What to Wear on a First Date

By December 22, 2018Consulting, Dating

As the saying goes, one only has one chance to make a first impression. You can be sized up literally, in a matter of five seconds, so make that first impression count. “Dating” clothing doesn’t have to cost an arm and a leg, and you can do magic with accessories. Here are some tips:


  1. What time of the day and what’s the venue? IF you are going on a coffee date, consider easy and casual-wear a cute pair of jeans that is figure flattering, and a top or sweater that shows your assets but doesn’t show all that you have to offer, so to speak.
  2. Your make-up should be suitable for day; not overdone and be sure not to spray your bottle of perfume into every single pore. (Many people are scent sensitive, so not wearing perfume may be a better bet until you understand the persons likes/dislikes.)
  3. Wear something that makes you feel great in your own skin. Confidence is key when dating, and if you feel good, and like who you are sitting across from, you may get your flirt on-BIG TIME. Now, we all feel great in our yoga pants, but that doesn’t mean we should wear them on a date. Wear something that gives you girl power and confidence, and get that attitude going. For me, it’s a pair of boots. When I was younger, it was rocking my Doc Martens. Now…. it’s my Paul Green boots.
  4. If you are seeing someone for the first time for a dinner date, wear something simple, yet sophisticated. Accessories can take a dominant role here and really create your own wonderful style. A little black dress, paired with drop dead gorgeous jewelry is a show stopper. Make sure you keep things to a hush versus a scream when it comes to the jewelry, as you don’t want the jewelry to overpower YOUR presence.
  5. Wear a heel. Heels make a girl feel powerful. Heels make your legs look better, heels give you more height and heels, even a kitten heel, are sexy. Need I say more?


If you have the opportunity to check out the venue online before heading off, even better. Best to dress appropriately versus over or under dressed. You truly want your focus to be determining if your date is a good fit for you, your wants and your needs!

Best Wishes,

Lori Mendelsohn, Uncommon Man

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