Winged Eyeliner For Deep-Set Sunken Eyes

Not like this.  Just so we're clear.
Kevyn Aucoin for Vogue, model Toneya Bird.

My eye shape isn't very common. It's a result of a bone structure that has the highest point of my cheekbone (actually it's the zygomatic bone, if I'm not mistaken) sitting not at the far out perimeter of the face pointing towards the temple, but an inch and a half closer to the center of my face and protruding straight ahead, casting a pronounced shadow on the entire under-eye area, as well as the very deep crease typical to regular deep-set eyes that comes with a very visible mobile lid.

My attempt at illustrating (copy/pasting various parts and lines, that is) my general eye shape.

This is what happens when trying to do a regular flick/wing. My sharp crease breaks the line and the colors actually pools inside.

This face situation has various consequences when it comes to makeup. Contour placement is extremely tricky if not completely useless. More frustrating than that is how my eye makeup needs to account for an under-eye shadow that can be slightly brightened but not erased. Nowadays it's fairly common to use fillers under the eye to make the area flat. However, I'm utterly freaked out by procedures this close to my eyes. My sight has been going downhill at an alarming pace and I'd rather not take any unnecessary risks, even the most remote and unlikely. I already know to expect cataracts in both eyes by the time I reach 60 (genetics. Thanks, dad and grandpa). I'm not happy about it, so I'm letting my eyes be until they need real medical intervention.

More than you've bargained for. No filters and no makeup other than a hint of concealer (Etude House BB Concealer) around the nose and Charlotte Tilbury Hollywood Filter across the cheeks for the sake of dimension.

Back to makeup. the only color makeup I apply under the eyes is light and bright, never a full-on grungy black smoky eye.  Also, since my mobile lid sits so low (deep) under the bone, I can't just run a line from the lashline to the brow bone. A regular wing or a cat-eye simply can't work because the start and finish points would never align. Still, I wear eyeliner, and quite a bit of it. I even like to cheat a winged look quite often. One way to do it is by placing a few clusters (or a chopped strip) of false lashes right at the outer corner of the eye and curl them up to outer space (actress Jamie-Lynn Sigler who shares a similar eye shape to mine* has worn this look on several red carpet occasions). I do that once in a very blue moon, but  can't say I enjoy messing with the glue and placement. What I do is draw the faux wing on the mobile lid itself using either a liquid or a liquid pen eyeliner (gel and an angled brush also work. It's just a matter of preference). I take advantage of the large space of my mobile lid and take the line up as far out as I can, so it's visible when the eye is open.

An action shot attempt. You can see I'm straining to control the various elements from the remote to the eyeliner wand, but the point is to show you where to take the line and how far one can go.

A key to this technique is using a magnifying mirror and turning my head slightly to the side opposite the wing while looking towards the eye I'm lining. This way I can see exactly how far I can take the wing. Once it's up I look straight ahead and fill the gap between the eyeliner and lash line as accurately as possible, then clean up mistakes where I've colored outside the line with a makeup wipe and blot it with a tissue. That's it. All done. The key, as with most things in life is not to hold one's breath while drawing your eyeliner. It's true no matter the eye shape or technique, because the second you involuntarily exhale your hand will move in the wrong direction (best case. Worst case is stabbing yourself in the eye).

In this demo I've used a bold color (Nyx Vivid Bright in Vivid Envy, $4.90 at Ulta, and now I finally know what possessed me to buy it. It definitely stands out even in bad lighting), so you can see exactly what I'm doing and where the line goes. Obviously it's the same thing with a black eyeliner, just without evoking Kermit the frog. The other eye makeup I used here and above (except in the  pre-makeup shot are a light champagne eye shadow all over the lid and a light/medium brown in the crease.  Both are from Chanel LES 9 OMBRES Multi-Effects Eyeshadow Palette in Quintessence ($70, Bloomingdale's), but obviously anything goes and this is not a full or even planned eye makeup look. I also used one coat of Lancome Monsieur Big mascara for balance and contras against the green.

That's my trick for a slightly more dramatic eyeliner application for a truly difficult eye shape. This basic line can be the finishing touch for a sophisticated eye shadow placement and go with a elongated shape created with a medium-dark eye shadow color, tightlining or a cut crease.


*Jamie-Lynn also had a similar nose to mine, but she took care of that early on, circa the second season of The Sopranos. Good for her.