six people on their first date outfit formulas

from across the gender identity spectrum

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can you guess what i was wearing?

Good morning dear reader. Last night, I went to a dopamine dressing event at the Freda Salvador store and got this live illustration of myself done. Cute, right!? It reminded me that I have a stash of Copic illustration markers sitting at home, and I ought to use them more (the furry mules you see in The Molehill logo were hand-drawn).

Today you’ll hear from six people about their first date outfit formulas, in the spirit of Valentine’s Day. It was important to me to feature a wide range of gender identities and expressions, because that’s a huge factor in how we choose to present ourselves for the possibility of romance or seduction.

Enjoy. And if you’re feeling chatty, I invite you to share your ideal first date outfit in the comments! Tomorrow, I will be sharing a few of my own V-day styled looks that honestly work for anytime of the year.

And for paid readers, there will also be a secondhand sonar drop on thrifted versions of my favorite NYFW collections (aka we have Anna Sui madcap heiress at home). Think: Victorian-style skirts, rosette detail dresses, fur-trim jackets, patterned knits and more.

Side note, I’ve been thinking about a comparative analysis of Anna Sui (age 60) and Sandy Liang (age 33) as two high-profile Chinese-American designers from distinct generations and how their work reflects the prevailing cultures of said generations. If anyone else is a nerd about this, I wanna know what you think.

Valentine’s Day Gift Guides:

• custom lockets and silk lingerie

• so you want to get your masc a starter chain

• the hottest thing you can gift for valentine's day is snail mail

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Danya Issawi

, 29, she/her

style: practical, playful, comfortable, whimsical

Depends on the season, but let's pretend it's winter. Nothing, to me, is more gorgeous/stunning/head-turning than a woman in sheer, black tights! The mystique!!!! I'd probably wear a pair of Calzedonia or Wolford black tights, a plain black miniskirt from literally anywhere, a black or gray, drapey "Bound" top from Entire Studios, and these stompin boots (the Joan High Boot) from Labucq.

First and foremost, when I'm meeting someone new who I MAYBE MIGHT want to impress, I want to feel equal parts sexy and comfortable. When I'm maxxing out these areas is when I'm able to reach confidence nirvana. I want to present as myself, sure, an elevated version, but still very much so me. Back in the day when I was still going on first dates, I always wore something a little edgy, almost never fully saccharine. I felt like this was indicative of my personality/what I would be like in a relationship.

Plus, I kind of just wanted men to know not to fuck with me? Typically, this was in the form of stompin' boots.

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Phillip, 30, any pronouns accepted

style: feminine asian grandfather

I would wear an oversized white button up, my favorite right now is an old YSL one, a maxi length black Issey Miyake skirt with an asymmetrical hem line, black Tabi loafers, and a grey coat with dropped shoulder from MM6.

My intention with this outfit is to communicate to the other person that I care about what I wear and how I present myself. I think dressing well for a first date also shows that you care about the other person. It's like, I'm presenting the best version of myself to them because I care about what they think.

I'm not necessarily trying to impress my date with my clothes, but I do want to look cute and be perceived well.

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Alexandra, 26, she/her

style: feminine, whimsical, playful, vintage

For a first date I’m wearing a dress! I have this gorgeous white cotton Iro Paris dress that I thrifted, I love that it has a high neck and is shorter on the bottom! I would wear my favorite Victorian lace up boots from Miz Mooz which are heeled yet SO comfortable and if it’s cold I’m throwing on a vintage trench or fur and maybe a fun pair of lacy tights!!! And of course, my statement rings and burgundy or red lipstick with nails to match.

It can be a little stressful trying to figure out an outfit for a first date with someone you really like, there are so many factors to think about and if you’re anything like me (an overthinker) it takes way too much time. To make it simple, I’m choosing an outfit that makes me feel beautiful and is an ode to my interests and personality—the main priority is that I’m comfortable and feel like the best version of me!!!

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Teeny, 24, he/they

style: skater, boyish, newsie, grunge, british

8053 brown leather low top Doc Martens, vintage brown denim Levi 501’s, faded tan t-shirt, black vintage 80s Cobra race car jacket (cobra patch, one white stripe)/a solid colored vintage overshirt.

There is a hybrid of factors when putting together this date outfit that can be best boiled down to two words: confidence and coolness. My personal confidence is largely determined by my expression through clothing. I am very precise and meticulous when deciding pieces to wear that accentuate the more masculine parts of my body and that hide or cover my curves, so to speak. This pair of Levi’s fit perfectly, they aren’t baggy but they are not tight, they have a sun fade and wear to them which I think makes them cooler than an average pair of light wash jeans or black pants. The tan t-shirt is boxy, it fits me like no other t-shirt ever has and thus feels lucky.

I know it looks good on me in the case of me getting hot and needing to remove the jacket. The jacket I chose because it is the newest addition to my wardrobe and I’m looking for a reason to wear it, it’s a simple and classic look but the Cobra patch is colorful and unique. The docs are my favorite pair of shoes and make every outfit look better.

All of this screams that I’m addicted to Depop of course. But also shows I care. That I make choices everyday when I wake up about how I want to be seen. And this outfit feels appropriate for various date settings (bar, walk in park, dinner, coffee).

My relationship with fashion has been changed and influenced by all sorts of things. I take inspiration from countless butch and transmasc creators online who post outfit videos and show how they tailor the cuts of their shirts to look more masculine. I only buy from thrift stores and on Depop. Depop is a dangerous game, but has also been the most helpful resource in my style development. If you make specific searches on there enough, if you purchase a few things that fall within your realm of style, the algorithmic technology on Depop begins to understand what kinds of clothes and accessories you like and generates pages of options for you. I’ve been extremely rewarded for the amount of time l’ve invested into browsing through that interface.

I’m sort of at this place where I describe my style as somewhere between Malcolm in the Middle and Jackass. A lot of 90s one-stripe shirts that the pesky little brother on a sitcom would wear.

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Griffith, 29, he/him

style: comfortable, seasonal, wool socks

Black T-Shirt - Heavyweighttshirt.com is my fav t shirt company ever. I've got like 10 of them.

Navy Overshirt - I have one from Mango that I really love. You need layers in the Bay.

Black trousers - I'd advise baggy so you can avoid any potential wedgie situations. Brand: whatever you dig.

Wool socks - I get cold, what can I say? I'm team smartwool-til-I-die.

Anything without laces - I have these square toed black clogs from Olive Clothing that are pretty great.

Watch (maybe?) - I'm not a big jewelry guy, but I have a tonneau-shaped watch that my dad gave me, and I wear it almost every day.

I'm not a very loud person, so I think subtle clothing suits my personality pretty well. I assumed the date was at night in the previous question, so I went with darker clothes. I definitely want to be comfortable and I don't want to think about my clothes at all once I've left the house.

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June, 28, she/her

style: schoolgirl, gemini, kawaii, 90s nostalgia

Sandy Liang black cutout top and a coat, go-to bottoms are either Miu Miu black pleated skirt or Simone Rocha black skort, shoes are Simone Rocha black platforms or Margiela knee-high tabi boots + knee-high socks.

I try to consider who I’m going on a date with (are they in a creative field, do they seem interested or familiar with fashion, are they around my age or older, how do they present themselves in person or on a dating app, etc), where I’m going (indoor vs outdoor, concert vs seated dinner/drinks, casual atmosphere or more formal?). As a trans girl, there are conscious and unconscious factors that also play a factor.

Safety is my #1 priority, so I always factor in if I’m taking a car or public transit. I’m also thinking about how I’m going to be perceived by the men I’m dating, I go toward outfits that are feminine and somewhat classic/easy to understand (simple silhouettes, closer to the body but not too tight), but hopefully still represent me and my style (I stick to the designers that i love and feel most confident and feminine in like Simone, Sandy, and Miu Miu).

The more dates I go on as a trans girl, the more confident I feel not just in my identity, but also in being able to assert myself in a situation where I am feeling disrespected or when I don’t feel safe.

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Thank you to everyone who shared their first date outfit wisdom.

Hope you loved reading this as much as I did!

xoxo viv