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LESSON 5 · Style Rules for Men

Date Night Strategy

Date night dressing means looking intentional without looking like you tried too hard. Aim for one level above what the venue requires: if the restaurant is casual, go smart-casual; if it is smart-casual, lean slightly formal.

Fit matters more here than on any other occasion. Your clothes should follow your body cleanly without being tight. Dark jeans or chinos, a well-fitted button-down or quality polo, and clean shoes make a reliable date uniform. Skip loud logos and heavy cologne. Authenticity beats costume — your date wants to see who you actually are.