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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.
- Most Relevant
- Price (low-high)
- Price (high-low)
Available Sizes
- pcs.
Silver-tone curb-chain necklace with logo link
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Silver
Available Sizes
- pcs.
Blue-dial watch with link bracelet
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Silver
Available Sizes
- pcs.
Stratus chronograph watch with seven-link bracelet
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Silver
Available Sizes
- pcs.
PRINCIPLE MASTER Grey-textured-dial watch with multi-link bracelet
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Silver
Available Sizes
- pcs.
Stainless-steel link-bracelet watch with black dial
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Silver
Available Sizes
- pcs.
Principle Dress black-dial watch with H-link bracelet
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Silver
Available Sizes
- pcs.
Stratus green-dial chronograph watch with link bracelet
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Silver
Available Sizes
- pcs.
Lit black-dial watch with link bracelet
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Silver
Available Sizes
- pcs.
PRINCIPLE Link-bracelet watch with blue textured skeleton dial
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Silver
Available Sizes
- pcs.
Langford two-tone watch with five-link bracelet
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Silver
Available Sizes
- pcs.
TOURMASTER Blue-dial watch with multi-link bracelet
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Silver
Available Sizes
- pcs.
Silver-tone chain necklace with branded magnetic closure
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Silver
Available Sizes
- pcs.
Gold-tone curb-chain necklace with logo link
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Gold
Available Sizes
- pcs.
Grand Prix stainless-steel watch with silver-white dial
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Silver
Available Sizes
- pcs.
Sky Traveller silver-tone watch
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Silver
Available Sizes
- pcs.
Silver-tone watch with grey dial
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Silver
Available Sizes
- pcs.
Silver-tone watch
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Silver
Available Sizes
- pcs.
Style silver-tone watch with green dial
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Silver
Available Sizes
- pcs.
Style silver-tone watch with white dial
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Silver
Available Sizes
- pcs.
#GRAIL SPORT Silver-tone watch with blue dial
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Silver
Available Sizes
- pcs.
Leather-strap watch with silver-white dial
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Brown
Available Sizes
- pcs.
Silver-tone watch with textured skeleton dial
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Brown
Available Sizes
- 30/32
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- 32/32
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- 34/32
- 35/32
- 36/32
- 38/32
Relaxed-fit jeans in dark-blue soft cotton
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Dark Blue
Available Sizes
- 29/32
- 30/32
- 30/34
- 31/32
- 31/34
- 33/34
Slim-fit jeans in dark-blue stretch denim
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Dark Blue
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
- 36/32
- 36/34
Tapered-fit jeans in dark-blue stretch denim
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Dark Blue
Available Sizes
- 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
- 36/30
- 36/32
- 36/34
- 38/30
- 38/32
- 38/34
Straight-fit jeans in dark-blue stretch denim
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Dark Blue
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
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Dark Blue
Available Sizes
- 29/32
- 30/32
- 31/30
- 31/32
- 32/30
- 32/32
- 32/34
- 33/32
- 33/34
- 34/30
- 34/32
- 34/34
- 35/34
- 36/32
- 36/34
- 38/32
- 38/34
Slim-fit jeans in dark-blue stretch denim
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Dark Blue
Available Sizes
- 31/32
- 32/32
Slim-fit jeans in dark-blue comfort-stretch denim
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Blue
Available Sizes
- 30/30
- 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
- 35/36
- 36/30
- 36/32
- 36/34
- 38/32
- 38/34
Slim-fit jeans in dark-blue comfort-stretch denim
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Dark Blue
Available Sizes
- pcs.
Skytraveller multi-tone watch
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Silver
Available Sizes
- 36/32
Relaxed-fit jeans in dark-blue Japanese denim
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Dark Blue
Available Sizes
- 31/32
- 33/30
- 35/34
- 38/32
Maine regular-fit jeans in dark-blue extra-soft denim
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Dark Blue
Available Sizes
- pcs.
Telly stainless-steel watch with retro-inspired case
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Silver
Available Sizes
- pcs.
Telly two-tone watch with retro-inspired case
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Silver
Available Sizes
- 29/32
- 30/30
- 30/32
- 31/32
- 31/34
- 32/32
- 32/34
- 33/32
- 33/34
- 34/30
- 34/32
- 34/34
- 35/32
- 35/34
- 36/32
- 36/34
- 38/34
Regular-fit jeans in dark-blue denim
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Dark Blue
Available Sizes
- 30/32
- 31/32
- 32/32
- 32/34
- 34/32
- 34/34
- 36/32
Tapered-fit jeans in dark-blue stretch cotton
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Dark Blue
Available Sizes
- 29/32
- 30/32
- 31/32
- 32/32
- 32/34
- 33/32
- 33/34
- 34/32
- 34/34
- 35/32
- 36/32
- 36/34
- 38/32
- 38/34
Baggy-fit jeans in dark-blue rinse-washed denim
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Dark Blue
Available Sizes
- 30/32
- 31/32
- 32/30
- 32/32
- 32/34
- 33/30
- 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
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Dark Blue
Available Sizes
- 29/32
- 30/32
- 30/34
- 31/32
- 31/34
- 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
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Dark Blue
40 products out of 248