Date night dresses under $300. Layer-friendly, warm but not bulky. Boots-friendly

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For date night, we curated dresses around your budget that feel effortlessly polished—easy to layer under a blazer or coat, warm yet sleek (think knits and long sleeves over heavy padding), and perfectly proportioned for boots. Want a specific color, length, size, or retailer? Add it in the search bar or use Smart Filters.

Norma Kamali

Jersey minidress

$225

Mytheresa

GANNI

Alpaca and wool-blend minidress

$187

$375

Mytheresa

MAJE

Jersey-paneled checked tweed midi dress

$187

$415

Outnet

Loulou Studio

Idon wool-twill mini dress

$90

$300

Outnet

GAUGE81

Kores draped stretch-jersey turtleneck mini dress

$177

$590

Outnet

MORRIS & CO. X PAIGE

Bodega ruffled floral-print silk-georgette mini wrap dress

$100

$399

Outnet

TOTEME

Mesh-paneled stretch-knit midi dress

$246

$820

Outnet

Theory

Draped crepe mini dress

$223

$495

Outnet

IRO Micha mesh-paneled tiered crepe mini dress

IRO

Micha mesh-paneled tiered crepe mini dress

$194

$645

Outnet

rag & bone

Ribbed-knit midi dress

$113

$375

Outnet

Veronica Beard

Wilkin ribbed-knit and stretch-cotton poplin mini dress

$175

$499

Outnet

New

REDValentino

Ribbed-knit mini dress

$279

$795

Outnet

Veronica Beard

Farha floral-print shirred cotton-voile mini dress

$180

$398

Outnet

IRO

Alofi plissé-mesh midi dress

$91

$455

Outnet

Diane von Furstenberg

Minx off-the-shoulder wool-blend jersey dress

$129

$428

Outnet

Ulla Johnson

Tilda cotton-blend minidress

$186

$465

Mytheresa

Another Tomorrow

Ribbed wool-blend turtleneck midi dress

$298

$850

Outnet

Naadam

Cashmere mini dress

$105

$350

Outnet

GANNI

Ruched asymmetric velvet minidress

$190

$380

Mytheresa

Another Tomorrow

Ruched jersey midi dress

$70

$350

Outnet

BRAND RECOMMENDATION

Ronny Kobo

Ronny Kobo is a standout for luxe, figure-flattering knit dresses that layer beautifully, keeping you warm without adding bulk. Their silhouettes always feel modern and sophisticated, making them perfect for a memorable date night with boots.

View Brand

Ronny Kobo

Eire open-back cable-knit midi dress

$125

$498

Outnet

Ronny Kobo

Madelyn knitted maxi dress

$148

$590

Outnet

Ronny Kobo

Mariana wrap-effect ruched jersey mini dress

$112

$448

Outnet

Ronny Kobo

Scorpio Dress

$244

$488

Shopbop

Ronny Kobo

Tonchi Dress

$231

$578

Ronny Kobo

Cindie Dress

$105.6

$528

Shopbop

Ronny Kobo

Matthieu Dress

$278

$448

Revolve

Ronny Kobo

Carissa ruched floral-jacquard mini dress

$130

$518

Outnet

Ronny Kobo

Eire open-back cable-knit midi dress

$125

$498

Outnet

Ronny Kobo

Madelyn knitted maxi dress

$148

$590

Outnet

Ronny Kobo

Mariana wrap-effect ruched jersey mini dress

$112

$448

Outnet

Ronny Kobo

Scorpio Dress

$244

$488

Shopbop

Ronny Kobo

Tonchi Dress

$231

$578

Ronny Kobo

Cindie Dress

$105.6

$528

Shopbop

Ronny Kobo

Matthieu Dress

$278

$448

Revolve

Ronny Kobo

Carissa ruched floral-jacquard mini dress

$130

$518

Outnet

BRAND RECOMMENDATION

Ronny Kobo

Eire open-back cable-knit midi dress

$125

$498

Outnet

Ronny Kobo

Madelyn knitted maxi dress

$148

$590

Outnet

Ronny Kobo

Mariana wrap-effect ruched jersey mini dress

$112

$448

Outnet

Ronny Kobo

Scorpio Dress

$244

$488

Shopbop

View brand

GANNI

Pleated denim minidress

$225

$375

Mytheresa

GAUGE81

Kores draped stretch-jersey turtleneck mini dress

$236

$590

Net-a-Porter

Veronica Beard

Lauper ribbed-knit mini shirt dress

$249

$498

Outnet

NBD

Cortado Dress

$68

$168

Revolve

3.1 Phillip Lim

Ribbed cotton-blend dress

$138

$550

Outnet

Alexander Wang

Mélange ribbed-knit mini dress

$268

$595

Outnet

THEORY PROJECT

Crepe midi dress

$87

$345

Outnet

Vince

Knitted jersey midi dress

$203

$290

Mytheresa

HALSTON

Kayleigh cutout jersey mini dress

$89

$445

Outnet

Isabel Marant

Verikio ruffled floral-print silk mini dress

$279

$1,395

Outnet

PAIGE

Ysabel ruffled leopard-print devoré-velvet mini dress

$171

$379

Outnet

Proenza Schouler

White Label Nina cotton-blend midi dress

$206

$295

Mytheresa

FRAME

Jacquard-knit mini dress

$150

$498

Outnet

Antik Batik

Eros floral-print cotton-gauze dress

$139

$307

Outnet

Sold Out NYC

The Turtleneck Dress in Black

$265

Soldout Nyc

Norma Kamali

Draped turtleneck midi dress

$295

Mytheresa

Diane von Furstenberg

Savannah jacquard-knit midi wrap dress

$252

$558

Outnet

Polo Ralph Lauren

Velvet midi dress

$194

$485

Mytheresa

Marant Étoile

Ruffled printed cotton-mousseline wrap dress

$115

$460

Outnet

Rick Owens

Ribbed jersey midi dress

$137

$390

Outnet