Date night dresses under $300. Layer-friendly, warm but not bulky. Boots-friendly
For a captivating date night, opt for midweight dresses that offer warmth without any bulky feel. We curated layer-friendly pieces designed to style beautifully with your favorite boots—all around your budget. If you have a preferred shade or silhouette, type it directly or use our Smart Filters to refine.
Another Tomorrow
Another Tomorrow Ribbed Wool-Blend Turtleneck Midi Dress
$128
$850
Outnet
GAUGE81
Flora metallic cotton-blend jersey turtleneck midi dress
$213
$710
Net-a-Porter
Staud
Lois off-the-shoulder ribbed-knit midi dress
$89
$295
Net-a-Porter
Splendid
Marigold Mini Sweater Dress
$248
Shopbop
DEREK LAM 10 CROSBY
Derek Lam 10 Crosby Diana Wool Turtleneck Midi Dress
$223
$495
Outnet
PETER DO
Peter Do Open-Back Ribbed Silk-Blend Maxi Dress
$284
$1,890
Outnet
Staud
Eva asymmetric cable-knit wool-blend dress
$198
$395
Net-a-Porter
Victoria Beckham
VB Body one-shoulder stretch-knit midi dress
$267
$890
Net-a-Porter
KHAITE
Khaite Aerica Off-the-Shoulder Ruched Mini Dress
$297
$1,980
Outnet
La Ligne
Sloane stretch-knit midi dress
$158
$395
Net-a-Porter
SANDRO
Sandro Ruffled Ribbed-Knit Maxi Dress
$201
$445
Outnet
Cult Gaia
Natacha cable-knit wool and cashmere-blend dress
$280
$700
Net-a-Porter
Tuckernuck
Brown Draped Long Sleeve Maxi Dress
$230
Tuckernuck
Tuckernuck
Cranberry Averie Polo Rib Sweater Dress
$194
$298
Tuckernuck
SIMKHAI
Genna ribbed-knit midi dress
$273
$545
Net-a-Porter
Tuckernuck
Cranberry Vivianne Midi Dress
$148
Tuckernuck
Bec + Bridge
KARINA TUCK MIDI DRESS - SANGRIA
$300
Bec + Bridge
Tuckernuck
Chocolate Vivianne Midi Dress
$148
Tuckernuck
Proenza Schouler White Label
Ezme paneled knitted midi dress
$203
$675
Net-a-Porter
LESET
Rozzi layered ribbed jersey midi dress
$72
$240
Net-a-Porter
Meshki
Chloe Peached Jersey One Shoulder Midi Dress - Ivory
$149
Meshki
Meshki
Natascha Drop Waist Cotton Midi Dress - Chocolate
$215
Meshki
Meshki
Euphemia Cupro Midi Wrap Dress - Chocolate
$159
Meshki
Meshki
Sharon Scuba Jersey Midi Dress - Ivory
$145
Meshki
Meshki
Liam Faux Suede Maxi Dress - Dark Chocolate
$79
$175
Meshki
Meshki
Sharon Scuba Jersey Midi Dress - Cacao Brown
$145
Meshki
Meshki
Malone Bandage Knit Midi Dress - Ivory
$149
Meshki
Meshki
Noelle Sleeveless Roll Neck Midi Dress - Dark Chocolate
$105
Meshki
Meshki
Chloe Peached Jersey One Shoulder Midi Dress - Ivory
$149
Meshki
Meshki
Natascha Drop Waist Cotton Midi Dress - Chocolate
$215
Meshki
Meshki
Euphemia Cupro Midi Wrap Dress - Chocolate
$159
Meshki
Meshki
Sharon Scuba Jersey Midi Dress - Ivory
$145
Meshki
Tuckernuck
Almond Knit Anya Midi Dress
$148
Tuckernuck
SIMKHAI
SIMKHAI Skyla Cotton and Cashmere-Blend Midi Wrap Dress
$178
$445
Outnet
Tuckernuck
Dark Cherry Rayna Bubble Sleeve Tweed Mini Dress
$164
Tuckernuck
GANNI
GANNI Ribbed-Knit Midi Dress
$37
$245
Outnet
SIMKHAI
Simkhai Albanie Ribbed Wool-Blend Turtleneck Mini Dress
$186
$465
Outnet
PAIGE
Kalindi Dress
$279
Shopbop
Herve Leger
Hervé Léger Bethany Draped Satin and Crepe Dress
$293
$650
Outnet
Vince
Short Sleeve Side Rouche Dress
$208.6
$298
Shopbop
self-portrait
Embellished ribbed-knit and poplin maxi dress
$266
$665
Net-a-Porter
o.p.t
Nicole Dress
$198
Shopbop
Tuckernuck
Olive Wide Wale Corduroy Tara Shirt Dress
$139
$198
Tuckernuck
Tuckernuck
Oxblood Knit Conrad Midi Swing Dress
$148
Tuckernuck
arch4
Arch4 Lily Cashmere Turtleneck Midi Dress
$279
$795
Outnet
rag & bone
rag & bone Luca Draped Stretch-Modal Jersey Maxi Dress
$148
$328
Outnet
Meshki
Chloe Peached Jersey One Shoulder Midi Dress - Ivory
$149
Meshki
Tuckernuck
Marron Fabiana Midi Dress
$214
$535
Tuckernuck
Entire Studios
Flop wool maxi dress
$276
$395
Mytheresa
rag & bone
rag & bone Dawson Ribbed-Knit Midi Dress
$119
$395
Outnet
TOTEME
Toteme Poplin-Trimmed Ribbed-Knit Maxi Dress
$248
$620
Outnet
Meshki
Natascha Drop Waist Cotton Midi Dress - Chocolate
$215
Meshki
