Women's Preppy Outfits

(41)

Women's preppy outfits exude a polished yet approachable vibe. Think tailored skirts, crisp button-down shirts, and clean lines—perfect for a sophisticated yet relaxed look. Pair with loafers or sneakers to complete your ensemble, and discover HUGO BOSS pieces that embrace the preppy style with refined sophistication.

Show more
Filter Filter
Most Relevant Sorting
  • Most Relevant
  • Price (low-high)
  • Price (high-low)
Select filter Close section
Brand
Open Section
Brand Line
Open Section
Category
Open Section
Size
Open Section
Colour
Open Section
Fit
Open Section
Price Open Section
Gender
Open Section
SLEEVES
Open Section
Collar
Open Section
Neckline
Open Section
Pleated mini skirt with micro check
Pleated mini skirt with micro check

Available Sizes

  • 6
  • 8
  • 10
  • 12
  • 14

Pleated mini skirt with micro check

With a micro-check pattern and preppy pleats, this HUGO Womenswear skirt is crafted in stretch fabric blended with cotton. Side zip with logo puller.
£189.00
  • Colour Patterned
Pleated skirt in stretch cotton with integrated shorts
Pleated skirt in stretch cotton with integrated shorts

Available Sizes

  • S
  • L
  • XL

Pleated skirt in stretch cotton with integrated shorts

Featuring integrated shorts for effortless wear, this versatile HUGO Womenswear skirt is crafted in soft stretch cotton. Pressed pleats.
£59.00
  • Colour Black
Equestrian cropped sweater in wool and cashmere

Available Sizes

  • XS
  • L
  • XL

Equestrian cropped sweater in wool and cashmere

A signature sweater by BOSS Womenswear. This cropped sweater is knitted with an interesting cable structure in soft yarns made from wool blended with luxurious cashmere. A logo patch completes this layer.
£219.00
  • Colour Brown
Regular-fit blazer in cotton-blend bouclé
Regular-fit blazer in cotton-blend bouclé

Available Sizes

  • 6
  • 10
  • 12
  • 14
  • 16

Regular-fit blazer in cotton-blend bouclé

Updating the classic cropped blazer, this straight-fit HUGO Womenswear jacket is made in cotton-rich bouclé yarn. Polished golden square buttons.
£269.00
  • Colour Natural
V-neck top in a knitted alpaca blend
V-neck top in a knitted alpaca blend

Available Sizes

  • S
  • M
  • L
  • XL
  • XXL

V-neck top in a knitted alpaca blend

Featuring a detailed V neckline, this BOSS Womenswear top is ideal for layering. Soft alpaca-blend yarn with a touch of wool.
£189.00
  • Colour Light Green
V-neck sweater in an open-knit cotton blend
V-neck sweater in an open-knit cotton blend

Available Sizes

  • XS
  • S
  • M
  • L

V-neck sweater in an open-knit cotton blend

Featuring a fresh open knit and distinctive collar, this BOSS Womenswear sweater is crafted with Italian yarn in a cotton blend. Straight fit.
£189.00
  • Colour Natural
Leather loafers with chain trim and logo detail
Leather loafers with chain trim and logo detail

Available Sizes

  • 3
  • 4
  • 5
  • 6
  • 7
  • 8
  • 9

Leather loafers with chain trim and logo detail

Featuring a statement chain trim with logo detailing, these versatile BOSS Womenswear loafers are shaped in leather with an almond toe. Expertly crafted in Portugal. This product contains at least 80% better raw materials. The leather used to make this product has been sourced from Leather Working Group Gold-certified tanneries.
£239.00
  • Colour Black
Bodycon dress with grosgrain trims
Bodycon dress with grosgrain trims

Available Sizes

  • 4
  • 6
  • 8
  • 10
  • 12
  • 14
  • 16
  • 18

Bodycon dress with grosgrain trims

Offering an elegant workwear look, this BOSS Womenswear dress has a bodycon fit in wrinkle-resistant, comfort-stretch material. Flattering darts and grosgrain details.
£319.00
  • Colour Dark Blue
Leather loafers with chain trim and logo detail
Leather loafers with chain trim and logo detail

Available Sizes

  • 3
  • 4
  • 5
  • 6
  • 7
  • 8
  • 9

Leather loafers with chain trim and logo detail

Featuring a statement chain trim with logo detailing, these versatile BOSS Womenswear loafers are shaped in leather with an almond toe. Expertly crafted in Portugal. This product contains at least 80% better raw materials. The leather used to make this product has been sourced from Leather Working Group Gold-certified tanneries.
£239.00
  • Colour Brown
Leather loafers made in Portugal
Leather loafers made in Portugal

Available Sizes

  • 3
  • 4
  • 8

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.
£289.00
  • Colour Black
Suede loafers with leather outsole
Suede loafers with leather outsole

Available Sizes

  • 4
  • 5
  • 6
  • 7
  • 8

Suede loafers with leather outsole

Lightweight and flexible, these BOSS Womenswear loafers are crafted in suede for classic appeal. Made in Portugal with a durable leather outsole. This product contains at least 80% better raw materials. The leather used to make this product has been sourced from certified tanneries.
£289.00
  • Colour Light Beige
Leather moccasins with Double B monogram
Leather moccasins with Double B monogram

Available Sizes

  • 3
  • 4
  • 5
  • 6
  • 7
  • 8
  • 9

Leather moccasins with Double B monogram

With a penny trim and soft leather uppers, these BOSS Womenswear moccasins are an everyday must. Trimmed with a Double B monogram charm. This product contains at least 80% better raw materials. The leather used to make this product has been sourced from Leather Working Group Gold-certified tanneries.
£199.00
  • Colour Black
Leather moccasins with Double B monogram
Leather moccasins with Double B monogram

Available Sizes

  • 3
  • 4
  • 5
  • 6
  • 7
  • 8
  • 9

Leather moccasins with Double B monogram

With a penny trim and soft leather uppers, these BOSS Womenswear moccasins are an everyday must. Trimmed with a Double B monogram charm. This product contains at least 80% better raw materials. The leather used to make this product has been sourced from Leather Working Group Gold-certified tanneries.
£199.00
  • Colour Light Brown
Leather loafers with penny trim and stacked logo
Leather loafers with penny trim and stacked logo

Available Sizes

  • 3
  • 4
  • 5
  • 6

Leather loafers with penny trim and stacked logo

Featuring a stacked logo in a gold effect, these HUGO Womenswear loafers are a modern everyday choice. Soft leather with classic penny trim. Lightweight sole.
£169.00
  • Colour Black
Stacked-logo loafers in faux leather
Stacked-logo loafers in faux leather

Available Sizes

  • 3
  • 4
  • 5
  • 6
  • 7
  • 8

Stacked-logo loafers in faux leather

Set on a chunky rubber outsole with uppers in smooth synthetic coated fabric, these HUGO Womenswear loafers are a modern must. Polished stacked-logo trim. 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.
£189.00
  • Colour Black
Leather moccasins with stacked logo
Leather moccasins with stacked logo

Available Sizes

  • 3
  • 4
  • 5
  • 6
  • 7

Leather moccasins with stacked logo

Featuring a subtle serrated trim, these classic HUGO Womenswear moccasins are shaped in smooth leather. Embossed stacked logo on the vamp.
£189.00
  • Colour Black
Knitted waistcoat with merino wool
Knitted waistcoat with merino wool

Available Sizes

  • XS
  • S
  • M
  • L
  • XXL

Knitted waistcoat with merino wool

Blended with luxuriously soft, superfine merino wool, this BOSS Womenswear waistcoat will become a casual favourite. Button front.
£169.00
  • Colour Light Beige
Leather trainers with embossed logos
Leather trainers with embossed logos

Available Sizes

  • 2
  • 3
  • 4
  • 5
  • 6
  • 7
  • 8
  • 9

Leather trainers with embossed logos

A minimum of 60% of the leather used to make this product has been sourced from certified tanneries. With a cushioning insole, these BOSS Womenswear trainers are an everyday staple. Crafted in smooth leather with a supportive rubber outsole.
£169.00
  • Colour White
Cupsole trainers in leather with logo details
Cupsole trainers in leather with logo details

Available Sizes

  • 2
  • 3
  • 4
  • 5
  • 6
  • 7
  • 8
  • 9

Cupsole trainers in leather with logo details

Cupsole trainers with branding throughout in signature red by HUGO. We continuously look for more responsible ways to produce and finish our products. A minimum of 60% of the leather used to make this product has been sourced from certified tanneries.
£189.00
  • Colour White
Suede moccasins with hand-stitched apron toe
Suede moccasins with hand-stitched apron toe

Available Sizes

  • 3
  • 4
  • 5
  • 6
  • 7
  • 8
  • 9

Suede moccasins with hand-stitched apron toe

Featuring precise hand stitching at the apron toe, these BOSS Womenswear moccasins are crafted in rich suede. Classic lacing and contrast rubber sole. This product contains at least 80% better raw materials. The leather used to make this product has been sourced from Leather Working Group Gold-certified tanneries.
£199.00
  • Colour Brown
Straight-fit biker jacket in leather with zipped details
Straight-fit biker jacket in leather with zipped details

Available Sizes

  • XS
  • S
  • M

Straight-fit biker jacket in leather with zipped details

A mainstay of any modern wardrobe, this HUGO Womenswear jacket has classic biker styling. Regular fit in rich leather. Asymmetric front zip. Epaulettes.
£389.00
  • Colour Black
Stand-collar biker jacket in soft leather
Stand-collar biker jacket in soft leather

Available Sizes

  • 6
  • 8
  • 10
  • 12
  • 14
  • 16

Stand-collar biker jacket in soft leather

The leather used to make this product has been sourced from Leather Working Group Gold certified tanneries. An expertly crafted biker jacket by BOSS Womenswear. Made from soft leather with a delicate waxed finish.
£389.00
  • Colour Black
Stretch-silk blouse with gathered details
Stretch-silk blouse with gathered details

Available Sizes

  • 6
  • 8
  • 10
  • 12
  • 14
  • 16
  • 18

Stretch-silk blouse with gathered details

Offering natural thermo regulation, this adaptable BOSS Womenswear blouse is made in luxuriously soft silk with added stretch. Concealed closure. Easy straight fit.
£269.00
  • Colour Light Yellow
Low-top trainers with suede trims
Low-top trainers with suede trims

Available Sizes

  • 3
  • 4
  • 5
  • 6
  • 7
  • 8

Low-top trainers with suede trims

With a comfy insole and rich suede trims, these HUGO Womenswear trainers balance comfort and modern style. Zigzag details and stacked logo.
£159.00
Relaxed-fit blouse in sandwashed silk
Relaxed-fit blouse in sandwashed silk

Available Sizes

  • 6
  • 8
  • 10
  • 12
  • 14
  • 16

Relaxed-fit blouse in sandwashed silk

With modern shoulder darts and a notch neckline, this BOSS Womenswear blouse offers tailored styling. Sandwashed silk with a weighty feel. Long sleeves.
£269.00
  • Colour Natural
Regular-fit tailored blouse in stretch silk
Regular-fit tailored blouse in stretch silk

Available Sizes

  • 6
  • 8
  • 10
  • 12
  • 14
  • 16

Regular-fit tailored blouse in stretch silk

A BOSS Womenswear blouse in a regular fit. Made from lightweight, breathable stretch silk for all-day comfort. Perfect for transitioning from day to night.
£239.00
  • Colour Light Green
Stretch-silk blouse with gathered details
Stretch-silk blouse with gathered details

Available Sizes

  • 4
  • 6
  • 8
  • 14
  • 16
  • 18

Stretch-silk blouse with gathered details

Offering natural thermo regulation, this adaptable BOSS Womenswear blouse is made in luxuriously soft silk with added stretch. Concealed closure. Easy straight fit.
£269.00
  • Colour Black
Stretch-silk blouse with gathered details
Stretch-silk blouse with gathered details

Available Sizes

  • 4
  • 6
  • 8
  • 10
  • 12
  • 14
  • 16
  • 18

Stretch-silk blouse with gathered details

Offering natural thermo regulation, this adaptable BOSS Womenswear blouse is made in luxuriously soft silk with added stretch. Concealed closure. Easy straight fit.
£269.00
  • Colour Natural
Stretch-silk blouse with gathered details
Stretch-silk blouse with gathered details

Available Sizes

  • 4
  • 6
  • 8
  • 10
  • 12
  • 14
  • 16
  • 18

Stretch-silk blouse with gathered details

Offering natural thermo regulation, this adaptable BOSS Womenswear blouse is made in luxuriously soft silk with added stretch. Concealed closure. Easy straight fit.
£269.00
  • Colour Brown
Stretch-silk blouse with gathered details
Stretch-silk blouse with gathered details

Available Sizes

  • 4
  • 6
  • 8
  • 10
  • 12
  • 14
  • 16
  • 18

Stretch-silk blouse with gathered details

Offering natural thermo regulation, this adaptable BOSS Womenswear blouse is made in luxuriously soft silk with added stretch. Concealed closure. Easy straight fit.
£269.00
  • Colour Light Blue
Sleeveless blouse in sandwashed silk with V neckline
Sleeveless blouse in sandwashed silk with V neckline

Available Sizes

  • 4
  • 6
  • 8
  • 10
  • 12
  • 14
  • 16

Sleeveless blouse in sandwashed silk with V neckline

Create a variety of looks with the modern V neckline of this straight-fit BOSS Womenswear blouse. Crafted in weighty yet soft sandwashed silk.
£199.00
  • Colour Green
Collarless regular-fit blouse in stretch silk
Collarless regular-fit blouse in stretch silk

Available Sizes

  • 14
  • 16
  • 18

Collarless regular-fit blouse in stretch silk

A feminine blouse crafted in stretch-silk satin by BOSS Womenswear. This collarless piece is cut to a regular fit with gatherings at the neckline.
£269.00
  • Colour light pink
Collarless regular-fit blouse in stretch silk
Collarless regular-fit blouse in stretch silk

Available Sizes

  • 4
  • 6
  • 8
  • 10
  • 12
  • 14
  • 16
  • 18

Collarless regular-fit blouse in stretch silk

A feminine blouse crafted in stretch-silk satin by BOSS Womenswear. This collarless piece is cut to a regular fit with gatherings at the neckline.
£269.00
  • Colour Black
Collarless regular-fit blouse in stretch silk
Collarless regular-fit blouse in stretch silk

Available Sizes

  • 4
  • 6
  • 8
  • 10
  • 12
  • 14
  • 16
  • 18
  • 20
  • 22

Collarless regular-fit blouse in stretch silk

A feminine blouse crafted in stretch-silk satin by BOSS Womenswear. This collarless piece is cut to a regular fit with gatherings at the neckline.
£269.00
  • Colour Natural
Regular-fit blouse in sandwashed silk with tie neck
Regular-fit blouse in sandwashed silk with tie neck

Available Sizes

  • 4
  • 6
  • 8
  • 10
  • 12
  • 14
  • 16

Regular-fit blouse in sandwashed silk with tie neck

Crafted in elevated sandwashed silk, this regular-fit BOSS Womenswear blouse is perfect for work or special occasions. Feminine bow tie collar.
£229.00
  • Colour Natural
Slim-fit T-shirt in cotton-silk blend with embroidered logo
Slim-fit T-shirt in cotton-silk blend with embroidered logo

Available Sizes

  • XS
  • S
  • M
  • L
  • XL

Slim-fit T-shirt in cotton-silk blend with embroidered logo

A slim-fit T-shirt by BOSS Womenswear, crafted from a soft cotton-silk blend for a luxurious feel. Features an embroidered double B logo at the chest.
£89.00
  • Colour Dark Blue
Slim-fit T-shirt in cotton-silk blend with embroidered logo
Slim-fit T-shirt in cotton-silk blend with embroidered logo

Available Sizes

  • XS
  • S
  • M
  • L
  • XL

Slim-fit T-shirt in cotton-silk blend with embroidered logo

A slim-fit T-shirt by BOSS Womenswear, crafted from a soft cotton-silk blend for a luxurious feel. Features an embroidered double B logo at the chest.
£89.00
  • Colour Light Yellow
Sleeveless top in stretch silk
Sleeveless top in stretch silk

Available Sizes

  • 4
  • 6
  • 8
  • 10
  • 12
  • 14
  • 16
  • 18

Sleeveless top in stretch silk

Create a variety of everyday looks with the soft stretch silk and regular fit of this BOSS Womenswear top. Scoop neckline and side slits. For certain materials, like wool, we mix recycled and virgin content so we can provide a high quality product.
£189.00
  • Colour Natural
Sleeveless blouse in sandwashed silk with V neckline
Sleeveless blouse in sandwashed silk with V neckline

Available Sizes

  • 8
  • 10
  • 12

Sleeveless blouse in sandwashed silk with V neckline

Create a variety of looks with the modern V neckline of this straight-fit BOSS Womenswear blouse. Crafted in weighty yet soft sandwashed silk.
£199.00
  • Colour Natural
Regular-fit T-shirt with stretch-silk front

Available Sizes

  • XS
  • XL

Regular-fit T-shirt with stretch-silk front

Easy to style for business or leisure, this regular fit BOSS Womenswear T shirt features a stretch silk front. Sleeves and back in soft touch fabric.
£159.00
  • Colour Natural

Explore more

Festival Outfits Women's Holiday Outfits Rave Outfits Men's Holiday Outfits Party Outfits for Women Relaxed fit overshirts for men Light cotton trousers for men Cotton button down shirt Men's Chains Drawstring cotton trousers Gift Ideas for Boyfriend Casual long sleeve shirts for men Leather Black trainers Ripstop trousers