If you live in a warm climate like Los Angeles, a beach date could definitely be a possibility. 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 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 nice dinner, I always suggest a nice black dress or black jeans with a cute top. MORE: The Transgender Woman’s Field Guide to Dating General Outfit Adviceįirst date options are endless. You’re going on a date to get to know one another, not to think about your outfit the entire time. 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. Based on the vibe of the date-whether it be casual or fancy-it’s more important to dress for yourself first. Rule #5: Don’t overdo it, unless that’s your personal aesthetic. If you’ll need a jacket, drape it over your shoulders to give your body some air (plus, it looks cool and effortless). If you sweat easily, like I did in my initial transition phase, wear shorter sleeves or a tank. Hormone changes can cause acne breakouts, weight gain, and sweating during your physical transition. 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. This plays into how you should style your hair and do your makeup. The setting says a lot about the type of outfit you should be wearing. Rule #2: Consider where your date is taking place. 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). 30 Can’t-Miss Clothing Sales to Shop Right Now: Zara, Nordstrom, Amazon, & More 5 Rules to Follow When Dressing for a Date
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