Men's Date Night Outfits

(150)

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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-38%
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 £49.00
  • Colour Black
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
-29%
TROPER AUTOMATIC Stainless-steel watch with Japanese automatic movement
TROPER AUTOMATIC Stainless-steel watch with Japanese automatic movement

Available Sizes

  • pcs.

TROPER AUTOMATIC Stainless-steel watch with Japanese automatic movement

Featuring a partially visible automatic movement front and back, this BOSS Menswear watch adds performance style to any look. Integrated link bracelet. 100m water resistance.
£279.00 £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
-41%
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 £129.00
  • Colour Silver
Silver-tone watch with black grooved dial
Silver-tone watch with black grooved dial

Available Sizes

  • pcs.

Silver-tone watch with black grooved 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
Strike stainless-steel watch with ridged dial
Strike stainless-steel watch with ridged dial

Available Sizes

  • pcs.

Strike stainless-steel watch with ridged dial

With cool steel and a distinctive textured dial, this BOSS Menswear watch adds understated luxury touch to any look. H-link bracelet for custom fitting.
£179.00
  • 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.
£279.00
  • Colour Silver
-41%
Link-bracelet digital watch with black dial
Link-bracelet digital watch with black dial

Available Sizes

  • pcs.

Link-bracelet digital watch with black dial

A directional digital watch by HUGO. Featuring a black dial and distinctive case shape, this modern accessory secures with a stainless-steel link bracelet.
£169.00 £99.00
  • 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
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
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.
£199.00
  • Colour Silver
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
-29%
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.
£279.00 £199.00
  • 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
GRAND PRIX 44 Green-dial watch with steel bracelet
GRAND PRIX 44 Green-dial watch with steel bracelet

Available Sizes

  • pcs.

GRAND PRIX 44 Green-dial watch with steel bracelet

Crafted in silver-tone steel offset by a brushed green dial, this BOSS Menswear watch embraces a luxe, racing-inspired look. Integrated five-link bracelet.
£329.00
  • 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
TROPER SPORT Green-dial watch with steel bracelet
TROPER SPORT Green-dial watch with steel bracelet

Available Sizes

  • pcs.

TROPER SPORT Green-dial watch with steel bracelet

Featuring applied indexes on a green, sunray-brushed dial, this BOSS Menswear watch is inspired by diving styles. Rotating bezel with aluminium insert.
£229.00
  • Colour Silver
TROPER SPORT Black-dial watch with steel bracelet
TROPER SPORT Black-dial watch with steel bracelet

Available Sizes

  • pcs.

TROPER SPORT Black-dial watch with steel bracelet

Add a sporty touch with this diving-inspired BOSS Menswear watch. Cool steel offset by a black dial and rotating bezel with aluminium insert.
£229.00
  • 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.
£279.00
  • 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
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
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
TOURMASTER Green-dial watch with two-tone bracelet
TOURMASTER Green-dial watch with two-tone bracelet

Available Sizes

  • pcs.

TOURMASTER Green-dial watch with two-tone bracelet

With a multi-level, green dial inside domed glass, this BOSS Menswear watch fuses heritage and racing-inspired style. Sporty tachymeter. Two-tone steel bracelet.
£329.00
  • Colour Silver
TOURMASTER Blue-dial watch with two-tone bracelet
TOURMASTER Blue-dial watch with two-tone bracelet

Available Sizes

  • pcs.

TOURMASTER Blue-dial watch with two-tone bracelet

Engineered with a multi-level dial inside domed glass, this BOSS Menswear watch is a racing-inspired classic. Tachymeter bezel. Carnation-gold-tone accents.
£329.00
  • 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
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
Two-tone chronograph watch with olive dial
Two-tone chronograph watch with olive dial

Available Sizes

  • pcs.

Two-tone chronograph watch with olive dial

Combining olive, golden and silver tones, this BOSS Menswear watch takes inspiration from the sleek lines of classic cars. Dashboard-style subeyes for maximum function.
£349.00
  • Colour Silver
Link-bracelet chronograph watch with green grooved dial
Link-bracelet chronograph watch with green grooved dial

Available Sizes

  • pcs.

Link-bracelet chronograph watch with green grooved dial

Featuring a creative grooved dial, this BOSS Menswear watch balances aquatic-inspired tones of silver and green. Integrated H-link bracelet. Hands with luminescent fill.
£279.00
  • Colour Silver
SKYTRAVELLER Two-tone chronograph watch with blue dial
SKYTRAVELLER Two-tone chronograph watch with blue dial

Available Sizes

  • pcs.

SKYTRAVELLER Two-tone chronograph watch with blue dial

Featuring brushed and polished indexes, this aviation-inspired BOSS Menswear watch is designed in golden and silver-tone steel. Blue dial with sunray brushing.
£329.00
  • Colour Silver
Two-tone chronograph watch with grey dial
Two-tone chronograph watch with grey dial

Available Sizes

  • pcs.

Two-tone chronograph watch with grey dial

Mixing golden, silver and grey tones, this BOSS Menswear watch is inspired by the adrenaline-fuelled world of car racing. Dial features dashboard-style subeyes.
£349.00
  • Colour Silver
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
Black-dial chronograph watch with steel bracelet
Black-dial chronograph watch with steel bracelet

Available Sizes

  • pcs.

Black-dial chronograph watch with steel bracelet

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
Black-dial watch with multi-link bracelet
Black-dial watch with multi-link bracelet

Available Sizes

  • pcs.

Black-dial watch with multi-link bracelet

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
Blue-dial watch with stainless-steel bracelet
Blue-dial watch with stainless-steel bracelet

Available Sizes

  • pcs.

Blue-dial watch with stainless-steel bracelet

In cool steel with a blue dial, this multi-function HUGO Menswear watch is an instant classic. Stamped-up branding. Moulded indexes. Elegant link bracelet.
£179.00
  • Colour Silver
GRAND PRIX 40 Gold-tone watch with silver-white dial
GRAND PRIX 40 Gold-tone watch with silver-white dial

Available Sizes

  • pcs.

GRAND PRIX 40 Gold-tone watch with silver-white dial

In gold-tone steel with an integrated bracelet, this BOSS Menswear watch embraces a luxe, racing-inspired design. Silver-white dial with multiple subeyes.
£379.00
  • Colour Gold
HERO 2.0 Green-dial chronograph watch with steel bracelet
HERO 2.0 Green-dial chronograph watch with steel bracelet

Available Sizes

  • pcs.

HERO 2.0 Green-dial chronograph watch with steel bracelet

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
HERO 2.0 Black-dial chronograph watch with two-tone bracelet
HERO 2.0 Black-dial chronograph watch with two-tone bracelet

Available Sizes

  • pcs.

HERO 2.0 Black-dial chronograph watch with two-tone bracelet

Featuring a sporty tachymeter bezel and layered dial, this racing-inspired BOSS Menswear watch is a modern way to accessorise. Two-tone bracelet. Chronograph movement.
£379.00
  • 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

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