Classic Fit Midi Dresses

Explore the elegance of classic fit midi dresses at Ann Taylor. Featuring flattering silhouettes and versatile designs, these dresses effortlessly transition from day to night, making them perfect for any occasion. Embrace timeless style with our collection of chic midi dresses.

Show 156 Results
Drop Waist Flare Midi Dress
198.00
84.94
$84.94
$198.00
EXTRA 50% OFF! PRICE AS MARKED.
Flare Midi Dress in Denim
189.00
64.94
$64.94
$189.00
EXTRA 50% OFF! PRICE AS MARKED.
Peplum Flare Midi Dress
189.00
67.44
$67.44
$189.00
EXTRA 50% OFF! PRICE AS MARKED.
Peplum Flare Midi Dress
189.00
67.44
$67.44
$189.00
EXTRA 50% OFF! PRICE AS MARKED.
Lace Trim Satin Slip Midi Dress
219.00
89.94
$89.94
$219.00
EXTRA 50% OFF! PRICE AS MARKED.
Weekend Floral Gathered Midi Dress
179.00
72.44
$72.44
$179.00
EXTRA 50% OFF! PRICE AS MARKED.
Night Sky
Belted Sweater Dress
$87.44 -
$125.40
$125.40
$209.00
EXTRA 50% OFF! PRICE AS MARKED.
Purest Plum
Flare Midi Dress in Linen Blend
198.00
40.00
$40.00
$198.00
BEST DEAL!
Coastal Glow
Striped Lace Collar Midi Shirtdress
198.00
84.94
$84.94
$198.00
EXTRA 50% OFF! PRICE AS MARKED.
White-Blue
Floral Flare Midi Dress in Linen Blend
209.00
89.94
$89.94
$209.00
EXTRA 50% OFF! PRICE AS MARKED.
Rich Walnut
Striped Midi Dress
189.00
40.00
$40.00
$189.00
BEST DEAL!
Rich Walnut
Floral Belted Flare Midi Dress
198.00
40.00
$40.00
$198.00
BEST DEAL!
Black
Pleated Polo Midi Dress
198.00
79.94
$79.94
$198.00
EXTRA 50% OFF! PRICE AS MARKED.
V-Neck Chambray Flare Midi Dress
189.00
40.00
$40.00
$189.00
BEST DEAL!
Dark Indigo
Gingham Midi Dress in Linen Blend
189.00
40.00
$40.00
$189.00
BEST DEAL!
Moonlight
Belted Midi Shirtdress
198.00
77.44
$77.44
$198.00
EXTRA 50% OFF! PRICE AS MARKED.
Puff Sleeve Midi Dress in Linen Blend
189.00
40.00
$40.00
$189.00
BEST DEAL!
Weekend Floral Smocked Midi Dress
179.00
40.00
$40.00
$179.00
BEST DEAL!
Vista Blue
Embroidered Peplum Flare Midi Dress
229.00
92.44
$92.44
$229.00
EXTRA 50% OFF! PRICE AS MARKED.
The Pinstripe Midi Dress in Linen Blend
179.00
40.00
$40.00
$179.00
BEST DEAL!
White
Crew Neck Flare Midi Dress
179.00
72.44
$72.44
$179.00
EXTRA 50% OFF! PRICE AS MARKED.
Geo Belted Midi Dress
179.00
40.00
$40.00
$179.00
BEST DEAL!
Black
Asymmetric Twist Shoulder Midi Dress
179.00
40.00
$40.00
$179.00
BEST DEAL!
Fresh Cut Green
Eyelet Drop Waist Midi Dress
229.00
97.44
$97.44
$229.00
EXTRA 50% OFF! PRICE AS MARKED.
White 9000
Button Midi Dress in Linen Blend
189.00
79.94
$79.94
$189.00
EXTRA 50% OFF! PRICE AS MARKED.
Satin Dotted Midi Dress
189.00
42.44
$42.44
$189.00
EXTRA 50% OFF! PRICE AS MARKED.
Night Sky
The Twist Sheath Dress
169.00
67.44
$67.44
$169.00
EXTRA 50% OFF! PRICE AS MARKED.
Studio Eyelet Midi Dress
249.00
99.94
$99.94
$249.00
EXTRA 50% OFF! PRICE AS MARKED.
Boatneck Sheath Dress
159.00
40.00
$40.00
$159.00
BEST DEAL!
Lace Trim Satin Midi Slip Dress
209.00
125.40
$125.40
$209.00
40% OFF! PRICE AS MARKED.
Purest Plum
Horsebit Print Midi Shirtdress
198.00
99.00
$99.00
$198.00
STYLE STEAL!
Sand Shell
Polka Dot Tie Neck Midi Shirtdress
198.00
99.00
$99.00
$198.00
STYLE STEAL!
Purest Plum
Floral Flare Midi Dress
198.00
84.94
$84.94
$198.00
EXTRA 50% OFF! PRICE AS MARKED.
Winter White
Sleeveless Pleated Midi Dress
179.00
99.00
$99.00
$179.00
STYLE STEAL!
Collared Wrap Midi Dress
189.00
99.00
$99.00
$189.00
STYLE STEAL!
Harbor Side Blue
Draped Midi Sheath Dress
169.00
99.00
$99.00
$169.00
STYLE STEAL!
Night Garden
Floral Crew Neck Midi Dress
198.00
84.94
$84.94
$198.00
EXTRA 50% OFF! PRICE AS MARKED.
Black - Yellow
Pleated Crew Neck Midi Dress
209.00
89.94
$89.94
$209.00
EXTRA 50% OFF! PRICE AS MARKED.
Striped Midi Flare Dress
189.00
74.94
$74.94
$189.00
EXTRA 50% OFF! PRICE AS MARKED.
Dark Forest Green
Gathered Midi Dress
169.00
99.00
$99.00
$169.00
STYLE STEAL!
Shadowy Jade
Plaid Crew Neck Midi Dress
179.00
74.94
$74.94
$179.00
EXTRA 50% OFF! PRICE AS MARKED.
Blue Plaid
Floral Midi Shirtdress
179.00
99.00
$99.00
$179.00
STYLE STEAL!
Belted Pleated Midi Dress
189.00
49.94
$49.94
$189.00
EXTRA 50% OFF! PRICE AS MARKED.
Collared Midi Shirtdress
189.00
79.94
$79.94
$189.00
EXTRA 50% OFF! PRICE AS MARKED.
Bright Poppy
Mixed Media Flare Midi Dress
189.00
99.00
$99.00
$189.00
STYLE STEAL!
Pleated Polo Midi Dress
Best Seller
209.00
125.40
$125.40
$209.00
40% OFF! PRICE AS MARKED.
Sleeveless Collared Midi Shirtdress
179.00
72.44
$72.44
$179.00
EXTRA 50% OFF! PRICE AS MARKED.
Lace Flutter Sleeve Midi Dress
229.00
97.44
$97.44
$229.00
EXTRA 50% OFF! PRICE AS MARKED.
Floral Collared Midi Shirtdress
189.00
99.00
$99.00
$189.00
STYLE STEAL!
French Mocha
Belted Midi Shirtdress
179.00
99.00
$99.00
$179.00
STYLE STEAL!
Pleated Midi Dress in Faux Leather
229.00
137.40
$137.40
$229.00
40% OFF! PRICE AS MARKED.
Floral Puff Sleeve Midi Dress
179.00
62.44
$62.44
$179.00
EXTRA 50% OFF! PRICE AS MARKED.
Purest Plum
Belted Lace Midi Shirtdress
198.00
99.00
$99.00
$198.00
STYLE STEAL!
Paisley Draped Midi Sheath Dress
179.00
99.00
$99.00
$179.00
STYLE STEAL!
Flare Midi Dress in Faux Leather
189.00
113.40
$113.40
$189.00
40% OFF! PRICE AS MARKED.
Midnight Mahogany
Geo Print Flare Midi Dress
189.00
79.94
$79.94
$189.00
EXTRA 50% OFF! PRICE AS MARKED.
French Mocha
Weekend Floral Midi Shirtdress
189.00
79.94
$79.94
$189.00
EXTRA 50% OFF! PRICE AS MARKED.
Boatneck Column Midi Dress
179.00
62.44
$62.44
$179.00
EXTRA 50% OFF! PRICE AS MARKED.
Caper Shadow
Animal Print Collared Midi Shirtdress
189.00
42.44
$42.44
$189.00
EXTRA 50% OFF! PRICE AS MARKED.
Cafe Au Lait B
Animal Print Mock Neck Midi Dress
169.00
59.94
$59.94
$169.00
EXTRA 50% OFF! PRICE AS MARKED.
Cafe Au Lait B
Paisley Puff Sleeve Midi Dress
179.00
99.00
$99.00
$179.00
STYLE STEAL!
Paisley Boatneck Column Midi Dress
189.00
64.94
$64.94
$189.00
EXTRA 50% OFF! PRICE AS MARKED.
Safari Foliage
Weekend Cable Polo Midi Dress
189.00
99.00
$99.00
$189.00
STYLE STEAL!
Studio Collection Boatneck Midi Dress in Genuine Silk
448.00
268.80
$268.80
$448.00
40% OFF! PRICE AS MARKED.
Dark Fuchsia Bloom
Studio Collection Paisley Midi Dress in Genuine Silk
498.00
298.80
$298.80
$498.00
40% OFF! PRICE AS MARKED.
Night Sky
Haven Well Within Cotton Blend Textured Midi Skirt
88.00
52.80
$52.80
$88.00
40% OFF! PRICE AS MARKED.
Ivory
Haven Well Within Organic Cotton Stripe Midi Dress
148.00
88.80
$88.80
$148.00
40% OFF! PRICE AS MARKED.
Haven Well Within Linen Pintuck Midi Dress
158.00
94.80
$94.80
$158.00
40% OFF! PRICE AS MARKED.
Sandstone
Haven Well Within Organic Cotton Interlock Stripe Midi Dress
128.00
76.80
$76.80
$128.00
40% OFF! PRICE AS MARKED.
Twilight Blue Heather
Haven Well Within Cotton Crochet Scalloped Midi Dress
189.00
113.40
$113.40
$189.00
40% OFF! PRICE AS MARKED.
Natural
Haven Well Within Organic Cotton Poplin Smocked Gingham Midi Dress
178.00
106.80
$106.80
$178.00
40% OFF! PRICE AS MARKED.
Night Navy
Haven Well Within Organic Cotton Ribbed Midi Dress
189.00
113.40
$113.40
$189.00
40% OFF! PRICE AS MARKED.
Nightfall Wash
Plaid Mock Neck Sweater Dress
198.00
99.00
$99.00
$198.00
STYLE STEAL!
French Mocha
The Seamed V-Neck Flare Dress in Classic Canvas
169.00
101.40
$101.40
$169.00
40% OFF! PRICE AS MARKED.
Haven Well Within Organic Cotton Rib Knit V-Neck Midi Dress
128.00
76.80
$76.80
$128.00
40% OFF! PRICE AS MARKED.
Vetiver
The Seamed Crew Neck Flare Dress in Fluid Crepe
169.00
101.40
$101.40
$169.00
40% OFF! PRICE AS MARKED.
Haven Well Within Ramie Blend Pleated Maxi Dress
268.00
160.80
$160.80
$268.00
40% OFF! PRICE AS MARKED.
Deep Turquoise
Ribbed Turtleneck Sweater Dress
189.00
99.00
$99.00
$189.00
STYLE STEAL!
Soft Mink Melange
Plaid Cowl Neck Midi Dress
179.00
99.00
$99.00
$179.00
STYLE STEAL!
Paisley Twist Sheath Dress
198.00
99.00
$99.00
$198.00
STYLE STEAL!
Night Garden
Pinstripe Crew Neck Sheath Dress
179.00
107.40
$107.40
$179.00
40% OFF! PRICE AS MARKED.
Dark Neutral Pinstripe
The Seamed V-Neck Sheath Dress in Bi-Stretch
169.00
101.40
$101.40
$169.00
40% OFF! PRICE AS MARKED.
The V-Neck Sheath Dress in Ponte
159.00
95.40
$95.40
$159.00
40% OFF! PRICE AS MARKED.
Pure Chocolate
Draped Midi Dress
New
198.00
118.80
$118.80
$198.00
40% OFF! PRICE AS MARKED.
Lace Midi Sheath Dress
New
198.00
118.80
$118.80
$198.00
40% OFF! PRICE AS MARKED.
Belted Midi Shirtdress
New
198.00
118.80
$118.80
$198.00
40% OFF! PRICE AS MARKED.
Paisley Crew Neck Midi Dress
Best Seller
198.00
118.80
$118.80
$198.00
40% OFF! PRICE AS MARKED.
Deep Forest Pine
Mixed Stitch Sweater Dress
Best Seller
198.00
118.80
$118.80
$198.00
40% OFF! PRICE AS MARKED.
Weekend Contrast Trim Sweater Dress
New
198.00
118.80
$118.80
$198.00
40% OFF! PRICE AS MARKED.
Plum Multi
Lace Trim Midi Shirtdress
New
198.00
118.80
$118.80
$198.00
40% OFF! PRICE AS MARKED.
Purest Plum
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
Paisley Jacquard Midi Sweater Dress
Best Seller
209.00
125.40
$125.40
$209.00
40% OFF! PRICE AS MARKED.
Shadow Grey
Floral Mock Neck Midi Dress
New
189.00
113.40
$113.40
$189.00
40% OFF! PRICE AS MARKED.
Ribbed Mock Neck Sweater Dress
Best Seller
189.00
113.40
$113.40
$189.00
40% OFF! PRICE AS MARKED.
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