Tomboy Makeup Made Glam For The Holidays

Here's how I get glam for the holidays while staying true to my boyish style.
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Here's how I get glam for the holidays while staying true to my boyish style.

If you ask my mom, "tomboy" is code for being lazy about your appearance. But it’s really about being comfortable in my own skin, and the times when I’m most comfortable, I’m probably not wearing makeup and I'm wearing jeans and a flannel.

That's not to say that I don’t ever dress up or even that I don’t LIKE dressing up--I love it. Finding a look that is simultaneously glamorous and true to my tomboy style might seem paradoxical, but if you remember what tomboy style is all about (simplicity, efficiency, and confidence) it makes total sense.

Tomboy Fragrances To Layer 

Fragrance is one of my favorite ways to express tomboy glamour. Here are two combos I’ll be taking out on the town a lot this winter.

juniper ridge big sur

L-R: Creed Fleurs de Gardenia; Juniper Ridge Big Sur Backpacker Cologne. Is there anything more glamorous than Creed? I’m not sure there is.

Juniper Ridge Big Sur Backpacker Cologne (named for my favorite place in the world) smells exactly like the air when you’re hiking through the coastal redwoods of central California. It’s woody, herbal, and it has a touch marine. Creed Fleurs de Gardenia is a greener take on a big white floral that plays shockingly well with Big Sur. The effect is like being hugged by a lumberjack and his gorgeous wife at the same time (file under: life goals).

kiehls original musk

L-R: Kiehl’s Original Musk and In Fiore Fumee D’Ambre. A sexy pair.

I’ve written about both In Fiore Fumee D’Ambre and Kiehl's Original Musk before, and they pair amazingly. They both have notes of patchouli, but the round amber and the verdant musk work to create layers and keep it from becoming a head shop mess. It’s a sultry combination that gives me a little rush every time I smell it.

Tomboy Makeup Made Glam For The Holidays 

Tomboy makeup is (I guess) the same as “effortless beauty,” but I hate that term because it’s a lie and it doesn’t mean anything. 

For me, it’s about an even glowing complexion, well-defined eyes, and your favorite lip. Since it’s the holiday season and we’re talking about glamour, I thought I’d throw in a little sparkle for good measure.

makeup products

Top Row: Lipstick Queen Medieval, Lipstick Queen Sinner, Make Up For Ever Smoky Extravagant Mascara, BECCA Shimmering Skin Perfector, Estee Lauder Double Wear Stay-in-Place Makeup. Middle Row: Laura Mercier Secret Camouflage, Make Up For Ever Aqua Brows, Hourglass Ambient Lighting Powder, NARS Blush. Bottom Row: Clio Gelpresso Waterproof Pencil Gel Liner.

I started out with Estée Lauder Double Wear Light Stay-in-Place Makeup to create the flawless skin I do not have. Since special occasions deserve special effort, I used Laura Mercier Secret Camouflage (thanks for the heads up, DaMonica!) to deal with my dark circles and some pimples. I filled in my brows a little heavier than usual (night brows are a thing, right?) with Make Up For Ever Aqua Brows and got ready to play.

foundation applied after

Foundation, concealer, and brows applied. Working on my Night Brows…

I am obsessed with this Clio Gelpresso Waterproof Pencil Gel Liner in Golden Black. It’s just as dramatic as plain black liner but the gold flecks give it sparkle and dimension. I use this to tightline my upper and lower lash line. After letting that set for a second, I add another thin line on the upper lash line, smudging it lightly. Finish the look by loading up lashes with Make Up For Ever Smoky Extravagant Mascara in Black, which is my go-to for night time.

tighline lash line

Eyes lined and lightly smudged, three coats of mascara, top and bottom lashes.

Y’all, Hourglass Ambient Lighting Powder is just the best. It is so finely milled that when applied, it makes your skin look airbrushed. It blends so well you can’t tell where the glow is coming from, it just looks like there’s light radiating from your skin. I use the Radiant Light shade to highlight my cheekbones, temples, down the middle of my nose, forehead, Cupid’s bow, and chin. 

Afterward, I apply NARS Blush in Seduction (a deep berry) to the apples of my cheeks and blend back towards my hairline. After I’ve blended my blush and highlight I add a little extra shimmer (all gold everything, please) to my cheekbones using my other favorite highlight, BECCA Shimmering Skin Perfector in Topaz.

For my lips I apply two coats of Lipstick Queen Sinner in Wine blotting after each layer. I'm not going for a perfectly applied lip, I just want to deeply stain my lips with the color. I top this off with Lipstick Queen Medieval (a super hydrating sheer red). The end result is a lush and shiny plum-stained lip, very Studio 54, which fills me with delight.

lipstick queen sinner wine

Top: lips stained with Sinner in Wine. Bottom: Medieval applied on top.

The final look ends up being elevated and glamorous while still maintaining a minimalist aesthetic.

glamorous holiday makeup


makeup swatches after

Top to Bottom: Clio Gelpresso Waterproof Pencil Gel Liner in Golden Black, Ambient Lighting Powder in Radiant Light, NARS Blush in Seduction, BECCA Shimmering Skin Perfector in Topaz, Lipstick Queen Sinner in Wine, Lipstick Queen Medieval.

Give me an excellent button-down shirt and this tomboy’s ready for a night on the town.

  • Any other tomboys out there who also like to glam it up?
  • What’s your version of tomboy glamour?
  • Can anyone explain why Ambient Lighting Powder is so good? Is it made of angels? Seriously, what is that stuff?!