The Million Dollar Question

July 25, 2017



The million dollar question. What do you wear on a first date? Some guys prefer not to tell you where you’re going, but coming from an Orthodox Jewish home, the first date tends to take place at a cute café or an upscale hotel lobby for drinks. But… what does one wear? Coming from a fashion blogger who lives and breathes everything the runways give us to drool over, I do and still struggle to find the perfect ensemble.

A first date is not the time to experiment with the latest trends, but rather this is the time to trust your gut. You probably want to wait a minute before you bust out in full runway garb (I’m talking to myself here), but if this date eventually blooms into a relationship, it should be clear that you wear what you want because you want to. Don’t dumb down your style for a stranger! By simplifying your favorite silhouettes and highlighting your accents you can very subtly enhance your favorite features.

Ladies I know and feel your pain. The struggle of getting dressed for that first date and not being able to decide what wear… but there is a solution: Wear your absolute favorite items! You’ll feel more confident in something you already know you love and look good in. Comfort is key no matter what. If you feel good in what you’re wearing you’ll look good.

First dates can be terrifying, but planning your outfit doesn’t have to be. Below I have listed a few options of my favorite date outfits.

1.This is my go to outfit. It’s simple, but chic. I know it’s all black, but I feel good and confident in this. This outfit is great, since it easily transitions for any occasion or season! You can always change it up with different accessories or shoes! I added this fun gold sequin clutch for a pop of color.

2.A denim skirt which is casual but can be dressed up as well. Pair it with a causal tee and bomber jacket or leather jacket. You can wear this to a more casual first date like a coffee date and recycle it for a day date 😉

For makeup, keep it light and natural. Don’t over do it and keep your hair down. If your planning on wearing open toe shoes make sure you’ve recently gotten a pedi 😉

Stay tuned for my next couple of looks where you’ll find inspiration you can copy for your upcoming dates whether it’s a daytime date, night escapade, fancy dinner or casual lunch.

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1 Comment

  • Reply Chana rachel July 25, 2017 at 6:17 am

    Nice post! Love the looks but the shoes look super uncomfortable. What other shoes do you suggest?

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