Makeup finally forced me out of the closet - 57 and completely lost
Hi everyone! My name is Samantha, and this is my very first post here, or anywhere.
Makeup is actually the thing that finally pushed me to come out of the closet and make a post.
I'll try to keep this fairly short. I'm a 57-year-old crossdresser who has always known Samantha was there, but I only started dressing about two years ago. It's been a slow but really enjoyable journey, and during that time I feel like I've started to develop my own sense of style.
The next step in my evolution is makeup… and honestly, it has completely humbled me.
I've been trying to learn for about a month, but I keep running into the same problem. Every tutorial I find assumes I already know the basics. Even something as simple as eyeliner feels like it's explained as if I've been doing makeup my whole life.
I've watched most of the videos listed in the r/crossdressing resource section, but they all seem to assume:
• I have the skin of a 16-year-old
• I already understand makeup tools
• I have basic application skills
Unfortunately… I have none of those things.
I’ve attached the best result I've managed so far.
One thing that is extremely important to me is not looking clownish. I'm not expecting miracles, but I do want to improve and look natural. I'm also realistic enough to see the obvious issues:
• white around my eyes (I have dark circles and small skin tags)
• my lipstick application clearly needs work
• my jawline is quite square
• my nose is fairly large
• my eyebrows are completely untouched
• I have absolutely no idea what I'm doing with eyeliner
• I did try blush, but it's barely visible
The wig I'm wearing is an $18 Shein wig, though I'm saving for a better one eventually (Ellen Wille, Raquel Welch, or Jon Renau).
From the research I've done so far, I think a Soft Glam look would suit me best. It seems appropriate for my age, I really like the aesthetic, and it also looks relatively minimal — which matters because I only get about one day a week to dress, so time is precious.
I also believe I fall into the Autumn color palette.
Below are the products I currently own. They're mostly e.l.f., since budget is always a factor.
Tools
• Real Techniques Makeup Brush Set (4) + 2 sponges
Eyes
• L'Oréal Gel Pencil - Brown
Lips
• Revlon ColorStay Lip Liner - Red (not used yet)
Face
• e.l.f. Halo Glow Setting Powder - Light Medium
• e.l.f. Soft Glam Satin Foundation
• e.l.f. Camo Color Corrector - Orange (works best for me)
• e.l.f. Camo Color Corrector - Peach
• e.l.f. Putty Blush - Tahiti
• e.l.f. 16HR Camo Concealer - Fair Warm
• e.l.f. 16HR Camo Concealer - Medium Neutral
• e.l.f. Powder Contour Palette (not used yet)
Right now I'm thinking about buying a warm rose or soft coral lipstick, but I'm struggling to commit to one since money is always a concern.
At this point I honestly feel a little overwhelmed.
If anyone has advice on where I should start, especially for:
• beginner techniques
• soft glam for mature skin
• fixing dark circles
• eyeliner for absolute beginners
• shaping or dealing with eyebrows
• lip colors that might suit me
I would really appreciate the help.
Thank you for reading.
- Samantha
Posted Mar 14, 2026, 7:18 AM UTC