Boys In Lipstick, Just Because

This story was originally published on Feb. 14, 2015.

When I dreamed up the concept of this shoot, inspired partially by all the men-wearing-makeup think pieces and that genius Tom Ford Lips & Boys collection, I was repeatedly met with one question by women all over R29 HQ: "Why?"

My answer: Why the hell not? I am a man who has worn makeup every single day since I can remember, and I know how much joy it gives me. I also know, though, that a lot of women don't see makeup as a joy — rather, they see it as an obligation or a chore. That's probably because society has told us that women need to wear makeup, and that's a damn shame. Nobody needs to wear anything they don't want to. (Except maybe underwear. Please wear underwear.)

I've had boyfriends who have come to me in times of dire need, begging for makeup, even though they began our relationship insisting it wasn't necessary. I have brothers who have needed concealer before big events. There's a lot of delight in introducing someone to makeup for the first time, and showing them what they can do with their face — something they see in the mirror every day and think they know so well. That delight, or, rather, awe, is contagious, almost palpable.

So, when thinking about how to best showcase some of the season's most exciting new lip shades, I was envisioning plenty of things: kisses on cocktail napkins, close-ups of pouts, animated GIFs of mouths moving, talking, kissing, eating, etc. But, then I thought, Why not let boys show us the lipsticks? Women constantly appear in beauty editorials — why would it be weird to let boys do the same?

Men wearing lipstick is not a novelty for me: In my world, as a beauty editor and a gay man, it's a regular occurrence. But, I appreciate the men here taking time out from their jobs to sit down, pick out lipsticks that spoke to them, and try something new for the day. The lipsticks ended up enhancing their looks; making them cooler.

Ahead, 15 stunning new shades we think you should consider for spring — plus, a little more about the men who tried them on.
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Photographed by M Studio.
Keenan, commercial real estate sales, wearing Tatcha Lipstick in Kyoto Red

Do you wear makeup, or have you ever worn makeup before?
"No, never."

What did you think about the color you chose?
"I think it matched my skin tone well and brought out my beauty. I trusted the expert, which is how I decided on this color."

How did wearing lipstick feel?
"It felt interesting because physically it felt restrictive, but emotionally it felt expressive and really garnered a sense of childish freedom. It was almost like — it took me back to a place where you had a carefree attitude about life and nothing mattered. So, that probably felt empowering in a way. It made me feel I were being made stage-ready, as if I were about to perform. It made me feel special because of the attention and the time it took, but most importantly, it made me feel energetic, and I relate that to running a marathon, being tired, and someone giving you a high five, and it giving you a crazy boost."

How did it feel looking at your photo for the first time?
"Surprisingly amazing! One, it forced me to look at myself through a different lens. Two, through that lens, I saw an expressive side of myself that I rarely see. I think, also, it was so uncomfortable that it forced me to be comfortable."

Can you remember a time you felt particularly beautiful?
"When I put on my favorite tailored suit — that’s when I feel it. I have my dress shoes shined to the nines and, most importantly, I have on my favorite pair of crazy socks."

Can you remember a time you felt particularly self-conscious about your appearance?
"Anytime I walk into a room full of people...any casual environment where I see people I don’t know. When it’s business, I’m on because I’m wearing my suit, but when it’s casual, I don’t have as diverse of a casual closet."
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Photographed by M Studio.
Glenn, hairstylist, wearing Maybelline ColorSensational Rebel Bloom Lipstick in Orchid Ecstasy

Do you wear makeup, or have you ever worn makeup before?
"I don’t wear makeup daily, but I’ve worn it before for Halloween or going out to house parties in downtown L.A. when I was 17. I used to wear checkered lipstick, actually, just to do something fun."

What did you think about the color you chose?
"I like the color I chose — I definitely think it will define someone’s personal style. It’s a good added extra touch. Purple is also my favorite color."

How did wearing lipstick feel?
"The lipstick felt just like ChapStick, to be honest. It felt good!"

How did it feel looking at your photo for the first time?
"I actually was surprised at how good I looked! I thought it was interesting to look at — to see myself in a way I’ve never seen myself before... I normally don’t range myself outside of doing something very feminine, because I never felt comfortable doing that…but I felt comfortable wearing lipstick."

Can you remember a time you felt particularly beautiful?
"I wouldn’t say beautiful — I’d say particularly handsome. I’m a hairstylist and I’m behind the scenes, and I’ve never gotten my photo taken before, so it was interesting to be on the other side and be the model. I felt really good about seeing my photo. I felt really confident and good in myself."

Can you remember a time you felt particularly self-conscious about your appearance?
"At the White Party in Palm Springs! There are so many hot men there, and I felt like I needed to hit up the gym more."
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Photographed by M Studio.
Matt, designer, wearing Chanel Rouge Coco in Insoumise

Do you wear makeup, or have you ever worn makeup before?
"I don’t wear makeup every day, but I’ve worn it for photo shoots."

What did you think about the color you chose?
"The people on set drew me towards it. I was not at all intimidated by it."

How did wearing lipstick feel?
"It felt just like ChapStick — I didn’t really notice it, to be honest."

How did it feel looking at your photo for the first time?
"I look like my mom. I thought it looked good, but there was…a lot of mom."

Can you remember a time you felt particularly beautiful?
"There were times when I felt more confident, but I don’t really pay too much attention to beauty. I don’t wash my hair and I don’t wash my face, but I guess...it’s just when I feel super-confident."

Can you remember a time you felt particularly self-conscious about your appearance?
"Yeah, just when I notice when it’s like cold, dark, or gloomy, and I haven’t worked out in a while. Or, I haven’t gone for a run or been active."
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Photographed by M Studio.
Darien, student, wearing Make Lipstick in Magma

Do you wear makeup, or have you ever worn makeup before?
"No, never ever."

What did you think about the color you chose?
"I thought it was fun! I thought it would brighten anyone’s gloomy day."

How did wearing lipstick feel?
"My lips have never felt so moisturized — they felt like butter. Now that I’ve taken it off, they feel dry."

How did it feel looking at your photo for the first time?
"Uncomfortable. It’s hard to look at the photos because, for me as a person with large lips, I feel like highlighting them is slightly terrifying. I think that naturally, the color of my lips doesn’t make them so obvious, but when they’re highlighted, you can see how large they are."

Can you remember a time you felt particularly beautiful?
"At the beginning of every day, because I think that the feeling of a fresh shower and the start of a new day wakes me up. By 4 p.m., I feel the worst."

Can you remember a time you felt particularly self-conscious about your appearance?
"I spent a large part of my life being overweight, so for me, that was a big deal up until the 10th grade... I think it was part biological — growing — and part increasing activity in changing myself."
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Photographed by M Studio.
Kevin, model, wearing Marc Jacobs Le Marc Lip Crème in the color Scandal 226

Do you wear makeup, or have you ever worn makeup before?
"I do not currently wear makeup, but I have in the past."

What did you think about the color you chose?
"I really liked the color I chose; I think it works well with tanner complexions and dark clothes."

How did wearing lipstick feel?
"I was surprised how beautiful I thought the lipstick looked."

How did it feel looking at your photo for the first time?
"I was confused. I didn't know if I was sexy or handsome, but it felt cool!"

Can you remember a time you felt particularly beautiful?
"I feel beautiful when I'm being myself — or getting a massage, for some reason."

Can you remember a time you felt particularly self-conscious about your appearance?
"I feel self-conscious a lot! Pick a day, I probably felt self-conscious then."
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Photographed by M Studio.
Logan, artist, wearing NARS Lipstick in Liguria

Do you wear makeup, or have you ever worn makeup before?
"I don’t on a regular basis. Actually, sometimes I wear POREfessional from Benefit if I’m having a particularly porous day. But, I have definitely worn makeup before, for various photo shoots from being a model — but that’s a secret. Modeling is a secret."

What did you think about the color you chose?
"I liked it because of my new blonde hair color — I like it because it feels really current, the '90s are coming back, and beige is pretty '90s."

How did wearing lipstick feel?
"My lips are dryer than they were when I came in."

How did it feel looking at your photo for the first time?
"I looked good! It ended up being [almost] identical to my hair color, so it was cool. It was like a more editorial kind of look for my everyday style."

Can you remember a time you felt particularly beautiful?
"There was a shoot I did once in Miami, and it was all Dior. My hair was slicked back, and I thought I looked great at that point in time — it was sunny outside and we were at a pool. I felt pretty gorg. But, on an everyday basis, I feel my best-looking when I’m in the clothes I feel most comfortable in and when my hair decides to lay flat."

Can you remember a time you felt particularly self-conscious about your appearance?
"When I lived in Arkansas, in high school. I'm tall and skinny, and I was treated as really weird. It was somehow linked to being gay if you were tall and skinny and didn’t play sports, so I was most self-conscious until 10th grade, until I discovered the Internet and realized I wasn’t alone. Then, I moved here and people started telling me I was beautiful."
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Photographed by M Studio.
Derek, student, wearing Clé de Peau in De la Maitre de L'ecole

Do you wear makeup, or have you ever worn makeup before?
"I do not wear makeup, but I did on Halloween in '98. Cleaning it off was such a nightmare that I swore I would never do it again. I guess I lied."

What did you think about the color you chose?
"The makeup artist did a three-shade blend; I was surprised how natural it looked."

How did wearing lipstick feel?
"I tried not to move my lips too much, because I didn't want to mess it up. I know that's not really how it works, but I felt a little out of my element."

How did it feel looking at your photo for the first time?
"It was unfamiliar seeing this particular transformation of myself, but I like living in a world where you can be whatever you want with a little effort."

Can you remember a time you felt particularly beautiful?
"My 185-millionth great-grandfather was a fish; I feel beautiful every day."

Can you remember a time you felt particularly self-conscious about your appearance?
"Probably, every day between fifth grade and 8th grade. Humans believe there is some universal meaning to things like beauty, but it differs every day depending on who you ask and what time period you find yourself in. Beauty is nothing more than being comfortable with who and what you are."
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Photographed by M Studio.
Peter, celebrity hairstylist, wearing Sephora Collection Cream Lip Stain in 08 Whipped Blush

Do you wear makeup, or have you ever worn makeup before?
"I have worn makeup before for TV appearances."

What did you think about the color you chose?
"The HOT-pink Miley Cyrus lipstick was a laugh! Why not choose the boldest and brightest if you're going to do it?"

How did wearing lipstick feel?
"I felt like a bearded man wearing lipstick — it was a laugh for me. I enjoyed the experience."

How did it feel looking at your photo for the first time?
"Looking at the monitor was a bit awkward, but it wasn't like I was at the DMV." (laughs)

Can you remember a time you felt particularly beautiful?
"I feel really beautiful [and] most attractive now. Right now in my life."

Can you remember a time you felt particularly self-conscious about your appearance?
"Phillip, I've never had an awkward phase...ever."
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Photographed by M Studio.
Tilton, account executive, wearing Charlotte Tilbury Matte Revolution Lipstick in Lost Cherry

Do you wear makeup, or have you ever worn makeup before?
"I have never worn makeup before. Well, yeah, during Halloween — I was a pharaoh."

What did you think about the color you chose?
"Maybe it was the packaging, maybe it was how toned-down it looked, [but I liked it.]"

How did wearing lipstick feel?
"I didn’t feel anything! I couldn’t even tell it was on."

How did it feel looking at your photo for the first time?
"It looked pretty natural, oddly enough. I guess I don’t look at my nude lips enough to notice the difference."

Can you remember a time you felt particularly beautiful?
"Pretty much every time I commit to buying a new jacket — looking in the mirror and knowing some piece of clothing I just bought or am about to buy looks good. The second right after that."

Can you remember a time you felt particularly self-conscious about your appearance?
"I guess, maybe, in grade school, having a big head."
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Photographed by M Studio.
Ryan, visual merchandiser, wearing Tom Ford Lip Color in Preston

Do you wear makeup, or have you ever worn makeup before?
"No, I don’t wear makeup during the normal day — only for fun. I wore it for Halloween when I was a 'Juicy Couture girl.' I wore a little tracksuit, and red lipstick by MAC and eyeliner."

What did you think about the color you chose?
"It was very soft and feminine, and I can see it being a very popular color for spring. It was a color that looked approachable and realistic."

How did wearing lipstick feel?
"It felt sexy!"

How did it feel looking at your photo for the first time?
"I wasn’t shocked, surprisingly! I feel like the color highlighted the shape of my mouth, which was nice because I feel like my lips are big, but people don’t notice them. So, coloring them showed how big they actually are."

Can you remember a time you felt particularly beautiful?
"When I’m in love."

Can you remember a time you felt particularly self-conscious about your appearance?
"Probably, like, when I first moved to New York because I was a tan Miami boy in a very pale, 2008 post-Misshapes New York."
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Photographed by M Studio.
Phillip, beauty editor, wearing Armani Rouge Ecstasy Lipstick in #512

Do you wear makeup, or have you ever worn makeup before?
"I wear makeup every day and have since I was about 11. This includes concealer, foundation, highlighter, bronzer, eyeshadows, cheek color, etc."

What did you think about the color you chose?
"The makeup artist Kate Lee once told me I should consider wearing red lipstick, because it would make my eyes pop! This was an exciting way to try it out."

How did wearing lipstick feel?
"The Armani lipsticks are super-hydrating on the lips, which is really quite lovely considering their opacity. We painted this one on super-precisely, and I ended up wearing it for a few hours without it budging much at all. In fact, the edges just blurred a little bit as I drank water or ate, and it was quite nice."

How did it feel looking at your photo for the first time?
"I felt like I looked significantly more feminine than the other gentlemen in this shoot! Everyone else still maintained this masculine sort of appeal, but I'm not sure that's quite the vibe in my photo... It's also nice to see my lips so defined! I enjoyed my Cupid's bow."

Can you remember a time you felt particularly beautiful?
"Yes — I had just started seeing someone, and it was the first night I had spent at his place. He had this giant window next to his bed, so there was loads of natural light pouring through. I opened my eyes, and he was already awake...we had been tossing and turning for an hour or so, and I guess we were in-between consciousness. Anyways, when I woke up, the sun was in my eyes, and he was looking at me, and he just said, 'You're so beautiful.' I felt vulnerable initially, because I was obviously without makeup and my hair was unkempt, but something about that moment made me really believe him."

Can you remember a time you felt particularly self-conscious about your appearance?
"Gosh. I had just broken out with this horrible guttate psoriasis, and I had patches on my forehead and down my neck, and they were mean, red, and irritated. Regardless, I had to be on camera the next TWO days: once with Candice Swanepoel, and the other with the Pixiwoo sisters. I've never been more horrified of myself in my life, but it was a really great reminder that I'm a whole lot more than the makeup I put on my face."
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Photographed by M Studio.
Will, fitness professional, wearing RMS Lip Shine in Royal

Do you wear makeup, or have you ever worn makeup before?
"Yes, I used to do theatre, and I used to wear concealer and bronzer because my skin was uneven, and I had tired eyes from college."

What did you think about the color you chose?
"I thought it was pretty! I want to take it home. I probably wouldn’t wear it, but I still want to take it home."

How did wearing lipstick feel?
"My lips felt soft and moist without being sticky — I was more aware of them, so I was giving pouty face."

How did it feel looking at your photo for the first time?
"It was cute! I don’t take myself too seriously, so I thought it was just another New York moment."

Can you remember a time you felt particularly beautiful?
"For me, beauty is not on the outside, it’s what you accomplish and do with your life. So, days I feel particularly beautiful are when I graduated college, when I moved to New York City; those days when you feel really great about yourself in all aspects."

Can you remember a time you felt particularly self-conscious about your appearance?
"Always. Growing up, I was always in front of people. I was a cheerleader since I was in first grade...and my mom was always doing my hair and making sure my hair was perfect. I modeled when I was young, and so I was always aware of what I looked like. And, in the professional world, especially in fitness, people look at you for inspiration. So, if you’re put-together and if your body is great, and face is good, and hair’s good, you feel like everyone’s looking at you to be that example, either consciously or subconsciously."
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Photographed by M Studio.
Adam, hairstylist, wearing Uslu Airlines BYC Lipstick in Yacuiba

Do you wear makeup, or have you ever worn makeup before?
"Yes — I wear it strictly for professional reasons, like for doing camera work or appearing on-air. I like to be ‘camera-ready.’ That generally consists of moisturizer, concealer, a light foundation, and that’s it...just something to even out the skin tone."

What did you think about the color you chose?
"The metallic! I think with my vibe of rock ’n’ roll, it was right up my alley. And, it can tend to swing masculine if you’re going to wear a lipstick."

How did wearing lipstick feel?
"I actually enjoy the texture. Some mattes can be sticky, but this has a creamy texture to it that moves."

How did it feel looking at your photo for the first time?
"It felt exhilarating! I’m not used to seeing lipstick on myself, so it was very different!"

Can you remember a time you felt particularly beautiful?
"My wedding day — I felt timeless. Wearing a tuxedo and a bow-tie, and having my slicked, Clark Gable hair…and it was one of the happiest moments of my life, therefore making me feel beautiful."

Can you remember a time you felt particularly self-conscious about your appearance?
"Definitely my latter high-school years. I was working for a fashion company, and I was constantly judged for my appearance — people were criticizing how I looked, the way I dressed, and they reflected that into homosexuality. That caused a lot of self-conscious issues where I broke myself down. It took moving from Pennsylvania to California to rediscover my self-confidence and build it up."
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Photographed by M Studio.
Chris, photographer, wearing Lipstick Queen Bête Noire Lipstick in Possessed Intense

Do you wear makeup, or have you ever worn makeup before?
"The last time I wore makeup was in a high-school musical. I played the Cat in the Hat in Seussical, and my makeup was applied by a 16-year-old girl."

What did you think about the color you chose?
"I chose a darker color, because it reminded me of the Lorde 'Tennis Court' music video."

How did wearing lipstick feel?
"At first, I didn’t know if I could move my lips, but eventually you don’t realize it’s on. But, I am constantly checking my teeth."

How did it feel looking at your photo for the first time?
"I thought it was really cool to see a sort of different look for myself, and you guys made me look great."

Can you remember a time you felt particularly beautiful?
"Usually, in the summer on Fire Island because I love being tan and my hair bleaches out a little, and salt air makes me feel the best. I grew up on Cape Cod."

Can you remember a time you felt particularly self-conscious about your appearance?
"I was really heavy my first two years of college before I came out, and that was all based on that. It was a shame weight. I wanted to be attractive, and I wanted to feel attractive to someone...so I started taking better care of myself."
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Photographed by M Studio.
John, investment banker, wearing Revlon Ultra HD Lipstick in Hydrangea

Do you wear makeup, or have you ever worn makeup before?
"Sure — I would look like a zombie most days, given my pale complexion and long hours at the office without it."

What did you think about the color you chose?
"I thought it was cool, like what a goth drag queen would wear."

How did wearing lipstick feel?
"It made me much more aware of my lips. It's not an area of my face I really give much thought, but once the lipstick was on them I thought, Wow, I have big lips."

How did it feel looking at your photo for the first time?
"I remember thinking, Whoa, that is bold. My pale skin against the dark lipstick seemed pretty ballsy to me... Definitely a badass choice."

Can you remember a time you felt particularly beautiful?
"'Beautiful' isn't a word I usually use to self-describe, but I did feel damn fine the first time I bought a suit that fit me well."

Can you remember a time you felt particularly self-conscious about your appearance?
"When ginger jokes became a thing in middle school, it wasn't a confidence-booster. Now, my hair color is one of my favorite things about my appearance."
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