Rerun

My Size

What to Wear for a Winter Weekend Getaway in Upstate NY

Upstate New York in winter sees temperatures in the low 20s to high 30s °F, calling for warm, layered outfits that balance function and style. Think insulated outerwear, cozy knits, and practical yet chic footwear. The right layers will keep you comfortable indoors and prepared for snowy, breezy outings. If you have more details about your itinerary, style preferences, or budget, let me know for truly personalized suggestions!

@kieunse

Insulated Down Parka

An insulated parka offers essential protection against Upstate NY’s cold winds and potential snow. Choose a longer length for added warmth and a timeless, versatile appearance.

See all

THE NORTH FACE

Aconcagua Parka

$250

Revolve

THE NORTH FACE

Women's Nuptse Parka

$450

Shopbop

Canada Goose

Junction Parka

$1,275

Shopbop

Prada

Re-Nylon shearling-trimmed down coat

$5,300

Mytheresa

Save The Duck

Samantha Coat

$598

Shopbop

Whitespace

Insulated Parka Jacket

$500

Revolve

MONCLER GRENOBLE

Rochelairs down coat

$2,680

Mytheresa

Canada Goose

Chelsea Parka

$1,350

Shopbop

Moncler

Erysimum hooded down coat

$2,700

Mytheresa

Cecilie Bahnsen

The North Face x Cecilie Bahnsen Himalayan Parka

$1,250

Shopbop

Rick Owens

X Moncler Flight Parka

$2,245

FWRD

Canada Goose

Elmvale Parka

$1,175

Shopbop

Canada Goose

Shelburne cotton-blend down parka

$1,475

Mytheresa

rag & bone

Taki Convertible Jacket

$678

Shopbop

Canada Goose

Clair Coat

$1,050

Shopbop

Yves Salomon

Hooded shearling-trimmed down coat

$1,324

$1,655

Mytheresa

THE NORTH FACE
Aconcagua Parka
$250
Revolve
THE NORTH FACE
Women's Nuptse Parka
$450
Shopbop
Canada Goose
Junction Parka
$1,275
Shopbop
Prada
Re-Nylon shearling-trimmed down coat
$5,300
Mytheresa
Save The Duck
Samantha Coat
$598
Shopbop
Whitespace
Insulated Parka Jacket
$500
Revolve
MONCLER GRENOBLE
Rochelairs down coat
$2,680
Mytheresa
Canada Goose
Chelsea Parka
$1,350
Shopbop
Moncler
Erysimum hooded down coat
$2,700
Mytheresa
Cecilie Bahnsen
The North Face x Cecilie Bahnsen Himalayan Parka
$1,250
Shopbop
Rick Owens
X Moncler Flight Parka
$2,245
FWRD
Canada Goose
Elmvale Parka
$1,175
Shopbop
Canada Goose
Shelburne cotton-blend down parka
$1,475
Mytheresa
rag & bone
Taki Convertible Jacket
$678
Shopbop
Canada Goose
Clair Coat
$1,050
Shopbop
Yves Salomon
Hooded shearling-trimmed down coat
$1,324
$1,655
Mytheresa

Insulated Down Parka

@kieunse

An insulated parka offers essential protection against Upstate NY’s cold winds and potential snow. Choose a longer length for added warmth and a timeless, versatile appearance.

THE NORTH FACE

Aconcagua Parka

$250

Revolve

THE NORTH FACE

Women's Nuptse Parka

$450

Shopbop

Canada Goose

Junction Parka

$1,275

Shopbop

Prada

Re-Nylon shearling-trimmed down coat

$5,300

Mytheresa

Thermal Base Layer Set

Layering starts here: moisture-wicking thermal tops and leggings keep your core warm without bulk, making all-day comfort achievable whether you’re hiking, exploring, or relaxing indoors.

See all

Halfdays

Fay Merino Top

$130

Shopbop

TOTEME

Jacquard-knit top

$128

$320

Net-a-Porter

Varley

Always Warm Mock Neck Baselayer

$98

Shopbop

Bogner Fire+Ice

Bogner Fire + Ice x LoveShackFancy Margo Top

$250

Shopbop

ÉTERNE

Oversized Thermal Top

$175

Shopbop

PERFECT MOMENT

1/4 Zip Base Layer Top

$250

Shopbop

Alo Yoga

Alosoft Finesse jersey top

$100

Mytheresa

Beach Riot

Kamara Top

$138

Shopbop

Halfdays

Fay Merino Top

$130

Shopbop

PERFECT MOMENT

Printed Base Layer Leggings

$225

Shopbop

Polo Ralph Lauren

Base Layer Leggings

$68

Shopbop

Rhone

Houndstooth Seamless Quarter Zip

$128

Shopbop

PERFECT MOMENT

Jazzy jacquard-knit wool and cashmere-blend hoodie

$425

$850

Net-a-Porter

SET

Airluxe Breathe Long Sleeve Top

$70

Shopbop

Splits59

Stevie Half Zip Top

$134

Shopbop

SET

Airluxe Breathe Long Sleeve Top

$70

Shopbop

Halfdays
Fay Merino Top
$130
Shopbop
TOTEME
Jacquard-knit top
$128
$320
Net-a-Porter
Varley
Always Warm Mock Neck Baselayer
$98
Shopbop
Bogner Fire+Ice
Bogner Fire + Ice x LoveShackFancy Margo Top
$250
Shopbop
ÉTERNE
Oversized Thermal Top
$175
Shopbop
PERFECT MOMENT
1/4 Zip Base Layer Top
$250
Shopbop
Alo Yoga
Alosoft Finesse jersey top
$100
Mytheresa
Beach Riot
Kamara Top
$138
Shopbop
Halfdays
Fay Merino Top
$130
Shopbop
PERFECT MOMENT
Printed Base Layer Leggings
$225
Shopbop
Polo Ralph Lauren
Base Layer Leggings
$68
Shopbop
Rhone
Houndstooth Seamless Quarter Zip
$128
Shopbop
PERFECT MOMENT
Jazzy jacquard-knit wool and cashmere-blend hoodie
$425
$850
Net-a-Porter
SET
Airluxe Breathe Long Sleeve Top
$70
Shopbop
Splits59
Stevie Half Zip Top
$134
Shopbop
SET
Airluxe Breathe Long Sleeve Top
$70
Shopbop

Thermal Base Layer Set

Layering starts here: moisture-wicking thermal tops and leggings keep your core warm without bulk, making all-day comfort achievable whether you’re hiking, exploring, or relaxing indoors.

Halfdays

Fay Merino Top

$130

Shopbop

TOTEME

Jacquard-knit top

$128

$320

Net-a-Porter

Varley

Always Warm Mock Neck Baselayer

$98

Shopbop

Bogner Fire+Ice

Bogner Fire + Ice x LoveShackFancy Margo Top

$250

Shopbop

@fredrika_ekerot

Chunky Wool or Cashmere Sweater

A thick knit sweater in wool or cashmere offers both insulation and elevated style. Pair with jeans or leggings for cozy downtime or cafe visits.

See all

Rachel Comey

Prescot Sweater

$311.5

$445

Shopbop

Bottega Veneta

Cable-knit wool sweater

$2,200

Mytheresa

Gabriela Hearst

Larenzo cashmere and wool sweater

$1,183

$1,690

Mytheresa

KHAITE

Natt Sweater in Sepia

$2,600

KHAITE

Milo Sweater in Indigo

$1,280

KHAITE

Jardin des Orangers

Wool and cashmere sweater

$368

$460

Mytheresa

KHAITE

Wolfe cashmere sweater

$1,176

$1,680

Net-a-Porter

Jardin des Orangers

Oversized wool and cashmere sweater

$650

Mytheresa

KHAITE

Mae Sweater in Warm Grey

$1,580

KHAITE

Gabriela Hearst

Lawrence cashmere sweater

$1,638

$2,340

Mytheresa

Brunello Cucinelli

Wool and cashmere sweater

$1,950

$3,900

Mytheresa

Extreme Cashmere

Lovely ribbed-knit cashmere sweater

$1,214

Mytheresa

La Ligne

Solid Marin Sweater

$350

Shopbop

LISA YANG

Julina cashmere turtleneck sweater

$860

Mytheresa

Brunello Cucinelli

Cashmere sweater

$3,500

$5,000

Mytheresa

The Row

Ophelia wool and cashmere sweater

$1,550

Mytheresa

Rachel Comey
Prescot Sweater
$311.5
$445
Shopbop
Bottega Veneta
Cable-knit wool sweater
$2,200
Mytheresa
Gabriela Hearst
Larenzo cashmere and wool sweater
$1,183
$1,690
Mytheresa
KHAITE
Natt Sweater in Sepia
$2,600
KHAITE
KHAITE
Milo Sweater in Indigo
$1,280
KHAITE
Jardin des Orangers
Wool and cashmere sweater
$368
$460
Mytheresa
KHAITE
Wolfe cashmere sweater
$1,176
$1,680
Net-a-Porter
Jardin des Orangers
Oversized wool and cashmere sweater
$650
Mytheresa
KHAITE
Mae Sweater in Warm Grey
$1,580
KHAITE
Gabriela Hearst
Lawrence cashmere sweater
$1,638
$2,340
Mytheresa
Brunello Cucinelli
Wool and cashmere sweater
$1,950
$3,900
Mytheresa
Extreme Cashmere
Lovely ribbed-knit cashmere sweater
$1,214
Mytheresa
La Ligne
Solid Marin Sweater
$350
Shopbop
LISA YANG
Julina cashmere turtleneck sweater
$860
Mytheresa
Brunello Cucinelli
Cashmere sweater
$3,500
$5,000
Mytheresa
The Row
Ophelia wool and cashmere sweater
$1,550
Mytheresa

Chunky Wool or Cashmere Sweater

@fredrika_ekerot

A thick knit sweater in wool or cashmere offers both insulation and elevated style. Pair with jeans or leggings for cozy downtime or cafe visits.

Rachel Comey

Prescot Sweater

$311.5

$445

Shopbop

Bottega Veneta

Cable-knit wool sweater

$2,200

Mytheresa

Gabriela Hearst

Larenzo cashmere and wool sweater

$1,183

$1,690

Mytheresa

KHAITE

Natt Sweater in Sepia

$2,600

KHAITE

@lisonseb

Fleece-Lined Leggings or Thermal Pants

Stay warm during outdoor activities with leggings or pants lined in fleece or technical thermals—they fit seamlessly under skirts or dresses as well.

See all

Polo Ralph Lauren

Travelers Leggings

$68

Shopbop

Frankies Bikinis

Milo Cloud Knit Capri Pant

$140

Revolve

Wolford

Perfect Fit Leggings

$295

Shopbop

Bogner Fire+Ice

Bogner Fire + Ice x LoveShackFancy Lovely Leggings

$190

Shopbop

Helsa

Corinne Footed Legging

$248

Revolve

Commando

Perfect Control Ankle Leggings

$118

Shopbop

SER.O.YA

Mish Knit Legging

$248

Revolve

Another Tomorrow

Stretch-LENZING™ Lyocell leggings

$175

$350

Net-a-Porter

437

The V Legging

$95

Revolve

Commando

Fast Track Leggings

$138

Shopbop

Sweaty Betty

Modal Jacquard Base Layer Ankle Leggings

$78

Shopbop

Naked Cashmere

TULSA RIBBED LEGGINGS

$295

Naked Cashmere

Wolford

Scuba Leggings

$170

Revolve

ÉTERNE

High Rise Legging

$185

FWRD

Halfdays

Hallie Merino Wool Leggings

$130

Shopbop

LESET

Rio Stirrup Pant

$200

Revolve

Polo Ralph Lauren
Travelers Leggings
$68
Shopbop
Frankies Bikinis
Milo Cloud Knit Capri Pant
$140
Revolve
Wolford
Perfect Fit Leggings
$295
Shopbop
Bogner Fire+Ice
Bogner Fire + Ice x LoveShackFancy Lovely Leggings
$190
Shopbop
Helsa
Corinne Footed Legging
$248
Revolve
Commando
Perfect Control Ankle Leggings
$118
Shopbop
SER.O.YA
Mish Knit Legging
$248
Revolve
Another Tomorrow
Stretch-LENZING™ Lyocell leggings
$175
$350
Net-a-Porter
437
The V Legging
$95
Revolve
Commando
Fast Track Leggings
$138
Shopbop
Sweaty Betty
Modal Jacquard Base Layer Ankle Leggings
$78
Shopbop
Naked Cashmere
TULSA RIBBED LEGGINGS
$295
Naked Cashmere
Wolford
Scuba Leggings
$170
Revolve
ÉTERNE
High Rise Legging
$185
FWRD
Halfdays
Hallie Merino Wool Leggings
$130
Shopbop
LESET
Rio Stirrup Pant
$200
Revolve

Fleece-Lined Leggings or Thermal Pants

@lisonseb

Stay warm during outdoor activities with leggings or pants lined in fleece or technical thermals—they fit seamlessly under skirts or dresses as well.

Polo Ralph Lauren

Travelers Leggings

$68

Shopbop

Frankies Bikinis

Milo Cloud Knit Capri Pant

$140

Revolve

Wolford

Perfect Fit Leggings

$295

Shopbop

Bogner Fire+Ice

Bogner Fire + Ice x LoveShackFancy Lovely Leggings

$190

Shopbop

@mihamcqueen

Waterproof Insulated Snow Boots

High-traction, waterproof snow boots protect against snow and icy sidewalks, keeping feet warm and dry for winter walks or exploring town.

See all

Sorel

Out N About IV Chillz Boots

$140

Shopbop

BOGNER

La Plagne lace-up snow boots

$325

Mytheresa

Prada

Re-Nylon gabardine snow boots

$1,390

Mytheresa

BOGNER

Chamonix 11 suede ankle boots

$620

Mytheresa

BOGNER

La Plagne snow boots

$325

Mytheresa

Inuikii

Technical Performance snow boots

$290

Mytheresa

Sorel

Caribou Horizon Gtx

$350

FWRD

Hunter Boots

Maribel S3 Boots

$180

Shopbop

GOLDBERGH

Snowy leopard-print snow boots

$680

Mytheresa

MOON BOOT

LTrack Low snow boots

$240

Mytheresa

GOLDBERGH

Frederica snow boots

$680

Mytheresa

BOGNER

La Plagne lace-up snow boots

$350

Mytheresa

BOGNER

Chamonix shearling-lined suede ankle boots

$710

Net-a-Porter

MOON BOOT

Icon Nylon Boots

$240

Shopbop

Miu Miu

Padded knee-high nylon boots

$1,470

Mytheresa

BOGNER

Chamonix shearling-trimmed suede snow boots

$690

Mytheresa

Sorel
Out N About IV Chillz Boots
$140
Shopbop
BOGNER
La Plagne lace-up snow boots
$325
Mytheresa
Prada
Re-Nylon gabardine snow boots
$1,390
Mytheresa
BOGNER
Chamonix 11 suede ankle boots
$620
Mytheresa
BOGNER
La Plagne snow boots
$325
Mytheresa
Inuikii
Technical Performance snow boots
$290
Mytheresa
Sorel
Caribou Horizon Gtx
$350
FWRD
Hunter Boots
Maribel S3 Boots
$180
Shopbop
GOLDBERGH
Snowy leopard-print snow boots
$680
Mytheresa
MOON BOOT
LTrack Low snow boots
$240
Mytheresa
GOLDBERGH
Frederica snow boots
$680
Mytheresa
BOGNER
La Plagne lace-up snow boots
$350
Mytheresa
BOGNER
Chamonix shearling-lined suede ankle boots
$710
Net-a-Porter
MOON BOOT
Icon Nylon Boots
$240
Shopbop
Miu Miu
Padded knee-high nylon boots
$1,470
Mytheresa
BOGNER
Chamonix shearling-trimmed suede snow boots
$690
Mytheresa

Waterproof Insulated Snow Boots

@mihamcqueen

High-traction, waterproof snow boots protect against snow and icy sidewalks, keeping feet warm and dry for winter walks or exploring town.

Sorel

Out N About IV Chillz Boots

$140

Shopbop

BOGNER

La Plagne lace-up snow boots

$325

Mytheresa

Prada

Re-Nylon gabardine snow boots

$1,390

Mytheresa

BOGNER

Chamonix 11 suede ankle boots

$620

Mytheresa

@jeanwang

Turtleneck Sweater Dress

A cozy sweater dress with a turtleneck makes cold-weather dressing feel effortless and refined. Style with leggings and knee-high boots for a polished daytime look.

See all

Veronica Beard

Wool and cashmere sweater dress

$536

$670

Mytheresa

Jardin des Orangers

Wool and cashmere sweater dress

$400

$500

Mytheresa

Lemaire

Turtleneck wool-blend midi dress

$417

$695

Mytheresa

Brunello Cucinelli

Cashmere midi dress

$3,360

$4,800

Mytheresa

Max Mara

Trudy wool turtleneck sweater dress

$675

$965

Mytheresa

Jil Sander

Cashmere turtleneck midi dress

$1,254

$2,090

Mytheresa

Brunello Cucinelli

Bead-embellished wool-blend jersey turtleneck midi dress

$1,398

$3,495

Outnet

Victoria Beckham

Wool-blend sweater dress

$903

$1,290

Mytheresa

Lemaire

Trompe l'œil wool-blend midi dress

$486

$695

Mytheresa

Jil Sander

Knitted cashmere midi dress

$1,254

$2,090

Mytheresa

Alaïa

Faux shearling-trimmed virgin wool midi dress

$3,090

Mytheresa

Lemaire

Turtleneck wool-blend midi dress

$486

$695

Mytheresa

LESET

Lauren turtleneck minidress

$144

$240

Mytheresa

Sablyn

Gab Turtleneck Rib Dress

$375

Shopbop

Missoni

Zigzag midi dress

$1,128

$1,410

Mytheresa

Veronica De Piante

Viola stretch-knit turtleneck midi dress

$486

$1,080

Outnet

Veronica Beard
Wool and cashmere sweater dress
$536
$670
Mytheresa
Jardin des Orangers
Wool and cashmere sweater dress
$400
$500
Mytheresa
Lemaire
Turtleneck wool-blend midi dress
$417
$695
Mytheresa
Brunello Cucinelli
Cashmere midi dress
$3,360
$4,800
Mytheresa
Max Mara
Trudy wool turtleneck sweater dress
$675
$965
Mytheresa
Jil Sander
Cashmere turtleneck midi dress
$1,254
$2,090
Mytheresa
Brunello Cucinelli
Bead-embellished wool-blend jersey turtleneck midi dress
$1,398
$3,495
Outnet
Victoria Beckham
Wool-blend sweater dress
$903
$1,290
Mytheresa
Lemaire
Trompe l'œil wool-blend midi dress
$486
$695
Mytheresa
Jil Sander
Knitted cashmere midi dress
$1,254
$2,090
Mytheresa
Alaïa
Faux shearling-trimmed virgin wool midi dress
$3,090
Mytheresa
Lemaire
Turtleneck wool-blend midi dress
$486
$695
Mytheresa
LESET
Lauren turtleneck minidress
$144
$240
Mytheresa
Sablyn
Gab Turtleneck Rib Dress
$375
Shopbop
Missoni
Zigzag midi dress
$1,128
$1,410
Mytheresa
Veronica De Piante
Viola stretch-knit turtleneck midi dress
$486
$1,080
Outnet

Turtleneck Sweater Dress

@jeanwang

A cozy sweater dress with a turtleneck makes cold-weather dressing feel effortless and refined. Style with leggings and knee-high boots for a polished daytime look.

Veronica Beard

Wool and cashmere sweater dress

$536

$670

Mytheresa

Jardin des Orangers

Wool and cashmere sweater dress

$400

$500

Mytheresa

Lemaire

Turtleneck wool-blend midi dress

$417

$695

Mytheresa

Brunello Cucinelli

Cashmere midi dress

$3,360

$4,800

Mytheresa

@emilylafitte

Quilted or Puffer Vest

Layering a lightweight vest over a sweater adds core warmth without restricting movement—a classic choice for outdoor adventures or lounging with hot cocoa.

See all

Moncler

Alpiste quilted down vest

$1,195

Mytheresa

Max Mara

Tregic quilted zip-up vest

$1,095

Mytheresa

Moncler

Butor quilted down vest

$1,950

Mytheresa

Moncler

Spicules down vest

$1,100

Mytheresa

Moncler

Igens logo down vest

$1,150

Mytheresa

Moncler

Igens down vest

$1,150

Mytheresa

Max Mara

The Cube Tregic quilted down vest

$796

$995

Mytheresa

BARBOUR

Barbour Otterburn Gilet

$165

Shopbop

Veronica Beard

Patra Mixed Media Jacket

$598

Shopbop

New

Moncler

Vigny quilted linen vest

$777

$1,295

Outnet

Moncler

Quilted down vest

$1,195

Mytheresa

Moncler

Liane cropped down vest

$1,045

Mytheresa

Moncler

Igens down vest

$1,150

Mytheresa

Moncler

Down-paneled virgin wool cardigan

$1,380

Mytheresa

Max Mara

The Cube technical puffer vest

$1,050

Mytheresa

Moncler

Down-paneled virgin wool cardigan

$1,195

Mytheresa

Moncler
Alpiste quilted down vest
$1,195
Mytheresa
Max Mara
Tregic quilted zip-up vest
$1,095
Mytheresa
Moncler
Butor quilted down vest
$1,950
Mytheresa
Moncler
Spicules down vest
$1,100
Mytheresa
Moncler
Igens logo down vest
$1,150
Mytheresa
Moncler
Igens down vest
$1,150
Mytheresa
Max Mara
The Cube Tregic quilted down vest
$796
$995
Mytheresa
BARBOUR
Barbour Otterburn Gilet
$165
Shopbop
Veronica Beard
Patra Mixed Media Jacket
$598
Shopbop
New
New
Moncler
Vigny quilted linen vest
$777
$1,295
Outnet
Moncler
Quilted down vest
$1,195
Mytheresa
Moncler
Liane cropped down vest
$1,045
Mytheresa
Moncler
Igens down vest
$1,150
Mytheresa
Moncler
Down-paneled virgin wool cardigan
$1,380
Mytheresa
Max Mara
The Cube technical puffer vest
$1,050
Mytheresa
Moncler
Down-paneled virgin wool cardigan
$1,195
Mytheresa

Quilted or Puffer Vest

@emilylafitte

Layering a lightweight vest over a sweater adds core warmth without restricting movement—a classic choice for outdoor adventures or lounging with hot cocoa.

Moncler

Alpiste quilted down vest

$1,195

Mytheresa

Max Mara

Tregic quilted zip-up vest

$1,095

Mytheresa

Moncler

Butor quilted down vest

$1,950

Mytheresa

Moncler

Spicules down vest

$1,100

Mytheresa

@azalia_lomakina

Flannel or Wool Long Sleeve Shirt

A staple for Upstate escapes, flannel and wool shirts add both softness and rustic charm, pairing well with jeans or under chunky sweaters.

See all

Frank & Eileen

Relaxed Button-Up Shirt

$258

Shopbop

Frank & Eileen

Relaxed Button-Up Shirt

$258

Shopbop

The Row

Pino virgin wool shirt

$1,650

Mytheresa

Max Mara

Tebaide cashmere-blend shirt

$1,870

Mytheresa

Vince

Twill shirt

$234

$468

Outnet

The Row

Caroline virgin wool shirt

$1,490

Mytheresa

Bottega Veneta

Oversized wool-blend shirt

$1,500

Mytheresa

The Row

Pino virgin wool shirt

$1,650

Mytheresa

Frank & Eileen

Relaxed Button-Up Shirt

$258

Shopbop

Stella McCartney

Wool-blend shirt

$318

$795

Mytheresa

The Row

Komako wool and cashmere shirt

$1,650

Mytheresa

Frank & Eileen

Relaxed Button-Up Shirt

$258

Shopbop

The Row

Komako wool and cashmere shirt

$1,650

Mytheresa

Prada

Checked wool shirt

$2,150

Mytheresa

Miu Miu

Oversized Button Up Top

$2,450

FWRD

Burberry

Heidi Top

$430

$895

FWRD

Frank & Eileen
Relaxed Button-Up Shirt
$258
Shopbop
Frank & Eileen
Relaxed Button-Up Shirt
$258
Shopbop
The Row
Pino virgin wool shirt
$1,650
Mytheresa
Max Mara
Tebaide cashmere-blend shirt
$1,870
Mytheresa
Vince
Twill shirt
$234
$468
Outnet
The Row
Caroline virgin wool shirt
$1,490
Mytheresa
Bottega Veneta
Oversized wool-blend shirt
$1,500
Mytheresa
The Row
Pino virgin wool shirt
$1,650
Mytheresa
Frank & Eileen
Relaxed Button-Up Shirt
$258
Shopbop
Stella McCartney
Wool-blend shirt
$318
$795
Mytheresa
The Row
Komako wool and cashmere shirt
$1,650
Mytheresa
Frank & Eileen
Relaxed Button-Up Shirt
$258
Shopbop
The Row
Komako wool and cashmere shirt
$1,650
Mytheresa
Prada
Checked wool shirt
$2,150
Mytheresa
Miu Miu
Oversized Button Up Top
$2,450
FWRD
Burberry
Heidi Top
$430
$895
FWRD

Flannel or Wool Long Sleeve Shirt

@azalia_lomakina

A staple for Upstate escapes, flannel and wool shirts add both softness and rustic charm, pairing well with jeans or under chunky sweaters.

Frank & Eileen

Relaxed Button-Up Shirt

$258

Shopbop

Frank & Eileen

Relaxed Button-Up Shirt

$258

Shopbop

The Row

Pino virgin wool shirt

$1,650

Mytheresa

Max Mara

Tebaide cashmere-blend shirt

$1,870

Mytheresa

@feve__r

Fleece-Lined Jeans

These bring the best of two worlds: classic denim warmth and winter-ready coziness, ideal for everything from casual strolls to drinks by the fire.

See all

rag & bone

Miramar Fleece Wide Leg Jeans Jeans

$228

Revolve

DAZE

The Cozy Jean Wide Leg Pull-On Jeans

$98

Shopbop

Miu Miu

High-rise boyfriend jeans

$1,350

Mytheresa

Dries Van Noten

Velvet-trimmed mid-rise wide-leg jeans

$573

$955

Net-a-Porter

Meshki

Laina Mid Rise Diamante Denim Jeans - Midnight Blue

$159

Meshki

Madewell

Madewell x Kaihara Denim Pieced Barrel Leg Jeans

$138.6

$198

Shopbop

TWP Jetties Beach Jean in Vintage Wash Denim

TWP

Jetties Beach Jean in Vintage Wash Denim

$495

TWP

New

RE/DONE

The Rewind Jeans

$375

Shopbop

rag & bone

Miramar Fleece Pull On Joggers

$228

Shopbop

Dries Van Noten

Jeans

$573

$955

Net-a-Porter

Splendid

Lounge Denim Pants

$168

Shopbop

rag & bone

Miramar Terry Jogger Pants

$198

Shopbop

New

rag & bone

Miramar Terry Sweatpants

$198

Shopbop

rag & bone

Miramar Terry Track Pants Pull On

$218

Shopbop

Brunello Cucinelli

Pleated tapered jeans

$1,800

Mytheresa

Madewell

Low-Slung Baggy Jeans in Airy Denim

$158

Shopbop

rag & bone
Miramar Fleece Wide Leg Jeans Jeans
$228
Revolve
DAZE
The Cozy Jean Wide Leg Pull-On Jeans
$98
Shopbop
Miu Miu
High-rise boyfriend jeans
$1,350
Mytheresa
Dries Van Noten
Velvet-trimmed mid-rise wide-leg jeans
$573
$955
Net-a-Porter
Meshki
Laina Mid Rise Diamante Denim Jeans - Midnight Blue
$159
Meshki
Madewell
Madewell x Kaihara Denim Pieced Barrel Leg Jeans
$138.6
$198
Shopbop
TWP
Jetties Beach Jean in Vintage Wash Denim
$495
TWP
New
New
RE/DONE
The Rewind Jeans
$375
Shopbop
rag & bone
Miramar Fleece Pull On Joggers
$228
Shopbop
Dries Van Noten
Jeans
$573
$955
Net-a-Porter
Splendid
Lounge Denim Pants
$168
Shopbop
rag & bone
Miramar Terry Jogger Pants
$198
Shopbop
New
New
rag & bone
Miramar Terry Sweatpants
$198
Shopbop
rag & bone
Miramar Terry Track Pants Pull On
$218
Shopbop
Brunello Cucinelli
Pleated tapered jeans
$1,800
Mytheresa
Madewell
Low-Slung Baggy Jeans in Airy Denim
$158
Shopbop

Fleece-Lined Jeans

@feve__r

These bring the best of two worlds: classic denim warmth and winter-ready coziness, ideal for everything from casual strolls to drinks by the fire.

rag & bone

Miramar Fleece Wide Leg Jeans Jeans

$228

Revolve

DAZE

The Cozy Jean Wide Leg Pull-On Jeans

$98

Shopbop

Miu Miu

High-rise boyfriend jeans

$1,350

Mytheresa

Dries Van Noten

Velvet-trimmed mid-rise wide-leg jeans

$573

$955

Net-a-Porter

@jeneenaylor

Over-the-Knee Boots

Elevate your evening or brunch outfits with these boots—worn over leggings or a sweater dress, they provide both style and extra insulation for chilly nights.

See all

Stuart Weitzman

Stuart Power Boots 75

$850

Shopbop

JIMMY CHOO

Turner 110 stretch-suede over-the-knee boots

$727

$2,075

Outnet

Stuart Weitzman

Gillian 60 microstretch and suede over-the-knee boots

$318

$795

Outnet

New

Stuart Weitzman

Gillian 60 suede over-the-knee boots

$383

$850

Outnet

Stuart Weitzman

Gillian 60 microstretch and leather over-the-knee boots

$477

$795

Outnet

Stuart Weitzman

Jocey stretch-suede over-the-knee boots

$314

$895

Outnet

Stuart Weitzman

Jocey stretch-suede over-the-knee boots

$398

$795

Outnet

MANOLO BLAHNIK

Lupasca suede over-the-knee boots

$1,225

$1,750

Mytheresa

AQUAZZURA

Zenn 65 suede knee-high boots

$1,436

$1,795

Mytheresa

KHAITE

Colt Over-the-Knee Heel Boot in Bordeaux Leather

$2,800

KHAITE

Stella McCartney

Ivy over-the-knee boots

$309

$1,235

Outnet

Tory Burch

Leather over-the-knee boots

$436

$728

Mytheresa

MANOLO BLAHNIK

Gore suede over-the-knee boots

$1,522

$2,175

Mytheresa

GIANVITO ROSSI

Elise 55 suede knee-high boots

$1,396

$1,995

Mytheresa

Stuart Weitzman

City microstretch and leather over-the-knee boots

$268

$763

Outnet

Stuart Weitzman

Stretch-suede over-the-knee boots

$240

$798

Outnet

Stuart Weitzman
Stuart Power Boots 75
$850
Shopbop
JIMMY CHOO
Turner 110 stretch-suede over-the-knee boots
$727
$2,075
Outnet
Stuart Weitzman
Gillian 60 microstretch and suede over-the-knee boots
$318
$795
Outnet
New
New
Stuart Weitzman
Gillian 60 suede over-the-knee boots
$383
$850
Outnet
Stuart Weitzman
Gillian 60 microstretch and leather over-the-knee boots
$477
$795
Outnet
Stuart Weitzman
Jocey stretch-suede over-the-knee boots
$314
$895
Outnet
Stuart Weitzman
Jocey stretch-suede over-the-knee boots
$398
$795
Outnet
MANOLO BLAHNIK
Lupasca suede over-the-knee boots
$1,225
$1,750
Mytheresa
AQUAZZURA
Zenn 65 suede knee-high boots
$1,436
$1,795
Mytheresa
KHAITE
Colt Over-the-Knee Heel Boot in Bordeaux Leather
$2,800
KHAITE
Stella McCartney
Ivy over-the-knee boots
$309
$1,235
Outnet
Tory Burch
Leather over-the-knee boots
$436
$728
Mytheresa
MANOLO BLAHNIK
Gore suede over-the-knee boots
$1,522
$2,175
Mytheresa
GIANVITO ROSSI
Elise 55 suede knee-high boots
$1,396
$1,995
Mytheresa
Stuart Weitzman
City microstretch and leather over-the-knee boots
$268
$763
Outnet
Stuart Weitzman
Stretch-suede over-the-knee boots
$240
$798
Outnet

Over-the-Knee Boots

@jeneenaylor

Elevate your evening or brunch outfits with these boots—worn over leggings or a sweater dress, they provide both style and extra insulation for chilly nights.

Stuart Weitzman

Stuart Power Boots 75

$850

Shopbop

JIMMY CHOO

Turner 110 stretch-suede over-the-knee boots

$727

$2,075

Outnet

Stuart Weitzman

Gillian 60 microstretch and suede over-the-knee boots

$318

$795

Outnet

New

Stuart Weitzman

Gillian 60 suede over-the-knee boots

$383

$850

Outnet

Shop More

Vince

Cozy Long Sleeve Funnel Neck Dress

$187.6

$268

Shopbop

Favorite Daughter

The Millie Dress

$159.6

$228

Shopbop

Cult Gaia

Carline Dress

$488.6

$698

Shopbop

Show Me Your Mumu

Lorraine Maxi Sweater Dress

$188

Shopbop

Staud

Vanya Dress

$270

$450

Shopbop

Splendid

Splendid x Cella Jane Off The Shoulder Sweater Dress

$55.2

$138

Shopbop

rag & bone

Loren Long Belted Dress

$498

Shopbop

New

Mango

Knitted dress with bell sleeves

$59.99

$89.99

Mango

L'Academie

Deena Maxi Dress

$144

$218

Revolve

Staud

CANAL MIDI DRESS | CHARCOAL

$270

$450

Staud

SIMKHAI

Skyla Wrap Dress

$445

Shopbop

New

Mango

Devoré floral dress

$89.99

$149.99

Mango

KHAITE

Oron ruched jersey midi dress

$1,036

$1,480

Mytheresa

TOTEME

Wool midi dress

$342

$570

Net-a-Porter

Jardin des Orangers

Wool and cashmere wrap dress

$346

$495

Mytheresa

o.p.t

Nicole Dress

$198

Shopbop

Aya Muse

Hale one-shoulder silk-blend maxi dress

$684

$855

Mytheresa

KHAITE

Jaime cashmere maxi dress

$875

$1,250

Mytheresa

Solid & Striped

The Dora Dress

$278

Shopbop

o.p.t

Nicole Dress

$198

Shopbop

Magda Butrym

Wool, silk, and cashmere maxi dress

$2,072

$2,590

Mytheresa

Isabel Marant

Ormany jersey bouclé maxi dress

$695

$1,390

Mytheresa

Marant Étoile

Jelina gathered jersey maxi dress

$357

$595

Mytheresa

Brunello Cucinelli

Cashmere midi dress

$2,765

$3,950

Mytheresa

Lemaire

Belted sweater dress

$345

$690

Mytheresa

Lemaire

Trompe-l'œil cotton midi dress

$507

$1,015

Mytheresa

New

Cara Cara

Margie Dress

$695

Cara Cara

Loro Piana

Merano cashmere sweater dress

$3,200

Mytheresa

Vince

Short Sleeve Side Rouche Dress

$298

Shopbop

Meshki

Baxter Off Shoulder Fluffy Knit Midi Dress - Taupe Marle

$129

Meshki

Isabel Marant

Salina Maxi Dress

$346.5

$990

Shopbop

Entire Studios

Draped wool maxi dress

$297

$425

Mytheresa

Seven Wonders

Greta One Shoulder Knit Maxi Dress

$149

Shopbop

ASTR the Label

Tilde Sweater Dress

$103.6

$148

Shopbop

SIMKHAI

Skyla Cotton Cashmere Wrap Dress

$445

SIMKHAI

Naked Cashmere

KATERINA CASHMERE KAFTAN

$395

Naked Cashmere

Veronica De Piante

Viola stretch-knit turtleneck midi dress

$486

$1,080

Outnet

Apiece Apart

Volta Long Sleeve Dress

$195

$325

Shopbop

TOTEME

Wool and alpaca-blend dress

$267

$890

Outnet

Christopher Esber

Salacia maxi dress

$840

$1,050

Mytheresa