Men's Date Night Outfits

(235)

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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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
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
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
Langford two-tone watch with five-link bracelet
Langford two-tone watch with five-link bracelet

Available Sizes

  • pcs.

Langford two-tone watch with five-link bracelet

An elevated dress watch by BOSS Menswear, featuring a two-tone case and five-link bracelet. The curved sunray dial includes a practical date window.
£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
Grand Prix stainless-steel watch with silver-white dial
Grand Prix stainless-steel watch with silver-white dial

Available Sizes

  • pcs.

Grand Prix stainless-steel watch with silver-white dial

With contrasting subeyes on a silver-white dial and luminescent-filled hands, this BOSS Menswear chronograph watch delivers high-octane style. Crafted in stainless steel.
£329.00
  • Colour Silver
Silver-tone watch
Silver-tone watch

Available Sizes

  • pcs.

Silver-tone watch

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
Sky Traveller silver-tone watch
Sky Traveller silver-tone watch

Available Sizes

  • pcs.

Sky Traveller silver-tone watch

Combining cool silver and blue tones, this BOSS Menswear watch delivers a modern pilot-inspired look. Sunray-brushed dial with shaped indexes and two subeyes.
£279.00
  • 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 watch
Silver-tone watch

Available Sizes

  • pcs.

Silver-tone watch

Crafted in silver-tone steel with a black textured dial, this BOSS Menswear watch embraces a classic look. Vertical subdials. Elegant multi-link bracelet.
£229.00
  • 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
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
Skytraveller multi-tone watch
Skytraveller multi-tone watch

Available Sizes

  • pcs.

Skytraveller multi-tone watch

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
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
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
Relaxed-fit jeans in dark-blue Japanese denim

Available Sizes

  • 36/32

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

Available Sizes

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

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
Principle Ark watch with black textured dial
Principle Ark watch with black textured dial

Available Sizes

  • pcs.

Principle Ark watch with black textured dial

A timeless watch by BOSS Menswear crafted in stainless steel. It features a distinctive case shape and a black textured dial with elegant Roman numerals.
£229.00
  • Colour Silver
Hero 2.0 steel watch
Hero 2.0 steel watch

Available Sizes

  • pcs.

Hero 2.0 steel watch

With its tachymeter bezel and chronograph movement, this BOSS Menswear watch delivers racing-inspired style. Cool steel elevated by a black, two-layered dial.
£349.00
  • Colour Silver
Hero 2.0 steel watch
Hero 2.0 steel watch

Available Sizes

  • pcs.

Hero 2.0 steel watch

This BOSS Menswear chronograph watch offers a modern, racing-inspired look with its tachymeter bezel and layered dial. Cool steel with green sunray-brushed dial.
£349.00
  • Colour Silver
Blue-dial watch with mesh bracelet
Blue-dial watch with mesh bracelet

Available Sizes

  • pcs.

Blue-dial watch with mesh bracelet

In silver-tone steel offset by a blue, textured dial featuring different levels, this BOSS Menswear watch exudes effortless elegance. Vertical subeyes.
£229.00
  • Colour Silver
Cheswick stainless-steel watch
Cheswick stainless-steel watch

Available Sizes

  • pcs.

Cheswick stainless-steel watch

Featuring a grey, sunray-brushed dial inside a slimline case, this stainless-steel BOSS Menswear watch has a distinctive fluted bezel. Elegant domed-link bracelet.
£229.00
  • Colour Silver
Cheswick two-tone watch with fluted bezel
Cheswick two-tone watch with fluted bezel

Available Sizes

  • pcs.

Cheswick two-tone watch with fluted bezel

Featuring gold and silver tones with a blue, sunray-brushed dial, this BOSS Menswear watch makes a refined impression. Elegant fluted bezel. Domed-link bracelet.
£249.00
  • Colour Silver
Stratus chronograph watch in two-tone steel
Stratus chronograph watch in two-tone steel

Available Sizes

  • pcs.

Stratus chronograph watch in two-tone steel

With an intricate link bracelet and blue, multi-functional dial, this BOSS Menswear watch delivers vintage-inspired sophistication. Stainless steel in gold and silver tones.
£279.00
  • Colour Silver
Grand Prix Vitesse blue-dial watch with integrated bracelet
Grand Prix Vitesse blue-dial watch with integrated bracelet

Available Sizes

  • pcs.

Grand Prix Vitesse blue-dial watch with integrated bracelet

Prominent subeyes and a black tachymeter bezel sharpen the racing aesthetic of this chronograph watch by BOSS Menswear. Blue sunray dial. Integrated bracelet.
£329.00
  • Colour Silver
Skytraveller Pro black-dial watch with sapphire crystal
Skytraveller Pro black-dial watch with sapphire crystal

Available Sizes

  • pcs.

Skytraveller Pro black-dial watch with sapphire crystal

A pilot-style chronograph watch by BOSS Menswear, featuring a scratch-resistant sapphire crystal and black dial. Distinctive bezel with grip detail. Elegant link bracelet.
£329.00
  • Colour Silver
Principle Ark two-tone watch with blue textured dial
Principle Ark two-tone watch with blue textured dial

Available Sizes

  • pcs.

Principle Ark two-tone watch with blue textured dial

This BOSS Menswear watch makes a sophisticated statement. Featuring a distinctively shaped, gold-tone case offset by a blue textured dial. Elegant two-tone bracelet.
£249.00
  • Colour Silver
#Style 3H green-dial watch with mesh bracelet
#Style 3H green-dial watch with mesh bracelet

Available Sizes

  • pcs.

#Style 3H green-dial watch with mesh bracelet

This modern dress watch by HUGO Menswear features a slim case and a minimalist, vertically brushed dial in green. Adjustable mesh bracelet.
£119.00
  • Colour Silver
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
  • 32/30
  • 33/30
  • 34/30
  • 34/34
  • 35/32
  • 35/34
  • 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
GRAND PRIX 40 Black-dial watch with steel bracelet
GRAND PRIX 40 Black-dial watch with steel bracelet

Available Sizes

  • pcs.

GRAND PRIX 40 Black-dial watch with steel bracelet

Add a sports-luxe touch to your look with this racing-inspired BOSS Menswear watch. Minimalist black dial with multiple subeyes. Integrated link bracelet.
£329.00
  • Colour Silver

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