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My Size

Winter Dresses for Seamless Desk-to-Dinner Style in New York City

For winter in New York City, choose dresses that balance warmth, elegance, and versatility—think cozy knits, tailored silhouettes, and rich textures that easily move from the office to an evening out. Below are detailed suggestions to help you stay polished during the day and effortlessly chic at night. If you have a specific color palette, preferred length, or budget, let us know for even more tailored picks!

@simkinstyle

Long-Sleeve Sheath Dress

A classic sheath in a neutral or jewel tone offers a polished, streamlined silhouette ideal for professional meetings and pairs easily with bold jewelry or a sleek belt for dinner.

See all

Victoria Beckham

Wool crepe midi dress

$1,150

Mytheresa

Tuckernuck

Black Hunter Dress

$297

$495

Tuckernuck

Black Halo

Marissa Sheath Dress

$273

$390

Shopbop

Pucci

Cady midi dress

$1,205

Mytheresa

Carolina Herrera

Crêpe midi dress

$1,249

$1,785

Mytheresa

Safiyaa

Off-shoulder crêpe midi dress

$1,228

$1,535

Mytheresa

Safiyaa

Draped crêpe midi dress

$962

$1,375

Mytheresa

Safiyaa

Off-shoulder crêpe midi dress

$1,074

$1,535

Mytheresa

Dolce&Gabbana

Crystal-embellished wool-blend crepe midi dress

$1,548

$3,095

Outnet

Roland Mouret

Floral-appliqué crêpe midi dress

$928

$1,160

Mytheresa

Black Halo

3/4 Sleeve Jackie O Dress

$390

Shopbop

Roland Mouret

Floral-appliqué crêpe midi dress

$928

$1,160

Mytheresa

Pucci

Printed jersey minidress

$1,085

Mytheresa

Stella McCartney

Bell-sleeve knit dress

$630

$1,575

Mytheresa

Roksanda

Ruffled midi dress

$1,450

Mytheresa

Stella McCartney

Off-shoulder jersey midi dress

$1,194

$1,990

Mytheresa

Victoria Beckham
Wool crepe midi dress
$1,150
Mytheresa
Tuckernuck
Black Hunter Dress
$297
$495
Tuckernuck
Black Halo
Marissa Sheath Dress
$273
$390
Shopbop
Pucci
Cady midi dress
$1,205
Mytheresa
Carolina Herrera
Crêpe midi dress
$1,249
$1,785
Mytheresa
Safiyaa
Off-shoulder crêpe midi dress
$1,228
$1,535
Mytheresa
Safiyaa
Draped crêpe midi dress
$962
$1,375
Mytheresa
Safiyaa
Off-shoulder crêpe midi dress
$1,074
$1,535
Mytheresa
Dolce&Gabbana
Crystal-embellished wool-blend crepe midi dress
$1,548
$3,095
Outnet
Roland Mouret
Floral-appliqué crêpe midi dress
$928
$1,160
Mytheresa
Black Halo
3/4 Sleeve Jackie O Dress
$390
Shopbop
Roland Mouret
Floral-appliqué crêpe midi dress
$928
$1,160
Mytheresa
Pucci
Printed jersey minidress
$1,085
Mytheresa
Stella McCartney
Bell-sleeve knit dress
$630
$1,575
Mytheresa
Roksanda
Ruffled midi dress
$1,450
Mytheresa
Stella McCartney
Off-shoulder jersey midi dress
$1,194
$1,990
Mytheresa

Long-Sleeve Sheath Dress

@simkinstyle

A classic sheath in a neutral or jewel tone offers a polished, streamlined silhouette ideal for professional meetings and pairs easily with bold jewelry or a sleek belt for dinner.

Victoria Beckham

Wool crepe midi dress

$1,150

Mytheresa

Tuckernuck

Black Hunter Dress

$297

$495

Tuckernuck

Black Halo

Marissa Sheath Dress

$273

$390

Shopbop

Pucci

Cady midi dress

$1,205

Mytheresa

@alexandrapereira

Wool Turtleneck Sweater Dress

Warm and sophisticated, a turtleneck sweater dress is both comfortable in the winter chill and chic enough for evening plans. Choose a tailored fit for maximum versatility.

See all

TOTEME

Wool and silk sweater dress

$493

$705

Mytheresa

TOTEME

Wool and silk-blend turtleneck dress

$420

$700

Net-a-Porter

Victoria Beckham

Wool-blend sweater dress

$903

$1,290

Mytheresa

Veronica Beard

Wool and cashmere sweater dress

$536

$670

Mytheresa

Jardin des Orangers

Wool and cashmere sweater dress

$400

$500

Mytheresa

Alaïa

Faux shearling-trimmed virgin wool midi dress

$3,090

Mytheresa

Brunello Cucinelli

Bead-embellished wool-blend jersey turtleneck midi dress

$1,398

$3,495

Outnet

Lemaire

Turtleneck wool-blend midi dress

$417

$695

Mytheresa

TOTEME

Wool and cashmere-blend sweater dress

$896

$1,120

Mytheresa

Max Mara

Cable-knit wool and cashmere-blend turtleneck maxi dress

$880

$1,760

Net-a-Porter

TOVE

Suzette wool and silk-blend turtleneck midi dress

$418

$835

Net-a-Porter

Allude

Wool and cashmere-blend turtleneck maxi dress

$640

Net-a-Porter

Another Tomorrow

Ribbed wool-blend turtleneck midi dress

$298

$850

Outnet

RIXO

Elliette wool and cashmere midi dress

$605

Mytheresa

JOSEPH

Ribbed-knit turtleneck wool and silk dress

$525

$750

Mytheresa

Lemaire

Belted wool-blend turtleneck midi dress

$372

$620

Net-a-Porter

TOTEME
Wool and silk sweater dress
$493
$705
Mytheresa
TOTEME
Wool and silk-blend turtleneck dress
$420
$700
Net-a-Porter
Victoria Beckham
Wool-blend sweater dress
$903
$1,290
Mytheresa
Veronica Beard
Wool and cashmere sweater dress
$536
$670
Mytheresa
Jardin des Orangers
Wool and cashmere sweater dress
$400
$500
Mytheresa
Alaïa
Faux shearling-trimmed virgin wool midi dress
$3,090
Mytheresa
Brunello Cucinelli
Bead-embellished wool-blend jersey turtleneck midi dress
$1,398
$3,495
Outnet
Lemaire
Turtleneck wool-blend midi dress
$417
$695
Mytheresa
TOTEME
Wool and cashmere-blend sweater dress
$896
$1,120
Mytheresa
Max Mara
Cable-knit wool and cashmere-blend turtleneck maxi dress
$880
$1,760
Net-a-Porter
TOVE
Suzette wool and silk-blend turtleneck midi dress
$418
$835
Net-a-Porter
Allude
Wool and cashmere-blend turtleneck maxi dress
$640
Net-a-Porter
Another Tomorrow
Ribbed wool-blend turtleneck midi dress
$298
$850
Outnet
RIXO
Elliette wool and cashmere midi dress
$605
Mytheresa
JOSEPH
Ribbed-knit turtleneck wool and silk dress
$525
$750
Mytheresa
Lemaire
Belted wool-blend turtleneck midi dress
$372
$620
Net-a-Porter

Wool Turtleneck Sweater Dress

@alexandrapereira

Warm and sophisticated, a turtleneck sweater dress is both comfortable in the winter chill and chic enough for evening plans. Choose a tailored fit for maximum versatility.

TOTEME

Wool and silk sweater dress

$493

$705

Mytheresa

TOTEME

Wool and silk-blend turtleneck dress

$420

$700

Net-a-Porter

Victoria Beckham

Wool-blend sweater dress

$903

$1,290

Mytheresa

Veronica Beard

Wool and cashmere sweater dress

$536

$670

Mytheresa

@melodiebanfield

Velvet Midi Dress

Velvet’s plush texture is not only winter-appropriate but adds instant elegance for after-hours. Opt for deeper hues like burgundy or forest green, which look professional by day and luxe by night.

See all

Velvet

Kandace velvet midi dress

$273

$456

Mytheresa

Velvet

Velvet midi dress

$415

Mytheresa

Emilia Wickstead

Camilla cotton velvet midi dress

$2,568

Mytheresa

Max Mara

Carl embellished silk velvet midi dress

$1,212

$1,515

Mytheresa

Shoshanna

Audrey Dress

$214.5

$429

Shopbop

Rebecca Vallance

Edwiena embellished velvet midi dress

$970

Mytheresa

Sea

Alia devoré-velvet midi dress

$198

$395

Net-a-Porter

Sea Cailyn ruched crushed-velvet midi dress

Sea

Cailyn ruched crushed-velvet midi dress

$130

$325

Net-a-Porter

ALFIE

Malu Dress

$331

$560

FWRD

Alaïa

Velvet maxi dress

$3,490

Mytheresa

Polo Ralph Lauren

Velvet midi dress

$194

$485

Mytheresa

Emilia Wickstead

Nyla cotton velvet midi dress

$1,050

$1,751

Mytheresa

Alessandra Rich

Velvet midi dress

$952

$1,905

Mytheresa

Tuckernuck

Winetasting Velvet Lace Delaney Dress

$262

$328

Tuckernuck

Liberowe

Arya draped velvet midi dress

$800

$1,600

Net-a-Porter

Rasario

Velvet midi dress

$1,098

$1,830

Mytheresa

Velvet
Kandace velvet midi dress
$273
$456
Mytheresa
Velvet
Velvet midi dress
$415
Mytheresa
Emilia Wickstead
Camilla cotton velvet midi dress
$2,568
Mytheresa
Max Mara
Carl embellished silk velvet midi dress
$1,212
$1,515
Mytheresa
Shoshanna
Audrey Dress
$214.5
$429
Shopbop
Rebecca Vallance
Edwiena embellished velvet midi dress
$970
Mytheresa
Sea
Alia devoré-velvet midi dress
$198
$395
Net-a-Porter
Sea
Cailyn ruched crushed-velvet midi dress
$130
$325
Net-a-Porter
ALFIE
Malu Dress
$331
$560
FWRD
Alaïa
Velvet maxi dress
$3,490
Mytheresa
Polo Ralph Lauren
Velvet midi dress
$194
$485
Mytheresa
Emilia Wickstead
Nyla cotton velvet midi dress
$1,050
$1,751
Mytheresa
Alessandra Rich
Velvet midi dress
$952
$1,905
Mytheresa
Tuckernuck
Winetasting Velvet Lace Delaney Dress
$262
$328
Tuckernuck
Liberowe
Arya draped velvet midi dress
$800
$1,600
Net-a-Porter
Rasario
Velvet midi dress
$1,098
$1,830
Mytheresa

Velvet Midi Dress

@melodiebanfield

Velvet’s plush texture is not only winter-appropriate but adds instant elegance for after-hours. Opt for deeper hues like burgundy or forest green, which look professional by day and luxe by night.

Velvet

Kandace velvet midi dress

$273

$456

Mytheresa

Velvet

Velvet midi dress

$415

Mytheresa

Emilia Wickstead

Camilla cotton velvet midi dress

$2,568

Mytheresa

Max Mara

Carl embellished silk velvet midi dress

$1,212

$1,515

Mytheresa

@chloelecareux

Knit Wrap Dress

The wrap design flatters most body types, and a fine knit ensures both comfort and warmth. Add a tailored blazer at work, then swap for statement earrings at dinner.

See all

Elie Tahari

Margaux Ruched Dress

$221

$368

Elie Tahari

Jardin des Orangers

Wool and cashmere wrap dress

$346

$495

Mytheresa

Enza Costa

Ribbed-knit midi wrap dress

$88

$352

Outnet

Jardin des Orangers

Wool and cashmere wrap dress

$555

Mytheresa

Diane von Furstenberg

Astrid wool and cashmere-blend midi wrap dress

$280

$560

Outnet

Diane von Furstenberg

Chelsea wrap-effect jacquard-knit dress

$243

$538

Outnet

JOSEPH

Linen-blend midi wrap dress

$239

$795

Outnet

SIMKHAI

Skyla Cotton Cashmere Dress

$445

SIMKHAI

Diane von Furstenberg

Edwina intarsia-knit mini wrap dress

$196

$558

Outnet

By Malene Birger

Gilena ribbed ECOVERO™-blend midi wrap dress

$200

$500

Outnet

SIMKHAI

Skyla Wrap Dress

$445

Revolve

Veronica Beard

Salomez Knit Dress

$479

$598

Revolve

MAJORELLE

Candella Faux Fur Wrap Dress

$175

$218

Revolve

Diane von Furstenberg

Luella floral-print wool-jersey wrap dress

$243

$538

Outnet

Veronica Beard

Salomez wool and cashmere wrap midi dress

$600

Mytheresa

Staud

Spritz Dress

$147

$245

Shopbop

Elie Tahari
Margaux Ruched Dress
$221
$368
Elie Tahari
Jardin des Orangers
Wool and cashmere wrap dress
$346
$495
Mytheresa
Enza Costa
Ribbed-knit midi wrap dress
$88
$352
Outnet
Jardin des Orangers
Wool and cashmere wrap dress
$555
Mytheresa
Diane von Furstenberg
Astrid wool and cashmere-blend midi wrap dress
$280
$560
Outnet
Diane von Furstenberg
Chelsea wrap-effect jacquard-knit dress
$243
$538
Outnet
JOSEPH
Linen-blend midi wrap dress
$239
$795
Outnet
SIMKHAI
Skyla Cotton Cashmere Dress
$445
SIMKHAI
Diane von Furstenberg
Edwina intarsia-knit mini wrap dress
$196
$558
Outnet
By Malene Birger
Gilena ribbed ECOVERO™-blend midi wrap dress
$200
$500
Outnet
SIMKHAI
Skyla Wrap Dress
$445
Revolve
Veronica Beard
Salomez Knit Dress
$479
$598
Revolve
MAJORELLE
Candella Faux Fur Wrap Dress
$175
$218
Revolve
Diane von Furstenberg
Luella floral-print wool-jersey wrap dress
$243
$538
Outnet
Veronica Beard
Salomez wool and cashmere wrap midi dress
$600
Mytheresa
Staud
Spritz Dress
$147
$245
Shopbop

Knit Wrap Dress

@chloelecareux

The wrap design flatters most body types, and a fine knit ensures both comfort and warmth. Add a tailored blazer at work, then swap for statement earrings at dinner.

Elie Tahari

Margaux Ruched Dress

$221

$368

Elie Tahari

Jardin des Orangers

Wool and cashmere wrap dress

$346

$495

Mytheresa

Enza Costa

Ribbed-knit midi wrap dress

$88

$352

Outnet

Jardin des Orangers

Wool and cashmere wrap dress

$555

Mytheresa

Blazer Dress

A structured blazer dress exudes contemporary professionalism. Cinch the waist with a statement belt and switch up shoes for a sleek evening transformation.

See all

Max Mara

Odessa wrap-effect wool dress

$596

$1,490

Net-a-Porter

Max Mara

Sella virgin wool shirt dress

$1,288

$1,840

Mytheresa

Alaïa

Hooded virgin wool minidress

$4,620

Mytheresa

Mango

Double-breasted blazer-style dress

$139.99

Mango

MILLY

Noora Blazer Dress

$441

$495

Revolve

Cinq à Sept

Cayleigh Dress

$222.5

$445

Cinq a Sept

Mango

Blazer-style dress with belt

$79.99

$139.99

Mango

Ralph Lauren Collection

Camden Blazer Dress

$2,790

FWRD

Balmain

Button-embellished cotton-twill mini dress

$1,945

$3,890

Net-a-Porter

Black Halo

Madeline Sheath Dress

$415

Shopbop

Veronica Beard

Elianna crepe mini tuxedo dress

$405

$898

Outnet

Balmain

Wool mini dress

$809

$2,695

Outnet

EAVES

Myah Mini Blazer Dress

$278

$295

Revolve

Mugler

Scuba minidress

$820

$2,050

Mytheresa

PRISCAVera

Mini Jacket Dress

$174

$695

FWRD

Theory

Cropped crepe jacket

$196

$490

Outnet

Max Mara
Odessa wrap-effect wool dress
$596
$1,490
Net-a-Porter
Max Mara
Sella virgin wool shirt dress
$1,288
$1,840
Mytheresa
Alaïa
Hooded virgin wool minidress
$4,620
Mytheresa
Mango
Double-breasted blazer-style dress
$139.99
Mango
MILLY
Noora Blazer Dress
$441
$495
Revolve
Cinq à Sept
Cayleigh Dress
$222.5
$445
Cinq a Sept
Mango
Blazer-style dress with belt
$79.99
$139.99
Mango
Ralph Lauren Collection
Camden Blazer Dress
$2,790
FWRD
Balmain
Button-embellished cotton-twill mini dress
$1,945
$3,890
Net-a-Porter
Black Halo
Madeline Sheath Dress
$415
Shopbop
Veronica Beard
Elianna crepe mini tuxedo dress
$405
$898
Outnet
Balmain
Wool mini dress
$809
$2,695
Outnet
EAVES
Myah Mini Blazer Dress
$278
$295
Revolve
Mugler
Scuba minidress
$820
$2,050
Mytheresa
PRISCAVera
Mini Jacket Dress
$174
$695
FWRD
Theory
Cropped crepe jacket
$196
$490
Outnet

Blazer Dress

A structured blazer dress exudes contemporary professionalism. Cinch the waist with a statement belt and switch up shoes for a sleek evening transformation.

Max Mara

Odessa wrap-effect wool dress

$596

$1,490

Net-a-Porter

Max Mara

Sella virgin wool shirt dress

$1,288

$1,840

Mytheresa

Alaïa

Hooded virgin wool minidress

$4,620

Mytheresa

Mango

Double-breasted blazer-style dress

$139.99

Mango

@carlacrnt

A-Line Wool Dress

A wool A-line silhouette provides cozy warmth and works well for full days on the go. Add a statement necklace and swap flats for heeled boots after office hours.

See all

Brunello Cucinelli

Belted pleated wool midi dress

$2,550

$5,100

Net-a-Porter

Dolce&Gabbana

Virgin wool minidress

$1,396

$1,995

Mytheresa

Emilia Wickstead

Leontine wool crêpe midi dress

$1,224

$2,040

Mytheresa

Emilia Wickstead

Camilla midi dress

$2,845

Mytheresa

self-portrait

Belted wool-blend midi dress

$660

$825

Net-a-Porter

Gabriela Hearst

Rebus wool, silk and cashmere-blend midi dress

$1,750

Net-a-Porter

Giuliva Heritage

The Dora belted wool-jersey midi shirt dress

$1,011

$1,685

Net-a-Porter

Patou

Vinyl-trimmed wool-blend mini dress

$609

$1,015

Net-a-Porter

Oscar de la Renta

Embellished belted wool-blend midi dress

$3,690

Net-a-Porter

Emilia Wickstead

Georgie wool midi dress

$1,860

$3,100

Mytheresa

Valentino Garavani

Embellished wool and silk-blend crepe midi dress

$3,250

$6,500

Net-a-Porter

Valentino

Crepe Couture minidress

$2,660

$3,800

Mytheresa

Valentino Garavani

Embellished leopard-print wool and silk-blend midi dress

$3,720

$6,200

Net-a-Porter

Brandon Maxwell

The Sophie Prince of Wales checked wool-tweed mini dress

$825

$1,650

Net-a-Porter

Valentino

Embellished wool and silk minidress

$2,800

$3,500

Mytheresa

Veronica De Piante

Elsie grain de poudre wool mini dress

$948

$1,895

Net-a-Porter

Brunello Cucinelli
Belted pleated wool midi dress
$2,550
$5,100
Net-a-Porter
Dolce&Gabbana
Virgin wool minidress
$1,396
$1,995
Mytheresa
Emilia Wickstead
Leontine wool crêpe midi dress
$1,224
$2,040
Mytheresa
Emilia Wickstead
Camilla midi dress
$2,845
Mytheresa
self-portrait
Belted wool-blend midi dress
$660
$825
Net-a-Porter
Gabriela Hearst
Rebus wool, silk and cashmere-blend midi dress
$1,750
Net-a-Porter
Giuliva Heritage
The Dora belted wool-jersey midi shirt dress
$1,011
$1,685
Net-a-Porter
Patou
Vinyl-trimmed wool-blend mini dress
$609
$1,015
Net-a-Porter
Oscar de la Renta
Embellished belted wool-blend midi dress
$3,690
Net-a-Porter
Emilia Wickstead
Georgie wool midi dress
$1,860
$3,100
Mytheresa
Valentino Garavani
Embellished wool and silk-blend crepe midi dress
$3,250
$6,500
Net-a-Porter
Valentino
Crepe Couture minidress
$2,660
$3,800
Mytheresa
Valentino Garavani
Embellished leopard-print wool and silk-blend midi dress
$3,720
$6,200
Net-a-Porter
Brandon Maxwell
The Sophie Prince of Wales checked wool-tweed mini dress
$825
$1,650
Net-a-Porter
Valentino
Embellished wool and silk minidress
$2,800
$3,500
Mytheresa
Veronica De Piante
Elsie grain de poudre wool mini dress
$948
$1,895
Net-a-Porter

A-Line Wool Dress

@carlacrnt

A wool A-line silhouette provides cozy warmth and works well for full days on the go. Add a statement necklace and swap flats for heeled boots after office hours.

Brunello Cucinelli

Belted pleated wool midi dress

$2,550

$5,100

Net-a-Porter

Dolce&Gabbana

Virgin wool minidress

$1,396

$1,995

Mytheresa

Emilia Wickstead

Leontine wool crêpe midi dress

$1,224

$2,040

Mytheresa

Emilia Wickstead

Camilla midi dress

$2,845

Mytheresa

@therealmilanj

Ribbed Knit Midi Dress

Ribbed knits are trending for winter 2025 because of their flattering fit and comfort. A midi version feels modern for the office and easily transitions to dinner with a change of accessories.

See all

Another Tomorrow

Deep V Tank Knit Dress - Resale | Black

$495

$990

ANOTHER TOMORROW

Another Tomorrow

Rib Knit Dress | Black

$1,190

ANOTHER TOMORROW

LE BOP

Ringer Midi Dress

$248

Shopbop

Theory

Ribbed merino wool-blend midi dress

$156

$345

Outnet

LISA YANG

Isabela Dress

$645

Shopbop

alice + olivia

Wright ribbed wool-blend midi dress

$99

$395

Outnet

Dolce&Gabbana

Midi dress

$1,347

$1,925

Mytheresa

Altuzarra

Trey ruffled ribbed-knit gown

$735

$1,050

Mytheresa

Tuckernuck

Plum Shimmer Knit Midi Dress

$125

Tuckernuck

Max Mara

Egizio ribbed-knit midi dress

$925

Mytheresa

o.p.t

Nicole Dress

$118.8

$198

Shopbop

Brunello Cucinelli

Ribbed-knit lamé midi dress

$3,300

Mytheresa

Theory

Ribbed-knit midi dress

$149

$425

Outnet

Elie Tahari

Knit Midi Dress

$119

$298

Elie Tahari

Mugler

Ribbed-knit midi dress

$984

$1,230

Mytheresa

self-portrait

Ribbed-knit midi dress

$650

Mytheresa

Another Tomorrow
Deep V Tank Knit Dress - Resale | Black
$495
$990
ANOTHER TOMORROW
Another Tomorrow
Rib Knit Dress | Black
$1,190
ANOTHER TOMORROW
LE BOP
Ringer Midi Dress
$248
Shopbop
Theory
Ribbed merino wool-blend midi dress
$156
$345
Outnet
LISA YANG
Isabela Dress
$645
Shopbop
alice + olivia
Wright ribbed wool-blend midi dress
$99
$395
Outnet
Dolce&Gabbana
Midi dress
$1,347
$1,925
Mytheresa
Altuzarra
Trey ruffled ribbed-knit gown
$735
$1,050
Mytheresa
Tuckernuck
Plum Shimmer Knit Midi Dress
$125
Tuckernuck
Max Mara
Egizio ribbed-knit midi dress
$925
Mytheresa
o.p.t
Nicole Dress
$118.8
$198
Shopbop
Brunello Cucinelli
Ribbed-knit lamé midi dress
$3,300
Mytheresa
Theory
Ribbed-knit midi dress
$149
$425
Outnet
Elie Tahari
Knit Midi Dress
$119
$298
Elie Tahari
Mugler
Ribbed-knit midi dress
$984
$1,230
Mytheresa
self-portrait
Ribbed-knit midi dress
$650
Mytheresa

Ribbed Knit Midi Dress

@therealmilanj

Ribbed knits are trending for winter 2025 because of their flattering fit and comfort. A midi version feels modern for the office and easily transitions to dinner with a change of accessories.

Another Tomorrow

Deep V Tank Knit Dress - Resale | Black

$495

$990

ANOTHER TOMORROW

Another Tomorrow

Rib Knit Dress | Black

$1,190

ANOTHER TOMORROW

LE BOP

Ringer Midi Dress

$248

Shopbop

Theory

Ribbed merino wool-blend midi dress

$156

$345

Outnet

Plaid Shirt Dress

A plaid shirt dress brings smart-casual polish during the day. Belt it for more definition and add knee-high boots for an elevated evening look.

See all

Burberry

Ribbon Check silk shirt dress

$2,275

$3,250

Mytheresa

RRL Selina belted checked cotton-flannel maxi shirt dress

RRL

Selina belted checked cotton-flannel maxi shirt dress

$277

$395

Net-a-Porter

Burberry

Burberry Check cotton shirt dress

$805

$1,150

Mytheresa

Woolrich

Checked wool-blend shirtdress

$219

$365

Mytheresa

Tuckernuck

Isle of Skye Plaid Callahan Shirt Dress

$89

$148

Tuckernuck

Polo Ralph Lauren

Checked cotton-blend shirt dress

$339

$485

Mytheresa

Polo Ralph Lauren

Collared Long Sleeve Dress

$238.8

$398

Shopbop

Polo Ralph Lauren

Belted plaid cotton-blend shirt dress

$400

Mytheresa

Tuckernuck

Tartan Martine Maxi Bubble Dress

$136

$248

Tuckernuck

Burberry

Burberry Check cotton shirt dress

$1,000

$1,250

Mytheresa

Tuckernuck

Isle Of Skye Plaid Cherie Dress

$136

$248

Tuckernuck

Marant Étoile

Yalisa cotton shirt

$304

$435

Mytheresa

Emilia Wickstead

Marione belted tartan wool-blend midi dress

$3,655

Mytheresa

Veronica Beard

Barrett midi dress

$500

Mytheresa

THE ATTICO

Checked cotton-blend shirt dress

$794

$1,135

Mytheresa

Emilia Wickstead

Jody checked midi dress

$2,490

Mytheresa

Burberry
Ribbon Check silk shirt dress
$2,275
$3,250
Mytheresa
RRL
Selina belted checked cotton-flannel maxi shirt dress
$277
$395
Net-a-Porter
Burberry
Burberry Check cotton shirt dress
$805
$1,150
Mytheresa
Woolrich
Checked wool-blend shirtdress
$219
$365
Mytheresa
Tuckernuck
Isle of Skye Plaid Callahan Shirt Dress
$89
$148
Tuckernuck
Polo Ralph Lauren
Checked cotton-blend shirt dress
$339
$485
Mytheresa
Polo Ralph Lauren
Collared Long Sleeve Dress
$238.8
$398
Shopbop
Polo Ralph Lauren
Belted plaid cotton-blend shirt dress
$400
Mytheresa
Tuckernuck
Tartan Martine Maxi Bubble Dress
$136
$248
Tuckernuck
Burberry
Burberry Check cotton shirt dress
$1,000
$1,250
Mytheresa
Tuckernuck
Isle Of Skye Plaid Cherie Dress
$136
$248
Tuckernuck
Marant Étoile
Yalisa cotton shirt
$304
$435
Mytheresa
Emilia Wickstead
Marione belted tartan wool-blend midi dress
$3,655
Mytheresa
Veronica Beard
Barrett midi dress
$500
Mytheresa
THE ATTICO
Checked cotton-blend shirt dress
$794
$1,135
Mytheresa
Emilia Wickstead
Jody checked midi dress
$2,490
Mytheresa

Plaid Shirt Dress

A plaid shirt dress brings smart-casual polish during the day. Belt it for more definition and add knee-high boots for an elevated evening look.

Burberry

Ribbon Check silk shirt dress

$2,275

$3,250

Mytheresa

RRL

Selina belted checked cotton-flannel maxi shirt dress

$277

$395

Net-a-Porter

Burberry

Burberry Check cotton shirt dress

$805

$1,150

Mytheresa

Woolrich

Checked wool-blend shirtdress

$219

$365

Mytheresa

@shlaikovaelena

High-Neck Midi Dress

A high neckline adds sophistication perfect for meetings, while the midi length is equally suited for dinner engagement. Dark colors or subtle prints keep it city-appropriate.

See all

Roland Mouret

Cady midi dress

$1,180

Mytheresa

Cult Gaia

Keller Dress

$463

$798

Revolve

Roland Mouret

Bridal cady midi dress

$1,200

Mytheresa

Roland Mouret

Cady midi dress

$801

$1,145

Mytheresa

Roland Mouret

High neck cady midi dress

$1,130

Mytheresa

alice + olivia

Nida stretch-crepe dress

$117

$465

Outnet

Mango

High-neck godet dress

$99.99

Mango

A-line turtleneck dress

$49.99

$99.99

Mango

Roland Mouret

Cady midi dress

$1,200

Mytheresa

Mango

Dress with scarf detail

$139.99

Mango

St. Agni

St Agni Soft Sculptural Dress

$376

$399

Revolve

Mango

Long dress with draped neck

$99.99

Mango

Vince

Turtleneck midi dress

$220

$315

Mytheresa

Vince

Knitted midi dress

$123

$245

Outnet

Roland Mouret

Crêpe midi dress

$1,215

Mytheresa

Cult Gaia

Katara Dress

$454

$498

Revolve

Roland Mouret
Cady midi dress
$1,180
Mytheresa
Cult Gaia
Keller Dress
$463
$798
Revolve
Roland Mouret
Bridal cady midi dress
$1,200
Mytheresa
Roland Mouret
Cady midi dress
$801
$1,145
Mytheresa
Roland Mouret
High neck cady midi dress
$1,130
Mytheresa
alice + olivia
Nida stretch-crepe dress
$117
$465
Outnet
Mango
High-neck godet dress
$99.99
Mango
Mango
A-line turtleneck dress
$49.99
$99.99
Mango
Roland Mouret
Cady midi dress
$1,200
Mytheresa
Mango
Dress with scarf detail
$139.99
Mango
St. Agni
St Agni Soft Sculptural Dress
$376
$399
Revolve
Mango
Long dress with draped neck
$99.99
Mango
Vince
Turtleneck midi dress
$220
$315
Mytheresa
Vince
Knitted midi dress
$123
$245
Outnet
Roland Mouret
Crêpe midi dress
$1,215
Mytheresa
Cult Gaia
Katara Dress
$454
$498
Revolve

High-Neck Midi Dress

@shlaikovaelena

A high neckline adds sophistication perfect for meetings, while the midi length is equally suited for dinner engagement. Dark colors or subtle prints keep it city-appropriate.

Roland Mouret

Cady midi dress

$1,180

Mytheresa

Cult Gaia

Keller Dress

$463

$798

Revolve

Roland Mouret

Bridal cady midi dress

$1,200

Mytheresa

Roland Mouret

Cady midi dress

$801

$1,145

Mytheresa

@thebstinger

Sweater Dress with Belt

A belted sweater dress offers cozy structure. Pair with tights and ankle boots at work; swap in bold earrings and a clutch for dinner.

See all

Brunello Cucinelli

Belted knitted midi dress

$3,570

$5,100

Mytheresa

Victoria Beckham

Wool-blend sweater dress

$903

$1,290

Mytheresa

Elie Tahari

Cashmere Long Sleeve Belted Dress

$198

$495

Elie Tahari

Gabriela Hearst

Imagene belted ribbed pointelle-knit wool midi dress

$810

$1,350

Net-a-Porter

Gabriela Hearst

Imagene belted wool midi dress

$1,824

Mytheresa

Shoshanna

Sam Dress

$276

$460

Shopbop

Alaïa

Wool-blend minidress

$3,470

Mytheresa

self-portrait

Belted ribbed-knit midi dress

$552

$690

Net-a-Porter

Gabriela Hearst

Imagene wool midi dress

$1,085

$1,550

Mytheresa

Elie Tahari

Sleeveless Cashmere Belted Dress

$190

$475

Elie Tahari

Shoshanna

Tara Dress

$220

$440

Shopbop

L'Academie

By Marianna Leslia Belted Midi Dress

$213

$259

FWRD

Elie Tahari

Cashmere Long Sleeve Belted Dress

$198

$495

Elie Tahari

Gabriela Hearst

Meier belted ribbed wool and cashmere-blend midi dress

$500

$1,250

Net-a-Porter

Gabriela Hearst

Meier wool and cashmere maxi dress

$1,315

Mytheresa

Proenza Schouler

Lauryn Dress

$298

$990

FWRD

Brunello Cucinelli
Belted knitted midi dress
$3,570
$5,100
Mytheresa
Victoria Beckham
Wool-blend sweater dress
$903
$1,290
Mytheresa
Elie Tahari
Cashmere Long Sleeve Belted Dress
$198
$495
Elie Tahari
Gabriela Hearst
Imagene belted ribbed pointelle-knit wool midi dress
$810
$1,350
Net-a-Porter
Gabriela Hearst
Imagene belted wool midi dress
$1,824
Mytheresa
Shoshanna
Sam Dress
$276
$460
Shopbop
Alaïa
Wool-blend minidress
$3,470
Mytheresa
self-portrait
Belted ribbed-knit midi dress
$552
$690
Net-a-Porter
Gabriela Hearst
Imagene wool midi dress
$1,085
$1,550
Mytheresa
Elie Tahari
Sleeveless Cashmere Belted Dress
$190
$475
Elie Tahari
Shoshanna
Tara Dress
$220
$440
Shopbop
L'Academie
By Marianna Leslia Belted Midi Dress
$213
$259
FWRD
Elie Tahari
Cashmere Long Sleeve Belted Dress
$198
$495
Elie Tahari
Gabriela Hearst
Meier belted ribbed wool and cashmere-blend midi dress
$500
$1,250
Net-a-Porter
Gabriela Hearst
Meier wool and cashmere maxi dress
$1,315
Mytheresa
Proenza Schouler
Lauryn Dress
$298
$990
FWRD

Sweater Dress with Belt

@thebstinger

A belted sweater dress offers cozy structure. Pair with tights and ankle boots at work; swap in bold earrings and a clutch for dinner.

Brunello Cucinelli

Belted knitted midi dress

$3,570

$5,100

Mytheresa

Victoria Beckham

Wool-blend sweater dress

$903

$1,290

Mytheresa

Elie Tahari

Cashmere Long Sleeve Belted Dress

$198

$495

Elie Tahari

Gabriela Hearst

Imagene belted ribbed pointelle-knit wool midi dress

$810

$1,350

Net-a-Porter

Shop More

Black Halo

Marissa Sheath Dress

$273

$390

Shopbop

Tuckernuck

Brown Houndstooth Smith Dress

$198

$248

Tuckernuck

Vince

Long Sleeve Collar Stand Shirt Dress

$274

$548

Shopbop

Black Halo

Madeline Sheath Dress

$415

Shopbop

Tuckernuck

Navy Ponte Clifton Dress

$168

Tuckernuck

Black Crepe Haley Dress

$248

Tuckernuck

S Max Mara

Orione midi dress

$623

$890

Mytheresa

Norma Kamali

Long Sleeve Side Draped Dress

$117

$195

Shopbop

Tuckernuck

Black Hunter Dress

$297

$495

Tuckernuck

Black Dupioni Tassel Downing Dress

$198

Tuckernuck

Chocolate Brown Zarah Midi Dress

$142

$178

Tuckernuck

Charcoal Clifton Dress

$168

Tuckernuck

Marron Fabiana Midi Dress

$214

$535

Tuckernuck

Mango

Long dress with draped neck

$89.99

Mango

Cinq à Sept

Tovianna Dress

$255

$425

Cinq a Sept

Tuckernuck

Black Side Tie Elspeth Maxi Dress

$178

Tuckernuck

Sold Out NYC

The Turtleneck Dress in Black

$265

Soldout Nyc

Cinq à Sept

Cayleigh Dress

$222.5

$445

Cinq a Sept

Tuckernuck

Grenache Robb Dress

$318

$795

Tuckernuck

Apiece Apart

Volta Long Sleeve Dress

$162.5

$325

Shopbop

BRAND RECOMMENDATION

SIMKHAI

Simkhai shines for modern, city-sleek dresses with expert tailoring and a knack for making luxurious, winter-ready fabrics feel fresh and approachable. Their versatile silhouettes move seamlessly from morning meetings to intimate dinners, capturing the polished yet subtly daring vibe perfect for New York winters.

View Brand

SIMKHAI

Skyla Wrap Dress

$267

$445

Shopbop

SIMKHAI

Skyla Wrap Dress

$311.5

$445

Shopbop

SIMKHAI

Ribbed knit-paneled satin-crepe midi dress

$298

$745

Outnet

SIMKHAI

Genna Knit Midi Dress

$545

SIMKHAI

Marabella Draped Satin Midi Dress

$645

SIMKHAI

Abilene knitted pleated midi dress

$668

$955

Mytheresa

SIMKHAI

Adelle Draped Satin Gown

$845

SIMKHAI

Frances knitted satin midi dress

$476

$680

Mytheresa

SIMKHAI

Skyla Wrap Dress

$267

$445

Shopbop

SIMKHAI

Skyla Wrap Dress

$311.5

$445

Shopbop

SIMKHAI

Ribbed knit-paneled satin-crepe midi dress

$298

$745

Outnet

SIMKHAI

Genna Knit Midi Dress

$545

SIMKHAI

Marabella Draped Satin Midi Dress

$645

SIMKHAI

Abilene knitted pleated midi dress

$668

$955

Mytheresa

SIMKHAI

Adelle Draped Satin Gown

$845

SIMKHAI

Frances knitted satin midi dress

$476

$680

Mytheresa

BRAND RECOMMENDATION

SIMKHAI

Skyla Wrap Dress

$267

$445

Shopbop

SIMKHAI

Skyla Wrap Dress

$311.5

$445

Shopbop

SIMKHAI

Ribbed knit-paneled satin-crepe midi dress

$298

$745

Outnet

SIMKHAI

Genna Knit Midi Dress

$545

SIMKHAI

View brand

Black Halo

3/4 Sleeve Jackie O Dress

$390

Shopbop

Norma Kamali

Turtleneck Gown

$133

$190

Shopbop

Tuckernuck

Black Cherry Dena Midi Dress

$400

$795

Tuckernuck

Elie Tahari

Cashmere Long Sleeve Belted Dress

$198

$495

Elie Tahari

Courrèges

Twill minidress

$668

$835

Mytheresa

Another Tomorrow

Panelled Dress - Resale | Black

$495

$990

ANOTHER TOMORROW

Tuckernuck

Black Gio Maxi Dress

$128

Tuckernuck

Long Sleeve Shirt Dress in Crepe

$795

Tuckernuck

Winetasting Side Tie Elspeth Maxi Dress

$178

Tuckernuck

Mango

Fitted dress with bell sleeves

$49.99

$99.99

Mango

Tuckernuck

Black Kingston Knit Dress

$198

Tuckernuck

Staud

MERCER DRESS | BLACK

$275

Staud

Mango

A-line dress with godets

$59.99

$99.99

Mango

Tuckernuck

Chocolate Lysandra A Line Midi Dress

$278

Tuckernuck

Black Jersey Knit Wilbanks Midi Dress

$214

$268

Tuckernuck

Emilia Wickstead

Elta wool midi dress

$1,351

$1,930

Mytheresa

Tuckernuck

Black Cape Leah Dress

$168

Tuckernuck

Mei Mei J

Long Sleeve Midi Scuba Dress

$231

$330

Shopbop

Tuckernuck

Navy Crepe Samantha Dress

$168

Tuckernuck

Noir Vivianne Midi Dress

$81

$148

Tuckernuck