What To Wear On A Date

August 23, 2024

I was 31 the first time I went on a date. I’d had relationships—I was even engaged once—but I’d always met my partners through family, friends, or work. Suddenly, I was in my thirties, sitting across the table from a lawyer studying psychology named Mark (not his real name) who I’d met on a dating app. Getting ready for the date had taken hours: I’d put on my favourite pair of Esse trousers, only to realise the wide leg (the very same thing I loved most about these pants) made me feel shapeless; I tried a grey St Agni suit, then worried the colour was giving both boardroom and boredom. I was lost in front of the mirror; the certainty I felt in my wardrobe, I no longer had.

It goes without saying that if you only own one pair of something, it probably means it doesn’t reflect your personal style. Nevertheless, I located a single pair of opaque tights at the bottom of my sock drawer, styled them with a black miniskirt and tucked in a white tailored shirt, opening the buttons so that it showed (just enough but not too much of) my décolletage. I had never worn this outfit before. Not once. Although, technically, I did own the individual pieces. I was dressed for the date but I still felt lost—I didn’t recognise myself at all. (I needn't have worried so much about what to wear—Mark didn’t ask me a single question, however he did tell me about his university thesis in great detail. I never saw him again).

What I was wearing was a particular representation of my personal style, with adjustments made through the lens of what I thought heterosexual men found conventionally attractive. In other words, I was dressing for “the male gaze”, a term coined by film theorist Laura Mulvey in an essay she wrote in 1975 titled Visual Pleasure and Narrative Cinema. “It is the way in which visual arts and literature depict the world and women from a masculine point of view, presenting women as objects of male pleasure,” translates Joey Solloway, an American television director and writer, adding, “It’s in pretty much everything. Everything you’ve ever seen.”

If we take this concept away from film theory, how does it relate to our role in getting dressed for a date? When we follow Mulvey’s argument, it’s the way in which we think about how men would perceive us and adjust our appearance accordingly. For me personally, it’s been about confronting the ways I adjust my appearance to cater to men, even when it’s left me feeling less comfortable and less confident. But that’s where it gets complex, because Mulvey would argue that women have already internalised the male gaze within ourselves, making the influence of the outside male perspective all but inescapable. In other words, we always view ourselves through the lens of men, even when no men are present. How does this relate to the context of a date, when the whole idea—at least for straight women like me—is that men are present?

While answering these questions for myself, I’ve also had to acknowledge the potential transaction taking place. As a single woman on the dating scene, aren’t I contributing to a context in which the male gaze is prevalent? Haven’t I become a form of capital in some way? And aren’t dates, by nature, to some extent transactional anyway? For instance, by agreeing to go on the date, am I agreeing to look good on the date? Where does the idea of wanting to look presentable end, and the concept of dressing for the male gaze begin?

This is where I’ve landed with it all: I choose to dress for dates in a way that honours my personal style, but leans towards a more sensual version of what I’d usually wear. I’ve learned to weigh up my own very real desire to feel sexy, with my desire to feel stylish. I see it as another part of dating etiquette: learning to dress for the date.

What does this look like? I’d describe my personal style as classic and I lean towards tailoring, with timeless silhouettes. No colour. For a date I went on recently, this translated to wearing my favourite brown wool Hyde & Stone trousers, but leaving the matching blazer at home, and instead opting for a simple black knit that felt really sexy to wear. I added an earring that I know draws the focus toward my eyes. These are all small adjustments that don’t betray my personal style—it’s simply a more considered way of dressing. And it’s all of this, while acknowledging there is no need to appear sexy 24/7—that is definitely the male gaze speaking. I’ve started to view the whole thing as simply adjusting my outfits for my target audience. I find this helps.

My advice would be to dress for yourself versus who you're trying to attract, knowing that when it comes to dating, if you feel good, then you’ll project a good energy. An important question to ask is: would you still wear this if you were going out to dinner solo? If yes, then I don’t think you’re betraying yourself, or your personal style.