It really is that simple. This should go without saying, but a prospective date will want to judge you sober. Details can come in the form of a pocket square and colour-matched belt and shoes. What should we talk about? For women, a classic date dress is hard to beat. Dating can be a tricky business. Pair with comfortable heels or embellished flats, a pair of statement earrings or a chunky necklace, and an appropriate outer layer.
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Dress to impress: what to wear on a first date
What look is best for dating? Who should pay on a first date? Main menu Open search menu. For men, smart jeans or khakis are also a good choice for a day date outfit. Again, this area used to be strictly male territory. After your time is up, the organizer will ring a bell. As it turns out, what to wear on a first date actually matters a whole lot more than any of us were aware of.