Women's Preppy Outfits

(56)

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
Season
Open Section
Heel
Open Section
-27%
Half-pleated mini skirt in blue rigid denim
Half-pleated mini skirt in blue rigid denim

Available Sizes

  • XS
  • S
  • M
  • L
  • XL

Half-pleated mini skirt in blue rigid denim

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 £65.00
  • Colour Blue
-27%
Pleated mini skirt in checked cotton twill
Pleated mini skirt in checked cotton twill

Available Sizes

  • 8
  • 10
  • 12
  • 14

Pleated mini skirt in checked cotton twill

Create modern looks with the fresh check of this HUGO Womenswear pleated mini skirt. Straight fit in soft cotton. Chunky side zip. Happy HUGO logo.
£89.00 £65.00
  • Colour Light Blue
-51%
Pleat-front cargo skirt in cotton twill
Pleat-front cargo skirt in cotton twill

Available Sizes

  • 4
  • 6
  • 8
  • 12
  • 16

Pleat-front cargo skirt in cotton twill

A contemporary skirt with open front pleats by HUGO Womenswear. Crafted in soft twill, this piece features cargo pockets for utilitarian edge. This product is made with organic cotton. Our organic standards do not allow the use of synthetic fertilisers, pesticides or genetically modified seeds.
£79.00 £39.00
  • Colour Beige
-50%
Mini skirt in pinstripe flannel
Mini skirt in pinstripe flannel

Available Sizes

  • 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.
£169.00 £85.00
  • Colour Beige
-28%
Pleated mini skirt in melange stretch flannel
Pleated mini skirt in melange stretch flannel

Available Sizes

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

Pleated mini skirt in melange stretch flannel

Ideal teamed with the matching blazer, this straight-fit HUGO Womenswear skirt is cut in pleated melange flannel with stretch. Side zip with logo puller.
£179.00 £129.00
  • Colour Light Grey
-32%
Equestrian cropped sweater in wool and cashmere
Equestrian cropped sweater in wool and cashmere

Available Sizes

  • XS
  • S
  • M
  • 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 £149.00
  • Colour Brown
Equestrian cardigan with knitted pattern
Equestrian cardigan with knitted pattern

Available Sizes

  • XS
  • S
  • M
  • L
  • XL

Equestrian cardigan with knitted pattern

With large buttons and a statement pattern inspired by Norwegian styles, this regular-fit BOSS Womenswear cardigan will be your favourite way to layer this season. Blended with soft, breathable cotton.
£159.00
  • Colour White
Regular-fit blouse in stretch-silk satin
Regular-fit blouse in stretch-silk satin

Available Sizes

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

Regular-fit blouse in stretch-silk satin

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.
£239.00
  • Colour White
-29%
Relaxed-fit cardigan in furry yarn
Relaxed-fit cardigan in furry yarn

Available Sizes

  • XS
  • M
  • L
  • XL

Relaxed-fit cardigan in furry yarn

Layer this buttoned HUGO Womenswear cardigan over any look for a touch of cosy luxury. Furry yarn. Relaxed fit. Swirled logo embroidery.
£139.00 £99.00
  • Colour White
-30%
Long-sleeved blouse in silk organza
Long-sleeved blouse in silk organza

Available Sizes

  • 6
  • 10
  • 12
  • 14
  • 16

Long-sleeved blouse in silk organza

Topped with a point collar, this BOSS Womenswear blouse puts a fresh twist on a tailored favourite. Crafted in finest silk organza. Double B monogram.
£269.00 £189.00
  • Colour Light Grey
-31%
Regular-fit blouse in stretch silk
Regular-fit blouse in stretch silk

Available Sizes

  • 4
  • 6
  • 8
  • 10
  • 12

Regular-fit blouse in stretch silk

Cut to a straight fit with a collar detail, this BOSS Womenswear blouse is crafted in drapey satin made from stretch silk. Modern wrap front.
£229.00 £159.00
  • Colour White
-30%
Crew-neck cardigan in merino wool with stacked logo
Crew-neck cardigan in merino wool with stacked logo

Available Sizes

  • XS
  • S
  • M
  • L
  • XL

Crew-neck cardigan in merino wool with stacked logo

Layer this versatile HUGO Womenswear cardigan over everyday looks for comfort and style. Temperature regulating merino wool. For us, responsibly sourced means mulesing free, and meeting the standards of the Five Freedoms of animal welfare.
£169.00 £119.00
  • Colour White
-31%
Relaxed-fit blouse in sand-washed silk
Relaxed-fit blouse in sand-washed silk

Available Sizes

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

Relaxed-fit blouse in sand-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.
£289.00 £199.00
  • Colour Natural
V-neck top with knitted structure
V-neck top with knitted structure

Available Sizes

  • XS
  • S
  • M
  • L
  • XL
  • XXL

V-neck top with knitted structure

Knitted with stretch in a flattering fit, this BOSS Womenswear top has a creative structure to add texture to your look. Subtle V neckline. This product is made with cellulose fibres, derived from natural raw wood material and sourced from responsibly managed forests. We cooperate with external organisations to ensure respectful treatment of virgin and endangered forests.
£179.00
  • Colour Natural
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
-32%
V-neck knitted sweater with degradé effect
V-neck knitted sweater with degradé effect

Available Sizes

  • XS
  • S
  • M
  • L
  • XL

V-neck knitted sweater with degradé effect

With a modern degradé effect, this BOSS Womenswear sweater has an intricate open knit to refresh your layers. Blended with wool and alpaca. V neckline.
£189.00 £129.00
  • Colour Red
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 Light Beige
Relaxed-fit cardigan in cashmere with ribbed trims
Relaxed-fit cardigan in cashmere with ribbed trims

Available Sizes

  • XS
  • S
  • M
  • L
  • XL
  • XXL

Relaxed-fit cardigan in cashmere with ribbed trims

Layer with luxury in the cashmere knit of this BOSS Womenswear cardigan. Cut to a laid-back fit with cashmere-blend ribbed trims. Buttoned closure.
£379.00
  • Colour White
-40%
Sleeveless knitted top with cut-out details
Sleeveless knitted top with cut-out details

Available Sizes

  • M
  • L
  • XL

Sleeveless knitted top with cut-out details

A V-neck top by BOSS Womenswear, knitted in stretch fabric featuring a ribbed structure and cut-out details. This product is made with cellulose fibres, derived from natural raw wood material and sourced from responsibly managed forests. We cooperate with external organisations to ensure respectful treatment of virgin and endangered forests.
£159.00 £95.00
  • Colour Natural
-50%
Short-sleeved knit polo in wool-blend

Available Sizes

  • XS
  • S
  • M
  • L

Short-sleeved knit polo in wool-blend

A short-sleeved sweater by BOSS, crafted in temperature-regulating and moisture-wicking fabric. This versatile top features a polo collar and button placket. This product is made with responsibly sourced wool. For us, responsibly sourced means mulesing free, and meeting the standards of the Five Freedoms of animal welfare.
£179.00 £89.00
  • Colour Light Grey
Regular-fit tuxedo-inspired blouse with pintuck pleats
Regular-fit tuxedo-inspired blouse with pintuck pleats

Available Sizes

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

Regular-fit tuxedo-inspired blouse with pintuck pleats

Whether worn with denim or tailoring, this regular fit BOSS Womenswear blouse adds effortless elegance with tuxedo styling. Semi sheer fabric featuring silk and wool.
£199.00
  • Colour Black
-50%
Platform trainers in patent faux leather
Platform trainers in patent faux leather

Available Sizes

  • 3
  • 4
  • 5
  • 6
  • 7
  • 8

Platform trainers in patent faux leather

Ideal with any outfit, these HUGO Womenswear trainers are made in glossy synthetic coated fabric. Tonal patched heel logo. Modern pumped-up outsole. 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.
£169.00 £85.00
  • Colour White
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
-29%
Mixed-material lace-up trainers with counter logo
Mixed-material lace-up trainers with counter logo

Available Sizes

  • 3
  • 4
  • 5
  • 6
  • 7
  • 8

Mixed-material lace-up trainers with counter logo

Contemporary trainers with tonal laces and contrast branding by HUGO Womenswear. This sporty pair is crafted in a combination of materials.
£139.00 £99.00
  • Colour White
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

Featuring suede trims and stacked logo details, these HUGO Womenswear trainers will go with any outfit. Comfort boosting insole. The leather used to make this product has been sourced from certified tanneries.
£159.00
  • Colour White
-30%
Lace-up trainers in leather with logo details
Lace-up trainers in leather with logo details

Available Sizes

  • 2
  • 3
  • 4
  • 8
  • 9

Lace-up trainers in leather with logo details

Low-top trainers with a lace-up closure by BOSS, shaped in nappa leather featuring logo details on the side and backtab.
£199.00 £139.00
  • Colour White
Leather trainers with inner wedge
Leather trainers with inner wedge

Available Sizes

  • 3
  • 4
  • 5
  • 6
  • 8
  • 9

Leather trainers with inner wedge

Give your look a little boost with the lightweight outsole and hidden wedge of these Italian crafted BOSS Womenswear trainers. Smooth leather uppers. A minimum of 60% of the leather used to make this product has been sourced from certified tanneries.
£429.00
  • Colour White
-29%
Leather lace-up trainers with suede trims
Leather lace-up trainers with suede trims

Available Sizes

  • 3
  • 4
  • 5
  • 6

Leather lace-up trainers with suede trims

Modern leather trainers with a low profile by BOSS. Designed with suede trims these shoes feature brand detailing.
£209.00 £149.00
  • Colour White
Collarless regular-fit blouse in stretch silk
Collarless regular-fit blouse in stretch silk

Available Sizes

  • 4
  • 6
  • 8
  • 10
  • 12

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 Dark Purple
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
-31%
Regular-fit blouse in stretch silk
Regular-fit blouse in stretch silk

Available Sizes

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

Regular-fit blouse in stretch silk

Cut to a straight fit with a collar detail, this BOSS Womenswear blouse is crafted in drapey satin made from stretch silk. Modern wrap front.
£229.00 £159.00
  • Colour light pink
-29%
Ruched-neck blouse in stretch-silk crepe de Chine
Ruched-neck blouse in stretch-silk crepe de Chine

Available Sizes

  • 4
  • 6
  • 8
  • 10
  • 16
  • 18

Ruched-neck blouse in stretch-silk crepe de Chine

An opaque blouse in luxurious stretch-silk crepe de Chine by BOSS Womenswear, with a ruched neckline, concealed closure and rear logo trim.
£239.00 £169.00
  • Colour Black
-29%
Ruched-neck blouse in stretch-silk crepe de Chine
Ruched-neck blouse in stretch-silk crepe de Chine

Available Sizes

  • 16
  • 18
  • 20

Ruched-neck blouse in stretch-silk crepe de Chine

An opaque blouse in luxurious stretch-silk crepe de Chine by BOSS Womenswear, with a ruched neckline, concealed closure and rear logo trim.
£239.00 £169.00
  • Colour White
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
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 Dark Red
-41%
Colour-blocked trainers with logo details
Colour-blocked trainers with logo details

Available Sizes

  • 3
  • 4
  • 5
  • 6
  • 7
  • 8

Colour-blocked trainers with logo details

Blocked in two tones and finishes for a modern look, these HUGO Womenswear trainers are so easy to style. Perforated toe and logo details.
£169.00 £99.00
  • Colour Black
-31%
Knitted vest top with layered design
Knitted vest top with layered design

Available Sizes

  • XS
  • S
  • M
  • L
  • XL
  • XXL

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.
£129.00 £89.00
  • Colour Black
-38%
Knitted top in stretch fabric with mixed structures
Knitted top in stretch fabric with mixed structures

Available Sizes

  • M
  • L

Knitted top in stretch fabric with mixed structures

With its mixed structures and soft yarns, this BOSS Womenswear top is a chic option. Add the cardigan and trousers for a modern co-ord. This product contains at least 60% better raw materials. This product is partially made from recycled cellulose based fibres.
£89.00 £55.00
  • Colour Natural
-31%
Leather loafers with rhinestones and satin
Leather loafers with rhinestones and satin

Available Sizes

  • 3
  • 4
  • 5
  • 6
  • 9

Leather loafers with rhinestones and satin

Combining sparkling rhinestones with soft satin, these BOSS Womenswear penny loafers make a chic statement. Smooth leather trims. Made in Portugal.
£229.00 £159.00
  • Colour Black

Recommendations

Women's White Trainers Festival Outfits Women's Black Dresses Rave Outfits Women's Long Coats Light Chinos Black Swim Shorts Suede Loafers Relaxed-fit Cotton Polo Shirts Men's Navy Blazers