Women's Preppy Outfits

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-60%
Mini skirt in pinstripe flannel
Mini skirt in pinstripe flannel

Available Sizes

  • 4
  • 6
  • 8
  • 10
  • 12

Mini skirt in pinstripe flannel

Create a host of looks with this HUGO Womenswear mini skirt. Crafted in stretch flannel with a classic pinstripe and deep pleats. Stacked-logo charm.
$179.00 $72.00
  • Color Beige
Checked-bouclé skirt with A-line profile
Checked-bouclé skirt with A-line profile

Available Sizes

  • 0
  • 2
  • 4
  • 6
  • 8
  • 10
  • 12

Checked-bouclé skirt with A-line profile

With its A-line shape, front pleats and classic check in boucle fabric, this HUGO Womenswear skirt is a modern must. Shank buttons. Matching blazer available.
$199.00
  • Color Patterned
-40%
Blue rigid-denim mini skirt with half pleating
Blue rigid-denim mini skirt with half pleating

Available Sizes

  • XL

Blue rigid-denim mini skirt with half pleating

Washed to an authentic blue with embroidered motifs, this HUGO Womenswear mini skirt is made in rigid cotton denim. Half pleats for a modern silhouette.
$89.00 $53.00
  • Color Blue
Front-pleat dress with balloon skirt
Front-pleat dress with balloon skirt

Available Sizes

  • 0
  • 2
  • 4
  • 6
  • 8
  • 10

Front-pleat dress with balloon skirt

Cut in stretch crepe with a balloon silhouette, this HUGO Womenswear dress makes a modern statement. Strappy square neckline. Pleat front
$349.00
  • Color Black
Front-pleat dress with balloon skirt
Front-pleat dress with balloon skirt

Available Sizes

  • 2
  • 4
  • 8

Front-pleat dress with balloon skirt

Cut in stretch crepe with a balloon silhouette, this HUGO Womenswear dress makes a modern statement. Strappy square neckline. Pleat front
$349.00
  • Color Purple
Nappa-leather skirt with front seam
Nappa-leather skirt with front seam

Available Sizes

  • 4
  • 6
  • 8
  • 10
  • 12

Nappa-leather skirt with front seam

Modernize any look in an instant with the feminine cut and soft nappa leather of this BOSS Womenswear skirt. Front seam and hidden rear zip.
$549.00
  • Color Black
-60%
Faux-leather mini skort with wrap front
Faux-leather mini skort with wrap front

Available Sizes

  • 0
  • 4
  • 6
  • 8

Faux-leather mini skort with wrap front

With a wrap front and button detail, this HUGO Womenswear mini skort is a modern take on a classic. Crafted in soft synthetic coated fabric. Synthetic coated fabric, sometimes referred to as faux leather, is a fabric designed to resemble real leather, and/or display a matte, glossy, smooth, or textured, coated appearance.
$209.00 $84.00
  • Color Black
-39%
Mini skirt in faux leather

Available Sizes

  • 0
  • 2
  • 8
  • 12

Mini skirt in faux leather

Featuring a Happy HUGO logo, this mini skirt from HUGO Womenswear is crafted in synthetic coated fabric for a statement look. Pockets front and back. Synthetic coated fabric, sometimes referred to as faux leather, is a fabric designed to resemble real leather, and/or display a matte, glossy, smooth, or textured, coated appearance.
$89.00 $54.00
  • Color Black
-32%
Knitted cardigan with tie closure
Knitted cardigan with tie closure

Available Sizes

  • XS
  • S
  • M
  • L
  • XL

Knitted cardigan with tie closure

Featuring a minimalist tie-up closure, this BOSS Womenswear cardigan is blended with wool and alpaca for a fluffy texture. Regular fit V neckline.
$249.00 $170.00
  • Color Dark Blue
Superfine merino wool cardigan
Superfine merino wool cardigan

Available Sizes

  • XS
  • S
  • M
  • L
  • XL

Superfine merino wool cardigan

A timeless BOSS Womenswear cardigan, crafted from exceptionally soft merino wool. Natural breathability, moisture management, and odor control for year-round comfort.
$299.00
  • Color White
Superfine merino wool cardigan
Superfine merino wool cardigan

Available Sizes

  • XS
  • S
  • M
  • L

Superfine merino wool cardigan

A timeless BOSS Womenswear cardigan, crafted from exceptionally soft merino wool. Natural breathability, moisture management, and odor control for year-round comfort.
$299.00
  • Color White
Tie-front rib-knit cardigan with balloon sleeves
Tie-front rib-knit cardigan with balloon sleeves

Available Sizes

  • XS
  • S
  • M
  • L
  • XL

Tie-front rib-knit cardigan with balloon sleeves

In a modern, voluminous shape with a tie front, this BOSS Womenswear cardigan is knitted with a chunky ribbed structure.
$299.00
  • Color White
Leather loafers made in Portugal
Leather loafers made in Portugal

Available Sizes

  • 6
  • 7
  • 8
  • 9
  • 10

Leather loafers made in Portugal

Understated and elegant, these BOSS Womenswear loafers are crafted in smooth leather with a slick silhouette. Expertly made in Portugal. Leather lining for elevated comfort.
$299.00
  • Color Black
Leather loafers with square toe
Leather loafers with square toe

Available Sizes

  • 10

Leather loafers with square toe

Crafted in leather with a squared toe, these BOSS Womenswear loafers add polished elegance to any look. Double B monogram in golden hardware.
$299.00
  • Color Black
-46%
Furry-yarn cardigan in a relaxed fit
Furry-yarn cardigan in a relaxed fit

Available Sizes

  • XS
  • M
  • XL

Furry-yarn cardigan in a relaxed fit

Layer this buttoned HUGO Womenswear cardigan over any look for a touch of cozy luxury. Furry yarn. Relaxed fit. Swirled logo embroidery.
$179.00 $97.00
  • Color White
Superfine merino wool cardigan
Superfine merino wool cardigan

Available Sizes

  • XS
  • S
  • M
  • L
  • XL

Superfine merino wool cardigan

Offering natural comfort and odor control, this BOSS Womenswear cardigan is an everyday essential. Pill-resistant merino wool with temperature regulation.
$299.00
  • Color White
Linen-cotton cardigan with buttoned front
Linen-cotton cardigan with buttoned front

Available Sizes

  • XS
  • S
  • M
  • L
  • XL

Linen-cotton cardigan with buttoned front

Knitted in soft, breathable yarn made from linen and cotton, this BOSS Womenswear cardigan is a chic summer essential. Buttoned front. V neckline.
$349.00
  • Color White
Ribbed-trim cardigan in cashmere
Ribbed-trim cardigan in cashmere

Available Sizes

  • XS
  • S
  • M
  • L
  • XL

Ribbed-trim cardigan in cashmere

Layer with luxury in the cashmere knit of this BOSS Womenswear cardigan. Cut to a laid-back fit with cashmere-blend ribbed trims. Button closure
$549.00
  • Color White
Leather loafers with debossed-logo detail
Leather loafers with debossed-logo detail

Available Sizes

  • 6
  • 8

Leather loafers with debossed-logo detail

These lace-up leather trainers from BOSS Womenswear feature finely stitched details on the front for an intricate look. Completed with understated, debossed logo detailing at the sides and on the back tabs. This style was showcased on the BOSS Summer 26 Fashion Show runway in Milan.
$299.00
  • Color Black
Leather loafers with square toe
Leather loafers with square toe

Available Sizes

  • 9
  • 10

Leather loafers with square toe

Crafted in leather with a squared toe, these BOSS Womenswear loafers add polished elegance to any look. Double B monogram in golden hardware.
$299.00
  • Color White
Bodycon dress with rhinestone stripes
Bodycon dress with rhinestone stripes

Available Sizes

  • XS
  • S
  • M
  • L
  • XL

Bodycon dress with rhinestone stripes

Featuring sparkling rhinestone stripes and a fitted profile, this knitted HUGO Womenswear dress is perfect for parties. High neckline. Tonal embroidered stacked logo.
$349.00
  • Color Black
Ruched-detail loafers in suede
Ruched-detail loafers in suede

Available Sizes

  • 6
  • 7
  • 8
  • 9
  • 10

Ruched-detail loafers in suede

Updating a classic with textured ruching, these suede BOSS Womenswear loafers are a modern must. Gold-tone Double B monogram on heel.
$199.00
  • Color Brown
Suede moccasins with whipstitching
Suede moccasins with whipstitching

Available Sizes

  • 6
  • 7
  • 8
  • 9
  • 10
  • 11

Suede moccasins with whipstitching

Featuring classic lacing and intricate whipstitching, these BOSS Womenswear moccasins are crafted in finest suede. Made in Portugal. Double B monogram trim.
$270.00
  • Color Dark Brown
Ruched-detail moccasins in leather
Ruched-detail moccasins in leather

Available Sizes

  • 6
  • 7
  • 9

Ruched-detail moccasins in leather

With their distinctive ruching, these BOSS Womenswear moccasins add refinement to any look. Sleek leather uppers. Double B monogram trim.
$199.00
  • Color Black
-44%
Knitted vest top with layered design
Knitted vest top with layered design

Available Sizes

  • XS
  • S
  • M
  • L
  • XL

Knitted vest top with layered design

Blended with soft wool and alpaca, this BOSS Womenswear vest top is a versatile casual option. Two-tone layered design. Knitted structure.
$169.00 $94.00
  • Color Black
Loose-fit sweatshirt with V-cut hemline
Loose-fit sweatshirt with V-cut hemline

Available Sizes

  • XS
  • S
  • M
  • L
  • XL

Loose-fit sweatshirt with V-cut hemline

Designed in stretchy jersey with a loose fit, this sleeveless BOSS Womenswear sweatshirt has an inverted V-cut hemline. Embroidered Double B monogram.
$229.00
  • Color White
Leather biker jacket in a regular fit
Leather biker jacket in a regular fit

Available Sizes

  • 0
  • 4

Leather biker jacket in a regular fit

With classic biker styling including polished hardware, this BOSS Womenswear jacket is a modern essential. Cut to a straight fit in rich leather.
$799.00
  • Color Black
-57%
Grained-leather biker jacket with cropped length
Grained-leather biker jacket with cropped length

Available Sizes

  • 0
  • 2
  • 4
  • 8
  • 10

Grained-leather biker jacket with cropped length

Collarless and cropped, this BOSS Womenswear jacket is effortlessly chic. Authentic zip and hardware trims. Grained leather with a vintage-effect finish. Removable belt.
$699.00 $300.00
  • Color Brown
-44%
Cropped biker jacket with leopard jacquard
Cropped biker jacket with leopard jacquard

Available Sizes

  • 2
  • 4
  • 6
  • 8
  • 10
  • 12
  • 14

Cropped biker jacket with leopard jacquard

With biker styling and a leopard jacquard, this BOSS Womenswear jacket makes a modern co-ord with the matching skirt. Piping details.
$349.00 $195.00
  • Color Dark Brown
Suede biker boots with faux-fur trim
Suede biker boots with faux-fur trim

Available Sizes

  • 6
  • 7
  • 9
  • 10
  • 11

Suede biker boots with faux-fur trim

Combining a fluffy collar with rich suede, these cozy BOSS Womenswear boots update a biker classic. Buckle detail with monogram trim. Lightweight outsole. Warm insole.
$270.00
  • Color Black
-44%
Grained-leather biker jacket with cropped length
Grained-leather biker jacket with cropped length

Available Sizes

  • 0
  • 8

Grained-leather biker jacket with cropped length

Collarless and cropped, this BOSS Womenswear jacket is effortlessly chic. Authentic zip and hardware trims. Grained leather with a vintage-effect finish. Removable belt.
$699.00 $390.00
  • Color Black
Suede biker boots with faux-fur trim
Suede biker boots with faux-fur trim

Available Sizes

  • 6
  • 7
  • 8
  • 9
  • 10
  • 11

Suede biker boots with faux-fur trim

Combining a fluffy collar with rich suede, these cozy BOSS Womenswear boots update a biker classic. Buckle detail with monogram trim. Lightweight outsole. Warm insole.
$270.00
  • Color Light Brown
Embossed-logo trainers in leather
Embossed-logo trainers in leather

Available Sizes

  • 6
  • 7
  • 8
  • 9
  • 10
  • 11

Embossed-logo trainers in leather

Designed to go with any look, these BOSS Womenswear trainers are crafted in rich leather with embossed branding. Comfort-boosting insole design.
$230.00
  • Color White
Low-top trainers with suede and leather
Low-top trainers with suede and leather

Available Sizes

  • 6
  • 7
  • 8
  • 10
  • 11

Low-top trainers with suede and leather

Complete any look with the low profile and distinctive zigzag detailing of these HUGO Womenswear trainers. Stacked logo. Leather and suede details. Comfort insole.
$150.00
  • Color White
-44%
Logo-detail trainers with colour-blocking
Logo-detail trainers with colour-blocking

Available Sizes

  • 9

Logo-detail trainers with colour-blocking

Blocked in two tones and finishes for a modern look, these HUGO Womenswear trainers are so easy to style. Perforated toe and logo details.
$160.00 $90.00
  • Color White
Suede-trim trainers in faux leather
Suede-trim trainers in faux leather

Available Sizes

  • 9
  • 10

Suede-trim trainers in faux leather

Refresh your casuals with the retro design and Double B monogram of these BOSS Womenswear trainers. Soft suede and nylon combined with synthetic coated fabric. Synthetic coated fabric, sometimes referred to as faux leather, is a fabric designed to resemble real leather, and/or display a matte, glossy, smooth, or textured, coated appearance.
$199.00
  • Color White
Sock trainers with Double B monogram
Sock trainers with Double B monogram

Available Sizes

  • 7
  • 8
  • 9
  • 10
  • 11

Sock trainers with Double B monogram

Combining knitted sock uppers with soft suede trims, these BOSS Womenswear trainers have a Double B monogram on the side panel. Toweling-effect laces.
$199.00
  • Color White
-44%
Regular-fit blouse in stretch silk

Available Sizes

  • 8
  • 10
  • 12
  • 14

Regular-fit blouse in stretch silk

With a keyhole detail and gatherings at the neckline, this tailored BOSS Womenswear blouse is a contemporary choice. Luxurious stretch silk. Straight fit.
$349.00 $195.00
  • Color light pink
-50%
Relaxed-fit blouse in washed silk
Relaxed-fit blouse in washed silk

Available Sizes

  • 6
  • 12

Relaxed-fit blouse in washed silk

Crafted in soft, sand-washed silk with a fluid drape, this BOSS Womenswear blouse has half-buttoned sleeves for an adaptable look. Relaxed fit
$349.00 $175.00
  • Color White
Regular-fit blouse in stretch silk
Regular-fit blouse in stretch silk

Available Sizes

  • 0
  • 2
  • 4
  • 6
  • 8
  • 10
  • 14

Regular-fit blouse in stretch silk

Create a host of workwear and occasion looks with the soft, lustrous silk of this BOSS Womenswear satin blouse. Regular fit, plus stretch for comfort.
$349.00
  • Color White