Sherry Pie’s Drag Makeup Transformation: Step-by-Step Guide

Follow drag queen Sherry Pie’s stunning makeup transformation into the Mad Hatter in this detailed Cosmo Queens tutorial.

By Medha deb
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Sherry Pie’s Full Drag Makeup Transformation: Cosmo Queens Guide

In this Cosmo Queens episode, RuPaul’s Drag Race star Sherry Pie brings you inside her signature transformation process—from bare-faced to dramatic drag queen, embodying the Mad Hatter. Whether you’re a drag artist, a beauty enthusiast, or just curious about the artistry behind drag makeup, this step-by-step guide breaks down Sherry’s approach, revealing how to achieve a flawless, editorial-quality look at home. Sherry’s emphasis on strong contouring, bold shadow, and meticulous details makes this tutorial ideal for anyone aiming to perfect their makeup game.

Prepping the Base

Every flawless drag face starts with a smooth, well-primed base. Sherry begins by applying a light moisturizer to hydrate her skin, followed by a silicone-based primer to blur pores and create a seamless canvas. For foundation, she layers a medium-to-full coverage foundation with a moist beauty sponge, blending outward for a smooth finish. She then draws attention to color-correcting, especially for beard shadow—using a pinkish-red corrector under the foundation to neutralize any visible hair growth. This step is crucial for a convincing, gender-bending transformation.

Contouring 101: Sculpting the Face

Sherry’s signature drag look relies on dramatic contouring to sculpt facial features and create higher, more pronounced cheekbones, a slimmer nose, and a more defined jawline. She uses a brown powder to contour these areas, blending with a fluffy brush for a shadow effect, not a stripe. She contours her forehead to bring it forward, the sides of her nose to slim it, and her jawline to soften the masculine structure. This chiseled effect is the foundation of her glamorous, editorial drag face.

Baking for Longevity

To set her makeup and prevent shine, Sherry bakes her highlighted areas—applying a thick layer of translucent powder to her under-eyes, T-zone, and chin, then letting it sit while she does the rest of her makeup. After several minutes, she brushes off the excess, leaving a smooth, matte finish. This technique not only prevents creasing but also brightens and highlights the features, ensuring the makeup stays put through performances and photoshoots.

StepPurposeKey Product/Technique
MoisturizerHydrates skinLightweight moisturizer
PrimerSmooths and blursSilicone-based primer
FoundationEvens skin toneMedium-full coverage
Color correctorNeutralizes beard shadowRed/pink corrector under foundation
Contour powderSculpts featuresBrown powder, fluffy brush
BakingSets, brightensTranslucent powder, let sit

Eyeshadow and Highlighter

Sherry’s eye makeup is bold and colorful, inspired by the Mad Hatter. She creates a vibrant, editorial eye look by layering several shades of shadow, starting with a transition color, deepening the crease with a darker shade, and packing bold, metallic pigment onto the lid. She highlights her brow bone and inner corners for extra sparkle and definition. The highlighter is also used on her cheekbones and bridge of her nose for a glowing effect.

Eyebrows and Lashes

With her natural brows covered, Sherry draws new, arched brows using a pencil or pomade—placing them higher and more sculpted for a feminine, dramatic effect. For lashes, she applies falsies for maximum volume and curl, layering for extra drama. Mascara is used to blend natural and false lashes together, ensuring there are no gaps and eyes are fully accentuated.

Lip Artistry

Sherry overlines her lips for a plump, exaggerated pout, then fills in with a bold lipstick. She may add gloss or glitter for extra dimension, depending on the character she’s embodying. The lip color often coordinates with her eye makeup, tying the whole look together.

Frequently Asked Questions (FAQs)

Q: What kind of contour powder does Sherry Pie use?

A: Sherry uses a brown powder to contour, focusing on cheekbones, jawline, forehead, and nose, blending for a natural shadow effect.

Q: How does she deal with beard shadow?

A: She applies a red or pink corrector under her foundation to neutralize any visible beard shadow, ensuring a smooth, flawless base.

Q: What is baking, and why is it important in drag makeup?

A: Baking involves applying a thick layer of translucent powder to set and brighten key areas, preventing shine and creasing for a long-lasting finish.

Q: How does Sherry achieve such dramatic eyes?

A: She layers bold, colorful eyeshadows, uses false lashes, and highlights the brow bone and inner corners for extra dimension.

Q: What tools are essential for Sherry’s makeup look?

A: Key tools include sponges for foundation, fluffy brushes for blending contour, a fine pencil for brows, and lash glue for falsies.

Final Touches and Styling

After her makeup is complete, Sherry ties her look together with a Mad Hatter-inspired hat, colorful wig, and statement costume—proving that drag is as much about character and confidence as it is about makeup. Hair, nails, and accessories all play a role in elevating the overall effect.

Lessons from Sherry Pie’s Drag Transformation

Sherry’s transformation is a masterclass in drag artistry: it’s not just about covering masculine features, but about creating a new, glamorous face with strong structure, bold color, and theatrical flair. While her personal story and reputation have become controversial, her makeup techniques remain a valuable resource for drag artists and makeup lovers seeking to channel both glamour and camp.

Try It Yourself: Tips for Recreating the Look

  • Start with a clean, moisturized face and a good primer for a smooth base.
  • Contour first, highlight next—blend thoroughly for a natural, yet dramatic effect.
  • Experiment with bold colors for eyeshadow, don’t be afraid to layer and blend.
  • Set your under-eye and T-zone with translucent powder and bake for longevity.
  • For brows, draw them higher and more arched than your natural shape for an instantly feminine look.
  • Pair with a wig and costume to complete your transformation.

Conclusion

Sherry Pie’s Cosmo Queens makeup tutorial is a testament to the transformative power of makeup and drag. While the individual behind the makeup has faced controversy, the artistry, techniques, and creativity on display remain instructive for anyone interested in beauty, self-expression, and the world of drag. Whether you’re practicing at home, preparing for a gig, or simply seeking inspiration, this tutorial provides a comprehensive guide to achieving a bold, long-lasting drag face—one step at a time.

Medha Deb is an editor with a master's degree in Applied Linguistics from the University of Hyderabad. She believes that her qualification has helped her develop a deep understanding of language and its application in various contexts.

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