dating + going out

first date: over 40-something

what to wear 1st date over 40

In the post-divorce, over 40-something world, dating seems like a foreign language; something that if you haven't practiced in a while, you find yourself rusty and making some mistakes along the way. It's true, dating is different now and although once unconventional, meeting someone online is more than acceptable…but full of landmines.  Men tend to lie about their height (which is truly a minor infraction when you think about the big picture) and women, I am told, lie about their age (again, a minor infraction when you think about the reasons for why.)

So, what do you wear when you've met someone who ‘seems' like he's what you're looking for and you're ready to meet?  First off, although it's technically a first date, it's really a “Let's meet and see if we really have a connection and that no huge lies were told in getting to this point.” So, yes…look good but BE comfortable…because this ‘date' could last 5 minutes. Jeans and a cute top work in my book. There's no point in getting totally dressed up for something that unfortunately can turn into a Debbie Downer situation. Speaking from experience, it's best to go into the first meet with an open mind. If it turns out badly, you'll have a really good story to tell your friends.

So here's something that will work perfectly for those first dates, uh-hem, meets.

  • Jeans. Duh. Everyone is talking about these MOTHER jeans. They are super great because they don't stretch out and this cropped version is great for summer and then into Fall with boots.
  • Aqua or Blue Top. Why this color? If you have my free guide for what 5 colors you need to have, you'll know why. It's perfect for that first meeting. This double-strap top is by MICHAEL Michael Kors and it has great hardware details at the shoulders – perfect on all body types.
  • Statement Ring. I talked about this green agate ring last week. Good to deck him with if he makes a move you're not wanting. (Seriously kidding on that.)
  • Pleather Draped Jacket. This non-leather draped jacket is shown in tan and perfect to top off your outfit. It goes for $95.
  • ‘Mystery' Wedge Sandals. These 3″ heels have a 1″ platform so they feel like 2″. By Naot and named, appropriately, Mystery, these sandals go to 11.  Remember, never go into too much detail about your life the first meeting…you need to keep some mystery and hopefully these sandals will help remind you.

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