Updated: Aug 3, 2020
Makeup is extremely powerful, and can be an incredibly important (and fun!) part of life for literally any one who chooses to wear it! Just a quick sidebar before I respond to this question, I am a cis female and am in no way emphasizing the need for trans women to 'pass' or look 'more feminine'...I am simply offering makeup advice as a professional makeup artist that has been asked this question by someone interested in feminizing their features. Know that I love and support you regardless of how you choose to use (or not use) makeup! And now...let's get into it!
A lot of YouTube tutorials focus on contouring in order to reshape the face to look softer & fuller, but to be honest...contouring is a pretty advanced makeup skill! It's difficult to know where to place the contour to achieve your desired result, and how to apply it in a way that looks natural. Although eventually learning to contour can definitely be beneficial, I'd love to focus on a few things that are way easier...but still have a powerful effect!
1. Opening up the eyes with an eyelash curler. As male eyes are typically more recessed, smaller, and sometimes 'hooded' (meaning the skin above the eye droops down to cover the eyelid), it can be extremely beneficial to visually open the eyes back up to make them look larger and more awake. The easiest way to do this? Curl your lashes and apply a couple coats of mascara. The curling is what truly makes the difference, as it makes lashes more visible, and gives your eyes an instantly lifted appearance. If you've never curled your lashes before, check out my tutorial for it right here. Also, Shiseido makes my favorite lash curler, which you can get here. Don't sleep on lash curlers, y'all!
2. Create a smoother skin texture with foundation primer. Female skin typically has a more refined, smooth, and soft appearance, which is actually something that can be easily achieved with makeup. Developing a great skincare routine is key, but using a foundation primer over top will really help fill in and correct any uneven skin texture. Look for a primer that has 'smooth' or 'pore filling' somewhere in its description (like this one from Too Faced) and you're likely to get great results. Foundation primer can even be worn without foundation over top to gently smooth out the skin, although using foundation will enhance these results.
3. Give the brows a lift using concealer. On females, the brows typically have more space from the eye itself to the brow bone, which makes them look higher and also gives the eyes that lifted and larger appearance. Unfortunately, tweezing brows to look thinner and higher will not always be flattering, and can also be tricky to do on your own. Instead, a great trick to raise the brows is to pat a bit of concealer that is a few shades lighter than your skin tone just beneath the brow. The lighter concealer will make the distance between your eyes and brows look larger, and will also brighten and open everything up. Keep the concealer just on the brow bone itself —you can feel exactly where it is with your finger as it eventually drops off to the hollow of your eye socket.
4. Soften the lips with shine. Soft, plush lips are always very feminine, but don't get overly caught up in the idea that you have to have large lips—Kylie Jenner is not always our role model, y'all. Any lip product that has shine to it, whether it's a lip gloss, a sheer lipstick, or even a juicy lip balm will instantly soften the appearance of the lips, and can also make them look plumper.
I know makeup can be pretty intimidating, especially if it's brand new to you, but I'm here to tell you...it doesn't always have to be so hard! I specifically chose the tips above because they are extremely do-able, and don't involve any complex products or techniques. Outside of these quick tips, I have a bunch more to teach you about feminizing. You can check out this video tutorial I created with some additional tips, or this one to learn about how to use contour & highlight to feminize. I also offer great online makeup classes you might find useful, as well as one-on-one makeup mentoring done via Zoom. If you want to get advice that's fully tailored to your particular needs, plus answers to all of your makeup questions, that can be a great way to go.
Lastly, I am always available to directly answer your makeup questions! Feel free to email me at firstname.lastname@example.org or DM me on Instagram @the_pretty_fix, and I will gladly help you in any way I can. Thanks for being here and being interested in learning from me.