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What to Wear for a Winter Weekend Getaway in Upstate NY

Expect brisk temperatures ranging from 20°F to 35°F (-6°C to 2°C) during an Upstate New York winter getaway. Pack cozy, insulating layers and durable shoes suitable for cold, possibly snowy weather. Choose a mix of comfortable daywear, chic casual pieces, and outerwear that delivers both warmth and style. If you have special activities planned—outdoor hikes, fireside lounging, or evenings out—let us know for even more targeted suggestions!
@chloelecareux
1
Chunky Knit Sweater
Chunky textured knits are in focus this season, providing both warmth and tactile interest—perfect for cozy cabin settings or exploring quaint towns.
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1
Chunky Knit Sweater
@chloelecareux
Chunky textured knits are in focus this season, providing both warmth and tactile interest—perfect for cozy cabin settings or exploring quaint towns.
New
New
Lovers and Friends x Bridget Jolene Knit Sweater
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Lovers and Friends

x Bridget Jolene Knit Sweater

$138

Revolve

HEIRLOME Patricia Sweater
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HEIRLOME

Patricia Sweater

$695

$1,390

FWRD

Amiya Nuvola Scarf And Sweater
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Amiya

Nuvola Scarf And Sweater

$1,050

FWRD

Marea Beach Sweater
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Marea

Beach Sweater

$100.8

$168

Shopbop

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@mmequeenb
2
Oversized Quilted Puffer Jacket
Stay warm and on-trend in an oversized puffer. Quilted details add style; insulation is essential for outdoor activities and protection against winter winds.
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2
Oversized Quilted Puffer Jacket
@mmequeenb
Stay warm and on-trend in an oversized puffer. Quilted details add style; insulation is essential for outdoor activities and protection against winter winds.
Acne Studios Logo down jacket
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Acne Studios

Logo down jacket

$1,408

$1,760

Mytheresa

IENKI IENKI Michlin quilted cotton-blend down jacket
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IENKI IENKI

Michlin quilted cotton-blend down jacket

$386

$1,544

Outnet

Balenciaga C-SHAPE puffer micro-faille jacket
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Balenciaga

C-SHAPE puffer micro-faille jacket

$3,290

Mytheresa

Prada Funnel-neck down and cotton coat
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Prada

Funnel-neck down and cotton coat

$3,050

Mytheresa

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@elborn_doris
3
Funnel-Neck Coat
Elevate your outerwear with a funnel-neck coat, a modern update that keeps your neck shielded from the chill. This silhouette is a Fall 2025 standout.
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3
Funnel-Neck Coat
@elborn_doris
Elevate your outerwear with a funnel-neck coat, a modern update that keeps your neck shielded from the chill. This silhouette is a Fall 2025 standout.
Source Unknown Wool-Cashmere Blend Coat, Black
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Source Unknown

Wool-Cashmere Blend Coat, Black

$1,900

Source Unknown

The Row Aurore oversized cotton canvas coat
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The Row

Aurore oversized cotton canvas coat

$3,500

Mytheresa

Source Unknown Boucle Flight Coat, Alabaster
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Source Unknown

Boucle Flight Coat, Alabaster

$580

Source Unknown

Apparis Blair Mid-Length Coat
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Apparis

Blair Mid-Length Coat

$395

Shopbop

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@sofiaboman
4
Textured Cable Knit Cardigan
Cardigans are back, and a cable knit offers layering versatility—throw it over tees or dresses for added warmth whether indoors or outdoors.
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4
Textured Cable Knit Cardigan
@sofiaboman
Cardigans are back, and a cable knit offers layering versatility—throw it over tees or dresses for added warmth whether indoors or outdoors.
Loro Piana Cable-knit cashmere-blend cardigan
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Loro Piana

Cable-knit cashmere-blend cardigan

$4,740

Net-a-Porter

Bottega Veneta Cable-knit wool cardigan
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Bottega Veneta

Cable-knit wool cardigan

$2,300

Mytheresa

Polo Ralph Lauren Cable-knit wool and cashmere cardigan
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Polo Ralph Lauren

Cable-knit wool and cashmere cardigan

$300

Mytheresa

Brunello Cucinelli Metallic cable-knit cardigan
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Brunello Cucinelli

Metallic cable-knit cardigan

$1,880

$4,700

Outnet

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@jellyjelly00
5
Straight-Leg 90s Cut Jeans
A denim staple that’s easy to style with bulky winter layers. The straight fit is practical for boots and flatters most body types.
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5
Straight-Leg 90s Cut Jeans
@jellyjelly00
A denim staple that’s easy to style with bulky winter layers. The straight fit is practical for boots and flatters most body types.
Lioness Alabama Jeans
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Lioness

Alabama Jeans

$110

Shopbop

New
New
Mango Matilda medium-rise straight-fit jeans
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Mango

Matilda medium-rise straight-fit jeans

$69.99

Mango

Good American Good Standard Bootcut Jeans
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Good American

Good Standard Bootcut Jeans

$164

Shopbop

ICON DENIM LA Blue Jeans
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ICON DENIM LA

Blue Jeans

$111

$185

Shopbop

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@deborabrosa
6
Wide-Leg Corduroy Trousers
Corduroy adds warmth and texture, and wide-leg silhouettes are big for Fall 2025. Perfect for comfy weekends with a subtle vintage touch.
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6
Wide-Leg Corduroy Trousers
@deborabrosa
Corduroy adds warmth and texture, and wide-leg silhouettes are big for Fall 2025. Perfect for comfy weekends with a subtle vintage touch.
Joe's Jeans The Mia Corduroy Pants
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Joe's Jeans

The Mia Corduroy Pants

$152.6

$218

Shopbop

Veronica De Piante Anya cotton-corduroy wide-leg pants
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Veronica De Piante

Anya cotton-corduroy wide-leg pants

$398

$995

Net-a-Porter

Nili Lotan Florence Corduroy Pants
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Nili Lotan

Florence Corduroy Pants

$315

$450

Shopbop

Apiece Apart Adi Wide Leg Corduroy Trousers
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Apiece Apart

Adi Wide Leg Corduroy Trousers

$172.5

$345

Shopbop

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@alvasperle
7
Leather Midi Skirt
A leather midi skirt provides a dressed-up option for casual dinners or exploring stylish towns. Easily layered over tights for extra warmth.
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7
Leather Midi Skirt
@alvasperle
A leather midi skirt provides a dressed-up option for casual dinners or exploring stylish towns. Easily layered over tights for extra warmth.
Brandon Maxwell The Avery paneled leather midi skirt
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Brandon Maxwell

The Avery paneled leather midi skirt

$1,608

$2,680

Net-a-Porter

FRAME The Midaxi croc-effect leather midi skirt
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FRAME

The Midaxi croc-effect leather midi skirt

$649

$1,298

Net-a-Porter

Marni Paneled crinkled-leather midi skirt
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Marni

Paneled crinkled-leather midi skirt

$3,200

Net-a-Porter

A.L.C. Marta Skirt
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A.L.C.

Marta Skirt

$895

Shopbop

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@alicecatherine
8
Shearling-Lined Work Jacket
This cozy hybrid outerwear piece offers rugged warmth with plush lining—a trending statement and practical pick for wintry excursions.
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8
Shearling-Lined Work Jacket
@alicecatherine
This cozy hybrid outerwear piece offers rugged warmth with plush lining—a trending statement and practical pick for wintry excursions.
Schott Waxy Vintage Buffalo Trucker
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Schott

Waxy Vintage Buffalo Trucker

$1,150

FWRD

Giuliva Heritage + NET SUSTAIN Daria shearling jacket
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Giuliva Heritage

+ NET SUSTAIN Daria shearling jacket

$1,468

$3,670

Net-a-Porter

NOUR HAMMOUR Portia Jacket
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NOUR HAMMOUR

Portia Jacket

$1,600

FWRD

Lovers and Friends James Faux Leather Jacket
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Lovers and Friends

James Faux Leather Jacket

$279

Revolve

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@lemanm
9
Bohemian Long Sleeve Peasant Blouse
Billowy peasant blouses pair well with jeans or trousers and bring a soft, playful contrast to heavier winter layers. Boho details are still trending.
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9
Bohemian Long Sleeve Peasant Blouse
@lemanm
Billowy peasant blouses pair well with jeans or trousers and bring a soft, playful contrast to heavier winter layers. Boho details are still trending.
THE GREAT. The Journey embroidered cotton-gauze top
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THE GREAT.

The Journey embroidered cotton-gauze top

$140

$350

Net-a-Porter

Velvet Tie-neck cotton blouse top
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Velvet

Tie-neck cotton blouse top

$170

$284

Mytheresa

Marant Étoile Lynne embroidered cotton blouse
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Marant Étoile

Lynne embroidered cotton blouse

$427

$610

Mytheresa

FRAME Cotton and linen denim top
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FRAME

Cotton and linen denim top

$210

$350

Mytheresa

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@veneti.a
10
Slouchy Boots
A Fall 2025 footwear trend, slouchy boots are fashionable and functional for winter. They’re roomy for thick socks and comfy enough for walking snowy streets.
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10
Slouchy Boots
@veneti.a
A Fall 2025 footwear trend, slouchy boots are fashionable and functional for winter. They’re roomy for thick socks and comfy enough for walking snowy streets.
Isabel Marant Ademe leather ankle boots
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Isabel Marant

Ademe leather ankle boots

$480

$960

Net-a-Porter

Isabel Marant Ademe leather ankle boots
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Isabel Marant

Ademe leather ankle boots

$480

$960

Net-a-Porter

JIMMY CHOO Biker suede mid-calf boots
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JIMMY CHOO

Biker suede mid-calf boots

$1,255

Mytheresa

Dolce&Gabbana Leather biker boots
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Dolce&Gabbana

Leather biker boots

$965

Mytheresa

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Shop More
Vince Cozy Long Sleeve Funnel Neck Dress
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Vince

Cozy Long Sleeve Funnel Neck Dress

$268

Shopbop

Favorite Daughter The Millie Dress
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Favorite Daughter

The Millie Dress

$228

Shopbop

Cult Gaia Carline Dress
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Cult Gaia

Carline Dress

$698

Shopbop

Show Me Your Mumu Lorraine Maxi Sweater Dress
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Show Me Your Mumu

Lorraine Maxi Sweater Dress

$188

Shopbop

Staud Vanya Dress
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Staud

Vanya Dress

$450

Shopbop

Splendid Splendid x Cella Jane Off The Shoulder Sweater Dress
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Splendid

Splendid x Cella Jane Off The Shoulder Sweater Dress

$138

Shopbop

rag & bone Loren Long Belted Dress
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rag & bone

Loren Long Belted Dress

$498

Shopbop

Varley Axel Rib Knit Midi Dress
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Varley

Axel Rib Knit Midi Dress

$124.6

$178

Shopbop

New
New
Mango Perkins-neck knitted dress
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Mango

Perkins-neck knitted dress

$69.99

$89.99

Mango

L'Academie Deena Maxi Dress
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L'Academie

Deena Maxi Dress

$151

$218

Revolve

New
New
Mango Midi-dress with back neckline
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Mango

Midi-dress with back neckline

$22.99

$45.99

Mango

SIMKHAI Skyla Wrap Dress
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SIMKHAI

Skyla Wrap Dress

$445

Shopbop

KHAITE Oron ruched jersey midi dress
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KHAITE

Oron ruched jersey midi dress

$1,036

$1,480

Mytheresa

Jardin des Orangers Wool and cashmere wrap dress
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Jardin des Orangers

Wool and cashmere wrap dress

$346

$495

Mytheresa

o.p.t Nicole Dress
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o.p.t

Nicole Dress

$198

Shopbop

Aya Muse Hale one-shoulder silk-blend maxi dress
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Aya Muse

Hale one-shoulder silk-blend maxi dress

$684

$855

Mytheresa

KHAITE Jaime cashmere maxi dress
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KHAITE

Jaime cashmere maxi dress

$875

$1,250

Mytheresa

Solid & Striped The Dora Dress
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Solid & Striped

The Dora Dress

$278

Shopbop

o.p.t Nicole Dress
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o.p.t

Nicole Dress

$198

Shopbop

Magda Butrym Wool, silk, and cashmere maxi dress
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Magda Butrym

Wool, silk, and cashmere maxi dress

$2,072

$2,590

Mytheresa

Madison the Label Russo Maxi Dress
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Madison the Label

Russo Maxi Dress

$159

Shopbop

Ralph Lauren Collection Abrillong cashmere-blend midi dress
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Ralph Lauren Collection

Abrillong cashmere-blend midi dress

$2,790

Mytheresa

Isabel Marant Ormany jersey bouclé maxi dress
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Isabel Marant

Ormany jersey bouclé maxi dress

$695

$1,390

Mytheresa

Marant Étoile Jelina gathered jersey maxi dress
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Marant Étoile

Jelina gathered jersey maxi dress

$357

$595

Mytheresa

Brunello Cucinelli Cashmere midi dress
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Brunello Cucinelli

Cashmere midi dress

$2,765

$3,950

Mytheresa

Lemaire Belted sweater dress
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Lemaire

Belted sweater dress

$345

$690

Mytheresa

Altuzarra Milda draped knitted midi dress
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Altuzarra

Milda draped knitted midi dress

$748

$1,495

Net-a-Porter

Lemaire Trompe-l'œil cotton midi dress
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Lemaire

Trompe-l'œil cotton midi dress

$507

$1,015

Mytheresa

Loro Piana Merano cashmere sweater dress
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Loro Piana

Merano cashmere sweater dress

$3,200

Mytheresa

SIMKHAI Hathaway scarf-effect draped wool and recycled cashmere-blend midi dress
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SIMKHAI

Hathaway scarf-effect draped wool and recycled cashmere-blend midi dress

$489

$815

Net-a-Porter

Meshki Baxter Off Shoulder Fluffy Knit Midi Dress - Taupe Marle
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Meshki

Baxter Off Shoulder Fluffy Knit Midi Dress - Taupe Marle

$129

Meshki

Marant Étoile Salomon cotton jersey sweatshirt dress
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Marant Étoile

Salomon cotton jersey sweatshirt dress

$367

$525

Mytheresa

Isabel Marant Salina Maxi Dress
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Isabel Marant

Salina Maxi Dress

$594

$990

Shopbop

Entire Studios Draped wool maxi dress
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Entire Studios

Draped wool maxi dress

$297

$425

Mytheresa

New
New
Altuzarra Cuddy ribbed cashmere maxi dress
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Altuzarra

Cuddy ribbed cashmere maxi dress

$638

$1,595

Net-a-Porter

Seven Wonders Greta One Shoulder Knit Maxi Dress
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Seven Wonders

Greta One Shoulder Knit Maxi Dress

$149

Shopbop

ASTR the Label Tilde Sweater Dress
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ASTR the Label

Tilde Sweater Dress

$148

Shopbop

SIMKHAI Skyla Cotton Cashmere Wrap Dress
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SIMKHAI

Skyla Cotton Cashmere Wrap Dress

$445

SIMKHAI

New
New
Lemaire Belted wool-blend turtleneck midi dress
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Lemaire

Belted wool-blend turtleneck midi dress

$372

$620

Net-a-Porter

Fforme + NET SUSTAIN Ainsley wool-blend midi dress
save

Fforme

+ NET SUSTAIN Ainsley wool-blend midi dress

$960

$2,400

Net-a-Porter