We often get questions about what to wear on a first date.
Appropriately, the first thing that comes to mind is the “KISS principle”, a lesson from one of my most memorable elementary school teachers.
“Keep It Simple, Stupid!”.
You want to look sharp and put-together but also approachable and easy-going. Over thinking it with an elaborate outfit will make you seem nervous and less confident.
Here are some simple outfit ideas for Spring first dates using versatile pieces that you may (or should) already have in your wardrobe.
1. Movie Night
An unstructured cotton jacket is a great Spring piece for looking smart but relaxed.
By “unstructured” or “unconstructed” I mean a jacket without a chest canvas, lining or shoulder pads/sleeve heads . It’s really just a shell of a jacket. It feels very lightweight and “moldable” because it’s sewn more like a shirt than a traditional tailored jacket.
With slim chinos and a sharp tee (preferably long-sleeve) it’s one of those dressy-casual looks that is appropriate to go just about anywhere.
Leather driving shoes are sharper than sneakers without the stiffness of leather-bottom office loafers.
They’re also very comfortable and great for walking – which is important when the nerves are running up on a first date.
- Grey l/s cotton tee by Rich In Clothing
- Black cotton jacket by Theory
- Light grey cotton chinos by Michael Andrews Bespoke
- Black leather driving shoes with bamboo bit by Gucci