Women’s
Dresses & Skirts

From corduroy and linen to cotton and suede, shop Territory Ahead for a wide selection of women’s dresses and skirts. Our dresses are comfortable, casual styles that can go with you from day to night, work to dinner. Our skirts are the perfect complements to our flowy blouses and longer-length shirts. Browse our collection of women’s dresses and skirts designed with unique patterns and details that showcase your relaxed sense of style.

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Item 302630
$129.00
Gothic Paisley Knit Maxi Skirt from Isle®: A rich paisley print adorns this flowing knit maxi skirt. Featuring an easy full elastic waist and full-sweep bottom. Pull-on style. Rayon/poly/spandex. Machine washable. Imported. 38" length.
Item 302527
$119.00
Aranyani Paisley Knit Dress from Nally & Millie®: A rich paisley print and the flattering knit fabric make this dress work day to evening. Add a belt or necklace for added panache. Featuring a boat neck and long sleeves. Pull-on style. Poly/rayon/spandex. Hand wash. U.S. made. 39.5" length.
Item 302624
$69.50
$54.50 - $69.50
Save up to 22%
5.05

(1)

Crochet Maxi Skirt: Expect many compliments when you wear this lovely skirt covered with open crochet designs. With an elastic-stitched waist and full sweep bottom. 100% cotton; fully lined in cotton voile. Hand wash. Imported. 36.5" length.

5.05

(1)

5.05

(1)

Item 302629
$99.00
Makeda Tribal Print Knit Skirt: A gorgeous mix of earthtone geometrics covers this maxi skirt featuring a ruched elastic waistband that feels comfortable and flatters. The soft, drapey rayon has a subtle slubby texture and a touch of spandex gives it stretch for extra comfort. Pull-on style. Partially lined for coverage. Rayon/spandex. Hand wash. Imported. 45" length.
Item 302627
$79.50
5.05

(3)

Rhythm & Blue Denim Skirt: This five-star favorite works with almost everything in your wardrobe. You won't believe it's denim. It's that soft, and that drapey thanks to tinting, sandblasting and specially washing the lightweight cotton denim. Double godet insets. Goldenrod topstitching. Side zip. 100% cotton. Machine washable. Imported. 33.5" length (hits below the calf).

5.05

(3)

5.05

(3)

Item 302505
$79.50
$69.50 - $79.50
Save up to 13%
4.45

(5)

Top Of The Line Long Sleeve Peruvian Pima Dress: You asked... we said "Yes" to using a more substantial, 250-gram Peruvian pima cotton for our ultrasoft dress. Pull-on styling. Tagless neck. Machine washable. Imported. 37.75" length (hits below the knee).

4.45

(5)

4.45

(5)

Item 320160
$299.00
5.05

(3)

R & B Suede Skirt: Our iconic R&B skirt you've loved for years is now available in buttery, drapey goat suede. Same gorgeous details: Flared A-line silhouette with two godet insets, clean waistband, invisible side zip, ankle length. Fully lined in satin acetate. Professional leather clean. Imported. 33.5" length.
5.05

(3)

5.05

(3)

Item 356262
$79.50
$59.50
Save 25%
4.15

(42)

First Pick Textured Dress: It just gets better. Based on your feedback, we've improved our best-selling knit dress. First, we gave the textured cotton-rayon fabric a tighter tensile knit to create a smoother fabric that retains its shape. Then, we eased the elbow-length sleeves for a more comfortable fit, and added additional hidden snaps to support the front closure wood button. Same pull-on styling, scoop henley neckline and relaxed, slightly A-line silhouette. Knee length. Machine washable. Imported. 39" length.

4.15

(42)

4.15

(42)

Item 301556
$89.50
$69.50
Save 22%
4.55

(8)

Tiered Garment Dyed Linen Skirt: This midweight linen skirt is garment-dyed for soft, lived-in character. It's cut on the bias, ending in two tiers for a great flowy drape. Elastic waist. Pull-on style. Machine washable. Imported. 32" length.

4.55

(8)

4.55

(8)

Item 302511
$59.50
$39.50
Save 34%
4.85

(4)

A-List Sleeveless Dress: Made of the same 235-gram, Tanguis Peruvian cotton as our best-selling men's A-List collection, this garment washed dress is perfect as a beach cover-up. Details include zig-zag stitching, cap sleeves and two patch pockets. 100% Tanguis cotton. Machine washable. Imported. 39" length.

Buy any 2 & SAVE $3 each
Buy 3 or more & SAVE $5 each

NOTE: Buy more & save pricing is not available on sale and clearance colors.

4.85

(4)

4.85

(4)

Item 302504
$119.00
$99.00
Save 17%
4.85

(5)

Basilica Printed Knit Dress from Nally & Millie®: The rich, kaleidoscope print is inspired by a medieval basilica, and the flattering knit fabric makes this dress work day to evening. Add a belt or necklace for added panache. Styled with a scoop neck, long sleeves and flared hem. Pull-on style. Poly/rayon/spandex. Hand wash. U.S. made. 41" length.

4.85

(5)

4.85

(5)

Item 301415
$69.50
5.05

(2)

Rhythm & Blue Short Denim Skirt: Our long Rhythm & Blue Skirt has been an all-season favorite for years, so we decided to design a kicky short version for warmer weather. It features the same soft and drapey cotton denim that's been tinted, sandblasted and specially washed for built-in character. Double godet insets. Goldenrod topstitching. Machine washable. Imported. 23" length.
5.05

(2)

5.05

(2)

Item 302512
$79.50
$49.50
Save 38%

A-List Short Sleeve Wrap Dress: This soft knit dress is perfect for every occasion from the beach to cocktails to a cozy brunch with friends. Made from our best-selling, A-List 235-gram Tanguis cotton fabric that's pigment garment dyed and garment washed. The attached belt completes the look. Cool zig-zag stitching details. 100% Tanguis Peruvian cotton. Machine washable. Imported. 39" length.

Buy any 2 & SAVE $3 each
Buy 3 or more & SAVE $5 each

NOTE: Buy more & save pricing is not available on sale and clearance colors.

Item 302522
$89.50
$44.50
Save 50%
4.05

(4)

Alegre Sleeveless Linen Dress: A lovely chainlink design is laser printed onto this substantial, midweight linen dress that keeps you cool even on hot days. The flattering A-line silhouette is styled with an easy scoop neck, two side pockets and a center seam on front and back. 100% linen. Machine washable. Imported. 40" length.
4.05

(4)

4.05

(4)

Item 320377
$159.00
$30.00
Save 81%
3.75

(3)

Printed Silk Pintuck Dress: A feminine silhouette, pintuck details and button-through 3/4-sleeves define this lovely silk georgette dress. Pleated 6-button placket. Elasticized waist. Two front pockets. 100% silk shell. Lined in polyester. Dry clean. Imported. 39" length.

3.75

(3)

3.75

(3)

Item 302513
$79.50
$39.50
Save 50%
Sleeveless Knit Maxi Dress: This easy slub knit maxi is your go-to spring dress. Styled with a scoop neck, two on-seam pockets, side vents and back yoke detail with Territory Ahead logo. Cotton/rayon. Machine washable. Imported. 53" length.
Item 302515
$99.50
$69.50
Save 30%
4.55

(2)

"Un" Work Chambray Henley Shirtdress: The tie belt and darts at the yoke make this your comfortable go-to dress. True indigo yarns are made of tencel for a silky finish and slubby cotton for breathability. Contrasting twill tape at the inside neck and sleeves. Antiqued brass buttons. Shirttail hem with gusset on the sides. Tencel/cotton chambray. Machine washable. Imported. 39" length (from high point of shoulder to bottom hem).

4.55

(2)

4.55

(2)

Item 302523
$119.00
$79.50
Save 33%
4.05

(1)

Nally & Millie® Bonita Knit Dress: A gorgeous Aztec print covers this versatile knit dress. Styled with a soft, rounded ballet neckline and short sleeves. Poly/rayon/spandex. Hand wash. Imported. 41" length (hits at the knee).

4.05

(1)

4.05

(1)

Item 302705
$119.00
$99.00
Save 17%
5.05

(1)

Bellissimo Knit Dress from Nally & Millie®: A beautiful wave print in a mix of red, green and ivory on a turquoise background covers this versatile knit dress. Styled with a soft, rounded ballet neckline and short sleeves. Poly/rayon/spandex. Hand wash. U.S. made. 41" length.
5.05

(1)

5.05

(1)

Item 301669
$139.00
$99.00
Save 29%
5.05

(3)

Lake Tahoe Blanket Skirt: A vibrant Southwestern pattern covers this exceptionally soft pencil skirt. Great seaming and stitching details. Single back vent. Back Zip. Poly/acrylic/wool. Fully lined in poly. Dry clean. Imported. 24" length.
5.05

(3)

5.05

(3)

Item 320338
$79.50
$49.50
Save 38%
4.45

(5)

Sublime Slub Knit Dress: The wonderfully soft knit fabric is gently slubbed and it drapes elegantly. With a scoop neck and handkerchief hem. Cotton/rayon. Unlined. Machine washable. Imported. 49" length.

4.45

(5)

4.45

(5)

Item 320387
$139.00
$109.00
Save up to 22%
4.35

(7)

First In Line Fit & Flare Sweater Dress: This flattering fit and flare knit gains dramatic appeal with contrast ribbon stripes running vertically and spaced further apart along the sleeves. With a scoop neck and hemmed sleeves. 100% cotton. Machine washable. Imported. 41" length.

4.35

(7)

4.35

(7)

Item 310030
$89.00
$17.00
Save 81%
4.85

(8)

Padaro Knit Dress from Isabella Bird: Exceptionally soft, the special ponte knit blend has an ingenious way of skimming over the skin without clinging, making it the ultimate travel fabric. Beautifully tailored with seaming to fit and flatter. Styled with a subtle scoop neck and raglan sleeves. Princess and center seaming. Semifitted. Rayon/nylon/spandex. Machine washable. Imported. 37" length (hits above the knee).

4.85

(8)

4.85

(8)

Item 302518
$89.50
Sleeveless Print Maxi Dress from VASNA®: A bold red and gold abstract print floats on the black background of this easy, crinkle textured rayon crepe dress. The elasticized top features a scoop neck and gathers at the empire waist. The full-sweep hem drapes beautifully for a dramatic look. 100% rayon crepe. Machine washable. Imported. 50" length.
Item 302611
$74.50
$59.50
Save 20%
5.05

(2)

Mission Comfort Stretch Twill Skirt: We used our best-selling Mission Comfort twill fabric to create this super-comfy skirt with a hidden secret: inside waist tabs stretch up to three inches. Cotton twill is pigment garment dyed and heavy garment washed for a lived-in feel. Antiqued brass buttons, two front pockets with gussets and inside striped waist. Cotton with a bit of stretch. Machine washable. Imported. 22" length (hits above the knee).

5.05

(2)

5.05

(2)

Item 310017
$89.00
$17.00
Save 81%
4.05

(2)

Lace Trim Knit Dress from Isabella Bird: The long, seductive silhouette invites plenty of compliments. It's pure elegance in flowing rayon, with fanciful details like the lace-inset V-neck, 3/4-length bell sleeves, and crossover fabric panels at the bodice. Belted; ties at the back. Rayon/spandex. Dry clean. Imported. 46.5" length (hits at the ankle).

4.05

(2)

4.05

(2)

Item 302605
$69.50
$39.50
Save 43%
4.55

(2)

Hazel Button Front Denim Skirt from Jag® Jeans: This updated version of a classic pencil skirt has the right amount of stretch to flatter every curve. The top three buttons are functional while the bottom four are faux – this prevents gapping when you move or sit. Signature "J" embroidery at back pocket. Pull-on style. Cotton/spandex. Machine washable. Imported. 25.5" length.

4.55

(2)

4.55

(2)

Item 302500
$89.50
$69.50
Save 22%
Mix Master Sueded Jersey Hoodie Dress: Whether you're relaxing or on-the-go, the heavyweight, 300-gram cotton jersey keeps you warm and cozy. Pigment garment dyed and sueded for a lived-in look and feel. With elastic drawstring waist and drawstring hood. Quarter zip front. Hemmed sleeves. Antiqued brass zipper and hardware. 100% cotton. Machine washable. Imported. 36" length.
Item 302615
$79.50
$69.50
Save 13%
3.05

(1)

Zephyr Basketweave A-line Skirt: Back by popular demand... this versatile skirt is made from the same medium weight basketweave fabric as our men's Zephyr collection. It keeps you cool in warm weather –  wear it with your favorite T-shirts, tunics and lightweight sweaters. Detailed with two front slanted pockets, faux horn buttons, princess seams front and back, and Signature vintage turquoise trim at the inside waist. Center back zip. 100% cotton. Machine washable. Imported. 24" length.

3.05

(1)

3.05

(1)

Item 302506
$89.50
$59.50
Save 34%
4.45

(5)

Drop Waist Peruvian Pima Knit Dress: You asked... we said "Yes" to using a more substantial, 250-gram Peruvian pima cotton for this easy-wearing dress. The effortless silhouette drapes well and flatters nicely with a scoop neck, drop waist and 3/4-length sleeves. Pull-on style. 100% Peruvian pima cotton. Machine washable. Imported. 46" length (hits below the knee).

4.45

(5)

4.45

(5)

Item 302618
$129.00
$109.00
Save 16%
4.75

(3)

Mediterraneo Bandana Print Maxi Skirt From Isle: This soft and drapey maxi skirt is made of a cool knit fabric and features a ruched 4.5" elastic waistband that feels comfortable and flatters. The colorful digital print pairs beautifully with your favorite knit tee for an easy, casual look. Pull-on style. Rayon/poly/spandex. Machine washable. Made in Turkey. 38" length.

4.75

(3)

4.75

(3)

Item 320256
$269.00
$52.00
Save 81%
4.05

(1)

Luxe Lambskin Leather Skirt: The perfect year-round look in buttery soft lambskin that's super luxurious to the touch. Classic 5-pocket styling with belt loops and shank button closure. Fully lined in polyester. Single back vent. Have professionally leather cleaned. Imported. 23" length.

4.05

(1)

4.05

(1)

Item 320379
$179.00
$99.00
Save 45%
5.05

(1)

Space Dyed Sweater Scarf Dress: Indulge in this season's most versatile look -  a marled knit sweater dress with a detachable scarf. The unique colorblocking look features different colored, space-dyed panels for the body and sleeves, with contrast ribbing at the asymmetrical hem and sleeve edges, and a different knit fabric for the scarf. V-neck with full sweep bottom. Pullover style. Cotton/ramie. Hand wash. Imported. 38" length.

5.05

(1)

5.05

(1)

Item 320349
$130.00
$26.00
Save 80%
5.05

(1)

Both Sides Now Hi-lo Sweater Dress: This cotton knit dress looks and feels relaxed whether you're arriving or departing. Nautical stripes line up on the front, while the back is solid navy. Gentle V-neck with cap sleeves. Pull-on style. 100% cotton. Hand wash. Imported. 40" length.
5.05

(1)

5.05

(1)

Item 302621
$89.50
$74.50
Save 17%

Sunrise Basketweave Skirt: Rich, textured basketweave combines with a great melange of colors to create your go-to skirt of the season. The top three buttons are functional, while the bottom three are decorative. Two front pockets with split back and belt loops. Cotton/poly. Dry clean. Imported. 23" length (hits at the knee).

Item 301432
$99.50
$69.50
Save 30%
5.05

(1)

Wool Buffalo Check Wrap Skirt: A bold plaid print and button front waist give this classic wool wrap skirt a distinctively modern twist. 100% wool. Fully lined in poly. Dry clean. Imported. 24" length.

5.05

(1)

5.05

(1)

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