Kat Dennings, Before and After

“I hate to be predictable, but I think Marilyn Monroe put that seed in my head that red lipstick equals glamour and confidence,” says Kat Dennings. “Honestly now, if I’m not wearing a colourful lip or at least like a deep lip, I feel like my face looks weird.”1

The 36-year-old star of 2 Broke Girls and Dollface is so devoted to bold lipstick, she hasn’t walked the red carpet without it for a least a decade. (And she actually started wearing it as young as 14.)

But those of us who pay close attention to celebrity makeup looks noticed something else over the years—something underneath the lipstick. Kat’s upper lip has always been distinctly fuller than the lower one, which is not the norm.

That got me thinking. Was Kat the original Kylie Jenner? Or does she just know how to wield a lip pencil, and was overdrawing her lip line (long before that was a thing)?

Let’s take a closer look at her beauty evolution, and see how her lips—or any other features!—may have changed.

From 2001 to 2002: Kat as a Teen
At the 2001 WB Television Upfront

Our first pic dates back to 2001, when Kat was just 14. At this point, she’d already been acting for five years, and was graduating high school early in order to move to Los Angeles as a full-time actress. Here, she was wearing her beloved red lip colour. (“I’ve been wearing red lipstick since I was, like, 14 years old.”1) Also note how her nose was more prominent.

At the 2002 Starlight Children’s Foundation Fundraiser

The next year, she went even bolder with her makeup, and it’s actually pretty similar to some of the looks she’s worn more recently! “One holiday, my mom got me a book called Making Faces by Kevyn Aucoin. He was this unbelievable makeup artist, and this is an instructional book about how to put on makeup and to do different looks. I would go to my mirror, sit down, and just spend hours trying to re-create the photos.” Again, you can see that her nose bears little resemblance to the nose she has today.

From 2005 to 2011: Supporting Roles
At the 2005 Los Angeles Premiere of ‘The 40-Year-Old Virgin’

By age 19, her full-time acting career was taking off, thanks to supporting roles in movies like The 40-Year-Old Virgin. Even still, my guess is that she did this makeup herself, since it’s her favourite combination of a dark lip with a wash of smoky eyeshadow. I don’t think her features have changed… yet. Her top lip seems about equal in size to the lower one.

At the 2006 Los Angeles Premiere of ‘Big Momma’s House 2’

The makeup intensified in 2006, and sure, it’s a little overdone. On most people, it would look ridiculous, but there’s just something about Kat—she can pull off these deep and cool tones like nobody else. This is also a rare photo where we get to see her teeth, which weren’t Hollywood perfect (she has a couple little gaps).

At the 2007 World Premiere of ‘I Now Pronounce You Chuck & Larry’

The next year, she stepped out with a new look, but this time, I don’t think it was just the makeup. Sure, the application seems more polished (probably because she started working with a professional makeup artist, as celebs always do once they achieve career success). But it also seems like her nose is narrower, and her upper lip has suddenly inflated in size. Notice how her Cupid’s bow has disappeared.

At the 2008 Los Angeles Premiere of ‘The House Bunny’

Here, Kat finally ventured out of her red lip comfort zone and wore a bold pop of pink. Anything cool-toned just works so well with her colouring. The lipstick also matches the step and repeat banner that she’s posing in front of, which adds to the effect. With her nose less prominent now, her lips and eyes stand out much more. (I just don’t get the need for over-lining that top lip, when it’s already twice the size of the lower one!)

At the 2009 Nylon Young Hollywood Issue Party

The next year, Kat didn’t hold back on the dramatic makeup for this event. She later recalled: “I was a hot mess for a long time because I loved trying everything and I thought I was kind of a genius with my look, which I was, kind of, looking back.”2 It’s giving Goth vibes, but I actually don’t hate it!

At the 2010 Vanity Fair Oscar Party

Then, there was that one—and only—time that she experimented with warm tones. We’ve got gold and brown smoky eyes to match the extravagant gold jewellery, paired with a warm, brick-toned lipstick. Even her foundation shade looks slightly yellow. If there was any doubt that Kat looks best in cool-toned colours, this should settle the debate!

At the 2011 Los Angeles Premiere of ‘Thor’

That’s better! At age 25, she was the height of glamour in this 1980s-inspired look. I don’t know why she doesn’t wear her naturally curly hair like this more often. It’s so good with the equally dramatic lips and eyes (usually a no-no, but some beauty rules are meant to be broken!).

From 2012 to 2015: Not-So-Broke Girl
At the 2012 CBS, CW and Showtime Summer TCA Party

Kat made the move back to TV when she was cast in 2 Broke Girls. (“I was at a point where I was just like, ‘I really want people to see this work that I do.’ I don’t mean fame. I don’t mean money. I don’t mean any of that. But it’s been 15 years, and I would like to work hard and have it seen for once. This literally fell in my lap right at the moment I was feeling that way.”3)

Since TV shows don’t have the same budgets as films, I suspect that meant going back to doing her own makeup for certain events. Don’t get me wrong, I still think she looks great here—but I don’t think the eyeliner has the finesse of a pro makeup artist.

At the 2013 Grammy Awards

However, she did work with a celebrity makeup artist for this event—and the result was one of her best beauty moments of all time. It’s still all very “Kat,” what with the vampy lips, winged liner and smooth waves. It’s just more refined.

At the 2014 People’s Choice Awards

By 2014, the winged liner was here to stay. (She explained: “I don’t think it’s a secret that I love a cat eye. That’s my thing.”4) This time, she paired it with soft waves, a sparkly headband, and a brighter raspberry lipstick. Speaking of the latter, she doesn’t seem to be over-lining her top lip quite as much.

At the 2015 People’s Choice Awards

For the same event a year later, Kat stayed in her makeup wheelhouse. It’s yet another variation on the red lips, cat eyes and smoky eyeshadow that we’ve now seen many times before. While she used to play up her top lip, here it almost looks like she’s trying to tone down the size discrepancy with blotted, blurred effect on the upper edge.

From 2018 to 2019: Signature Style
At the 2018 Baby2Baby Gala

In recent years, Kat hasn’t been in the public eye as often, since 2 Broke Girls was cancelled in 2017. But she made a memorable return in 2018 with a bolder beauty look than we’ve ever seen before. She dialled up the drama with shimmery, smoky eyes, and then paired them with an equally intense matte berry lipstick. Honestly, I love it (and that’s saying a lot, because I’m a makeup minimalist!).

But that’s not all—she also deepened her hair colour to an almost-black shade. Here’s the reason why: “I don’t mind telling you that I have gotten so many gray hairs. It’s, like, making me really upset. I don’t know what to do about it. So I’m in this weird place of, like, do I start dyeing my hair? Do I just give in to this happening?”4

At the 2019 PaleyFest Fall TV Previews Presentation for ‘Dollface’

That brings us to one of Kat’s most recent appearances. Clearly, she’s found her signature style and she’s sticking to it! What I find most interesting here is that her lips are looking far more symmetrical than they once did. No, the Cupid’s bow hasn’t come back, but the top one is no longer dwarfing the lower one in size.

Kat Dennings Before and After
Kat in 2002 vs 2019

Some things about Kat haven’t changed at all in the 17 years between these photos. She still loves her dark lipstick, pink blush and eyeshadow. And even though she has started dyeing her hair, the new colour is pretty close to her natural hue.

But it’s clear to any observer that the shape of her nose is no longer the same, which suggests that she probably had a rhinoplasty surgery early on in her career. Her nose is noticeably narrower now, and you can see the distinct indentations on each side, likely from the removal of nasal cartilage.

The other feature that has changed is her lips. In her teenage years, her lips appeared about equal in proportion, and in 2005, you could clearly see her Cupid’s bow. But suddenly, her upper lip became much fuller, and looked unnatural. “The upper lip should be smaller than the lower lip by the golden ratio of phi, 1:1.6,” says Dr. Steven Weiner. “If the doctor does not abide by normal anatomic ratios, the lips look done and abnormal.”5

Another thing you may have noticed about Kat’s lips is that (until recently), the shape was always the same. That doesn’t happen with fillers, since the hyaluronic acid gets slowly absorbed by the body. So I’m wondering if she may have had a more permanent procedure, like a lip implant, back in the day. (I have the same theory about Jessica Biel. Lip fillers weren’t common when their careers were getting started!) That said, Kat’s lips do seem more proportionate now, so either her makeup techniques have improved, or she may have had a little revision.

Although we haven’t seen her teeth lately, she’s had some dental work, too, according to Dr. Sara Chen. “The teeth are looking a little bit different now, and I don’t think that these are porcelain veneers. It looks like the diastema [gap between her teeth] is a little bit smaller. The colour’s a lot lighter. This to me looks like bleaching plus Invisalign.”