How Dating Helped Me Rediscover My Personal Style

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There are three outstanding theories on who exactly women dress for: potential significant others they wish to attract (nope), other women, be them friends or coworkers (not likely), or themselves, and their reflection when they pass it in the mirror (bingo).

The thing is, while you’ll likely consider where you’ll be and who you’ll be with each day when getting dressed in the morning, ultimately, what you’re deciding is how you want to feel for any given occasion. Sometimes, of course, it’s possible to get distracted by these other factors. But I’ve come to find that when I convolute them with my true intentions, I’m much more self-conscious (and potentially unhappy) throughout my day. Yet, when it comes to getting dressed up for an all-important date, it’s certainly hard to keep your head on straight.

I’ll spare you the details of my last heartbreak—we’ve all been through them before—and we’ll skip straight to the recovery phase. Before I was even remotely interested in dating again, distraction was my coping mechanism; retail therapy was as close as I came to processing any real emotions. Despite a stream of new clothes and a renewed focus on socializing, something about my wardrobe, and my auxiliary plans, left me feeling empty. So I finally allowed myself time for a little introspective reflection, which led me to rediscover my personal style again, right? Well, no, it wasn’t quite like that.

When I finally sought the one distraction I hadn’t bothered with yet—dating—something interesting happened. I started having to talk about myself, a lot. I had to share what I liked and disliked, what I did and what I wanted to do. But the more I had to convince other people to find me interesting, the more I realized: I already liked myself. So by the time I was picking out date night outfits, I found I was much more excited about the process of getting dressed than I’d been in a really long time. I was feeling myself, if you will.

“Whilst many of us can be tempted to think about how other people would expect us to dress on a date and then choose outfits accordingly, ultimately, when you dress in a way that makes you feel authentically you and your best self, this will radiate when you’re dating,” says Laura Yates , blogger, coach, and podcaster, who specializes in helping people bounce back. When we chatted, she pinpointed exactly what I was feeling, explaining, “It’s really not about the clothes at all; it’s about the energy, confidence, and self-assurance you exude when you’re on a date.”

It was true. The more I focused on who I wanted to be and how I wanted to present myself, rather than what my date would think of me, the more confidence I had, and the more I enjoyed myself while I was out.

That’s not to say I didn’t have any moments of self-doubt. But as Laura pointed out, “We can get so caught up in what others think of us—whether it’s a dating situation, friends, or co-workers. When it comes to dating, unless the person is really shallow (in which case you don’t want to be dating them anyway!), they’re not looking at what we’re wearing.” She reassured, “If you’re wearing something you feel amazing in, you’re bound to then show your best self because you feel good on an inner level too.”

So as suggested, I ignored the voice that wondered if my date would think my jeans were weird (pro-tip: if you’re dating a fashion girl, compliment them anyways). I definitely still asked my friends to weigh in on which shoes to wear, but in reality, I was only using their opinions to validate my own gut instincts (and thankfully, they were willing to humor me).

I truly dressed for my own damn reflection, and it felt good.

Ultimately, prioritizing what I liked best, rather than mindlessly plucking up the newest trends or automatically feeding into other people’s expectations, finally made fashion fun for me again. I was able to tap back into my personal style, and was more honest with myself over which pieces truly made me happy and which might have just been for show. For a daytime date, I rediscovered the magic of a favorite dress I had forgotten about for years. For a first date, I didn’t feel guilty about buying a new top I loved at first sight, which I wouldn’t have had an excuse to purchase otherwise. Dating style fits a very niche category of clothing—it’s a little more flirty than you can be for work, and a little more dressy than you’re expected to be on weekends. It just so happens those are two of my favorite things to be.

Ahead, date-night outfits that make me happy…

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Dating Style 101

The first date

All I need is a pretty cami and my favorite pair of jeans to feel comfortable, confident, and just the right amount of dressed up for a first date.

Demi Lune Bag

$470

A.P.C.

Cowl Drape Camisole

$49

Astr The Label

Insider Crop Step Fray Not Rough Enough

$228

Mother Denim

Irene Hoop Earrings

$36

Shashi

Carrie Leather Slingback Sandals

$385

by FAR

The daytime date

A femme dress paired with a sporty sneaker is a flirty formula that can be translated in many ways, no matter your style.

Esplar Leather Sneaker

$120

Vejas

Frankfort Dress

$218

Reformation

The Velvet Mirror Sunglasses

$69

Crap Eyewear

The dinner date

A fitted bodysuit and silky midi skirt is always a winner. Dress your combination up with a simple pair of heels.

Parlanda Ankle Strap Sandals

$60

Nine West

Jackie Jaguar Jacquard Midi Skirt

$69

Urban Outfitters

Black Leather B-Link Bracelet Backpack

$1,495

Balmain

Mott Bodysuit

$165

Alix