Men's Date Night Outfits

(162)

For a sophisticated evening, men's date night outfits bring together timeless style and modern flair. From tailored blazers and crisp shirts to dark jeans and sleek shoes, these looks are perfect for making a lasting impression. Complete the look with a stylish watch or leather jacket for added polish, and explore HUGO BOSS pieces that ensure you’re dressed to impress.

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Slim-fit jeans in dark-blue stretch denim
Slim-fit jeans in dark-blue stretch denim

Available Sizes

  • 29/32
  • 30/32
  • 30/34
  • 31/32
  • 31/34
  • 32/34
  • 33/34
  • 34/34

Slim-fit jeans in dark-blue stretch denim

Regular-rise slim-fit jeans by HUGO Menswear. This straight-leg pair comes in dark-blue stretch cotton with a raw-denim look.
£99.00
  • Colour Dark Blue
Baggy-fit jeans in dark-blue denim
Baggy-fit jeans in dark-blue denim

Available Sizes

  • 29/32
  • 31/32
  • 32/32
  • 32/34
  • 33/32
  • 33/34
  • 34/32
  • 34/34
  • 35/32
  • 36/32

Baggy-fit jeans in dark-blue denim

Showcasing a hammer loop and painted trims, these HUGO Menswear jeans pair perfectly with the matching jacket. Dark-blue cotton denim. Baggy, straight fit.
£129.00
  • Colour Dark Blue
Tapered-fit jeans in dark-blue stretch denim
Tapered-fit jeans in dark-blue stretch denim

Available Sizes

  • 29/30
  • 29/32
  • 30/30
  • 30/32
  • 30/34
  • 31/30
  • 31/32
  • 31/34
  • 32/32
  • 32/34
  • 33/32
  • 33/34
  • 34/32
  • 34/34
  • 35/32
  • 36/34

Tapered-fit jeans in dark-blue stretch denim

Complement your everyday casuals with these tapered-fit jeans by HUGO Menswear. Dark-blue stretch denim. Regular-rise waist. Signature trims.
£99.00
  • Colour Dark Blue
Strike silver-tone watch with ridged dial
Strike silver-tone watch with ridged dial

Available Sizes

  • pcs.

Strike silver-tone watch with ridged dial

Combining cool steel with a textured black dial, this bold BOSS Menswear watch is a versatile accessory. H-link bracelet to achieve the perfect fit.
£179.00
  • Colour Silver
Straight-fit jeans in dark-blue stretch denim
Straight-fit jeans in dark-blue stretch denim

Available Sizes

  • 30/32
  • 30/34
  • 31/32
  • 31/34
  • 32/30
  • 32/32
  • 32/34
  • 33/30
  • 33/32
  • 33/34
  • 34/30
  • 34/32
  • 34/34
  • 35/32
  • 35/34
  • 36/30
  • 36/32
  • 36/34
  • 38/30
  • 38/32
  • 38/34

Straight-fit jeans in dark-blue stretch denim

Cut to a casual straight fit, these BOSS Menswear jeans have a versatile dark-blue tone. Stretch denim for comfort and shape recovery. Distinctive trims.
£159.00
  • Colour Dark Blue
Delaware slim-fit jeans in dark-blue denim
Delaware slim-fit jeans in dark-blue denim

Available Sizes

  • 29/34
  • 30/32
  • 30/34
  • 31/32
  • 31/34
  • 32/30
  • 32/32
  • 32/34
  • 33/30
  • 33/32
  • 33/34
  • 33/36
  • 34/30
  • 34/32
  • 34/34
  • 35/32
  • 35/34
  • 36/30
  • 36/32
  • 36/34
  • 38/30
  • 38/32
  • 38/34
  • 40/32
  • 42/34

Delaware slim-fit jeans in dark-blue denim

Regenerative agriculture prioritizes the preservation and restoration of natural environments, aiming to enhance biodiversity, maintain water quality, and improve soil health.
£139.00
  • Colour Dark Blue
Delaware slim-fit jeans in dark-blue denim
Delaware slim-fit jeans in dark-blue denim

Available Sizes

  • 29/32
  • 29/34
  • 30/32
  • 30/34
  • 31/32
  • 31/34
  • 32/30
  • 32/32
  • 32/34
  • 32/36
  • 33/30
  • 33/32
  • 33/34
  • 34/30
  • 34/32
  • 34/34
  • 35/34
  • 35/36
  • 36/30
  • 36/32
  • 36/34
  • 38/30
  • 38/32
  • 38/34
  • 38/36
  • 40/32
  • 40/36
  • 42/34
  • 42/36
  • 44/32
  • 44/34
  • 44/36
  • 46/32
  • 46/34
  • 48/32
  • 48/34

Delaware slim-fit jeans in dark-blue denim

Regenerative agriculture prioritises the preservation and restoration of natural environments, aiming to enhancebiodiversity, maintain water quality, and improve soil health.
£179.00
  • Colour Dark Blue
STRIKE Gold- and silver-tone watch with green grooved dial
STRIKE Gold- and silver-tone watch with green grooved dial

Available Sizes

  • pcs.

STRIKE Gold- and silver-tone watch with green grooved dial

Combining gold and silver tones with a green textured dial, this BOSS Menswear watch offers a luxe everyday look. H-link bracelet for a custom fit.
£199.00
  • Colour Silver
Silver-tone watch with green dial
Silver-tone watch with green dial

Available Sizes

  • pcs.

Silver-tone watch with green dial

With oversized markers on the green, brushed dial, this HUGO Menswear watch adds modern style to any look. Clean case and sleek mesh bracelet.
£179.00
  • Colour Silver
Silver-tone watch with grey dial
Silver-tone watch with grey dial

Available Sizes

  • pcs.

Silver-tone watch with grey dial

With oversized markers and an 'H' sweep tip, this HUGO Menswear watch has a masculine grey dial. Silver-tone steel with modern link bracelet.
£179.00
  • Colour Silver
Style silver-tone watch with green dial
Style silver-tone watch with green dial

Available Sizes

  • pcs.

Style silver-tone watch with green dial

Bauhaus inspired, this stainless-steel HUGO Menswear watch has a slim, comfortable profile. Vertically brushed dial in green for modern contrast. Mesh bracelet.
£149.00
  • Colour Silver
Style silver-tone watch with white dial
Style silver-tone watch with white dial

Available Sizes

  • pcs.

Style silver-tone watch with white dial

Featuring a slimline, compact case, this stainless-steel HUGO Menswear watch is inspired by the Bauhaus movement. Clean white dial with a vertically brushed finish.
£149.00
  • Colour Silver
#GRAIL SPORT Silver-tone watch with blue dial
#GRAIL SPORT Silver-tone watch with blue dial

Available Sizes

  • pcs.

#GRAIL SPORT Silver-tone watch with blue dial

With a silver-tone link bracelet, this HUGO Menswear watch has a blue, multi-eye dial featuring a moulded reflector ring. Branded case side.
£179.00
  • Colour Silver
Style silver-tone watch with blue dial
Style silver-tone watch with blue dial

Available Sizes

  • pcs.

Style silver-tone watch with blue dial

Inspired by minimalist Bauhaus style, this stainless-steel HUGO Menswear watch has a slim, compact case. Blue dial with modern vertical brushing. Mesh bracelet.
£149.00
  • Colour Silver
Square cufflinks with enamel core and logo
Square cufflinks with enamel core and logo

Available Sizes

  • pcs.

Square cufflinks with enamel core and logo

Sleek cufflinks in polished zinc with a square head, a coloured enamel core and an engraved logo by HUGO. Diameter: 1. 2cm
£49.00
  • Colour Black
Round cufflinks with enamel core and logo
Round cufflinks with enamel core and logo

Available Sizes

  • pcs.

Round cufflinks with enamel core and logo

Round minimalist cufflinks in polished zinc with an engraved logo and coloured enamel core by HUGO. Diameter: 1. 2cm
£49.00
  • Colour Silver
Round cufflinks with black-enamel insert
Round cufflinks with black-enamel insert

Available Sizes

  • pcs.

Round cufflinks with black-enamel insert

With subtle engraved branding, these BOSS Menswear cufflinks will complement any dress shirt. Crafted in highly polished brass with a black insert. Measurements: 1. 6 x 1. 6cms.
£79.00
  • Colour Black
Green-dial chronograph watch in silver-tone steel
Green-dial chronograph watch in silver-tone steel

Available Sizes

  • pcs.

Green-dial chronograph watch in silver-tone steel

With an improved comfort fit on the link bracelet, this BOSS Menswear watch is ideal for everyday wear. Green brushed dial with multiple subeyes.
£279.00
  • Colour Silver
GRAND PRIX 44 Silver-tone chronograph watch with blue dial
GRAND PRIX 44 Silver-tone chronograph watch with blue dial

Available Sizes

  • pcs.

GRAND PRIX 44 Silver-tone chronograph watch with blue dial

A sports-luxe essential, this BOSS Menswear watch is inspired by the lines of classic automobiles. Blue sunray-brushed dial with dashboard-style subeyes.
£329.00
  • Colour Silver
Enamel-insert cufflinks with Double B monogram
Enamel-insert cufflinks with Double B monogram

Available Sizes

  • pcs.

Enamel-insert cufflinks with Double B monogram

Freshen up your finishing touches with these polished BOSS Menswear cufflinks. Featuring a new shape with an enamel insert and Double B monogram. Measurements: 1. 8 x 1. 4cms.
£99.00
  • Colour Dark Blue
Leather-strap watch with silver-white dial
Leather-strap watch with silver-white dial

Available Sizes

  • pcs.

Leather-strap watch with silver-white dial

With Roman numerals on a silver-white dial, this BOSS Menswear watch has a curved case for modern elegance. Timeless brown alligator-embossed leather strap.
£199.00
  • Colour Brown
Silver-tone watch with textured skeleton dial
Silver-tone watch with textured skeleton dial

Available Sizes

  • pcs.

Silver-tone watch with textured skeleton dial

Daring and modern, this rectangular BOSS Menswear watch is set with a double-layered, textured dial with striking skeleton elements. Strap in rich brown leather.
£199.00
  • Colour Brown
Relaxed-fit jeans in dark-blue denim
Relaxed-fit jeans in dark-blue denim

Available Sizes

  • 31/32
  • 32/32
  • 32/34
  • 33/32
  • 33/34
  • 34/32
  • 34/34
  • 36/32

Relaxed-fit jeans in dark-blue denim

With a relaxed, tapered fit, these HUGO Menswear jeans are a casual essential. Crafted in cotton denim with a dark-blue, raw effect.
£159.00
  • Colour Dark Blue
Maine regular-fit jeans in dark-blue extra-soft denim
Maine regular-fit jeans in dark-blue extra-soft denim

Available Sizes

  • 30/32
  • 31/32
  • 33/30
  • 33/32
  • 33/34
  • 34/30
  • 34/34
  • 35/32
  • 35/34
  • 36/32
  • 38/30
  • 38/32

Maine regular-fit jeans in dark-blue extra-soft denim

With their dark blue tone and extra soft denim, these BOSS Menswear jeans will quickly become your favourite pair. Regular fit with tapered leg.
£179.00
  • Colour Dark Blue
Regular-fit jeans in dark-blue denim
Regular-fit jeans in dark-blue denim

Available Sizes

  • 30/32
  • 31/32
  • 32/32
  • 32/34
  • 33/32
  • 33/34
  • 34/32
  • 34/34
  • 35/32
  • 36/32
  • 36/34
  • 38/32

Regular-fit jeans in dark-blue denim

In authentic dark blue with five-pocket styling, these HUGO Menswear jeans are an easy casual foundation. Straight fit. Stretch denim with distressing.
£129.00
  • Colour Dark Blue
Maine regular-fit jeans in dark-blue stretch denim
Maine regular-fit jeans in dark-blue stretch denim

Available Sizes

  • 30/32
  • 31/32
  • 32/30
  • 32/32
  • 32/34
  • 33/30
  • 33/32
  • 34/30
  • 34/32
  • 34/34
  • 36/30
  • 36/32
  • 36/34
  • 38/30
  • 38/32
  • 38/34
  • 40/32

Maine regular-fit jeans in dark-blue stretch denim

Featuring a regular fit with a tapered leg, these BOSS Menswear jeans are a casual classic. Comfort-stretch denim with a rich dark-blue tone.
£99.00
  • Colour Dark Blue
Regular-fit jeans in dark-blue denim
Regular-fit jeans in dark-blue denim

Available Sizes

  • 29/32
  • 30/30
  • 30/32
  • 30/34
  • 31/32
  • 31/34
  • 32/30
  • 32/32
  • 32/34
  • 33/32
  • 33/34
  • 34/30
  • 34/32
  • 34/34
  • 35/32
  • 35/34
  • 36/32
  • 36/34
  • 38/32
  • 38/34

Regular-fit jeans in dark-blue denim

Straight-leg jeans with a regular rise by HUGO Menswear. This timeless pair is crafted in weighty raw denim with a dark-blue hue.
£99.00
  • Colour Dark Blue
Tapered-fit jeans in dark-blue stretch denim
Tapered-fit jeans in dark-blue stretch denim

Available Sizes

  • 29/32
  • 30/32
  • 30/34
  • 31/32
  • 31/34
  • 32/30
  • 32/32
  • 32/34
  • 33/32
  • 33/34
  • 34/32
  • 34/34
  • 35/32
  • 35/34
  • 36/32
  • 36/34
  • 38/32
  • 38/34

Tapered-fit jeans in dark-blue stretch denim

Signature-trim jeans cut to a tapered fit with a regular rise by HUGO. This pair has an authentic dark-blue tone. This product’s raw material is derived from regenerative agriculture: an approach focused on preservation and restoration that aims to increase biodiversity, preserve water quality and improve soil health while absorbing CO2. Regenerative agriculture also promotes animal welfare and fair working conditions for farmers.
£99.00
  • Colour Dark Blue
Slim-fit jeans in dark-blue comfort-stretch denim
Slim-fit jeans in dark-blue comfort-stretch denim

Available Sizes

  • 29/32
  • 30/32
  • 31/32
  • 31/34
  • 32/32
  • 32/34
  • 33/32
  • 33/34
  • 34/32
  • 34/34
  • 36/32
  • 36/34

Slim-fit jeans in dark-blue comfort-stretch denim

Featuring lived-in effects on dark-blue comfort-stretch denim, these HUGO Menswear jeans are so easy to style. Defined fit with a straight leg.
£139.00
  • Colour Dark Blue
Tapered-fit jeans in dark-blue comfort-stretch denim
Tapered-fit jeans in dark-blue comfort-stretch denim

Available Sizes

  • 29/34
  • 30/32
  • 30/34
  • 31/32
  • 31/34
  • 32/30
  • 32/32
  • 32/34
  • 33/30
  • 33/32
  • 33/34
  • 33/36
  • 34/30
  • 34/32
  • 34/34
  • 34/36
  • 36/34
  • 38/32
  • 38/34
  • 38/36

Tapered-fit jeans in dark-blue comfort-stretch denim

Regenerative agriculture prioritises the preservation and restoration of natural environments, aiming to enhancebiodiversity, maintain water quality, and improve soil health.
£119.00
  • Colour Dark Blue
Maine regular-fit jeans in dark-blue denim
Maine regular-fit jeans in dark-blue denim

Available Sizes

  • 29/34
  • 30/32
  • 30/34
  • 31/32
  • 31/34
  • 32/30
  • 32/32
  • 32/36
  • 33/30
  • 33/32
  • 33/34
  • 33/36
  • 34/30
  • 34/32
  • 34/34
  • 34/36
  • 35/32
  • 35/34
  • 36/30
  • 36/32
  • 36/34
  • 38/30
  • 38/32
  • 38/34
  • 38/36
  • 40/32
  • 40/34

Maine regular-fit jeans in dark-blue denim

With an extra soft feel, these BOSS Menswear jeans have a dark blue tone that's easy to style. Stretch denim.
£179.00
  • Colour Dark Blue
Delaware slim-fit jeans in dark-blue soft-motion denim
Delaware slim-fit jeans in dark-blue soft-motion denim

Available Sizes

  • 30/32
  • 30/34
  • 31/32
  • 31/34
  • 32/30
  • 32/32
  • 32/34
  • 33/30
  • 33/32
  • 33/34
  • 34/30
  • 34/32
  • 34/34
  • 35/32
  • 35/34
  • 36/32
  • 36/34
  • 38/32
  • 38/34

Delaware slim-fit jeans in dark-blue soft-motion denim

In blue denim with generous stretch and a soft slub effect, these BOSS Menswear jeans are an everyday essential. Cut to a slim fit.
£129.00
  • Colour Dark Blue
Grey-plated watch with leather strap
Grey-plated watch with leather strap

Available Sizes

  • pcs.

Grey-plated watch with leather strap

A contemporary three-hand watch by BOSS. Crafted in stainless steel with a grey-plated finish, this elegant watch is set with a two-layered dial in a silver-white tone with stamped-down numbers and a date window. This timepiece secures with a leather strap in grey for tonal appeal.
£219.00
  • Colour Silver
Telly stainless-steel watch with retro-inspired case
Telly stainless-steel watch with retro-inspired case

Available Sizes

  • pcs.

Telly stainless-steel watch with retro-inspired case

With its distinctive retro-inspired case shape, this HUGO Menswear watch is refreshingly unexpected. Minimalist silver-white dial. Seamless, fully integrated bracelet.
£139.00
  • Colour Silver
Telly two-tone watch with retro-inspired case
Telly two-tone watch with retro-inspired case

Available Sizes

  • pcs.

Telly two-tone watch with retro-inspired case

Crafted in steel with gold and silver finishes, this HUGO Menswear watch showcases an unexpected, retro-inspired design. Seamless, fully integrated bracelet.
£179.00
  • Colour Silver
Slim-fit jeans in dark-blue comfort-stretch denim
Slim-fit jeans in dark-blue comfort-stretch denim

Available Sizes

  • 30/32
  • 31/32
  • 31/34
  • 32/32
  • 32/34
  • 33/32
  • 34/32
  • 34/34
  • 36/32
  • 36/34

Slim-fit jeans in dark-blue comfort-stretch denim

Regenerative agriculture prioritises the preservation and restoration of natural environments, aiming to enhancebiodiversity, maintain water quality, and improve soil health.
£99.00
  • Colour Blue
Two-tone chronograph watch with green dial
Two-tone chronograph watch with green dial

Available Sizes

  • pcs.

Two-tone chronograph watch with green dial

A multifunctional design inspired by the spirit of aviation, this BOSS Menswear watch combines silver, green and gold tones for modern elegance. Bold reflector ring.
£279.00
  • Colour Silver
Stainless-steel chronograph watch with transparent dial
Stainless-steel chronograph watch with transparent dial

Available Sizes

  • pcs.

Stainless-steel chronograph watch with transparent dial

In silver and black tones, this architectural BOSS Menswear watch brings contemporary elegance to everyday looks. A transparent dial reveals the movement beneath.
£329.00
  • Colour Silver
Blue-dial watch with stainless-steel link bracelet
Blue-dial watch with stainless-steel link bracelet

Available Sizes

  • pcs.

Blue-dial watch with stainless-steel link bracelet

A sleek watch by BOSS, designed with a link bracelet and featuring stepped-down sub-eyes and faceted indexes on the blue brushed dial.
£199.00
  • Colour Silver
Stainless-steel link-bracelet watch with black dial
Stainless-steel link-bracelet watch with black dial

Available Sizes

  • pcs.

Stainless-steel link-bracelet watch with black dial

In stainless steel with a link bracelet, this multifunctional HUGO Menswear watch has a clean, everyday design. Brushed black dial with modern logo plate.
£169.00
  • Colour Silver

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