Men's Date Night Outfits

(248)

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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Blue-dial watch with link bracelet
Blue-dial watch with link bracelet

Available Sizes

  • pcs.

Blue-dial watch with link bracelet

Featuring a diving-inspired bezel with a silicone inlay, this HUGO Menswear watch offers multifunctional style. Silver-tone steel with blue dial. Distinctive subeyes.
£199.00
  • Colour Silver
Stratus chronograph watch with seven-link bracelet
Stratus chronograph watch with seven-link bracelet

Available Sizes

  • pcs.

Stratus chronograph watch with seven-link bracelet

With a sporty, vintage-inspired case shape, this BOSS Menswear watch has a black, multi-functional dial for maximum performance. Sophisticated seven-link bracelet.
£249.00
  • Colour Silver
PRINCIPLE MASTER Grey-textured-dial watch with multi-link bracelet
PRINCIPLE MASTER Grey-textured-dial watch with multi-link bracelet

Available Sizes

  • pcs.

PRINCIPLE MASTER Grey-textured-dial watch with multi-link bracelet

Elevated by a multi-level, textured dial in grey, this BOSS Menswear watch goes perfectly with tailoring. Silver-tone steel. Multifunctional movement with subdials.
£249.00
  • 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.
£199.00
  • 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
Principle Dress black-dial watch with H-link bracelet
Principle Dress black-dial watch with H-link bracelet

Available Sizes

  • pcs.

Principle Dress black-dial watch with H-link bracelet

Featuring a delicate dial pattern inside a modern, curved case, this stainless-steel BOSS Menswear watch showcases sophisticated elegance. Integrated H-link bracelet. Polished Roman numerals.
£229.00
  • Colour Silver
Stratus green-dial chronograph watch with link bracelet
Stratus green-dial chronograph watch with link bracelet

Available Sizes

  • pcs.

Stratus green-dial chronograph watch with link bracelet

With a vintage-inspired design, this stainless-steel BOSS Menswear watch is set with a green, multi-functional dial. Distinctive seven-link bracelet.
£249.00
  • Colour Silver
Lit black-dial watch with link bracelet
Lit black-dial watch with link bracelet

Available Sizes

  • pcs.

Lit black-dial watch with link bracelet

Contemporary and minimalist, this HUGO Menswear watch combines subtle angles with an integrated link bracelet. Silver-tone steel with a modern black dial.
£139.00
  • Colour Silver
Strike Black-dial chronograph watch with H-link bracelet
Strike Black-dial chronograph watch with H-link bracelet

Available Sizes

  • pcs.

Strike Black-dial chronograph watch with H-link bracelet

With its black, groove-textured dial, this BOSS Menswear chronograph watch strikes a refined look. Sporty H-link bracelet in stainless steel for a perfect fit.
£279.00
  • Colour Silver
PRINCIPLE Link-bracelet watch with blue textured skeleton dial
PRINCIPLE Link-bracelet watch with blue textured skeleton dial

Available Sizes

  • pcs.

PRINCIPLE Link-bracelet watch with blue textured skeleton dial

Featuring stepped sides on the rectangular case, this steel BOSS Menswear watch creates a powerful presence with its blue, double-layered skeleton dial. Link bracelet.
£229.00
  • Colour Silver
TOURMASTER Blue-dial watch with multi-link bracelet
TOURMASTER Blue-dial watch with multi-link bracelet

Available Sizes

  • pcs.

TOURMASTER Blue-dial watch with multi-link bracelet

Combining a sporty tachymeter with elegant, racing-inspired design details, this BOSS Menswear watch is an instant classic. Blue, multi-level dial inside domed glass.
£279.00
  • Colour Silver
Silver-tone curb-chain necklace with logo link

Available Sizes

  • pcs.

Silver-tone curb-chain necklace with logo link

Crafted in silver-tone steel with a chunky chain, this BOSS Jewelry necklace adds impact to any look. Logo-lettering link detail.
£149.00
  • Colour Silver
Gold-tone curb-chain necklace with logo link

Available Sizes

  • pcs.

Gold-tone curb-chain necklace with logo link

With its logo-lettering link detail, this BOSS Jewelry necklace adds distinctive BOSS DNA to everyday looks. Crafted in gold-tone steel with a curb chain.
£169.00
  • Colour Gold
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.
£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
Silver-tone chronograph watch with blue dial
Silver-tone chronograph watch with blue dial

Available Sizes

  • pcs.

Silver-tone chronograph watch with blue dial

With an improved fit on the bracelet, this BOSS Menswear watch is the ideal everyday choice. Silver-tone steel offset by a blue, multifunctional dial.
£299.00
  • 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
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.
£229.00
  • Colour Silver
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
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
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.
£299.00
  • Colour Silver
Relaxed-fit jeans in dark-blue Japanese denim
Relaxed-fit jeans in dark-blue Japanese denim

Available Sizes

  • 33/34

Relaxed-fit jeans in dark-blue Japanese denim

In a relaxed fit that tapers through the leg, these HUGO Menswear jeans cut a modern profile. Weighty Japanese denim with a clean blue tone.
£159.00
  • Colour Dark Blue
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
  • 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
Extra-slim-fit jeans in dark-blue stretch denim

Available Sizes

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

Extra-slim-fit jeans in dark-blue stretch denim

Our organic standards do not allow the use of synthetic fertiliser, pesticides or genetically modified seeds.
£129.00
  • Colour Dark Blue
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
  • 35/36
  • 36/30
  • 36/32
  • 36/34
  • 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
  • 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
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
THREEHAND Grey-plated watch with leather strap
THREEHAND Grey-plated watch with leather strap

Available Sizes

  • pcs.

THREEHAND 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
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
SKYTRAVELLER Two-tone chronograph watch with green dial
SKYTRAVELLER Two-tone chronograph watch with green dial

Available Sizes

  • pcs.

SKYTRAVELLER 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 automatic watch with green dial
Stainless-steel automatic watch with green dial

Available Sizes

  • pcs.

Stainless-steel automatic watch with green dial

Engineered with a Japanese automatic movement that's partially exposed front and back, this BOSS Menswear watch is ready for adventure. Link bracelet. 100m water resistance.
£349.00
  • Colour Silver
Black-dial watch and leather card holder gift set

Available Sizes

  • pcs.

Black-dial watch and leather card holder gift set

With a stainless-steel watch and textured-leather card holder, this two-piece BOSS Menswear set makes a refined gift. Presented in a branded box.
£229.00
  • Colour Silver

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