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Comfortable and Classy Cozy Dresses for Cold, Overcast Days

For chilly, overcast weather, opt for dresses in plush knits, heavier fabrics, or with thoughtful sleeve details. The following suggestions offer warmth, comfort, and elevated style. If you’d like recommendations tailored to a specific formality, color palette, or budget, feel free to share more details!
@itsyuyann
1
Long Sleeve Sweater Dress
Knit sweater dresses deliver maximum coziness while still looking refined. Choose a column or A-line silhouette for a polished appearance—great for withstanding cold temperatures.
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1
Long Sleeve Sweater Dress
@itsyuyann
Knit sweater dresses deliver maximum coziness while still looking refined. Choose a column or A-line silhouette for a polished appearance—great for withstanding cold temperatures.
Tuckernuck Winter White Vivianne Crewneck Dress
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Tuckernuck

Winter White Vivianne Crewneck Dress

$102

$128

Tuckernuck

Line & Dot Pippa Mini Dress
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Line & Dot

Pippa Mini Dress

$57.2

$143

Shopbop

Tuckernuck Black Anzu Puplum Sweater Mini Dress
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Tuckernuck

Black Anzu Puplum Sweater Mini Dress

$120

$150

Tuckernuck

Elie Tahari Cashmere Long Sleeve Belted Dress
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Elie Tahari

Cashmere Long Sleeve Belted Dress

$198

$495

Elie Tahari

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@hoskelsa
2
Turtleneck Knit Dress
A turtleneck provides extra warmth around your neck, making it ideal for cold, overcast days. The fitted shape and heavier knit maintain a classy feel.
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2
Turtleneck Knit Dress
@hoskelsa
A turtleneck provides extra warmth around your neck, making it ideal for cold, overcast days. The fitted shape and heavier knit maintain a classy feel.
Veronica Beard Cassidy Turtleneck Mini Dress
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Veronica Beard

Cassidy Turtleneck Mini Dress

$284

$568

Shopbop

TOTEME Wool and silk sweater dress
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TOTEME

Wool and silk sweater dress

$493

$705

Mytheresa

Susana Monaco Turtleneck Sweater Dress
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Susana Monaco

Turtleneck Sweater Dress

$91.2

$228

Shopbop

Veronica Beard Wool and cashmere sweater dress
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Veronica Beard

Wool and cashmere sweater dress

$536

$670

Mytheresa

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@therealmilanj
3
Ribbed Knit Midi Dress
The ribbed texture and midi length offer both comfort and a sophisticated, streamlined silhouette. Looks chic alone or layered under a jacket.
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3
Ribbed Knit Midi Dress
@therealmilanj
The ribbed texture and midi length offer both comfort and a sophisticated, streamlined silhouette. Looks chic alone or layered under a jacket.
Z Supply Linden Dress
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Z Supply

Linden Dress

$110

Shopbop

Tuckernuck Black Mixed Media Lizzie Dress
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Tuckernuck

Black Mixed Media Lizzie Dress

$198

Tuckernuck

Tuckernuck Pine Softest Rib Nursing Dress
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Tuckernuck

Pine Softest Rib Nursing Dress

$198

Tuckernuck

LISA YANG Lexie Dress
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LISA YANG

Lexie Dress

$575

Shopbop

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@clairerose
4
Long Sleeve Knit Wrap Dress
The wrap style flatters a variety of body shapes while keeping things soft and cozy. A knit version feels elevated enough for dressier settings.
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4
Long Sleeve Knit Wrap Dress
@clairerose
The wrap style flatters a variety of body shapes while keeping things soft and cozy. A knit version feels elevated enough for dressier settings.
Diane von Furstenberg Astrid wool and cashmere-blend midi wrap dress
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Diane von Furstenberg

Astrid wool and cashmere-blend midi wrap dress

$280

$560

Outnet

JOSEPH Linen-blend midi wrap dress
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JOSEPH

Linen-blend midi wrap dress

$239

$795

Outnet

Enza Costa Ribbed-knit midi wrap dress
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Enza Costa

Ribbed-knit midi wrap dress

$88

$352

Outnet

SIMKHAI Skyla Wrap Dress
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SIMKHAI

Skyla Wrap Dress

$445

Shopbop

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@mathildegoehler
5
Fit and Flare Sweater Dress
This silhouette offers a comfortable waist and skirt movement, while the knit fabric ensures a cozy, put-together look. Works well with tights and boots for extra warmth.
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5
Fit and Flare Sweater Dress
@mathildegoehler
This silhouette offers a comfortable waist and skirt movement, while the knit fabric ensures a cozy, put-together look. Works well with tights and boots for extra warmth.
LoveShackFancy Lavender Dress
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LoveShackFancy

Lavender Dress

$495

Shopbop

Fleur du Mal Henley Flared Corset Dress
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Fleur du Mal

Henley Flared Corset Dress

$485

Shopbop

Fleur du Mal Long Sleeve Flared Corset Dress
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Fleur du Mal

Long Sleeve Flared Corset Dress

$199.2

$498

Shopbop

Shoshanna Martha Dress
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Shoshanna

Martha Dress

$398

Shopbop

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@hintofglamour
6
Long Sleeve Knit Dress with Statement Sleeves
Add a sophisticated twist with dramatic sleeves—like puff or balloon styles—which are a seasonal trend and elevate a basic knit dress.
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6
Long Sleeve Knit Dress with Statement Sleeves
@hintofglamour
Add a sophisticated twist with dramatic sleeves—like puff or balloon styles—which are a seasonal trend and elevate a basic knit dress.
self-portrait Ribbed-knit midi dress
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self-portrait

Ribbed-knit midi dress

$650

Mytheresa

self-portrait Ribbed-knit midi dress
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self-portrait

Ribbed-knit midi dress

$465

$665

Mytheresa

Meshki Amirose Ruffle Knit Midi Dress - Plum
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Meshki

Amirose Ruffle Knit Midi Dress - Plum

$139

Meshki

Elie Tahari Cashmere Fit & Flare Dress
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Elie Tahari

Cashmere Fit & Flare Dress

$198

$495

Elie Tahari

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@kieunse
7
Shearling Trim Sweater Dress
Touches of shearling or faux shearling nod to current outerwear trends, offering additional warmth and a luxe, modern finish.
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7
Shearling Trim Sweater Dress
@kieunse
Touches of shearling or faux shearling nod to current outerwear trends, offering additional warmth and a luxe, modern finish.
Jean Paul Gaultier Ribbed-knit maxi dress
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Jean Paul Gaultier

Ribbed-knit maxi dress

$954

$1,590

Mytheresa

Steve Madden Riello Dress
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Steve Madden

Riello Dress

$129

Revolve

Valentino VLogo feather-trimmed turtleneck minidress
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Valentino

VLogo feather-trimmed turtleneck minidress

$4,000

Mytheresa

Markgong Sheath Henley Neckline Dress
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Markgong

Sheath Henley Neckline Dress

$504

Revolve

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@alvasperle
8
Cable Knit Midi Dress
Heavier and texturally interesting, cable knit midi dresses provide timeless comfort and a cozy, heritage-inspired vibe for low-light days.
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8
Cable Knit Midi Dress
@alvasperle
Heavier and texturally interesting, cable knit midi dresses provide timeless comfort and a cozy, heritage-inspired vibe for low-light days.
Tuckernuck Chocolate Cable Knit Fernie Midi Dress
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Tuckernuck

Chocolate Cable Knit Fernie Midi Dress

$85

$188

Tuckernuck

Tuckernuck Cream Freya Fringe Sweater Dress
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Tuckernuck

Cream Freya Fringe Sweater Dress

$142

$178

Tuckernuck

Elie Tahari Cashmere Fit & Flare Dress
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Elie Tahari

Cashmere Fit & Flare Dress

$198

$495

Elie Tahari

Elie Tahari Cashmere Long Sleeve Belted Dress
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Elie Tahari

Cashmere Long Sleeve Belted Dress

$198

$495

Elie Tahari

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@lovisabarkman
9
Belted Wool Blend Dress
A belted wool-blend dress provides snug warmth while the belt defines your shape for a more tailored, classy effect.
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9
Belted Wool Blend Dress
@lovisabarkman
A belted wool-blend dress provides snug warmth while the belt defines your shape for a more tailored, classy effect.
Another Tomorrow Wool Shirt Dress | Juniper
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Another Tomorrow

Wool Shirt Dress | Juniper

$750

ANOTHER TOMORROW

Prada Checked minidress
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Prada

Checked minidress

$2,200

Mytheresa

Max Mara Virgin wool midi dress
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Max Mara

Virgin wool midi dress

$339

$565

Mytheresa

Lemaire Turtleneck wool-blend midi dress
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Lemaire

Turtleneck wool-blend midi dress

$417

$695

Mytheresa

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Rue Sophie Mignet Midi Sweater Dress
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Rue Sophie

Mignet Midi Sweater Dress

$124

$248

Rue Sophie

Gabriela Hearst Tegea wool, cashmere and silk-blend midi dress
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Gabriela Hearst

Tegea wool, cashmere and silk-blend midi dress

$775

$1,550

Net-a-Porter

Mango Fitted sweater dress
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Mango

Fitted sweater dress

$59.99

Mango

Mango Draped combined dress
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Mango

Draped combined dress

$59.99

$79.99

Mango

Mango Knitted dress with bell sleeves
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Mango

Knitted dress with bell sleeves

$45.99

$89.99

Mango

moco Scoop Neck Loose Dress
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moco

Scoop Neck Loose Dress

$435

$480

moco

moco Straight Cut Midi Dress
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moco

Straight Cut Midi Dress

$205

$375

moco

KHAITE Ruth wool midi dress
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KHAITE

Ruth wool midi dress

$2,400

Net-a-Porter

Altuzarra Cuddy ribbed cashmere maxi dress
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Altuzarra

Cuddy ribbed cashmere maxi dress

$638

$1,595

Net-a-Porter

Brunello Cucinelli Ribbed wool midi dress
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Brunello Cucinelli

Ribbed wool midi dress

$4,100

Net-a-Porter

Gabriela Hearst Uriel Knit Maxi Dress in Black Brushed Cashmere
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Gabriela Hearst

Uriel Knit Maxi Dress in Black Brushed Cashmere

$4,670

Gabriela Hearst

Gabriela Hearst Hannah wool and cashmere-blend midi dress
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Gabriela Hearst

Hannah wool and cashmere-blend midi dress

$945

$1,890

Net-a-Porter

Johanna Ortiz Celestial Silence Dress
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Johanna Ortiz

Celestial Silence Dress

$995

Johanna Ortiz

LISA YANG Eliora cotton and cashmere-blend maxi dress
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LISA YANG

Eliora cotton and cashmere-blend maxi dress

$575

Net-a-Porter

Moncler Ribbed wool turleneck midi dress
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Moncler

Ribbed wool turleneck midi dress

$1,190

Net-a-Porter

Le Kasha Logan ribbed organic cashmere midi dress
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Le Kasha

Logan ribbed organic cashmere midi dress

$985

Net-a-Porter

TOVE Suzette wool and silk-blend turtleneck midi dress
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TOVE

Suzette wool and silk-blend turtleneck midi dress

$418

$835

Net-a-Porter

Another Tomorrow Rib Knit Dress | Black
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Another Tomorrow

Rib Knit Dress | Black

$1,190

ANOTHER TOMORROW

MARIA MCMANUS Ribbed recycled-cashmere and organic cotton-blend turtleneck midi dress
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MARIA MCMANUS

Ribbed recycled-cashmere and organic cotton-blend turtleneck midi dress

$387

$1,290

Net-a-Porter

Tuckernuck Squire Brown Rib Knit Crew Neck Long Sleeve A-Line Dress
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Tuckernuck

Squire Brown Rib Knit Crew Neck Long Sleeve A-Line Dress

$319

$398

Tuckernuck

BRAND RECOMMENDATION
JOSEPH
Joseph quietly excels at creating understated, beautifully made knitwear and wool dresses that feel simultaneously cozy and sophisticated. Their designs are beloved for their luxurious fabrics and modern, streamlined silhouettes—perfect for crisp, overcast days when you want a dress that balances comfort with a refined finish.
View Brand
BRAND RECOMMENDATION
JOSEPH
Joseph quietly excels at creating understated, beautifully made knitwear and wool dresses that feel simultaneously cozy and sophisticated. Their designs are beloved for their luxurious fabrics and modern, streamlined silhouettes—perfect for crisp, overcast days when you want a dress that balances comfort with a refined finish.
JOSEPH Knitted wool and silk maxi dress
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JOSEPH

Knitted wool and silk maxi dress

$542

$775

Mytheresa

JOSEPH Ribbed merino wool midi dress
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JOSEPH

Ribbed merino wool midi dress

$471

$785

Net-a-Porter

JOSEPH Wool midi dress
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JOSEPH

Wool midi dress

$416

$595

Mytheresa

JOSEPH Cashmere-blend sweater dress
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JOSEPH

Cashmere-blend sweater dress

$710

$1,015

Mytheresa

View brand
Mango Turtleneck knitted dress with brooch
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Mango

Turtleneck knitted dress with brooch

$59.99

$99.99

Mango

Veronica De Piante Anais ribbed wool midi dress
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Veronica De Piante

Anais ribbed wool midi dress

$539

$1,795

Net-a-Porter

Mango Perkins-neck knitted dress
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Mango

Perkins-neck knitted dress

$49.99

$89.99

Mango

Tuckernuck Red Long Sleeve Sara Maxi Dress
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Tuckernuck

Red Long Sleeve Sara Maxi Dress

$178

Tuckernuck

Jil Sander Cashmere midi dress
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Jil Sander

Cashmere midi dress

$1,463

$2,090

Mytheresa

Givenchy Paneled cashmere midi dress
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Givenchy

Paneled cashmere midi dress

$1,675

$3,350

Net-a-Porter

The Row Evins knitted midi dress
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The Row

Evins knitted midi dress

$1,075

$2,150

Net-a-Porter

MARIA MCMANUS Stretch-knit maxi dress
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MARIA MCMANUS

Stretch-knit maxi dress

$534

$890

Net-a-Porter

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

Tuckernuck Marron Fabiana Midi Dress
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Tuckernuck

Marron Fabiana Midi Dress

$241

$535

Tuckernuck

Vince Rib Scoop Neck Dress
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Vince

Rib Scoop Neck Dress

$328

Shopbop

Jil Sander Wool sweater dress
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Jil Sander

Wool sweater dress

$596

$1,490

Mytheresa

Le Kasha Logan ribbed organic cashmere midi dress
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Le Kasha

Logan ribbed organic cashmere midi dress

$985

Net-a-Porter

LOULOU DE SAISON Ari wool and cashmere-blend maxi dress
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LOULOU DE SAISON

Ari wool and cashmere-blend maxi dress

$300

$500

Net-a-Porter

Max Mara Sophia wool-blend midi dress
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Max Mara

Sophia wool-blend midi dress

$660

$1,100

Mytheresa

Lemaire Belted sweater dress
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Lemaire

Belted sweater dress

$345

$690

Mytheresa

SIMKHAI Skyla Cotton Cashmere Dress
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SIMKHAI

Skyla Cotton Cashmere Dress

$445

SIMKHAI

Cult Gaia Natacha cable-knit wool and cashmere-blend dress
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Cult Gaia

Natacha cable-knit wool and cashmere-blend dress

$420

$700

Net-a-Porter

Meshki Cleona Merino Wool Ribbed Long Sleeve Maxi Dress - Deep Chocolate
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Meshki

Cleona Merino Wool Ribbed Long Sleeve Maxi Dress - Deep Chocolate

$130

$185

Meshki

KHAITE Norla Dress in Black Silk Cashmere Jersey
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KHAITE

Norla Dress in Black Silk Cashmere Jersey

$1,880

KHAITE

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