a breezy morning in the Village. It’s cinematic in the best way.

With sturdy denim and ankle boots, you’re set for bookstore laps and leaf-crunching walks along tree-lined blocks.

Grey Baggy Jeans + Brown Adidas Sambas + Brown Sweater

Off-duty downtown, but cozy. Warm browns + relaxed denim + classic sneakers – perfect for coffee in Nolita and a lazy gallery stroll in Chelsea.

Effortless, practical, and very “yes, I live here.”

Striped Cute Shirt + Navy Blue Flared Jeans + Ankle Boots

Stripes are an NYC fall staple – a little preppy, a little bookish. Flares add retro charm; ankle boots keep it city-ready.

Ideal for museum Sundays and a hot cider detour on the way home.

Khaki Green Suede Jacket + Black Jeans + Black Longsleeve

Suede season is here. This combo reads polished without trying – throw a scarf in your bag for when the sun dips behind the brownstones.

Sharp enough for a meeting, easy enough for a downtown wander.

White Top + Navy Straight-Leg Jeans + Leather Brown Jacket

The capsule classic: navy + cognac. It turns a quick coffee run into a casual catch-up and looks great against every autumn backdrop.

Navy Plaid Mini Skirt + Navy Jean Jacket + White Turtleneck Sweater

Preppy with a wink. Add tights when the temperature dips and channel your inner Upper West Side heroine.

Yes, a takeaway latte is the finishing accessory.

Wool Beige Turtleneck Pullover + Grey Baggy Jeans + Ankle Boots

The fall uniform: a real wool knit, relaxed denim, ankle boots. Throw a trench or topcoat over it and you’re set for the day.

I wore this to Bryant Park and got more compliments than the pumpkin display.

Grey Wool Cardigan + Jeans + White Tank Top + Ballet Flats

Transitional perfection. Morning chill, afternoon sun – cardigan on, cardigan off. Swap flats for loafers if you’re walking the bridge.

Cream Zip Sweater + Light-Blue Jeans + Uggs

Cozy-girl Soho run: zip knit, broken-in denim, and comfy boots for bodega coffee and a Trader Joe’s line you definitely didn’t plan for.

Burgundy Sweater + Cream Scarf + Light Blue Jeans

Burgundy was made for October. Add a cream scarf and even grey days feel like golden hour on the Williamsburg waterfront.

Beige Knit Cardigan + Navy Blue Jeans + White Shirt

No-fuss, go-anywhere. Wear to Tribeca brunch, then somehow end up at a friend’s place in Brooklyn with a bottle of red. That’s fall magic.

White Knit Sweater + Brown Mini Skirt + Brown High-Leg Boots + Brown Leather Jacket

Main-character October. Picture crunchy leaves, a moody playlist, and a latte that warms your hands between photos.

10/10 with tights when the wind picks up.

Grey Pleated Mini Skirt + Grey Wool Sweater + High-Leg Boots

Monochrome grey is a fall sleeper hit. Soft textures, tall boots, and an easy stride from gallery to wine bar.

Burgundy Leather Mini Skirt + Beige Sweater + Brown High-Leg Boots

Going-out, but autumnal. Polished leather meets cozy knit – festive without trying too hard.

Dark Grey Baggy Jeans + White Top + Striped Navy Cardigan + Uggs

The clothing equivalent of a lazy Sunday in the West Village. Three errands, two cappuccinos, zero complaints. Bonus points for a tote full of apples from the market.

Lorelai Gilmore Vibes with Black Leather Jacket + Flared Jeans + Burgundy Knit Pullover

Flares, leather, sass – add a takeaway coffee and walk like you’ve got the best line in the episode. Peak leaf-peeping look for Riverside Park.

Retro headphones recommended.

Cream Knit Pullover + Brown Suede Jacket + Straight-Leg Jeans

Soft, timeless, endlessly wearable. Works with a trench at 10am and a wool coat at 8pm. Compliments guaranteed – even from friendly dogs.

Suede + October sidewalks = a love story (just watch the puddles).

Denim Mini Skirt + White Top + Cream Cardigan + Brown Boots

Cozy cardigan supremacy. Add tights when it’s chilly and detour for cider doughnuts. This is a brunch-to-bookshop uniform.

Navy Blue Mini Skirt + Brown Boots + Green Cardigan + White Top

Earthy tones that still feel polished. Forest-green cardigan = park-walk vibes with city polish.

Try not to adopt another plant on the way home. (No promises.)

Brown Suede Jacket + White Top + White Flowy Mini Skirt + Brown Boots

Romantic fall pairing – suede + swish. Wear for a slow ramble through Central Park and inevitably end up at a farmer’s market.

Beige Pullover + Black Leather Jacket + Denim Mini Skirt + Brown Boots

Leather + knit is the power couple of October. Add opaque tights, call a friend, and meet for mulled wine after work.

Flared Jeans + Off-Shoulder Black Top + Brown Leather Jacket

Confident, a little flirty, very downtown.

FAQ:

How should I dress in NYC in the fall?

If I’m in New York during fall, I always start with layers. You might wake up to chilly air, be sweating by lunch, and need a jacket again after sunset.

Think jeans or wide-leg trousers, a soft sweater or long-sleeve tee, and a jacket you can throw over your arm when it warms up. The trick is shoes – go for something comfortable but city-chic, like ankle boots or clean white sneakers.

Is fall cold in NYC?

Early fall? Not really – September can still feel a little summery.

But by mid-October, you’ll start getting crisp mornings and those golden, windy afternoons that call for a cozy scarf. November can get properly chilly, so you’ll be glad to have a wool coat or a warm jacket in your suitcase.

How to dress when visiting NYC?

If you don’t want to scream “tourist,” stick to classic, versatile pieces you can mix and match.

New Yorkers love neutral colors, well-cut coats, and shoes you can walk in for hours. Personally, I like to wear dark jeans, a blazer or leather jacket, and a good crossbody bag – it works for both sightseeing and a last-minute dinner reservation.

Do I need a jacket in New York in September?

If you’re there in early September, you can probably skip a heavy jacket – a denim jacket or light cardigan will do the job.

Late September tho, starts getting cooler at night. If you plan to be out after dark or near the waterfront, bring a medium-weight jacket just in case.

20+ NYC Fall Outfits You’ll Love to Wear on Your Next Trip