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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

New
New
HEIRLOME Patricia Sweater
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HEIRLOME

Patricia Sweater

$695

$1,390

FWRD

New
New
Amiya Nuvola Scarf And Sweater
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Amiya

Nuvola Scarf And Sweater

$1,050

FWRD

LE BOP Marina Pullover Sweater
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LE BOP

Marina Pullover Sweater

$138

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.
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

Jacquemus La Doudoune Capullo puffer jacket
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Jacquemus

La Doudoune Capullo puffer jacket

$1,015

$2,030

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.
Apparis Blair Mid-Length Coat
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Apparis

Blair Mid-Length Coat

$395

Shopbop

Moncler Flammette down coat
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Moncler

Flammette down coat

$2,210

Mytheresa

Apparis Blair Coat
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Apparis

Blair Coat

$395

Shopbop

New
New
Moncler Lombi quilted micro-ripstop down parka
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Moncler

Lombi quilted micro-ripstop down parka

$2,720

Net-a-Porter

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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.
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

Polo Ralph Lauren Cable-knit cotton cardigan
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Polo Ralph Lauren

Cable-knit cotton cardigan

$300

Mytheresa

TWP Chain Sweater Jacket
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TWP

Chain Sweater Jacket

$447.5

$895

Shopbop

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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

$129.5

$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

$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

$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.
New
New
A.L.C. Gwen studded leather midi skirt
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A.L.C.

Gwen studded leather midi skirt

$358

$895

Outnet

Balenciaga Leather midi skirt
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Balenciaga

Leather midi skirt

$4,690

Mytheresa

JOSEPH Blomfield leather midi skirt
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JOSEPH

Blomfield leather midi skirt

$1,046

$1,495

Mytheresa

JOSEPH Savana leather midi skirt
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JOSEPH

Savana leather midi skirt

$997

$1,425

Mytheresa

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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

Acne Studios Lessora Leather Jacket
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Acne Studios

Lessora Leather Jacket

$3,900

FWRD

Polo Ralph Lauren Shearling Aviator Jacket
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Polo Ralph Lauren

Shearling Aviator Jacket

$2,998

FWRD

Acne Studios Lella Leather Jacket
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Acne Studios

Lella Leather Jacket

$1,178

$3,100

FWRD

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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.
Etro Paisley silk top
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Etro

Paisley silk top

$328

$820

Mytheresa

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

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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.
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

Isabel Marant Ildred Boots
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Isabel Marant

Ildred Boots

$630

$1,050

Shopbop

GANNI Studs Crinkle Oleatex Low Boots
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GANNI

Studs Crinkle Oleatex Low Boots

$375

$625

Shopbop

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Shop More
Favorite Daughter The Millie Dress
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Favorite Daughter

The Millie Dress

$228

Shopbop

Guest In Residence Showtime Shirt Dress
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Guest In Residence

Showtime Shirt Dress

$357

$595

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

Varley Axel Rib Knit Midi Dress
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Varley

Axel Rib Knit Midi Dress

$178

Shopbop

New
New
Mango Perkins-neck knitted dress
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Mango

Perkins-neck knitted dress

$89.99

Mango

New
New
Mango Fitted sweater dress
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Mango

Fitted sweater dress

$59.99

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

$45.99

Mango

SIMKHAI Skyla Wrap Dress
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SIMKHAI

Skyla Wrap Dress

$445

Shopbop

New
New
Mango Devoré floral dress
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Mango

Devoré floral dress

$89.99

$149.99

Mango

KHAITE Oron ruched jersey midi dress
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KHAITE

Oron ruched jersey midi dress

$1,036

$1,480

Mytheresa

New
New
TOTEME Wool midi dress
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TOTEME

Wool midi dress

$342

$570

Net-a-Porter

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

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

New
New
Altuzarra Milda draped knitted midi dress
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Altuzarra

Milda draped knitted midi dress

$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

New
New
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

$815

Net-a-Porter

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

$693

$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

New
New
Mango Long halter-neck dress
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Mango

Long halter-neck dress

$69.99

Mango

ASTR the Label Tilde Sweater Dress
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ASTR the Label

Tilde Sweater Dress

$148

Shopbop

New
New
Veronica De Piante Viola stretch-knit turtleneck midi dress
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Veronica De Piante

Viola stretch-knit turtleneck midi dress

$486

$1,080

Outnet

New
New
Lemaire Belted wool-blend turtleneck midi dress
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Lemaire

Belted wool-blend turtleneck midi dress

$620

Net-a-Porter

Fforme + NET SUSTAIN Ainsley wool-blend midi dress
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Fforme

+ NET SUSTAIN Ainsley wool-blend midi dress

$1,200

$2,400

Net-a-Porter