What to Wear on a Date: Men's Date Night Outfits for Valentine's Day and Beyond

Quick Answer: What Should a Man Wear on a Date?

  • Upscale dinner: a sport jacket or suit with an open-collar dress shirt and leather shoes.
  • Drinks or a casual dinner: a fine-knit sweater or sport shirt with dark jeans or chinos.
  • Daytime or activity date: a polo or tee, chinos and clean sneakers.

Whatever the plan, prioritize fit, cleanliness and one thoughtful detail.

Whether it's Valentine's Day, a first date or a night out with your partner, what you wear sets the tone. You don't need to overdress. The goal is to look like you made an effort and feel like yourself. Here's what to wear for every kind of date.

Dinner at a Nice Restaurant

Go smart casual or a step above:

  • A sport jacket or blazer over a crisp dress shirt, no tie
  • Dark trousers or dark jeans
  • Black or cognac oxfords

A suit without a tie works too, especially for a special occasion.

Drinks or a Casual Dinner

Relaxed but put-together:

  • A fine-knit sweater over a collared shirt, or a sport shirt on its own
  • Dark jeans or chinos
  • Boots or clean leather sneakers

Daytime and Activity Dates

For a coffee, a walk or an outing:

  • A polo or quality tee
  • Chinos or dark jeans
  • Clean, comfortable sneakers

Valentine's Day Outfit Ideas

  • Classic: navy sport jacket, white shirt, grey trousers, cognac oxfords.
  • Moody: all black: black jacket, black dress shirt, dark trousers.
  • A touch of red: a burgundy sweater or pocket square for a subtle Valentine's nod.

The Details That Matter

  • Fit: well-fitting clothes look better than expensive ones that don't fit.
  • Clean shoes: they get noticed.
  • Grooming: a fresh haircut and a light touch of fragrance go a long way.
  • One thoughtful detail: a pocket square, a lapel pin or a great belt.

For more on the habits that make a man look well put-together, read 5 habits of a well-dressed man.

Want to make a strong first impression? See what women notice first about a man.

FAQ

What should I wear on a first date?

Smart casual is a safe bet: a collared shirt or fine-knit sweater, dark jeans or chinos and clean shoes.

Should I wear a suit on a date?

For an upscale dinner or special occasion, yes. Skip the tie for a more relaxed feel.

What colour should I wear on Valentine's Day?

Navy, black and charcoal are classic. Add a touch of burgundy or red for a subtle nod to the day.

Find Your Date Night Look at Tip Top

Browse sport jackets, sport shirts and sweaters, or read our smart casual guide. Or visit one of our 80+ locations across Canada to see the collection in person.

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