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(I always do this for my clients.) A great rule of thumb for the first date: Choose a color or outfit that you are often complimented on. The last thing you want to do is be fidgeting with your outfit—there are more important things to be thinking about!

Jamie: Let location be your guide–your look should reflect your environment!

It's not only unsightly, it creates a weird sort of forced intimacy.

Especially these days when everyone hugs everyone else — even casual acquaintances — hello and good-bye instead of shaking hands.

For a casual dinner, boyfriend jeans and a cute blouse or tee are always a great bet.

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(You can remove the jacket when you leave the office! A classic, fitted blazer is perfect for the occasion when worn the right way! This is what will make a great first impression and guarantee a second date! ) Jess: I can’t say it enough—wear what makes YOU feel good. If you feel good in what you’re wearing, it’ll show.

(And enough time to steam or iron your outfit beforehand!

) Being disheveled and stressed out until the second your date picks you up is no way to start out!

If you decide to wear something backless or low cut in the front, wear it with a maxi skirt or jeans.

Jamie: This might sound obvious, but give yourself plenty of time to plan out what you’re wearing.