× Dressing for First Date – Spring/Summer The Go-To: Sports Coat + Jeans/Khakis. Lighter weight cotton sport coat. While, light-colored, or checked button-down shirt. Wear a stylish accessory like a watch or pocket square. Dark denim jeans or khakis. Dark brown leather lace-up shoes with rounded toe. Always dress in layers. If it gets chilly, you can offer your date your coat. Fingernails cleaned and trimmed. The More Casual Date. Well-fitting polo shirt or casual button down shirt. Get your hair cut the week before the date and don’t try something new with it for your date. Go with your usual routine. Choose your shoes carefully – they say a lot about you and women always notice them. Canvas shoes or top-siders. Dark denim jeans or khakis. Field watch.

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