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Image from Beauty Tips Etc - this link includes rather helpful advice on how to choose the best eyeliner style for your eyes. Gold!

A friend of mine who wears little-to-no makeup recently asked me how I achieve my winged eyeliner look. I gave her the dreaded response that I used to loathe hearing: practice. Practice practice practice.

Upfront disclaimer: I’m useless with makeup. I imagine makeup professionals see my sloppy makeup job and cringe in the same way grammar snobs and literary types and long-term kinksters cringe when they read50 Shades of Grey. But I can manage a passable wingtip eyeliner these days so, for those of you who, like myself, struggle with makeup, I’m going to tell you how I finally managed it - in a little more depth than a casual shrug and nonchalant practice, doll. 

First: youtube tutorials. I watched dozens of them. Dozens and dozens. There’s no one correct way to manage the wingtip, so the more tutorials you watch, the better off you’ll be at finding a way (or combination of ways) that works for you. Some ladies recommend a bit of sticky tape along the eyeline. Others recommend a dot for you to connect. Others do this weird pencil angle in line with the end of your eye brows. Find a way that makes sense to you.

Second: try different applicators. You won’t know what’s right for you until you’ve tried a few different applicators. I started with a (cheap) pencil. It didn’t work out. Next I tried a sponge tip applicator. Again, fail. There was even some sort of felt-tip applicator. I finally settled on an angled brush from MAC.

Which leads me to: go to a makeup counter and talk to someone. Tell them what you want, and let them help you. I’d advise going at a time that’s unlikely to be busy so they can really help you rather than just giving you shitty “I’m in a rush” help. I went to a MAC counter at 9am on a weekday and spent half an hour with a young lady who showed me MAC’s range of eyeliner applicators. Weirdly the brush immediately stood out to me and I knew it would work before I’d even tried it - as odd as it might seem, I had a beautiful calligraphy style in my teens and then three years in Japan (lots of exposure to messages inked by slanted brushes) meant I had a bit of a feel for how to use an angled tip.

Also: you’ll hear this a lot, but you really do get what you pay for. My first black eyeliner pencil was some cheapy from a chemist. It smudged, the tip constantly broke or went blunt within two seconds … even if I’d been a pro at makeup, I couldn’t have got a decent line with that thing.

And now. Practice. Experiment. Put time aside to play with the different tools you’ve got, and do it over and over. Don’t expect to pay $40 for a brush and another $40 for a pot of ink and be able to whip something perfect up 30 minutes before you leave the house.

Personally, I use a combination of both a black pencil and the angled brushed with a pot of ‘ink’. I lightly pencil out my line above my eyelashes first, and only when I’m happy with that do I pick up the brush. I then use the angled brush to create my little ‘wingtips’ on each eye, and then I also paint over the pencil (I use a MAC one, and I find it smudges like hell if I don’t seal over it with the paint - I’m really just using it to lay down the groundwork).

Bonus tip: if you’re right handed, when you’re drawing your line, support your right elbow as much as possible, whether you’re leaning on your bench or against a mirror or simply propping with your left hand. If you’re left handed, vice versa.

And because I’m really quite crap and rarely, rarely create the perfect wingtip on the first try … I keep a heap of cotton buds on hand with some makeup remover, and if I need to I just gently ‘erase’ any messy bits. Or I’ll thin out a thick line and make it much more delicate and pointed, depending on the look I’m going for.

I’ve been wearing the wingtip eyeliner for two years now and still muck it up all the time, so I always start an hour before I leave the house. Inevitably I’ll end up with two neat and tidy lines - then when I stare at my face front on in the mirror I’ll realise they’re crooked and have to start over again!