
Our reader asks: “I love how eyeliner looks on other people, but when I try it, my eyes look weird and the line is never even. I’m fairly new to makeup, so where should I start if I want a more feminine look? -Trista”
In this article, we’ll cover:
- Lining your upper lashes
- Creating a small, lifted wing
- Applying liner to hooded eyes
- Making eyes look more open
- Fixing uneven eyeliner
Dear Trista,
Start with a thin line along your upper lashes. You don’t need a dramatic cat eye: a little definition and a slight lift at the outer corner can do plenty. If you’re learning to use eyeliner to make eyes look more feminine, less is more. You can add to a fine line much more easily than you can take a thick one away.

With decades of makeovers under our belt, one thing we always check is how the liner looks with the eyes open. It can look just right while someone’s eyelid is closed, then disappear into the crease as soon as they look up. Keep a mirror in front of you and look straight ahead now and then as you work.
I’d start with a smooth pencil. It gives you time to work, and you can soften an uneven edge with a small brush for a gentler look. Liquid liner gives a crisp line, but mistakes tend to show more, and it’s harder to blend out. Save it for when you’re comfortable with the shape you want. Brown can look softer for daytime; black will give you stronger definition.
Rest your elbow on a table to steady your hand. Make short strokes right beside your upper lashes, beginning around the middle of the eye and moving outward. Then fill out any little gaps between the strokes. Leave the line very fine toward the inner corner. If you’re wondering how to make eyes look bigger with eyeliner, that thin upper line is a good place to start. It defines the lashes without covering up too much of your eyelid.

Ready to try a wing? Place a tiny dot just past the outer corner and slightly above it. Join the dot to your upper lash line with two or three short strokes. For a sharper edge, place a small piece of skin-safe makeup tape beneath the outer corner, angled up toward your temple. Draw along the tape’s edge, then peel it off gently. Don’t put tape too close to your eye, and skip it if the skin there is irritated or sensitive.
If your eyelids are hooded, mark the wing while looking straight ahead with your eyes open. A flick drawn on a closed lid can bend or vanish in the fold. Keep it short enough that you can still see it when your face is relaxed. That little adjustment helps you use eyeliner to make eyes look more feminine on your own eye shape, instead of trying to copy a wing that was drawn on somebody else’s.
I’d also go easy on the lower lashes. A thick black line all the way around the eye can make it look smaller. If you want more definition underneath, soften a little pencil along just the outer part of the lower lash line with your brush. Step back from the mirror before adding more. What looks too subtle up close often looks lovely from a normal distance.

And Trista, your two eyes won’t be perfectly identical. If one wing goes astray, clean up its edge with a pointed cotton swab rather than making the other one bigger and bigger to match. Give yourself a few practice runs on a quiet evening, when you’re not trying to get out of the door. A pencil, a brush and five minutes of experimenting will teach you more about your eye shape than trying to draw one perfect line on the first attempt.
Using eyeliner to make eyes look more feminine is mostly about finding the small changes that suit YOUR face. Start thin, check your work with your eyes open, and stop when you like what you see. The wing can wait until you feel ready for it!
With love,
Katie
Remember, if you have any questions about crossdressing, Katie can help with everything from relationship advice to tucking to sizing. Ask away, and Katie will gladly answer all emails sent to [email protected]. Make sure to add ‘For Katie’ into the Subject Line.
