What should be considered when deciding what to wear on a first date? I once read that the ideal outfit is jeans, a white T-shirt and a black bra. Is this still true? — Gillian, Vancouver, Canada
First of all, there is no such thing as a single ideal outfit. People, of all ages, shapes, geographies and situations, are too gloriously varied. What I can offer, however, is a first-date fashion philosophy.
Also, a reference point.
In fact, when I first read this question, the cultural touchstone that came to mind was the 2004 Adam Sandler-Drew Barrymore film “50 First Dates” (for obvious reasons). But given that the woman in question has short-term amnesia and repeats the same day over and over again in pretty much the same clothes, I decided on consideration that a better reference would be the recent Netflix series “Nobody Wants This.” As a rom-com for our times, it’s about as good a guide to first-date fashion as I have seen.
Indeed, it has spawned a whole subgenre of TikToks devoted to what Kristen Bell’s character wears during her various encounters with her rabbi boyfriend, played by Adam Brody. I think that is because her wardrobe perfectly embodies what the designer Christopher John Rogers said was the ideal way to approach the first-date wardrobe: “understated, but with a touch of surprise.”
You should think about “what you wear every day, but amped up a bit,” he said. For example: Try jeans, a T-shirt — and a statement earring. Or a dress with sneakers. On the evening Ms. Bell’s character meets Mr. Brody’s, she has on black jeans and a black off-the-shoulder Abercrombie & Fitch bodysuit. On their actual first date, she wore jeans, low-heeled boots and a fitted black button-up shirt from Mango.
The point is to feel comfortable, in every sense of that word. This means clothes that are physically comfortable, sure. There is nothing worse on any date (but especially a first one) than wearing shoes that hobble you or clothing that is too tight to eat or anything that requires a lot of fiddling and tugging and otherwise distracts you from the person you are with.
But it also means clothes that are psychologically comfortable. You want to feel like the most relaxed, polished version of yourself, without necessarily giving too much away. A first date is, after all, simply the beginning of a process of discovery.
Most likely you want to look as if you have made an effort, but not too much of an effort. You want to look casual, but not too casual. (You don’t want to convey the idea that you don’t care at all.) You also don’t want to wear anything that could predispose whoever you are meeting to leap to stereotyped conclusions about who you are.
For example: When the two characters meet in “Nobody Wants This,” Ms. Bell is wearing a giant faux fur coat. Later, Mr. Brody deconstructs her in short order, announcing: “Walking into a party with a big-ass fur coat ’cause you’re scared not to be seen as special or different? Sorry, babe. You vulnerable.”
You may want to avoid that. Or not. Either way, remember that everything you wear will be read like tea leaves.
Oh, and one more tip, from a colleague: Stay away from wearing white, especially if you are going to a restaurant where red wine, soy sauce or any other potentially splattering comestible is likely to be encountered. While spilling on yourself is never a good look, worrying about it is even worse.
Your Style Questions, Answered
Every week on Open Thread, Vanessa will answer a reader’s fashion-related question, which you can send to her anytime via email or Twitter. Questions are edited and condensed.
The post What’s the Best Thing to Wear on a First Date? appeared first on New York Times.
