Never Wear Khakis
For many men, khakis are a first-date standby. But fashion experts recommend avoiding khakis for date nights. According to Bruce Pask, Bergdorf Goodman's men's director, khakis are not sexy at all. Jeans, on the other hand, are a better option. They are sexy, rugged and perfect for a relaxed casual look. These days, jeans are perfectly acceptable in almost all dating scenarios except for some fancy restaurants that have a strict dress code.
Style Tip: Wear a basic dark pair of slim-fit jeans with a t-shirt/dress shirt and layer it up with a sweater/blazer, knitted scarf, and a pair of boots or boat shoes.
[Photo via @colehaan]