Classic Tailored Dresses

Discover the elegance of classic tailored dresses at Ann Taylor. Featuring refined silhouettes and sophisticated details, these dresses are designed for a flattering fit and versatile style, perfect for both professional settings and special occasions, ensuring you always look polished and poised.

Show 123 Results
Weekend Collared Shirtdress
159.00
59.94
$59.94
$159.00
EXTRA 50% OFF! PRICE AS MARKED.
Weekend Belted Denim Shirtdress
179.00
72.44
$72.44
$179.00
EXTRA 50% OFF! PRICE AS MARKED.
Bright Medium Stone Wash
Polka Dot Linen Blend Sheath Dress
198.00
40.00
$40.00
$198.00
BEST DEAL!
White
Striped Lace Collar Midi Shirtdress
198.00
84.94
$84.94
$198.00
EXTRA 50% OFF! PRICE AS MARKED.
White-Blue
Collared Shift Dress
169.00
40.00
$40.00
$169.00
BEST DEAL!
Mixed Floral Sheath Dress
229.00
92.44
$92.44
$229.00
EXTRA 50% OFF! PRICE AS MARKED.
Winter White
The Pinstripe Midi Dress in Linen Blend
179.00
40.00
$40.00
$179.00
BEST DEAL!
White
Belted Collared Shirtdress
169.00
40.00
$40.00
$169.00
BEST DEAL!
Geo Belted Midi Dress
179.00
40.00
$40.00
$179.00
BEST DEAL!
Black
Polka Dot Square Neck Sheath Dress
169.00
72.44
$72.44
$169.00
EXTRA 50% OFF! PRICE AS MARKED.
Rich Walnut
Shift Dress in Linen
169.00
40.00
$40.00
$169.00
BEST DEAL!
The Twist Sheath Dress
169.00
67.44
$67.44
$169.00
EXTRA 50% OFF! PRICE AS MARKED.
Boatneck Sheath Dress
159.00
40.00
$40.00
$159.00
BEST DEAL!
Collared Belted Shirtdress
179.00
40.00
$40.00
$179.00
BEST DEAL!
Gingham Button Pocket Shift Dress
159.00
40.00
$40.00
$159.00
BEST DEAL!
Paisley Belted Midi Shirtdress
198.00
99.00
$99.00
$198.00
STYLE STEAL!
Purest Plum
Horsebit Print Midi Shirtdress
198.00
99.00
$99.00
$198.00
STYLE STEAL!
Sand Shell
Collared Midi Shirtdress
189.00
79.94
$79.94
$189.00
EXTRA 50% OFF! PRICE AS MARKED.
Bright Poppy
Striped Belted Collared Shirtdress
179.00
72.44
$72.44
$179.00
EXTRA 50% OFF! PRICE AS MARKED.
Blue Stripe
Paisley Twist Sheath Dress
198.00
99.00
$99.00
$198.00
STYLE STEAL!
Night Garden
Sleeveless Collared Midi Shirtdress
179.00
72.44
$72.44
$179.00
EXTRA 50% OFF! PRICE AS MARKED.
Collared Wrap Midi Dress
189.00
99.00
$99.00
$189.00
STYLE STEAL!
Harbor Side Blue
Floral Collared Midi Shirtdress
189.00
99.00
$99.00
$189.00
STYLE STEAL!
French Mocha
Floral Midi Shirtdress
179.00
99.00
$99.00
$179.00
STYLE STEAL!
The Seamed V-Neck Flare Dress in Classic Canvas
169.00
101.40
$101.40
$169.00
40% OFF! PRICE AS MARKED.
Animal Print Collared Midi Shirtdress
189.00
42.44
$42.44
$189.00
EXTRA 50% OFF! PRICE AS MARKED.
Cafe Au Lait B
The Plaid Flare Dress
179.00
107.40
$107.40
$179.00
40% OFF! PRICE AS MARKED.
Multi Plaid
Crew Neck Button Shift Dress in Tweed
189.00
74.94
$74.94
$189.00
EXTRA 50% OFF! PRICE AS MARKED.
Belted Sheath Dress in Tweed
179.00
64.94
$64.94
$179.00
EXTRA 50% OFF! PRICE AS MARKED.
Whipped Cream Multi
Crew Neck Twist Dress
189.00
64.94
$64.94
$189.00
EXTRA 50% OFF! PRICE AS MARKED.
Geo Print Collared Wrap Dress
169.00
99.00
$99.00
$169.00
STYLE STEAL!
Night Sky
Pinstripe Crew Neck Sheath Dress
179.00
107.40
$107.40
$179.00
40% OFF! PRICE AS MARKED.
Dark Neutral Pinstripe
The V-Neck Sheath Dress in Ponte
159.00
95.40
$95.40
$159.00
40% OFF! PRICE AS MARKED.
Pure Chocolate
The Square Neck Sheath Dress in Seasonless Stretch
159.00
95.40
$95.40
$159.00
40% OFF! PRICE AS MARKED.
Button Pocket Shift Dress
169.00
99.00
$99.00
$169.00
STYLE STEAL!
Caper Shadow
The Seamed V-Neck Sheath Dress in Bi-Stretch
169.00
101.40
$101.40
$169.00
40% OFF! PRICE AS MARKED.
The Seamed Crew Neck Flare Dress in Fluid Crepe
169.00
101.40
$101.40
$169.00
40% OFF! PRICE AS MARKED.
The Scoop Neck Dress In Bi-Stretch
159.00
95.40
$95.40
$159.00
40% OFF! PRICE AS MARKED.
The Scoop Neck Dress in Bi-Stretch
159.00
95.40
$95.40
$159.00
40% OFF! PRICE AS MARKED.
The Scoop Neck Sheath Dress in Bi-Stretch — Curvy Fit
159.00
95.40
$95.40
$159.00
40% OFF! PRICE AS MARKED.
The Scoop Neck Sheath Dress in Bi-Stretch — Curvy Fit
149.00
89.40
$89.40
$149.00
40% OFF! PRICE AS MARKED.
The Scoop Neck Zip Pocket Dress in Bi-Stretch
159.00
95.40
$95.40
$159.00
40% OFF! PRICE AS MARKED.
Draped Midi Sheath Dress
169.00
99.00
$99.00
$169.00
STYLE STEAL!
Night Garden
Paisley Draped Midi Sheath Dress
179.00
99.00
$99.00
$179.00
STYLE STEAL!
Weekend Plaid Belted Midi Shirtdress
Best Seller
198.00
118.80
$118.80
$198.00
40% OFF! PRICE AS MARKED.
Purest Plum
Double Breasted Blazer Midi Dress
New
229.00
137.40
$137.40
$229.00
40% OFF! PRICE AS MARKED.
Dark Berry
The Crew Neck Sheath Dress
New
169.00
101.40
$101.40
$169.00
40% OFF! PRICE AS MARKED.
The Wrap Effect Midi Dress in Fluid Crepe
New
169.00
101.40
$101.40
$169.00
40% OFF! PRICE AS MARKED.
Plaid Shift Dress
New
159.00
95.40
$95.40
$159.00
40% OFF! PRICE AS MARKED.
Crew Neck Twist Sheath Dress
179.00
40.00
$40.00
$179.00
BEST DEAL!
Sail Cloth
Eyelet Halter Maxi Dress
229.00
97.44
$97.44
$229.00
EXTRA 50% OFF! PRICE AS MARKED.
Belted Vest Slip Dress
209.00
77.49
$77.49
$209.00
EXTRA 50% OFF! PRICE AS MARKED.
Collared Midi Shirtdress
179.00
74.94
$74.94
$179.00
EXTRA 50% OFF! PRICE AS MARKED.
Shift Dress in Tweed
179.00
74.94
$74.94
$179.00
EXTRA 50% OFF! PRICE AS MARKED.
Striped Collared Halter Midi Dress
179.00
72.44
$72.44
$179.00
EXTRA 50% OFF! PRICE AS MARKED.
Vista Blue
Weekend Paisley Collared Shirtdress
169.00
67.44
$67.44
$169.00
EXTRA 50% OFF! PRICE AS MARKED.
Sea Haze
Weekend Belted Shirtdress in Chambray
189.00
64.99
$64.99
$189.00
EXTRA 50% OFF! PRICE AS MARKED.
Paisley Belted Collared Shirtdress
169.00
62.44
$62.44
$169.00
EXTRA 50% OFF! PRICE AS MARKED.
Popcorn B
$62.44 -
$67.44
$67.44
$169.00
EXTRA 50% OFF! PRICE AS MARKED.
Cheerful Blue
Weekend Striped Pleated Midi Shirtdress
189.00
40.00
$40.00
$189.00
BEST DEAL!
Rich Walnut
Belted Crew Neck Flare Dress
179.00
40.00
$40.00
$179.00
BEST DEAL!
Blush Haze
Weekend Floral Tie Waist Sheath Dress
159.00
40.00
$40.00
$159.00
BEST DEAL!
Night Sky
The Belted Shift Dress in Linen Blend
169.00
40.00
$40.00
$169.00
BEST DEAL!
Lime Slice
Tweed Square Neck Shift Dress
179.00
40.00
$40.00
$179.00
BEST DEAL!
Gold/White
Plaid Belted Mini Shirtdress
Tweed Button Shift Dress
The Crew Neck Sheath Dress
The Short Sleeve Sheath Dress in Bi-Stretch — Curvy Fit
$35.00 -
$95.40
$95.40
$159.00
40% OFF! PRICE AS MARKED.
The Short Sleeve Sheath Dress in Bi-Stretch
$40.00 -
$95.40
$95.40
$159.00
40% OFF! PRICE AS MARKED.
Halter Flare Midi Dress in Chambray
189.00
40.00
$40.00
$189.00
BEST DEAL!
Light Indigo Wash
The Midi Flare Dress in Double Knit
159.00
35.00
$35.00
$159.00
BEST DEAL!
The Flare Dress in Double Knit
159.00
35.00
$35.00
$159.00
BEST DEAL!
Petite Weekend Collared Shirtdress
159.00
59.94
$59.94
$159.00
EXTRA 50% OFF! PRICE AS MARKED.
Petite Striped Lace Collar Midi Shirtdress
198.00
84.94
$84.94
$198.00
EXTRA 50% OFF! PRICE AS MARKED.
White-Blue
Petite Belted Collared Shirtdress
169.00
40.00
$40.00
$169.00
BEST DEAL!
Petite Boatneck Sheath Dress
159.00
40.00
$40.00
$159.00
BEST DEAL!
Petite Horsebit Print Midi Shirtdress
198.00
99.00
$99.00
$198.00
STYLE STEAL!
Sand Shell
Petite Sleeveless Collared Midi Shirtdress
179.00
72.44
$72.44
$179.00
EXTRA 50% OFF! PRICE AS MARKED.
Petite Floral Midi Shirtdress
179.00
99.00
$99.00
$179.00
STYLE STEAL!
The Petite Seamed V-Neck Flare Dress in Classic Canvas
169.00
101.40
$101.40
$169.00
40% OFF! PRICE AS MARKED.
Petite Belted Sheath Dress in Tweed
179.00
64.94
$64.94
$179.00
EXTRA 50% OFF! PRICE AS MARKED.
Whipped Cream Multi
Petite Animal Print Collared Midi Shirtdress
189.00
42.44
$42.44
$189.00
EXTRA 50% OFF! PRICE AS MARKED.
Cafe Au Lait B
Petite Pinstripe Crew Neck Sheath Dress
179.00
107.40
$107.40
$179.00
40% OFF! PRICE AS MARKED.
Dark Neutral Pinstripe
Petite Button Pocket Shift Dress
169.00
99.00
$99.00
$169.00
STYLE STEAL!
Caper Shadow
The Petite V-Neck Sheath Dress in Ponte
159.00
95.40
$95.40
$159.00
40% OFF! PRICE AS MARKED.
Pure Chocolate
The Petite Square Neck Sheath Dress in Seasonless Stretch
159.00
95.40
$95.40
$159.00
40% OFF! PRICE AS MARKED.
The Petite Seamed Crew Neck Flare Dress in Fluid Crepe
169.00
101.40
$101.40
$169.00
40% OFF! PRICE AS MARKED.
Cool Dusk
The Petite Seamed V-Neck Sheath Dress in Bi-Stretch
159.00
95.40
$95.40
$159.00
40% OFF! PRICE AS MARKED.
The Petite Short Sleeve Sheath Dress in Bi-Stretch
159.00
95.40
$95.40
$159.00
40% OFF! PRICE AS MARKED.
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