I Let My Dad, My Boss, and a Dating Expert Dress Me for a Date

"It will be easy," my boss said. "Just put yourself out there." I spent six and a half of the past seven years in a serious relationship, and dipping my toe back into the dating pool has been painful. So when I found out I was being tasked with going on not one—but three—first dates, I inwardly cringed (no surprise there). But luckily I had a team in my corner to help me conquer one major task: figuring out what to wear.

In the name of journalism, I enlisted the help of my father, my boss, and a dating expert to break down their ideas of the ideal first-date look. But before you draw comparisons to Kate Hudson's character in How to Lose a Guy in 10 Days, I want to make one thing clear: This experiment was more about gauging my own internal reaction to what I wore. Yes, the way the date progressed was important, especially when my outfit picked up a compliment or two. But at the end of the day, my goal was to find the date-night look that best impressed me and my date

With admitted hesitation, I got busy navigating the murky waters of dating apps and friend-of-friend setups—all of which actually went pretty smoothly (and I'm sure most of you could have told me that, dear readers). In total, two margaritas, three sauvignon blancs, and one fancy, fruity cocktail were imbibed, and this dating-world rookie learned a lesson or two along the way (thanks to my mentors, of course).

So with three dates down (thanks to Tinder and the friends who set me up), how did things play out? After testing three very different looks, I learned that even though what you wear is important, it's mostly about how you feel in what you're wearing that counts. If I was confident in my ensemble, that is what my date really noticed. Still, let's not pretend testing out three mystery outfits wasn't tons of fun. 

Read on to see how it all went down! 

Look #1: My Dad's Pick

Photo:

Who What Wear/Paley Fairman

The Look: My parents aren't normally ones to usually offer up their opinions on my clothing. So when I first asked their thoughts on a first-date outfit, I was met with responses of "whatever you feel best in," a sentiment I appreciate but didn't get much help from. Finally after a bit of prodding my dad offered up this: "Your mom used to wear a beat-up jean jacket with a dress" (way to answer the question, Dad). Armed with the closest thing to an outfit pick I was going to get, and inspired by own mother's go-to date look, I was tasked with put a modern spin on his advice. The result: a distressed jacket styled over a silver dress. 

Photo:

Who What Wear/Paley Fairman

The Date: Figuring out the who part of the date was obviously more intimidating than figuring out what to wear. For this first date, I met up with a Tinder connection (admittedly it was my first time arranging an IRL meeting from the dating app—or really any dating app).

We stopped into a bar on the Lower East Side for a few glasses of wine (me) and beers (him) before heading our separate ways on a Saturday night. Since a dress can skew a little fancy for such an occasion, the distressed denim jacket added enough edge to fit the neighborhood's vibe.

Believe it or not, without any prompting, my date complimented my outfit choice, so things were off to a good start. I was confident in the look but also at ease (or as much as I could be on a first date), and when we parted ways at the end of the night, we made plans to get together again. Nice work, Dad. 

Photo:

Who What Wear/Paley Fairman

What I Wore: Rag & Bone Avenida Jacket ($395); Zara Shimmer Fabric Dress ($50) and Zara Polo Neck Top ($40); Phillip Lim Alix Clutch ($750); Prada heels. 

Look #2: My Boss's Pick

Photo:

Who What Wear/Paley Fairman

The Look: When it came time for my boss, Nicole, to share her input, her look of choice was, unsurprisingly, very similar to what I might choose on my own. In her words, the ideal look consisted of "a silky button-down blouse tucked into flattering blue jeans and a pair of low heels." The ensemble is simple but feels just dressed up enough for a first date—especially with the addition of a bright red lip. 

Photo:

Who What Wear/Paley Fairman

The Date: A Sunday night date in the East Village was just the right occasion to test this classic yet casual ensemble. I was meeting a friend of a friend, who suggested we head to a cozy, candlelit spot for drinks (great for a date but not as ideal for evaluating outfits up close).

It was a bit chilly, so I threw a leather jacket on over my ensemble, but promptly took it off once we sat down. Since jeans are probably what I consider most comfortable to wear, this outfit had me at ease. Block heels and a tucked-in blouse helped add a little extra sophistication, but luckily I didn't have to fuss around with them, meaning I could focus on the conversation instead of my aching feet or a top that wouldn't sit right. 

Photo:

Who What Wear/Paley Fairman

What I Wore: Equipment Signature Shirt ($220); Levi's jeans; Zara Leather Mid Heel Shoes ($80); Kara Tie Crossbody Bag ($475).

Look #3: An Expert's Pick

Photo:

Who What Wear/Paley Fairman

The Look: When I tapped matchmaker Nora DeKeyser of Three Day Rule for my story, her first advice for a successful date was to make sure I felt good in what I wore. "When a woman feels confident in her appearance, it exudes out of her," she told me. Then she got down to business, suggesting that if I was headed straight from work, a wrap dress was the way to go.

While I would say my usual office-to-drinks attire is a little more casual, this look felt just right for fancy cocktails in Midtown. So when the night came around, I headed out of the office ready to tackle my third and final date.

Photo:

Who What Wear/Paley Fairman

The Date: From the minute I arrived at our meet-up spot—a popular taco and margaritas joint in the Flatiron district—I had a feeling the night was going to be a fun one. I was meeting up with an acquaintance I'd been texting with for a while, so I was optimistic about the date-night chemistry.

As DeKeyser suggested, I made sure I felt comfortable in my ensemble. Yes, I wore heels, but went for ones I knew wouldn't kill my feet. And one quick glance around confirmed I wasn't the only one wearing a wrap dress. The result: I was definitely at ease (especially after a spicy margarita or two). After we decided to call it a night, my date texted me wanting to set plans to meet up again. It seems like I'm maybe getting the hang of this…

Photo:

Who What Wear/Paley Fairman

What I Wore: Diane von Furstenberg New Jeanne Wrap Dress ($368); Proenza Schouler Hava Bag ($2250); Zara Ballerina Heel ($70).

Curious to see more of my outfit experimenting? See how I wore concert merch IRL!