What To Wear on a First Date

Do you know who Carol Channing is? She's one of the loves of my life. If you too are a child of the 80's you might remember her from the rather frightening made-for-tv movie Alice in Wonderland. {The dance break starts at minute two. You're welcome.}

Well, I've met her soul sister who I adore just as much. Her name is E Jean Carroll. She happens to be just as over the top effervescent and fabulous, and thus is in my phone as E Jean Carroll Channing. When we hang up the phone I practically have tears in my eyes I just can't get over how delightful she is. Oh and smart. Like, you're writing things she says on post-it's mid-conversation smart.

And she can be your matchmaker.

Yes, you! If I'm a stylist for "real people with real budgets", E Jean {who by the way is a legendary advice columnist over at Elle Magazine} is all about love for "real people with real budgets". So, taking her years of matchmaking Manhattan's elite {you know Kristen Bell's Gossip Girl voice just popped into your head} she's newly partnered with How About We, to create an option for a betty just like you -- smart, charming, and ready to have someone do a bit of the dirty work of finding and setting up a date, so you can get down to the flirty work of what you're going to wear on one.


{Dress : Target: Similar | Belt : Primark: Similar | Necklace + Bracelets : Thrifted : Similar : Similar | Watch c/o Sperry Top Sider | Bag Coach Vintage : Similar | Shoes : DSW : Similar} + Brooklyn Photography by Bethany Michaela


So once Miss E Jean has a match for you, what do wear on a first blind date? An easy version of you on your best day.

A magazine is going to give you a bunch of outfit ideas but let's be honest, we all have wildly different style and that mini skirt plus blazer plus booties vision board they mocked up is going to look or feel not totally "you" on half the Dean St bettys. So I say disregard anyone who tries to give you a one-style-first-all quation.

1. An easy version of you: Soft hair, natural make-up, not too fancy, no striving.

2. On your best day: Not your average jeans and a tee day when you work from home, not your corporate suit you take off the moment you walk in the door. What you would wear to a chic brunch with girlfriends, out to drinks at that darling place you saw on Instagram. 

3. And give him something to compliment you on: A great color, pretty dress, nice shoes, cool bag, interesting piece of jewelry. I shared on Instagram yesterday about my newest experiment in dressing remarkably, worth of remarking upon. After all, the guy's probably nervous, right? So give him some help. Right off the bat, "You look great in that dress" is a solid way to ease into hellos and "Where did you get that necklace" saves a pause in conversation.

Oh and don't drink too much. Don't let him order a second round without ordering food first. Though you might not want to commit to dinner on a first date -- You know what, E Jean will handle the rest. Then email me afterwards and tell me all about it. {wink}


Matchmaker Girl

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* This post is sponsored by How About We Matchmaking. Personally, I'd say how about we meander around the Brooklyn Flea with two lattes. Vintage finds and wandering is always good for conversation, and E Jean once told me "A woman should be in motion on a first date. If she's sitting down, she's sitting on half her assets!" I told you she was good ...

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