BOSS Style Guide: What To Wear On A Date

If the key to presenting the best of yourself is feeling self-assured, then looking confident and comfortable will play a big part in your success on a date. 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 meeting for a casual day out or aiming to make a bold impression over dinner, BOSS has men’s and women’s date outfits to suit every setting. 

The Lunch Date 

When meeting for lunch, you have the day ahead of you, and as the conversation turns to shared interests you could find yourself spending the afternoon anywhere from a gallery to a concert. Be ready for any event in a clean-cut yet versatile ensemble. For men, a tailored jacket layered with a sweater can be made casual by removing the top layer, and a knitwear and trousers are an easy-to-wear combination. For women, a shirt-dress paired with boots is the perfect balance of dressed up and dressed down. 

The After-Work Drinks Date 

If you’re heading to a bar straight after work, your outfit has to do double duty. Consider a relaxed tailored look that works for both day and night. For men, try wearing your suit with a collarless shirt, or simply lose the tie. Adding casual derby shoes will keep you looking sharp. For women, go for a statement trouser suit over fitted knitwear, and complete the look with sleek leather boots. 

The Romantic Dinner for Two 

Once you’ve secured some great company and chosen the best restaurant in town, ensure the scene is completely set with an outfit to match. For men, a slim-cut suit and tie, or a fine-knit polo neck, will ensure you’re ready for formal dining. Meanwhile, women can opt for sleek separates or an elegant dress. Try a piece with a touch of sparkle to really light up the evening.

The Casual 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 sharp-cut jacket, or sneakers with tailoring. For women, a relaxed-cut skirt and top combination in a statement-making pattern will be sure to make an impact.