The Simple Rules
1. Dress one step above the venue. If others will be in T-shirts, wear a shirt or a nice top. 2. Fit beats fashion. Clothes that fit well look better than new or expensive ones. 3. Be comfortable. If you're tugging at a hem or limping in new shoes, it shows. 4. Look like yourself. Dress like the best version of how you usually look, so you're recognisable from your photos. 5. Get the details right: clean shoes, pressed clothes, and a recent haircut.
Outfits by Date Type
Coffee: men: plain T-shirt or polo, overshirt, dark jeans, white leather sneakers. Women: knit top or blouse, straight jeans, ankle boots or clean sneakers. Dinner: men: oxford shirt or fine knit, chinos or dark trousers, loafers or boots, and an unstructured blazer for a nicer restaurant. Women: a simple dress or silky top with tailored trousers, and shoes you can walk in.
Drinks: men: dark shirt or knitted polo, dark jeans, Chelsea boots. Women: a nice top with jeans or a slip skirt, and a jacket. Activity (walk, mini golf, gallery): clean casual: jeans, a T-shirt or sweater, a light jacket and comfortable sneakers.
Read more: Smart Casual for Men, Explained
Colour and Grooming
Wear a colour that suits your undertone near your face; see what colors look good on me. Some studies have linked red clothing to people being rated as more attractive, but later attempts to repeat them found smaller or no effects, so wear red only if you like it.
Grooming matters as much as clothes: tidy hair, trimmed beard or brows, clean nails and a light amount of fragrance, if any. For a bigger refresh before the date, see glow up tips.
Plan the Outfit in Advance
Try outfit ideas on a model set to your build in Ollie Stylist. The Clean classic and Minimal styles in Choose for me work for most first dates, and you can see a haircut that suits your face shape too.