Holiday Dresses

Discover the perfect holiday dresses at Ann Taylor, featuring elegant designs that blend comfort and style. From festive gatherings to cozy celebrations, our collection offers a variety of silhouettes, colors, and embellishments to ensure you shine during the holiday season.

Show 200 Results
Draped Midi Sheath Dress
New
169.00
118.30
$118.30
$169.00
30% OFF. PRICE AS MARKED.
Night Garden
Colorblock Midi Sweater Dress
189.00
79.94
$79.94
$189.00
EXTRA 50% OFF! PRICE AS MARKED.
Rich Walnut
Weekend Floral Smocked Midi Dress
179.00
74.94
$74.94
$179.00
EXTRA 50% OFF! PRICE AS MARKED.
Vista Blue
Denim Boatneck Shift Dress
169.00
67.44
$67.44
$169.00
EXTRA 50% OFF! PRICE AS MARKED.
Belted Midi Dress in Linen Blend
209.00
55.00
$55.00
$209.00
BEST DEAL!
Polka Dot Linen Blend Sheath Dress
198.00
84.94
$84.94
$198.00
EXTRA 50% OFF! PRICE AS MARKED.
White
Eyelet Halter Maxi Dress
229.00
97.44
$97.44
$229.00
EXTRA 50% OFF! PRICE AS MARKED.
Paisley Flare Dress
179.00
49.94
$49.94
$179.00
EXTRA 50% OFF! PRICE AS MARKED.
Multi
Button Ribbed Sweater Dress
198.00
84.94
$84.94
$198.00
EXTRA 50% OFF! PRICE AS MARKED.
Halter Flare Midi Dress in Linen Blend
189.00
55.00
$55.00
$189.00
BEST DEAL!
Gingham Midi Dress in Linen Blend
189.00
79.94
$79.94
$189.00
EXTRA 50% OFF! PRICE AS MARKED.
Moonlight
Striped Shirtdress
179.00
74.94
$74.94
$179.00
EXTRA 50% OFF! PRICE AS MARKED.
Cool Cascades
Split Neck Sheath Dress
169.00
67.44
$67.44
$169.00
EXTRA 50% OFF! PRICE AS MARKED.
Rose Clay
Scalloped Midi Dress
198.00
84.94
$84.94
$198.00
EXTRA 50% OFF! PRICE AS MARKED.
Gingham Belted Midi Dress in Linen Blend
229.00
55.00
$55.00
$229.00
BEST DEAL!
Sea Haze
Asymmetric Twist Shoulder Midi Dress
179.00
72.49
$72.49
$179.00
EXTRA 50% OFF! PRICE AS MARKED.
Fresh Cut Green
Satin Dotted Midi Dress
189.00
40.00
$40.00
$189.00
BEST DEAL!
Night Sky
Weekend Chambray Flare Midi Dress
189.00
55.00
$55.00
$189.00
BEST DEAL!
Light Indigo Wash
Mixed Media Flare Midi Dress
New
189.00
132.30
$132.30
$189.00
30% OFF. PRICE AS MARKED.
Paisley Twist Sheath Dress
New
198.00
138.60
$138.60
$198.00
30% OFF. PRICE AS MARKED.
Night Garden
Flare Midi Dress in Linen Blend
198.00
84.94
$84.94
$198.00
EXTRA 50% OFF! PRICE AS MARKED.
Coastal Glow
The Twist Sheath Dress
169.00
67.44
$67.44
$169.00
EXTRA 50% OFF! PRICE AS MARKED.
Belted Midi Dress in Linen Blend
198.00
74.99
$74.99
$198.00
EXTRA 50% OFF! PRICE AS MARKED.
Eyelet Halter Midi Dress
249.00
99.99
$99.99
$249.00
EXTRA 50% OFF! PRICE AS MARKED.
Lime Slice
Ombré Crochet Sweater Dress
229.00
55.00
$55.00
$229.00
BEST DEAL!
Pirouette
Ribbed Halter Sweater Dress
198.00
74.99
$74.99
$198.00
EXTRA 50% OFF! PRICE AS MARKED.
Aperol
Haven Well Within Linen Halter Maxi Dress
178.00
124.60
$124.60
$178.00
30% OFF. PRICE AS MARKED.
Haven Well Within Organic Cotton Stripe Midi Dress
148.00
103.60
$103.60
$148.00
30% OFF. PRICE AS MARKED.
Haven Well Within Ramie Blend Pleated Maxi Dress
268.00
187.60
$187.60
$268.00
30% OFF. PRICE AS MARKED.
Deep Turquoise
Haven Well Within Cotton Crochet Scalloped Midi Dress
189.00
132.30
$132.30
$189.00
30% OFF. PRICE AS MARKED.
Natural
169.00
40.00
$40.00
$169.00
BEST DEAL!
Aperol
Faux Leather Mini Dress
New
189.00
132.30
$132.30
$189.00
30% OFF. PRICE AS MARKED.
Polka Dot Square Neck Sheath Dress
169.00
40.00
$40.00
$169.00
BEST DEAL!
Rich Walnut
Weekend Mixed Media Crew Neck Midi Dress
179.00
74.94
$74.94
$179.00
EXTRA 50% OFF! PRICE AS MARKED.
Weekend Floral Shirred Dress
189.00
45.00
$45.00
$189.00
BEST DEAL!
B Dream Blue
Floral Belted Flare Midi Dress
198.00
138.60
$138.60
$198.00
30% OFF. PRICE AS MARKED.
Black
Ribbed Button Sweater Dress
189.00
40.00
$40.00
$189.00
BEST DEAL!
Mocha Meringue
Weekend Smocked Midi Dress
179.00
50.00
$50.00
$179.00
BEST DEAL!
Yellow Hibiscus
Floral Gathered Midi Dress
179.00
40.00
$40.00
$179.00
BEST DEAL!
Sail Cloth
Striped Collared Halter Midi Dress
179.00
72.49
$72.49
$179.00
EXTRA 50% OFF! PRICE AS MARKED.
Vista Blue
Floral Flare Midi Dress in Linen Blend
209.00
45.00
$45.00
$209.00
BEST DEAL!
Rich Walnut
Linen Blend Flare Dress
179.00
45.00
$45.00
$179.00
BEST DEAL!
V-Neck Chambray Flare Midi Dress
189.00
79.94
$79.94
$189.00
EXTRA 50% OFF! PRICE AS MARKED.
Dark Indigo
Halter Flare Midi Dress in Chambray
189.00
40.00
$40.00
$189.00
BEST DEAL!
Light Indigo Wash
Floral Belted Flare Midi Dress
198.00
50.00
$50.00
$198.00
BEST DEAL!
White-Blue
The Scoop Neck Sheath Dress in Bi-Stretch — Curvy Fit
159.00
111.30
$111.30
$159.00
30% OFF. PRICE AS MARKED.
Gathered Midi Dress
169.00
118.30
$118.30
$169.00
30% OFF. PRICE AS MARKED.
Shadowy Jade
Haven Well Within Organic Cotton Poplin Strappy Maxi Dress
168.00
117.60
$117.60
$168.00
30% OFF. PRICE AS MARKED.
Straw
Belted Crew Neck Flare Dress
179.00
55.00
$55.00
$179.00
BEST DEAL!
Blush Haze
Floral Sheath Dress
169.00
40.00
$40.00
$169.00
BEST DEAL!
Dream Blue
Ruffle Collar Mini Dress
169.00
40.00
$40.00
$169.00
BEST DEAL!
Rhododendron
Dotted Linen Blend Shift Dress
169.00
40.00
$40.00
$169.00
BEST DEAL!
Black
Eyelet Peplum Midi Dress
249.00
99.94
$99.94
$249.00
EXTRA 50% OFF! PRICE AS MARKED.
Tweed Square Neck Shift Dress
179.00
45.00
$45.00
$179.00
BEST DEAL!
Gold/White
Striped Crew Neck Mini Dress
179.00
125.30
$125.30
$179.00
30% OFF. PRICE AS MARKED.
Ocean Oasis Stripe
Animal Print Puff Sleeve Midi Dress
198.00
79.99
$79.99
$198.00
EXTRA 50% OFF! PRICE AS MARKED.
Cafe Au Lait
Weekend Gathered Maxi Dress
179.00
40.00
$40.00
$179.00
BEST DEAL!
Weekend Tie Strap Midi Dress
179.00
40.00
$40.00
$179.00
BEST DEAL!
Terra Toscana
Floral Gathered Maxi Dress
189.00
40.00
$40.00
$189.00
BEST DEAL!
Bright Cherry
Puff Sleeve Midi Dress in Linen Blend
189.00
74.99
$74.99
$189.00
EXTRA 50% OFF! PRICE AS MARKED.
Eyelet Shift Dress in Linen Blend
189.00
132.30
$132.30
$189.00
30% OFF. PRICE AS MARKED.
Weekend Denim Shift Dress
179.00
45.00
$45.00
$179.00
BEST DEAL!
The Pinstripe Midi Dress in Linen Blend
179.00
72.49
$72.49
$179.00
EXTRA 50% OFF! PRICE AS MARKED.
White
Floral Jacquard Sweater Dress
198.00
84.94
$84.94
$198.00
EXTRA 50% OFF! PRICE AS MARKED.
Palm Green
Floral Midi Wrap Dress in Linen Blend
198.00
45.00
$45.00
$198.00
BEST DEAL!
Rhododendron
Collared Shift Dress
169.00
32.44
$32.44
$169.00
EXTRA 50% OFF! PRICE AS MARKED.
The Scoop Neck Sheath Dress in Bi-Stretch — Curvy Fit
149.00
104.30
$104.30
$149.00
30% OFF. PRICE AS MARKED.
The Scoop Neck Zip Pocket Dress in Bi-Stretch
159.00
111.30
$111.30
$159.00
30% OFF. PRICE AS MARKED.
Shift Dress in Linen
169.00
67.49
$67.49
$169.00
EXTRA 50% OFF! PRICE AS MARKED.
Striped Square Neck Sweater Dress
209.00
146.30
$146.30
$209.00
30% OFF. PRICE AS MARKED.
Winding Ivy
Geo Belted Midi Dress
179.00
125.30
$125.30
$179.00
30% OFF. PRICE AS MARKED.
Black
Haven Well Within Organic Cotton Interlock Striped Short Sleeve Dress
118.00
82.60
$82.60
$118.00
30% OFF. PRICE AS MARKED.
Vetiver
Haven Well Within Organic Cotton Interlock Stripe Midi Dress
128.00
89.60
$89.60
$128.00
30% OFF. PRICE AS MARKED.
Twilight Blue Heather
Haven Well Within Ramie Blend Pintuck Maxi Dress
189.00
132.30
$132.30
$189.00
30% OFF. PRICE AS MARKED.
Floral Twist Midi Dress
169.00
40.00
$40.00
$169.00
BEST DEAL!
Cafe Au Lait
Striped Midi Dress
189.00
79.94
$79.94
$189.00
EXTRA 50% OFF! PRICE AS MARKED.
Rich Walnut
Embroidered Midi Dress in Linen Blend
229.00
92.44
$92.44
$229.00
EXTRA 50% OFF! PRICE AS MARKED.
Embroidered Peplum Flare Midi Dress
229.00
50.00
$50.00
$229.00
BEST DEAL!
Weekend Tie Waist Midi Dress
149.00
104.30
$104.30
$149.00
30% OFF. PRICE AS MARKED.
Sail Cloth
Floral Collared Shift Dress in Linen Blend
169.00
118.30
$118.30
$169.00
30% OFF. PRICE AS MARKED.
Bright Cherry
Polka Dot Maxi Dress in Satin
179.00
125.30
$125.30
$179.00
30% OFF. PRICE AS MARKED.
Night Sky B
Haven Well Within Organic Cotton Modal Strapless Dress
148.00
103.60
$103.60
$148.00
30% OFF. PRICE AS MARKED.
98.00
68.60
$68.60
$98.00
30% OFF. PRICE AS MARKED.
Haven Well Within Balance Active Dress
148.00
103.60
$103.60
$148.00
30% OFF. PRICE AS MARKED.
Halter Flare Midi Dress
198.00
40.00
$40.00
$198.00
BEST DEAL!
Eyelet Drop Waist Midi Dress
229.00
97.44
$97.44
$229.00
EXTRA 50% OFF! PRICE AS MARKED.
White 9000
Button Sweater Dress
169.00
30.00
$30.00
$169.00
BEST DEAL!
Crew Neck Flare Midi Dress
179.00
40.00
$40.00
$179.00
BEST DEAL!
The Scoop Neck Dress in Bi-Stretch
159.00
111.30
$111.30
$159.00
30% OFF. PRICE AS MARKED.
The Scoop Neck Dress In Bi-Stretch
159.00
111.30
$111.30
$159.00
30% OFF. PRICE AS MARKED.
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