Here’s a confession: When I look in the mirror, I see a woman who the feminine graces seemed to have passed over. My brows are unkempt, the dark circles under my eyes (a genetic inheritance from my Indonesian side, but also the result of a lifetime of insomnia) are generally visible because I only wear makeup at parties or on vacation. If I’m not going out in public, and sometimes even when I am, I prefer to hide in baggy men’s clothes. A form fitting outfit makes me feel uncomfortably exposed. I’ve always worn my tomboy persona like armour. Then I started getting invited to weddings.
In the past three years, I’ve been invited to about ten weddings, and that means more makeup, heels, and formal dresses than I thought I’d ever wear in my entire life. Yet I find myself drawn to the experience of donning a feminine costume for a day. I use the term “feminine” loosely — defined by attributes conventional society traditionally associates with women.
In theory, clothing should not be gendered and those qualities that people still think women best embody should be embraced by all genders. There’s also nothing wrong with wearing whatever you want, in whatever style, that makes you feel comfortable. You don’t have to change to fit any social convention. Yet I still can’t help but feel that the dresses I wear at weddings have helped me access a side of myself that I’ve buried—one that is vulnerable, outgoing, approachable. Dressing up gives me a chance to explore the world (both internal and external) outside of my comfort zone.
The outfits I wear to weddings make me feel like I’m playing an unfamiliar, but exciting character: That of a woman who feels inherently connected to, and comfortable with, her femininity. In reality, I’ve never been very good at embracing what our society considers to be feminine characteristics: nurturing, emotionally open, patient—even kind, at times.
My so-called femininity shouldn’t be something that I repress or try to hide. It can, in fact, be a source of power and strength, a way for me to nurture not just different sides of my personality that I usually ignore, but also my capacity for personal growth and change. In celebration of all the ways I have championed my feminine side, here are 9 of my favourite wedding outfits:
An ode to every outfit that I, a self-professed tomboy, have ever worn to a wedding
All businessI wanted to create a suit for this wedding so I wore a business-like black blazer, black silk tank top, and dark green velvet bell bottoms. This outfit probably best reflects my personal style, or at least what my personal style aspires to be. I felt a little like Lisa Luder in Romy and Michelle’s High School Reunion: super chic, distinguished, but a little bit cold and aloof.Elisabeth Sherman
Sandy from GreaseI wore this vintage yellow dress to a Mad Men party in college and recycled it for this wedding, the first one I ever attended with my now-partner. The princess vibe is strong with this dress, and it made me feel like I was wearing a theatre costume. In fact, it reminds me of something Sandy Olsson in Grease would wear—sweet and innocent—and I’ve always been more of Rizzo. Elisabeth Sherman
BombshellI was bridesmaid in this wedding. We wore jewel-toned dresses in the retro style. This is one of the first times I felt sexy, and it was a little bit of a revelation. I imagined myself slinking around like Jessica Rabbit (though I’m hardly that graceful). Never before or since have I felt like a “bombshell” but I’m totally fine with that being a one-time only experience. Elisabeth Sherman
The jumpsuitThis periwinkle jumpsuit was a win for me because of the wide legs. I’m most comfortable in formal outfits that aren’t body hugging and give me room to move. The culotte cut of the pants (reminiscent of those shorts Prince George wears on formal occasions) and the pale, understated colour maintain the tomboy appeal, which is nicely offset by the bow at the hip. Elisabeth Sherman
Peach RufflesI have a reputation for being blunt and speaking without a filter, so for this beachside wedding in Maine, I wanted to connect with a softer side of myself. I set aside my personal style principles and I picked the girliest dress I could find. The white flowers and the ruffles on the sleeves helped me live out a Cinderella fantasy I never really embraced in adulthood, but that I was enthralled with in childhood (my favorite game was taking out my tea set and pretending to serve my evil step sisters). Looking back, the dress amped up my imposter syndrome, but it was ultimately liberating to find out that a hyper-feminine look isn’t oppressive, or a betrayal of my politics. It’s actually empowering to feel vulnerable on my own terms, to embrace my body rather than feel pressured to hide it away. I know they teach that stuff in Feminism 101, but I’m a late learner—and I’m proud of myself for not just leaving, but completely abandoning, my comfort zone. (The guy on my arm is our longtime family friend, Peter.) Elisabeth Sherman
The inventor of Post-ItsI love the low-key sharpness and simplicity of this navy blue dress. The short sleeves are business-like and modest. It seems like with a different pair of shoes, it could work for a job interview. On the whole, the outfit made me feel like a serious business executive, maybe the inventor of Post-Its? (I’m posing with Peter’s wife, Jessica.)Elisabeth Sherman
Wide legged pantsI took a risk with these bright pink pants. Like my personality, they are bold and in your face. I wore dangly hot pink beaded earrings too, but the black crop top balanced the whole look out and I wore a blazer over it most of the night. I tried to find the sweet spot where my personal style gels with what’s appropriate for a wedding (an ongoing struggle!). As you may have noticed, wide-leg pants are my secret weapon. They’re formal and flattering but not restricting or too revealing either (although I’m a very sex-positive person, I’m a strictly conservative dresser on special occasions). It’s a tiny niche, but I try to only buy clothes that could double as fashionable pajamas. Elisabeth Sherman
A riskier choice (for me, at least)I remember feeling extremely anxious about wearing this dress because it’s so low cut. I wasn’t worried about exposing a breast, but I think the collarbone is particularly erotic and it felt completely out of character to tout my sexuality so openly. As I mentioned, I am fully capable of being extroverted, but conversely, I am sometimes intensely reserved around strangers. Here, I gave myself permission to embody the vibe of this dress, which is uninhibited and jovial. Basically, that meant taking a shot from the vodka luge. Elisabeth Sherman
Pulling an ElaineThis is my nineties-era ‘Elaine from Seinfeld’ dress. We now consider Elaine’s style iconic for good reason: She expertly towed the line between masculine and feminine with her full-length floral print dresses, loafers, and blazers. This is the most beautiful I’ve ever felt at a wedding, because I finally nailed a version of femininity that makes me feel at ease: Understated, simple, unfussy. Ultimately what I want from an outfit for any occasion is to feel at home in my body (which will take a lifetime of work to achieve, I’m certain), but I think I’m getting closer to understanding how my clothes can reflect the truest version of myself—all my insecurities and sometimes-confidence intact. Elisabeth Sherman