Dressing to Dominate the First Date

When I think of getting ready for a first date, I picture those old black-and-white movies with women in front of their vanity mirrors brushing their hair, applying lipstick and putting on their jewels. There is just something so ethereal and magical about the process to me. These days, it seems like people are always too stressed out about what to wear on a date to enjoy getting ready. To help you avoid some of that unnecessary stress, we’ll share tips for concocting the perfect date outfit. That way, you can focus on more important things—like enjoying the date!

The first suggestion, no matter the occasion, is to start with something very basic and add accessories, jackets or a fun bag to make things interesting. Building an outfit around an all-black base is where I like to begin—first, because it’s easy, and second, because the possibility of things you can do from there are endless.

Start with a pair of black pants and a black top. You can always dress them up or down depending on the occasion. All black makes a simple yet bold statement that’s perfect for any array of first date activities. I am a fan of wide leg pants and a tighter-fitting top combination, but if you are more of a skinny-jeans-and blouse-kinda girl, that works perfectly as well.

Now for the fun part: accessorizing!

Heading to an outdoor date like a winery tour or music festival? First things first—sunglasses. You always need a good pair of sunglasses! Then, grab your favorite crossbody bag and a pair of chic-yet-comfortable shoes, and you’re ready to go. We love a good pair of platform sneakers, flat boots or mules. If it’s a chilly outside, throw on a chunky knit to cap off the outfit.

Going out for dinner and drinks? Choose a pair of dainty heels to dress up your look and give you perfect posture when you make your entrance. You can also never go wrong with a statement necklace or pair of earrings for those fancy nights out.

First date happening in the dead of winter? I’ve recently become obsessed with statement outerwear and look for any excuse to incorporate it into my wardrobe. Faux fur, leather and bright colors are all great options to spice up your all-black look during the winter months.

Are you more of a dress girl, or just not into wearing pants on a first date? These tips can be applied to a black dress as well—even on the most casual occasions!

With a bit of luck, these tips will lead to stress-free dressing and a fun getting-ready process. Good luck! I hope he’s Mr. Right.

Co-creator of The Crystal Press, Rebecca Piersol is a stylist-turned-fashion blogger and contributing author to thredUP, an online thrift store that makes it easy to shop and sell high-quality secondhand women’s clothing. The wife of a Gatsby-obsessed high school English Teacher, Rebecca loves a classic white tee and a pair of flare jeans, and is a sucker for a good glass of bubbly.