There’s something timeless about red lipstick. It’s not just makeup—it’s a statement. Of power. Of confidence. Of refusing to shrink.
This National Lipstick Day, I’m celebrating the boldest shade of all—red—and what it means to wear it unapologetically at 56.
A Little Red Lipstick History
Red lipstick has been around for centuries—Cleopatra was said to crush beetles to make hers, and ancient Sumerians mixed gemstones with oils to tint their lips. But it really took off in the 20th century.
During World War II, women were encouraged to wear red lipstick as a symbol of strength and patriotism. It was worn by suffragettes, flappers, movie stars, and rule-breakers. In fact, red lipstick was once considered rebellious—too bold, too “much.” And that’s exactly what makes it powerful.
What Red Lipstick Means at Midlife
Wearing red lipstick at 56 isn’t about trying to reclaim youth. It’s about owning every year, every line, and every ounce of fire still burning inside.
It says:
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I’m here, and I’m not dimming down.
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I’ve earned this confidence.
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I don’t need permission to be bold.
For me, red lipstick is less about impressing anyone and more about remembering who I am, on the days I feel like I’ve forgotten.
Why It’s in the Wear the Damn Boots Confidence Kit
Red lipstick is an essential part of the Confidence Kit—not because it’s trendy or perfect, but because it’s transformational.
That little tube holds a message:
You can be bold. You can show up. You can take up space.
It’s for the mornings you need a reminder.
The dinners you almost talk yourself out of.
The days when confidence feels just out of reach—until you swipe it on and remember, oh right, she’s still in there.
Red lipstick is a tool, a symbol, and a secret weapon in every midlife woman’s toolkit.
Just like the damn boots—you put it on, and you step into your power.
How to Find Your Perfect Red
Red lipstick isn’t one-size-fits-all. The right shade can make your eyes brighter, your skin glow, and your whole mood shift. Here are a few tips to help you find a red that lights you up:
Based on Skin Tone:
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Fair Skin: Look for blue-based reds like cherry or true red. They balance cool undertones and make teeth look whiter.
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Medium/Olive Skin: Orange-reds, poppy, and brick tones flatter beautifully.
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Deep Skin: Try bold berry reds, oxblood, or classic scarlet—they’re rich and stunning.
Based on Hair Color:
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Gray or Silver Hair: True reds and cool-toned reds pop against silver and give a chic contrast.
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Brunettes: Deep reds like wine, crimson, and burgundy enhance warmth and richness.
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Blondes: Coral-reds or blue-reds offer a bright, balanced look.
Tip: Try it on and leave it on. Sometimes red feels “too much” at first—until you see how it changes your whole posture.
A Few of My Red Lip Favorites
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Jane Iredale ColorLuxe Hydrating Cream Lipstick– glides on smooth and wraps lips in moisture for the perfect lip. Candy Apple, a cool medium-dark red is my go-to red.
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RMS Beauty Legendary Serum Lipstick– a lipstick, serum, and lip stain hybrid with long-lasting color. Ruby Moon, a poppy orange-red, is my favorite.
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Ilia Balmy Tint Hydrating Lip Balm – a tinted lip balm, for sheer buildable color. Heartbeats, a warm red, looks great with anything.
- Jane Iredale HydroPure Hyaluronic Lip Gloss– a soft gloss for fuller, supple lips. Berry Red, sheer berry red is always in my purse.
So, Will You Wear the Red?
On National Lipstick Day, I invite you to do what women have done for centuries—reach for the red and claim your space.
Whether you’re running errands, heading to dinner, or just looking in the mirror, wear it for you. You don’t need a special occasion.
Red lipstick is the occasion.
P.S. If you’re nervous to try, start by blotting it down into a stain. Or wear it with your comfiest jeans. Confidence doesn’t come from the lipstick—it comes from the woman wearing it.
