What to wear on a date

If the key to winning someone over is being yourself and feeling self-assured, then looking confident and comfortable will play a big part in your success. For Valentine’s Day and beyond, it’s important to wear something that works for you and that’s right for the event. Whether you’re wooing over a casual day out, or aiming to make a bold impression over dinner, BOSS has the men’s and women’s date outfits for every occasion.

The lunch date

When meeting for a lunch date you have the day ahead of you, and as conversation turns to shared interests you could find yourself spending the afternoon anywhere from a gallery to a gig. Be ready for any event in a clean-cut yet versatile ensemble. For men, a casual jacket and tonal trousers is a combination that looks elevated when you opt for designs with minimal details. A tailored dress is the perfect choice for women, paired with white mule for a summery feel. Accessorize with a bag for all your must-haves and, for a more laid-back feel, simply swap shoes for sporty trainers.

The after-work drinks date

If you’re heading to a bar straight after work, your outfit has to do double duty. So, as a man choosing what to wear for drinks on a first date, take signature BOSS tailoring and relax the look a little by teaming a sharp suit with a fine-knit sweater. Adding casual Derby shoes will keep you looking on point. For women, experiment with a midi skirt with a tie-waist for an individual twist, and add warm knitwear for cozy confidence. Complete the look with a tonal pair of loafers.

The romantic dinner for two

Once you’ve secured some great company and chosen a stunning venue, ensure the scene is set with an impeccable BOSS outfit. For men, this masculine blazer in a soft wool blend pairs perfectly with tonal trousers for an an assured look that's ready for the finest restaurants around. Meanwhile, women can slip into this flirty dress that flatters any body shape.

The casual dinner date

While the venue might be informal, you'll still want to show that you’ve put some thought into your outfit. That's where casual tailoring comes into its own: it looks effortlessly relaxed, yet polished enough for that all-important first impression. For men, an understated look can be created with a jersey T-shirt layered under a shirt, completed with a lightly structured trench coat and athletic trainers. Women can team a feminine plissé dress with slingbacks and a bucket bag for easy elegance.

A stroll in the park

Bring an air of authentic BOSS to the outdoors with adaptable layers. Designed in complementary colors, BOSS collections can be put together effortlessly when deciding what to wear on a walking date. An on-trend windbreaker protects you from the chill, and can easily be carried to give you the chance to display a timeless T-shirt or sweater. Combine with casual chinos or neutral jeans for a fusion of comfort and style, and strike a sporty note with tennis shoes. Women can find confidence in a lightweight jacket - simply layer over a fluid blouse-dress and athletic trainers for an outfit that suits spending a day strolling in undone elegance.