I was really excited to create a “pretty pirate” look for Kassy when I found out which character she would be portraying. I hear a lot of repeat requests when it comes to Halloween makeup, but I can’t say that a glamorous Captain Hook is one of them. Because this character goes against the grain, so to speak, I wanted to challenge some makeup myths as well. Everyone has heard that they shouldn’t wear a dramatic eye and a dramatic lip together, and who better than a pirate to break the age old makeup rule?

THE EYES

I know black eyeshadow can be intimidating, but Halloween is not the time to be shy! Captain Hook has some serious attitude, and I wanted her smoky eye to be dark and hazy.

  1. As always, I started with an eyeshadow primer from lashline to browbone to keep the eyeshadow in place. Because I was working with a creamier base, I expected some creasing, but I actually think this adds to the grungy and smoky effect.
  2. I laid down a black Kajal liner as a base for the smoky eye. I chose the YSL Couture Kajal liner because it has a fat tip and is so easy to blend. I used the side of the pencil to get maximum coverage from Kassy’s lash line to her crease, and softly blended the colour upwards onto her orbital bone.
  3. I also carried the liner under the lower lash line, all the way into the inner corner and added it into the top and bottom waterline for extra blackness. I buffed the liner out with a precision smudge brush to create a round shape. It’s okay if your liner isn’t perfectly straight, that’s what a smoky eye is all about. You want the edges to be smudgy and hazy.
  4. To keep the eyes blended and beautiful, I used my favourite trick. I took a little bit of a warm coloured bronzer on my blending brush and swept it through the crease and under the eye in a circular motion, creating a halo effect. This not only helps break up the black, but also creates a more cohesive look by warming up this seriously smoky eye.
  5. I patted the blackest black shadow I know of, Saucebox “Black Widow” eyeshadow, on top of the eye with the bristles of my brush pointing downwards. This technique prevents fall out and ensures maximum colour payoff.
  6. After doing one last sweep with a clean blending brush to ensure any harsh lines were buffed away, I finished the lashes with a coat of super- black mascara.

 

THE COMPLEXION

I have to say, when it comes to complexion, I’m a full-coverage kind of gal. But as a makeup artist, I know that airbrush foundation photographs best.

  1. I always prep the skin with a moisturizer before applying any foundation. Kassy was a little on the drier side, so I made sure to really work the product into the skin, and even used a few drops of a beauty oil to help the skincare absorb.
  2. I followed the moisturizer with a hydrating primer and let it soak in for a full minute.
  3. Because the coverage of airbrush makeup is more lightweight, I like to use a concealer first in any areas that require additional coverage. I used a brightener under the eyes to colour correct any darkness, and a tiny bit of a cream concealer around the nose to hide redness.
  4. Many women require the most coverage in the center of the face, so that’s where I start with the airbrush. I hold the machine at arm’s length from my client and spray in circular motions until desired coverage is achieved.
  5. I always finish with a translucent setting powder to prolong the wear of the makeup and minimize any texture.

Captain Hook doesn’t strike me as a modest character, so I skipped blush on Kassy to give her a more rebellious look. We focused on contour to give her face shape and definition.

  1. I used a cool toned contour powder to mimic the look of a shadow. To enhance Kassy’s cheekbones, I started at the top of her ear and blended the colour towards the corner of her mouth. I always start way back in the hairline with my brush to ensure a diffused look.
  2. I also took the contour colour around the hairline on the forehead, and just at the edges of Kassy’s jawline to define her bone structure. When I contour these areas, I like to use a fluffier brush for a more transparent application of product.
  3. I sharpened up my cheekbone contour by dusting a matte highlight powder along the bottom edge of the contour. After letting it set for a moment or two, I dust away any excess to reveal a seriously sharp, dramatic cheek bone.
  4. On a kabuki brush, I picked up a little of the same bronzer shade I used to warm up Kassy’s smoky eye. I dusted the bronzer on the high points of her face to add a little warmth, without making her look too “innocent”.

 

THE DETAILS

  1. Every villain (or villainess) needs a bold brow. Kassy already had a great shape going, and I played up her arches with a dark brow powder to match her black wig. I always set the brows with a wax or gel to keep any rogue hairs in place.
  2. From the moment I found out Kassy was playing Captain Hook, I knew we had to dress her up in a red lip. I chose a matte shade that was a little on the warmer side to tie in with the bronzer. I started with a lip primer to keep the colour in place. I then defined her perfect lip shape with a liner and buffed it out using a lip brush so it wouldn’t appear too harsh. I finished with the lipstick to give her a saturated, vampy pout.
  3. To give Captain Hook a glamorous twist, we added some “Face Lace” to one eye in place of an eye patch. I trimmed the decal to suit Kassy’s eye shape and adhered it using a bit of clear eyelash glue.
  4. Glam makeup just isn’t glam enough without false lashes. To finish off Kassy’s look, we added a dramatic pair that weren’t too flared out at the ends. The shape of the lash should enhance, rather than distract from the eye look.

I always finish my makeup off with a generous spritz of finishing spray to keep the look in place all night! With a little compact powder in her “treasure chest” to touch up throughout the night, and of course, her signature red lipstick, this pirate was ready to party!