Applying a Base
Wash your hands thoroughly with soap before you start. You should always wash your hands before applying makeup, especially around the eyes. Oil can be transferred from your hands to your face, which can cause breakouts or blemishes.
Choose your base. You can use a regular concealer, or a product specifically designed as an eyeshadow primer. The base layer will smooth out your complexion and act as a blank slate for your eyeshadow, allowing it to adhere better.
Apply primer with your fingers. Taking a small amount, dab the base layer onto your upper eyelid. Smooth the primer into one thin and even layer that starts at the edge of your upper eyelid and up to the crease of your eye.
Do the same for your other eye. Apply the base in the same way, smoothing it across your whole eyelid. Make sure that you use the same thickness and shape on the other side of your face.
Using Your Eyeliner
Choose your eyeliner. Kohl pencils are perfect for the Jack Sparrow look, as they are made of compressed soot and other natural ingredients that make a smoother, softer line than regular eyeliners. Regular black eyeliner will work too, but it won’t blend as well.
Lift your eyelid. Using your non-dominant hand, pull your eyebrow up in the center to lift and smooth your eyelid. This will put tension on your eyelid and give you a firmer surface to work with.
Apply a medium sized line to your upper lid. Start at the inside corner of your upper lid, and draw a smooth and even line to the outside corner of your eyelid. The line should be the same thickness all the way across. Hold your elbow on a table or counter while drawing to help stabilize your arm.
Adjust as needed. Since this look uses a heavy amount of eyeliner and will be blended at the end, you can fill in gaps or mistakes with a little more liner as needed. The most important thing is to make sure it’s a strong line of even thickness.
Pull down your lower lid. Place your finger in the middle of your lower lid, again using your non-dominant hand. Gently pull down until you can see your water line, or the wet part of your lower eyelid.
Apply eyeliner to your bottom lid. Starting at the inside corner of your eyelid, draw your lower line with the same thickness as the eyeliner on your upper lid. Adjust as necessary to make sure it’s thick and even.
Line your other eye. Line both your upper and lower eyelids in exactly the same way as your first eye, with the same thickness and darkness. If you find one is dramatically different than the other when you finish, adjust as necessary, filling in any gaps or thickening up the thinner line.
Applying Eyeshadow
Choose your eyeshadow and brush. Any black or dark gray eyeshadow will do: the darker the better. You’ll also want a small, rounded brush to apply the shadow. You won’t need anything super expensive for this look, because it will all be blended together at the end, but look for brushes labeled “allover eye shadow” or “general use eye shadow”.
Apply the shadow on your upper lid. Go dark, using much more dark shadow than you normally might. Brush from the inside corner to the outside corner, sweeping up to the crease of your eyelid, where Jack Sparrow’s makeup stops. Make sure it’s smooth and even, with no gaps or darker spots.
Do the same underneath your eyes. Cover the whole of your bottom lid, again applying the makeup as thick as possible. You don’t want to apply as low on your lower eyelid as you did up on your upper eyelid: about half a centimeter down should do.
Apply eyeshadow to your other eye. Again, use the same technique on your other eye. Adjust if you find that one eye looks a bit different than the other.
Blending the Makeup
Use your fingers to blend both eyes. While there are some brushes specifically made for blending, the messy style worn by Jack Sparrow won’t need that kind of specialized brush. Again, make sure that your hands are clean and dry.
Use one finger to blend the upper lids. Blend the eyeshadow and eyeliner together to create a smoky, matte texture, starting at the inner corner of your eye and working up and out. Drag a bit of the powder up above your eyelid crease to create a bit of gradient.
Smooth your lower lids. Using the same finger, blend the eyeliner and shadow starting at the inner corner and working towards the outer corner. Jack Sparrow’s lower eyeliner is a bit more defined than that on his upper lid, so blend a little less than you did on the top lid.
Apply translucent powder. A little powder applied at the end will help set your makeup and keep it from moving or smearing more throughout the day. Use a large brush to gently place the powder over your look and set it.
Apply mascara if you want. Mascara can help make this look pop a bit more if you feel that your eyelashes are too thin. Use a black mascara that emphasizes volume and not length, as Jack Sparrow’s eyelashes aren’t particularly long.
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