Important Friday business here–we’re talking lipstick, specifically RED lipstick, the Little Black Dress of the makeup world. I started wearing lipstick when I was a teenager, awkwardly stumbling into the makeup world with a multi-year commitment to Revlon’s Toast of New York, a brownish almost red that was popular in the 90’s and was a safe enough step down from a fiery red for a churchy homeschooled girl who burned her BMG CD collection because it was worldly. The store aisle ads of Cindy Crawford said she was wearing Toast of New York, and everyone in the Speigel and Chadwicks catalogues at that time seemed to be wearing a similar combination of brown + red + pink, so I felt “in” with the lipstick crowd. It wasn’t until years later that I’d step into the magical Land of Red with a swipe of Ruby Woo, and ever since there’s been a tube of red at the bottom of every purse I own. While I don’t wear red lipstick everyday (I’m having a current affair with Red’s cousin, Pinky Nude), I will forever be entranced by its instant transformative powers. Red pulls me together when I’m falling apart. It’s the smoke and mirrors I need on days when I’m feeling tired or doubtful: “I’m awake!” “I’m feeling bold!” And it classically pairs both with a black dress or jeans & white t-shirt as if they were made for each other. However, while there aren’t that many shades of black when it comes to dresses, there are numerous shades of red lipstick; and not all are equal.

Before I get to my favorite reds, here are a few red rules I live by:

1)  ANYONE CAN WEAR RED LIPSTICK! TRY IT! It’s the same rule that applies to hats. Anyone can be “hat girl,” but people shy away from a hat they really want to wear because they feel awkward the first time they wear one. You do not have to have a history of bold fashion choices to make a bold fashion choice, and red lipstick isn’t just for risk-takers. It’s classic. No one’s thinking about your lipstick except you, so get out of your head and wear the lipstick–don’t let the lipstick wear you.

2) Go light on the rest of the make-up. It’s like jewelry. If you’re wearing statement earrings, don’t also wear a statement necklace. Red lips are a statement, and they need to be balanced with lighter make-up on the rest of the face. I love a good smoky eye but only with nude lips. When I wear red lipstick, I try and keep everything else light and bright. Leave the gun, take the cannoli. Skip the dark eyeshadow, wear the red lipstick.

3) Define the edges. I might be able to apply nude lipstick blindly in the car while I’m driving and get away with it, but not red. I use red lipliner when I’m wearing red lipstick–or at least a super tedious application so that there’s no red bleeding out past my lip line.

4) Shade and texture matter. Sometimes, if I’m wearing something orangey, I’ll wear an orangey red lipstick; but for the most part, I like a classic red that has cooler tones because it makes your teeth look whiter. This is also true with texture. I love a good matte lipstick, but anything too matte can highlight stained teeth and make your lips look dry. If I wear matte, I always swipe on a little lip balm first and sometimes a little on top as well.

My Favorite Reds

Stila Stay All Day Matte’ificent Lipstik in Bisou – I get compliments every time I wear this, and it’s my go-to red lately. It’s matte but really soft and moisturizing, and it’s the perfect shade of classic red.

Revlon Ultra HD Matte Lipcolor in Love (625) – It looks like a gloss but applies matte, and it’s fabulous. Also, bonus points for inexpensive. It’s a bright fire engine red and all you need for a red lipstick if you want to keep your makeup budget at the drug store level.

Sonia Kashuk Poppy Nude 03 Velvety Matte Lip Crayon – I don’t know why the word “nude” is in this color because it’s clearly red. This is a little warmer red–great for spring and summer–and I love it. I also love that it’s a crayon (looks like a fat pencil) because I can use it as both liner and lipstick, and it applies really clean. Bonus? Inexpensive, easy to pick up on a Target run.

MAC Ruby Woo – (matte) It’s a cult classic and probably MAC’s most “signature” red. I’ve worn this shade for years and I find old tubes in sweater pockets and old purses.

MAC Russian Red — (matte) A cool-toned crimson. Did you know it was created for Madonna for her Blonde Ambition tour in 1990? It was during her cone bra stage, and MAC made it to match that vampy vibe of the tour.

MAC Powder Kiss in Style Shocked– This is my favorite orangey red (when I’m wearing something coral or orange). And I love the finish–it’s a moisture matte. You still get the look of matte but without feeling like you’re dragging a broken crayon across your lips. Weightless and non-drying.