Relax: The Perfect First-Date Outfit Doesn't Exist

Jessica Schiffer

Style du Monde

Google “first-date outfit” and you’ll find over 4 million results weighing in on the subject, from expert opinions on what to wear to style mistakes to avoid at all costs. While the intentions are nice—help us score romantic points, sartorially—the reality is that these strict guidelines negate our individual personalities, sweeping our style quirks under the rug as if to say, Who you really are won’t do—try this on for size instead.

Not to mention the fact that never in the history of the world has a healthy, long-lasting relationship been formed by people hiding their true colours in lieu of something more palatable and, perhaps, mainstream (correct me if I’m wrong). So, while it may seem innocent enough, caving to outside opinions on the dos and don’ts of first-date wear that don’t necessarily align with your style is really just an effort in convincing your partner to fall for someone you’re not. What’s more, it’s an act of self-flagellation, a way of reinforcing that your inclination toward wide-leg culottes or jeans and a vintage tee renders you somehow less than dateable.

Opt for a little black dress; pair jeans with heels; show some skin; don’t wear anything too trendy—the list goes on.

I wholeheartedly reject these rules, as they feel both anti-feminist and anti-fun, quashing personal style quirks and the freedom that comes with fashion for the seemingly noble cause of romance. To that, I say nah—real connection transcends such frivolities, but can also only happen between two authentic parties (wearing what they like when they like).

Having occasionally caved to these rules myself, I also know the discomfort they bring, contributing to nerves and that audition-like feeling that first dates so often hold. Like me for who I’m only pretending to be, these looks seem to shout, followed by an inner monologue of Ohmigod why did I wear this? I’m so uncomfortable. Instead of paying attention to the person in front of me, I find myself expending way too much energy on the components of my outfit, wishing I could run back home and change into something more “me.”

When I forgo the rulebook, though, I feel my confidence rise—it’s that self-assuredness via style that drew me to fashion in the first place. Proudly wearing what I like to wear, even if it’s considered too casual or unsexy for a first date, reminds me to be proud of who I am and to look for someone who likes that person, not say, a sparklier, magazine-worthier version.

Scroll down to shop some of my quirky and comfortable first-date outfit picks…

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