5 Annie Lennox Inspired Makeup Looks, From The Black Eyeshadow Mask To The Edward Mapplethorpe Portrait

Annie Lennox is pretty incredible, isn't she? After a brief trip down musical memory lane the other day, I was inspired to recreate some of Annie Lennox's makeup looks made famous by various videos, album covers, and performances, in hopes of paying tribute to the enigmatic woman behind some of my favorite songs. For decades, Lennox has been influencing millions of fans with her bold, unabashedly original sense of style. From natural and demure, to striking, Bowie-esque transformations, Lennox never seems to shy away from a visual challenge (or from voicing her opinion regarding twerking, even when it contradicts popular opinion). Perhaps that's why even her most stark looks work so well — she couples them with fearlessness.

Of course, wild eye shadow combinations that speak more to '80s music videos and cartoon robbery costumes aren't necessarily makeup looks that we can use practically each day. Fearlessness, however, is something we can. And often, pushing the limits of our perceived norms teaches us a bit about our own fearlessness — even if we're only playing with fun makeup styles in our bathroom mirrors. In adapting someone else's (sometimes extreme) style for a bit, we have the opportunity to address our insecurities, to learn new techniques, and to add to our toolkit new methods of highlighting our strengths. So, I did just that, and took to my mirror, makeup in hand (or on counter, truthfully), ready to spend a few hours in Lennox's shoes, visually speaking.

1. Vogue

I began my trip down Lennox lane with a look she sported for About Face in Vogue, circa 1992, just after the release of her first solo album, Diva. It seemed an appropriate place to begin, since Vogue is well, Vogue, and within the article, Lennox and author Richard Alleman discuss Lennox's use of makeup and clothing during performances.

This look is pretty typical of the early '90s, and features strong brows, strong eyeliner, and rich lips. The understated, classic lines look lovely on Lennox's defined features, which are further highlighted by her ultra short pixie haircut.

So, to start my recreation (and each look, from here forth), I began with a light coat of primer and finishing powder. Since I'm not personally a big fan of foundation, I don't use much (my skin is happiest without), but obviously, feel free to cater this look to your needs, and use whatever basic base you normally start with. That being said, I wouldn't, however, pair this look with contouring, at least not to achieve the straight forward, clear skin Lennox features above.

From here, I used a white shadow to line below my brows as a highlight, bringing the color down to my lids, and applying a healthy amount near my inner lid and the corner of my eye. For this I switch between working with my finger, working with a medium rounded brush, and working with a petite detail brush.

Next, I focus on adding definition to my brows, which, in case I've failed to mention in the past, I hate. Bless your heart if you feel comfortable and confident in the land of strong brows, but when it comes to my face, applying them and wearing them in public is enough to make me cringe.

Blech. Look at those two gross caterpillars, just camping out above my eyes. Get off of me, will ya? Sheesh.

Anyway, getting back to the task at hand, it's time to refresh the white color on the corner of the inner eye, then apply a strong, black eyeliner. I choose to brush on my black eyeshadow (specifically the black from Kat Von D's Interstellar Eyeshadow Palette), since I feel I have greater control that way, and experience less irritation than with an eye pencil, but to each their own.

Urban Decay Perversion Mascara, $23, Sephora

To do this look justice, you'll want to fully line your upper lid, and the outer edge of your lower lid, gently tapering off your liner as you near the inner corner of your eye. Then, finish things off with a strong black mascara, like Urban Decay's Perversion Mascara.

2. Edward Mapplethorpe Portrait

Next up I tackled the look Lennox had suspended in time by portrait photographer Edward Mapplethorpe. This iconic image features makeup not far off from the look above, so I simply added to the existing base of strong brows, highlighted lids, and black eyeliner to create further depth and dimension.

To do this, I used my eyeliner brush to gently pull down the black line, giving it a softer, slightly smoky effect. Then, I added both a cocoa colored shadow and the same black shadow from the eyeliner to my crease and the outer corner of my eyelids, blending them gently around my lower brow.

Voila! Pretty simple.

Were I doing this look from scratch, I probably would have saved the eyeliner and mascara for last in order to create really rich color, but I think the look works well anyway. Here it is in black and white, for a better comparison. (Please excuse my shower curtain.)

3. Medusa

This makeup look is for all of my less is more ladies out there. On the cover of her Medusa album, Lennox went simple and understated, featuring a softer, more feminine image of herself. Since this isn't too far off from my daily comfort zone, I thought it would be a nice hat tip to Lennox and her current stance on wanting to remain as natural looking as possible as she ages.

On the cover of her most recent album, Nostalgia, Lennox opted for an image with very minimal retouching, and even less stylized makeup. Of course, that doesn't make for a very exciting recreation, so the cover of the Medusa album makes for a nice compromise.

I left my brows natural (phew!), added a bit of light beige eyeshadow just below my brows as a subtle highlight, and swept just a touch of a similar color to my lids. Then, I applied black eyeshadow as liner to my eyelids and water line, dragging the pigment away from the edge to create a smoky look. To top it off, I applied a light coat of nude lipstick to further subdue my lips. The final effect? Subtle, and a little bit sultry.

4. "Why"

Melodic and a bit haunting, Lennox's music video to the song "Why" features a very iconic look. It's a glam-pop sort of vibe, and exceptionally striking. I knew straight away it was a look I'd want to feature, but I also knew I'd be mellowing it out just slightly, since my color palette is slightly less vibrant these days.

However, thanks to a dear friend of mine who creates natural, mineral based makeup, I was able to create something fairly similar without having to spend extra on a new M.A.C. eyeshadow palette.

As you can see, this look began with lined lids, a touch of mascara, and a soft yellow shadow for a base. I applied the shadow beneath my brow, dragging it down to cover the entire lid, as a subtle foundation. Looking back at the end result, I wish I had applied a stronger coat of primer to begin with, to really help each color pop and blend.

Next, I began the process of blending in a rusty color to add some depth around the outer edges and crease of my brow. (Hello, awkward one-eyed glance!)

From here, things start to get a bit more interesting. I applied a salmon colored shadow to the inner edge of my eye, dragging it all the way around the eyelid to form a bright line of color.

To finish out the look, I added two more shades, beginning with a soft purple, mostly matte eyeshadow, which I blended into the salmon. Then, I created a smoky outer corner with a darker shade of eyeshadow, which I also used to redefine my eye line. Finally, I reapplied a coat of mascara. More subdued than Lennox's look overall, but something you might be able to use outside of a music video, and still quite a bit of fun, especially for summer.

5. "Under Pressure"

In 1992, Lennox and David Bowie sang Queen's "Under Pressure" as a duet during the Freddie Mercury Tribute Concert. The event was held in memory of Mercury, who had passed away of AIDS in 1991. During the stunning performance, Lennox wore a striking black metallic and tulle floor length gown, and donned a fierce black shadow mask coupled with pure red lips. If you're looking to step outside of your comfort zone, this is a look that will help you achieve just that.

Start out simple. Line your eyes with black liner or shadow, making sure to cover the water lines, since you're going for a rather stark effect. Apply mascara, then trace a rough outline with black eyeshadow, marking where you want your "mask" to lay. Fill in the remainder with more black eyeshadow, and...

Bam! There you are. A bit creepy? Maybe. Feeling somewhere between Furiosa of Mad Max: Fury Road and Lennox? Almost certainly. Inspired to new levels of fierceness? Without a doubt.

Images: Jen Schildgen; martinsrobertto, sharevolution, queenviqtoria, shesgotmoxiee, piririff/Instagram