With These Tips, A Transgender Woman Will Look Fabulous On Her Date

trans woman dressing on date

If you are a transgender woman and have more masculine-type traits now that you have transitioned, we would like to offer you some fabulous styling tips. They will help to conceal the masculine side of you now that you are a transgender woman and want to look feminine. Our tips will help you to find your own personal style, to keep you feeling confident, chic, feminine, and comfortable in your clothes – all meant to show off your beautiful authentic self.

Our first tip is to dress according to your body type

Look, we have given you some types of female body shapes. You are bound to find your body shape here! Then you can style your clothing according to your body shape. For instance, you might have a straight figure; then you might want to accentuate your waist area. Wearing form-fitting clothes might look excellent on you. So whether it is skirts, pants, or tops, clothing that is close to the body might work best for you.

What colors will suit you as a transgender woman?

It would be wise to embrace the darker colors and be more cautious with the very bold vivid doors or very light colors. The darker colors will conceal the more masculine part of your body and create excellent and convincing illusions. With lighter colors, you won’t be able to hide everything. Bold colors, as with all people, will draw a lot of attention to you, but if you really can’t resist the flashy colors, then it’s all up to you.

Pay attention to wearing clothes that have thin spaghetti straps

Use caution if you love the thought of wearing strapless designs. Remember, that men usually have broader shoulders than women do, and if you want to get away with strapless dresses, carry with you a wrap or jacket handy for you to cover up if necessary. You will realize that the wider straps will probably be more flattering for you.

What shoes?

Feminine shoes are to be found in most of the larger shoe stores if you have bigger feet or thicker ankles for instance. Pumps, boots, sandals, and sneakers all come in some of the available sizes so you probably won’t have a problem finding them. If you do want to wear high heels, perhaps you should start with a block heel or something lower, just for starters, to get the feel of how it feels to walk with high heels. Also if you are someone who is tall, wearing high heels will make you look a lot bigger and taller. But if this all doesn’t seem to work for you, there are fantastic sneakers in all kinds of colors which are very trendy as well!

What about accessories?

All the little details count a lot, like a ring, a bracelet, a simple necklace. These help to complete the outfit. Add some nail polish to your attractive accessories and you will instantly feel feminine. Remember too, if you have a larger Adam’s apple, then wearing a choker can conceal it more.

Don’t forget your makeup and we have got super tips and ideas for you here.

Consider where your date is taking place

  • The setting says a lot about the type of outfit you should be wearing. Base your clothing on the vibe of where you are going. Then you will also know how to style your hair and apply your makeup.
  • Don’t force yourself into smaller sizes or anything that will make you uncomfortable. It won’t flatter your physique and might make you feel uncomfortable and self-conscious on your date. When you look good, you feel confident.
  • Don’t wear something that looks and feels like you went out and spent a huge sum of money because you think your date won’t like you if you don’t look like a million dollars. Remember, you are going on a date to get to know each other.

Places and types of clothes

  • If you’re going to a nice dinner, a nice black dress or black jeans with a cute top will look just perfect.
  • If you are visiting a bar, wear jeans of any color with a comfy top and shoes with small to medium heels, as you never know where the night will take you.
  • For sporty events, you could wear a cute pair of sneakers with your jeans and casual shirt, with a denim jacket draped over your shoulders just in case it gets cold.
  • For very warm climates, it might be a beach date. A cute pair of shorts with a flattering tank top or T-shirt, with a sweater to throw on as the sun sets.
  • Dresses and skirts can become a bit more complicated, particularly on windy days and you’ve had gender affirmation surgery for instance – it could make you very uncomfortable for the rest of the day.
  • Winter makes an outfit simple to choose; just a pair of comfortable black jeans or leggings, an on-trend oversized sweater or hoodie, and a chic pea coat. You could accessorize with a warm scarf and fingerless gloves to polish off your cozy winter look.
  • If your date hasn’t disclosed the location, dressing can seem kind of impossible. But remember, the little black number is easy to accessorize into being very dressy or being much more casual.
  • Always ensure your hair is clean and style in case your date wants to run their fingers through it!
  • Another outfit if you are not sure where you are going that will be a good guess is a nice pair of black jeans, a weather-appropriate top, and a leather jacket.
  • Now to makeup which can get a bit tricky as well. You might love a full face of makeup for the occasion. Always remember that your date might see you one day without your makeup so you need to make sure you highlight your best attributes without going overboard. Always keep your lips clean and line-free, carrying a lip balm with you, preferably a tinted one. Choose lighter makeup on your first date, maybe some mascara, moist lips, and a bit of highlighter on the cheekbones, then you can wow your date with something more dramatic on your second or third date.


We hope our above tips have given you an idea of what will help you to look absolutely stunning and feminine! As a transgender woman, it’s important that you feel your absolute best when dressing to impress. This will get your date started off on the right start.

Don’t get frustrated with dressing your body. Remember, everyone’s body is different. Just because something fits you superbly won’t mean it is flattering your body. Don’t go for outrageously sexy or completely covered-up – rather dress comfortably and most of all dress in the way that represents your true self. Remember, first impressions count, and with the fab tips we’ve given you, you should be able to start your date off on a high note! Oh, and don’t forget – ENJOY!