What to Wear on a Date When You’re a Transgender Woman

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STYLECASTER | Trans Woman Date Dressing Guide
Photo: JEFF MUSOLINO/ART: ALLISON KAHLER/STYLECASTER

With Valentine’s Day rapidly approaching, you may find yourself being asked out on a date or making the first move yourself. No matter how you scored it, prepping and primping is customary and crucial for a first date with a promising new prospect. As a transgender woman, there’s a bit more pressure on dressing to impress. It’s important to feel your best in order to start the date off right, and from years of experience, I’ve created a few simple rules in preparation for any type of date.

5 Rules to Follow When Dressing for a Date

Rule #1: Keep your body type in mind. When shopping or tearing through your closet, remember that you want to wear something that flatters you, not just something that looks “sexy” (which is subjective, anyway).

Rule #2: Consider where your date is taking place. The setting says a lot about the type of outfit you should be wearing. This plays into how you should style your hair and do your makeup.

Rule #3: Don’t force yourself into smaller sizes or anything that will make you uncomfortable—it’s not worth it and most likely won’t flatter your physique. If you feel good, you’ll look great.

STYLECASTER | Trans Woman Date Dressing Guide

Jeff Musolino

Rule #4: Drape your jacket. Hormone changes can cause acne breakouts, weight gain, and sweating during your physical transition. If you sweat easily, like I did in my initial transition phase, wear shorter sleeves or a tank. If you’ll need a jacket, drape it over your shoulders to give your body some air (plus, it looks cool and effortless).

Rule #5: Don’t overdo it, unless that’s your personal aesthetic. Based on the vibe of the date—whether it be casual or fancy—it’s more important to dress for yourself first. Don’t wear something that feels unlike you, or spend an outrageous amount of money because you think they’ll only like you if you do. You’re going on a date to get to know one another, not to think about your outfit the entire time.

MORE: The Transgender Woman’s Field Guide to Dating

General Outfit Advice

First date options are endless. If you’re going to a nice dinner, I always suggest a nice black dress or black jeans with a cute top.

If you go to a bar, wear jeans (any color) with a comfortable top and booties with a small to medium heel, as you never know where the night will take you.

If you’re going to a sporty event, wear a cute pair of sneakers or Converse-style shoes with jeans and a casual shirt, and, of course, a denim jacket draped over your shoulders just in case it gets cold.

If you live in a warm climate like Los Angeles, a beach date could definitely be a possibility. If you’re riding bikes in Venice, strolling the Santa Monica Pier, or spending the day in Malibu, I suggest a cute pair of shorts, a flattering tank top or T-shirt, with a sweater to throw on as the sun sets.

Skirts and dresses can become complicated, especially with unexpected winds—if you’re pre-surgery (gender affirmation surgery), this could make you feel very uncomfortable throughout the day. Fashion-forward sandals are always a great idea for beach dates. A gladiator style is my personal go-to, as they have the ability to thin my foot and lengthen my legs, depending on the color and how thick the straps are.

STYLECASTER | Trans Woman Date Dressing Guide

Jeff Musolino

MORE: Why We Need to Destigmatize Trans Beauty Standards

Winter dates in a climate like New York make choosing an outfit simpler. Whether you walk through Central Park, go ice skating, or sip coffee comfortably inside, my outfit advice is simple: a pair of comfortable black jeans or leggings, an on-trend oversized sweater or hoodie, and a chic peacoat. Accessorize with a warm scarf and fingerless gloves to polish off your cozy winter look.

If your date location is undisclosed, dressing can seem nearly impossible, but don’t despair. A black dress can be accessorized to be dressy or casual. Make sure your hair is clean and styled so your date can’t help but want to run their fingers through it. You can never go wrong with nice pair of black jeans, a weather-appropriate top, and a leather jacket. A chunky heeled bootie is always a safe bet, or a pair of sleek platform sneakers. When it comes to the unknown, remember to KISS (Keep It Simple, Stupid.)

STYLECASTER | Trans Woman Date Dressing Guide

Jeff Musolino

MORE: ‘Why I Quit Wearing High Heels When I Turned 30’

The amount of makeup one should wear on a date is always a tricky. Personally, I’m a fan of the “no-makeup” makeup look. If you love a full face, and that’s what makes you feel more confident, go for it; just keep in mind that your date may very well see you without makeup one day, so make sure you’re highlighting your authentic attributes without going overboard.

Keep your lips clean and line-free. Always carry and apply a moisturizing lip balm (tinted is a plus), or for a plump natural lip, I swear by Aquaphor—but apply sparingly, as a little goes a long way with this one. I choose to do light makeup on the first date, with mascara, moisturized lips, and maybe some highlighter on my cheekbones. Then, wow them with a bolder look on the second or third.

And no matter what, remember that everyone’s body is different. Just because something fits doesn’t mean it’s flattering. Don’t go for overtly sexy or completely covered-up, unless that’s what truly makes you most comfortable. It’s important to represent your true self in the context of your appearance. It will be the first impression you give off and it should start on a high note.

Remember, too, that confidence is key. If you feel good, your confidence will shine from within. Whatever you choose to wear, don’t forget to enjoy yourself—you’ve got a date!

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