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What to Wear for a Winter Weekend Getaway in Upstate NY

A winter weekend in upstate New York means chilly temperatures, so focus on cozy layers, plush knits, warm outerwear, and sturdy shoes for snowy terrain. Think earthy and jewel tones, textural fabrics, and silhouettes that let you feel stylish and snug. If you’re planning specific activities (skiing, dinners out, etc.), or have personal style preferences, let me know for even more tailored picks!
@s.u.a.m.a.r
1
Chunky Knit Sweater in Earth Tones
A plush, textured knit in fall-inspired shades like caramel, forest green, or rust keeps you comfortable and on-theme with the winter scenery. Perfect for layering over tops or under outerwear, and one of the coziness-driven trends this season.
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1
Chunky Knit Sweater in Earth Tones
@s.u.a.m.a.r
A plush, textured knit in fall-inspired shades like caramel, forest green, or rust keeps you comfortable and on-theme with the winter scenery. Perfect for layering over tops or under outerwear, and one of the coziness-driven trends this season.
New
New
RE/DONE 90s Baja space-dyed knitted hoodie
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RE/DONE

90s Baja space-dyed knitted hoodie

$184

$525

Outnet

New
New
PISTOLA Quinn Sweater
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PISTOLA

Quinn Sweater

$198

Shopbop

Brunello Cucinelli Bead-embellished striped cotton sweater
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Brunello Cucinelli

Bead-embellished striped cotton sweater

$1,740

$2,900

Net-a-Porter

New
New
La Ligne Fluffy Marina merino wool-blend sweater
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La Ligne

Fluffy Marina merino wool-blend sweater

$450

Net-a-Porter

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@sobalera
2
Oversized Puffer Jacket
This outerwear staple offers superior warmth and pairs well with street or outdoor looks. The voluminous silhouette is a major trend for winter 2025, and it stands up to snowy upstate weather.
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2
Oversized Puffer Jacket
@sobalera
This outerwear staple offers superior warmth and pairs well with street or outdoor looks. The voluminous silhouette is a major trend for winter 2025, and it stands up to snowy upstate weather.
New
New
Balenciaga C-shape oversized hooded quilted shell jacket
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Balenciaga

C-shape oversized hooded quilted shell jacket

$1,293

$2,350

Outnet

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New
Norma Kamali Oversized padded shell bomber jacket
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Norma Kamali

Oversized padded shell bomber jacket

$595

Net-a-Porter

Marant Étoile Gally cotton-blend puffer coat
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Marant Étoile

Gally cotton-blend puffer coat

$556

$695

Mytheresa

Rick Owens Turtle oversized down jacket
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Rick Owens

Turtle oversized down jacket

$1,325

$2,650

Mytheresa

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@cheriedari
3
Long Sleeve Thermal Tops
Essential as a comfortable, heat-trapping base layer. Wear under sweaters or flannels for extra warmth during outdoor activities or strolls around town.
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3
Long Sleeve Thermal Tops
@cheriedari
Essential as a comfortable, heat-trapping base layer. Wear under sweaters or flannels for extra warmth during outdoor activities or strolls around town.
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New
ÉTERNE Long Sleeve Thermal Top
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ÉTERNE

Long Sleeve Thermal Top

$165

FWRD

New
New
Free People x We The Free Latte Blues Thermal Solid In Chocolate Grape
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Free People

x We The Free Latte Blues Thermal Solid In Chocolate Grape

$68

Revolve

New
New
Bobi Modal Thermal Top
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Bobi

Modal Thermal Top

$66

Revolve

New
New
Free People x We The Free Lucky Locket Tee
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Free People

x We The Free Lucky Locket Tee

$42

$68

Revolve

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@azalia_lomakina
4
Wide-Leg Corduroy Trousers
Corduroy is both classic and trending for fall/winter. Wide-leg and high-waisted fits are flattering, warm, and allow for easy layering with thermal leggings underneath.
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4
Wide-Leg Corduroy Trousers
@azalia_lomakina
Corduroy is both classic and trending for fall/winter. Wide-leg and high-waisted fits are flattering, warm, and allow for easy layering with thermal leggings underneath.
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The Row Tarley cotton-corduroy wide-leg pants
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The Row

Tarley cotton-corduroy wide-leg pants

$1,050

Net-a-Porter

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New
PAIGE Anessa 31" Corduroy Pants with Stitch Utility Pockets
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PAIGE

Anessa 31" Corduroy Pants with Stitch Utility Pockets

$259

Shopbop

New
New
Polo Ralph Lauren Corduroy Cropped Wide Leg Pants
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Polo Ralph Lauren

Corduroy Cropped Wide Leg Pants

$298

Shopbop

FRAME Le Slim Palazzo Corduroy Jeans
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FRAME

Le Slim Palazzo Corduroy Jeans

$298

Shopbop

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@elisalevallois
5
Pleated Wool Midi Skirt
A heavier pleated skirt in wool offers warmth and movement. Style with boots and knits for dinner out or dressier day trips—pleated midi skirts are a chic trend for 2025.
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5
Pleated Wool Midi Skirt
@elisalevallois
A heavier pleated skirt in wool offers warmth and movement. Style with boots and knits for dinner out or dressier day trips—pleated midi skirts are a chic trend for 2025.
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New
Gabriela Hearst Wesley wool and cashmere midi skirt
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Gabriela Hearst

Wesley wool and cashmere midi skirt

$1,330

Mytheresa

New
New
Gabriela Hearst Wesley pleated wool and cashmere-blend twill midi skirt
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Gabriela Hearst

Wesley pleated wool and cashmere-blend twill midi skirt

$1,330

Net-a-Porter

New
New
Mango Pleated skirt with belt
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Mango

Pleated skirt with belt

$99.99

Mango

New
New
Rue Sophie Ambre Skirt
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Rue Sophie

Ambre Skirt

$328

Revolve

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@olisusskind
6
Shearling-Lined Denim Work Jacket
This hybrid jacket provides both warmth and rustic style, nodding to upstate’s laid-back vibe. The plush interior keeps you insulated during outdoor adventures or casual outings.
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6
Shearling-Lined Denim Work Jacket
@olisusskind
This hybrid jacket provides both warmth and rustic style, nodding to upstate’s laid-back vibe. The plush interior keeps you insulated during outdoor adventures or casual outings.
New
New
Miu Miu Denim Jacket
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Miu Miu

Denim Jacket

$3,800

FWRD

New
New
Bottega Veneta Padded Denim Jacket
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Bottega Veneta

Padded Denim Jacket

$2,900

FWRD

New
New
Steve Madden Winona Jacket
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Steve Madden

Winona Jacket

$109

$149

Revolve

New
New
HEARTLOOM Elina Jacket
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HEARTLOOM

Elina Jacket

$169

Revolve

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@kieunse
7
Cable Knit Turtleneck Sweater
A cable knit is classic, warm, and always in style. The turtleneck protects against the chill and is excellent for layering under outerwear or vests.
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7
Cable Knit Turtleneck Sweater
@kieunse
A cable knit is classic, warm, and always in style. The turtleneck protects against the chill and is excellent for layering under outerwear or vests.
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New
DENIMIST Cable Turtleneck Sweater
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DENIMIST

Cable Turtleneck Sweater

$495

Shopbop

TOTEME Cable-knit wool and cotton turtleneck sweater
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TOTEME

Cable-knit wool and cotton turtleneck sweater

$600

$750

Mytheresa

New
New
Max Mara Alcazar wool and cashmere turtleneck sweater
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Max Mara

Alcazar wool and cashmere turtleneck sweater

$1,150

Mytheresa

New
New
Guest In Residence Cropped Cable Turtleneck
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Guest In Residence

Cropped Cable Turtleneck

$545

Shopbop

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@natalikim
8
Funnel-Neck Wool Coat
A structured wool coat with a funnel neckline is both practical and sophisticated, framing the face while protecting from cold winds. This outerwear trend elevates any winter look.
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8
Funnel-Neck Wool Coat
@natalikim
A structured wool coat with a funnel neckline is both practical and sophisticated, framing the face while protecting from cold winds. This outerwear trend elevates any winter look.
New
New
Mango Woollen coat with belt
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Mango

Woollen coat with belt

$299.99

Mango

New
New
Mango Manteco wool coat with belt
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Mango

Manteco wool coat with belt

$299.99

Mango

New
New
Mango Short virgin wool coat
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Mango

Short virgin wool coat

$299.99

Mango

New
New
Mango Turtleneck wool coat
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Mango

Turtleneck wool coat

$229.99

Mango

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@gemmatalbot
9
Shearling Boots
Perfect for snowy, icy conditions—shearling boots are extremely warm and add textural contrast to your winter outfits. Choose mid-calf or knee-high styles for maximum comfort.
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9
Shearling Boots
@gemmatalbot
Perfect for snowy, icy conditions—shearling boots are extremely warm and add textural contrast to your winter outfits. Choose mid-calf or knee-high styles for maximum comfort.
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New
Freda Salvador Winnie Boots
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Freda Salvador

Winnie Boots

$398

Shopbop

Inuikii Curly Sneakers
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Inuikii

Curly Sneakers

$369

Shopbop

New
New
Inuikii Curly Sneakers
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Inuikii

Curly Sneakers

$329

Shopbop

New
New
LEGRES 52 shearling ankle boots
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LEGRES

52 shearling ankle boots

$695

Net-a-Porter

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@dawn.tan
10
Maxi Dress with Layered Knit Vest
A cozy boho trend, pairing a soft maxi dress with a textured knit vest gives warmth, movement, and a layered look perfect for chilly weekends. Ideal for daytime exploring or casual dinners.
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10
Maxi Dress with Layered Knit Vest
@dawn.tan
A cozy boho trend, pairing a soft maxi dress with a textured knit vest gives warmth, movement, and a layered look perfect for chilly weekends. Ideal for daytime exploring or casual dinners.
The Row Agla stretch-knit maxi dress
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The Row

Agla stretch-knit maxi dress

$620

$1,550

Net-a-Porter

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New
Jil Sander Draped merino wool maxi dress
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Jil Sander

Draped merino wool maxi dress

$1,850

Net-a-Porter

Jil Sander Ribbed cotton maxi dress
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Jil Sander

Ribbed cotton maxi dress

$755

$1,510

Net-a-Porter

New
New
KHAITE Miriele tweed-paneled knitted maxi dress
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KHAITE

Miriele tweed-paneled knitted maxi dress

$1,320

$2,200

Net-a-Porter

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Shop More
Brunello Cucinelli Cashmere midi dress
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Brunello Cucinelli

Cashmere midi dress

$3,360

$4,800

Mytheresa

KHAITE Rivka Fair Isle cashmere-blend midi dress
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KHAITE

Rivka Fair Isle cashmere-blend midi dress

$3,840

$6,400

Mytheresa

Fforme Ainsley wool-blend shift dress
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Fforme

Ainsley wool-blend shift dress

$1,440

$2,400

Mytheresa

New
New
Jardin des Orangers Wool and cashmere maxi dress
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Jardin des Orangers

Wool and cashmere maxi dress

$356

$445

Mytheresa

Fforme Ainsley wool and cashmere shift dress
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Fforme

Ainsley wool and cashmere shift dress

$1,440

$2,400

Mytheresa

New
New
KHAITE Ava off-shoulder wool-blend maxi dress
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KHAITE

Ava off-shoulder wool-blend maxi dress

$2,086

$2,980

Mytheresa

Marni Cashmere sweater midi dress
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Marni

Cashmere sweater midi dress

$775

$1,550

Mytheresa

New
New
Cult Gaia Carline Dress
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Cult Gaia

Carline Dress

$698

Shopbop

Altuzarra Kasos cashmere maxi dress
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Altuzarra

Kasos cashmere maxi dress

$1,172

$1,465

Mytheresa

Max Mara Virgin wool midi dress
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Max Mara

Virgin wool midi dress

$339

$565

Mytheresa

Tom Ford Cashmere turtleneck gown
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Tom Ford

Cashmere turtleneck gown

$2,034

$3,390

Mytheresa

Jil Sander Asymmetric wool midi dress
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Jil Sander

Asymmetric wool midi dress

$906

$1,510

Mytheresa

Loro Piana Engadin pointelle-knit cashmere maxi dress
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Loro Piana

Engadin pointelle-knit cashmere maxi dress

$3,775

Net-a-Porter

KHAITE Hans ribbed-knit cashmere maxi dress
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KHAITE

Hans ribbed-knit cashmere maxi dress

$1,246

$1,780

Mytheresa

New
New
Victoria Beckham Draped Sleeveless Rib Dress
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Victoria Beckham

Draped Sleeveless Rib Dress

$1,250

Shopbop

Dries Van Noten Snake-print wool midi dress
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Dries Van Noten

Snake-print wool midi dress

$684

$1,710

Mytheresa

Stella McCartney Intarsia wool-blend hoodie dress
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Stella McCartney

Intarsia wool-blend hoodie dress

$837

$1,395

Mytheresa

The Row Gianna cashmere maxi dress
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The Row

Gianna cashmere maxi dress

$1,470

$2,450

Mytheresa

New
New
Veronica Beard Madden Knit Dress
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Veronica Beard

Madden Knit Dress

$648

Shopbop

The Row Nimah wool and mohair maxi dress
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The Row

Nimah wool and mohair maxi dress

$2,100

$4,200

Mytheresa

Acne Studios Cable-knit wool-blend minidress
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Acne Studios

Cable-knit wool-blend minidress

$343

$573

Mytheresa

The Row Reysha wool-blend maxi dress
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The Row

Reysha wool-blend maxi dress

$2,100

$5,250

Mytheresa

New
New
Cult Gaia Holland Dress
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Cult Gaia

Holland Dress

$428

FWRD

New
New
SIMKHAI Albanie Mini Dress
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SIMKHAI

Albanie Mini Dress

$465

Revolve

Etro Cashmere, wool, and silk midi dress
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Etro

Cashmere, wool, and silk midi dress

$1,925

$2,750

Mytheresa

New
New
LISA YANG Amannda Dress
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LISA YANG

Amannda Dress

$390

$1,025

Revolve

New
New
Ralph Lauren Collection Nora Dress
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Ralph Lauren Collection

Nora Dress

$2,190

FWRD

Valentino Wool and silk crêpe gown
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Valentino

Wool and silk crêpe gown

$3,850

$5,500

Mytheresa

S Max Mara Wool and cashmere sweater dress
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S Max Mara

Wool and cashmere sweater dress

$872

$1,090

Mytheresa

Emilia Wickstead Jenna wool flannel midi dress
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Emilia Wickstead

Jenna wool flannel midi dress

$1,190

$1,700

Mytheresa

Markarian Cybil wool midi dress
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Markarian

Cybil wool midi dress

$1,030

$2,060

Mytheresa

Loewe Ruffled sequined wool midi dress
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Loewe

Ruffled sequined wool midi dress

$2,880

$7,200

Net-a-Porter

Maison Margiela Checked wool midi dress
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Maison Margiela

Checked wool midi dress

$1,062

$1,770

Mytheresa

Stella McCartney Draped wool maxi dress
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Stella McCartney

Draped wool maxi dress

$532

$1,065

Mytheresa

The Row Stefos wool and silk gown
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The Row

Stefos wool and silk gown

$2,250

$3,750

Mytheresa

Emilia Wickstead Malinda wool crêpe gown
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Emilia Wickstead

Malinda wool crêpe gown

$1,944

$2,430

Mytheresa

New
New
Willy Chavarria Bustier Dress
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Willy Chavarria

Bustier Dress

$3,400

FWRD

New
New
KHAITE Quintin Dress in Ivory
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KHAITE

Quintin Dress in Ivory

$5,400

KHAITE

New
New
HERSKIND Adele Dress
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HERSKIND

Adele Dress

$695

Revolve

Fforme Wool-blend maxi dress
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Fforme

Wool-blend maxi dress

$2,272

$4,545

Mytheresa