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


With Valentine’s Day quickly approaching, you could end up being requested out on a date or making the primary transfer your self. No matter the way you scored it, prepping and primping is customary and essential for a primary date with a promising new prospect. As a transgender lady, there’s a bit extra strain on dressing to impress. It’s essential to really feel your greatest with a view to begin the date off proper, and from years of expertise, I’ve created a number of easy guidelines in preparation for any sort of date.

5 Rules to Follow When Dressing for a Date

Rule #1: Keep your physique sort in thoughts. When purchasing or tearing by way of your closet, keep in mind that you wish to put on one thing that flatters you, not simply one thing that appears “sexy” (which is subjective, anyway).

Rule #2: Consider the place your date is going down. The setting says quite a bit about the kind of outfit you ought to be sporting. This performs into how it’s best to type your hair and do your make-up.

Rule #3: Don’t pressure your self into smaller sizes or something that may make you uncomfortable—it’s not value it and most certainly received’t flatter your physique. If you are feeling good, you’ll look nice.

STYLECASTER | Trans Woman Date Dressing Guide

Jeff Musolino

Rule #4: Drape your jacket. Hormone modifications may cause zits breakouts, weight acquire, and sweating throughout your bodily transition. If you sweat simply, like I did in my preliminary transition section, put on shorter sleeves or a tank. If you’ll want a jacket, drape it over your shoulders to present your physique some air (plus, it seems cool and easy).

Rule #5: Don’t overdo it, except that’s your private aesthetic. Based on the vibe of the date—whether or not it’s informal or fancy—it’s extra essential to decorate for your self first. Don’t put on one thing that feels in contrast to you, or spend an outrageous sum of money since you assume they’ll solely such as you in case you do. You’re occurring a date to get to know each other, not to consider your outfit your entire time.

General Outfit Advice

First date choices are countless. If you’re going to a pleasant dinner, I at all times counsel a pleasant black costume or black denims with a cute high.

If you go to a bar, put on denims (any coloration) with a cushty high and booties with a small to medium heel, as you by no means know the place the evening will take you.

If you’re going to a sporty occasion, put on a cute pair of sneakers or Converse-style footwear with denims and an informal shirt, and, after all, a denim jacket draped over your shoulders simply in case it will get chilly.

If you reside in a heat local weather like Los Angeles, a seashore date may undoubtedly be a chance. If you’re using bikes in Venice, strolling the Santa Monica Pier, or spending the day in Malibu, I counsel a cute pair of shorts, a flattering tank high or T-shirt, with a sweater to throw on because the solar units.

Skirts and clothes can grow to be difficult, particularly with surprising winds—in case you’re pre-surgery (gender affirmation surgical procedure), this might make you are feeling very uncomfortable all through the day. Fashion-forward sandals are at all times an ideal thought for seashore dates. A gladiator type is my private go-to, as they’ve the power to skinny my foot and lengthen my legs, relying on the colour and the way thick the straps are.

STYLECASTER | Trans Woman Date Dressing Guide

Jeff Musolino

Winter dates in a local weather like New York make selecting an outfit less complicated. Whether you stroll by way of Central Park, go ice skating, or sip espresso comfortably inside, my outfit recommendation is straightforward: a pair of comfy black denims or leggings, an on-trend outsized sweater or hoodie, and an elegant peacoat. Accessorize with a heat scarf and fingerless gloves to shine off your cozy winter look.

If your date location is undisclosed, dressing can appear practically unattainable, however don’t despair. A black costume might be accessorized to be dressy or informal. Make certain your hair is clear and styled so your date can’t assist however wish to run their fingers by way of it. You can by no means go incorrect with good pair of black denims, a weather-appropriate high, and a leather-based jacket. A chunky heeled bootie is at all times a protected guess, or a pair of modern platform sneakers. When it involves the unknown, keep in mind to KISS (Keep It Simple, Stupid.)

STYLECASTER | Trans Woman Date Dressing Guide

Jeff Musolino

The quantity of make-up 1 ought to put on on a date is at all times a difficult. Personally, I’m a fan of the “no-makeup” make-up look. If you like a full face, and that’s what makes you are feeling extra assured, go for it; simply take into account that your date might very nicely see you with out make-up in the future, so be sure you’re highlighting your genuine attributes with out going overboard.

Keep your lips clear and line-free. Always carry and apply a moisturizing lip balm (tinted is a plus), or for a plump pure lip, I swear by Aquaphor—however apply sparingly, as just a little goes a great distance with this 1. I select to do mild make-up on the primary date, with mascara, moisturized lips, and perhaps some highlighter on my cheekbones. Then, wow them with a bolder look on the 2d or 3rd.

And it doesn’t matter what, keep in mind that everybody’s physique is totally different. Just as a result of one thing matches doesn’t imply it’s flattering. Don’t go for overtly horny or utterly covered-up, except that’s what actually makes you most comfy. It’s essential to signify your true self within the context of your look. It would be the first impression you give off and it ought to begin on a excessive notice.

Remember, too, that confidence is essential. If you are feeling good, your confidence will shine from inside. Whatever you select to put on, don’t neglect to take pleasure in your self—you’ve bought a date!

(Editor references)

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