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.

Sort By
Item 302610
Price $59.50

A-List Drawstring Skirt: Made from our Tanguis Peruvian cotton that's a substantial 280-gram weight, pigment garment dyed and garment washed. With an elastic waist, hidden inside waistband pocket and two side pockets. Pull-on style. Machine washable. Imported. 20" length (hits above the knee).

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 302512
Price $79.50

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 240-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 302611
Price $74.50

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).

Item 356262
$79.50
$19.50 - $79.50
Save up to 75%
4.25

(34)

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.

4.25

(34)

4.25

(34)

Item 302515
Price $99.50

"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).

Item 302621
Price $89.50

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 302615
Price $79.50

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.

Item 302618
Price $129.00

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.

Item 302627
Price $79.50

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).

Item 301415
$69.50
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.
Item 302523
Price $119.00

Bonita Knit Dress From Nally & Millie®: 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).

Item 301556
$89.50
4.65

(5)

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.

4.65

(5)

4.65

(5)

Item 302623
Price $99.50

Tencel Dobby Skirt: Flowy A-line in smooth tencel dobby. The inside tab closure and side zip allow for easy on and off, while the belt flatters your figure. Detailed with an aztec trim logo, zig-zag stitching and grosgrain tape at the inside waist. 100% tencel. Dry clean. Imported. 24.5" length (hits below the knee).

Item 302504
Price $119.00

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.

Item 302506
$89.50
$69.50
Save 22%

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).

Item 320338
$79.50
$59.50
Save 25%
5.05

(2)

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.

5.05

(2)

5.05

(2)

Item 302607
$69.50
$49.50
Save 29%
Mañana Corduroy Skirt: When you plan your next getaway, pack this travel-friendly skirt made from our famous Mañana 11-wale corduroy. Detailed with Sausalito trim zip front, two side pockets, plus coin pocket. Back vent. 100% cotton. Machine washable. Sizes: 4-16. 24" length (hits below the knee).
Item 302601
$79.50
$69.50
Marrakesh Heathered Wool Skirt: This versatile skirt is made of a great heathered wool blend, and can be dressed up or down. Featuring a slightly A-line silhouette with two front pockets. Back darts and back zip. Wool/poly; fully lined in poly acetate. Dry clean. Imported. 24" length (hits below the knee).
Item 301669
$139.00
$129.00
5.05

(1)

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

(1)

5.05

(1)

Item 536210
$79.50
$59.50
Save 25%
4.65

(37)

Rhythm And Blue Denim Skirt: 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. The indigo colorways feature goldenrod topstitching. Falls below the calf. Side zip. Machine washable. Imported. Length: 31.5". 

4.65

(37)

4.65

(37)

Item 302605
$69.50
$59.50

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.

Item 301438
Price $229.00

Touchstone Washable Suede Skirt: Enjoy the luxurious, liquid drape of fine suede without the inconvenience of dry cleaning. The classic A-line shape flares beautifully at the hem with godet panel insets. Clean styled waist for an easy fit. Side zip. Fully lined in poly. Machine washable. Imported. 35.5" length.

Item 320424
$89.00
$59.50
Save 33%
4.05

(4)

Scoop Neck Peruvian Pima Knit 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 from Peru. 46" length.

4.05

(4)

4.05

(4)

Item 320387
$139.00
$129.00
4.25

(4)

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.

4.25

(4)

4.25

(4)

Item 320384
$89.00
$29.50
Save 67%
2.05

(2)

Slub Knit Handkerchief-Hem Dress: This effortless silhouette dresses up or down, and the slub knit jersey fabric drapes well and offers non-stop comfort. With a boat neck, 3/4-length sleeves and uneven handkerchief hem. Pull-on style. Cotton/rayon. Machine washable. Imported. 41" length.

2.05

(2)

2.05

(2)

Item 320379
$179.00
$99.00
Save 45%

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.

Item 320377
$159.00
$49.50
Save 69%
3.05

(2)

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.

3.05

(2)

3.05

(2)

Item 310030
$89.00
$24.50 - $29.50
Save up to 72%
4.35

(3)

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).

4.35

(3)

4.35

(3)

Item 310017
$89.00
$19.50
Save 78%
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 301574
$99.50
$69.50
Save 30%
2.05

(1)

Pieced Ikat Cotton Maxi Skirt: A figure-flattering shape combines with a lovely, pieced ikat print to create your must-have skirt of the season. Full-sweep bottom. Side zip. 100% cotton. Machine washable. Imported. 36" length.

2.05

(1)

2.05

(1)

Item 301571
$69.50
$49.50
Save 29%
5.05

(2)

Peruvian Slub Knit Maxi Skirt: Relaxed A-line silhouette with elastic waist, two front pockets and shirring details. Pull-on style. 100% Peruvian cotton. Machine washable. Imported. 38" length.

5.05

(2)

5.05

(2)

Item 301549
$109.00
$87.00
Save 20%

Via Del Corso Hi Lo Pieced Linen Dress: A solid tank at the top contrasts with a finely striped body that drapes like a dream with an easy hi-lo hem. Sleeveless. Garment-dyed 100% linen. Machine washable. U.S. made of imported fabric. Sizes: S-XL. 36" front length; 41" back length.

Item 301548
$109.50
$87.50
Save 20%

Sleeveless Braid Trim Maxi Dress: This easy-draping, jersey knit dress is accented with braided trim at the empire waist and V-neckline. Full-sweep bottom. Pull-on style. Cotton/modal/spandex. Machine washable. U.S. made of imported fabric. 52" length.

Item 301302
$119.00
$49.50
Save 58%

Crushed Velvet Long Skirt From Isabella Bird: This shimmery velvet skirt has a liquid drape that accentuates the flattering, flared silhouette. Elastic waist. Pull-on style. Rayon/silk. Hand wash. Imported. 36" length.

Item 302603
$129.00
$109.00

Aspen Knit Maxi Skirt from Isle: A soft, sophisticated skirt featuring a wide banded waist with ruching at the side. Wear it with your favorite boots! Pull-on style. Rayon/poly/spandex. Machine washable. Imported. 38" length.

Item 302505
$79.50
$69.50

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).

  • Refine by:
  • Clear
    Type
    • Dresses
    • Skirts
  • Clear
    Color
    BLACK
    BLUE
    BROWN
    RED
    PATTERN
    GREEN
    GREY
    NEUTRAL
    ORANGE
    WHITE
    DENIM
    METALLIC
    PINK
    PURPLE
    YELLOW
  • Clear
    Size Range
    • Misses
    • Petite
    • Regular
  • Clear
    Size
    02
    04
    06
    06P
    08
    10
    12
    14
    16
    16P
    L
    M
    PXS
    S
    XL
    XS
  • Clear
    Material
    Cotton
    Denim
    Linen
    Silk
    Suede
    Wool
  • Clear
    Price
    • Under $50
    • $50 to $74.99
    • $75 to $99.99
    • $100 to $149.99
    • $150 & Above
  • Clear
    Rating
    4 Stars and Up
    3 Stars and Up
    2 Stars and Up
    1 Stars and Up