25 Women Talk About What Makes Them Feel Prettiest

I have collected dozens of amazing female friends and hold them all near and dear to my heart. They’re all ages and shapes and sizes and I adore them all and think each one is the most beautiful person in the world. But even though I find them beautiful all the time, I wanted to know when THEY think they’re the prettiest and why. Here’s what they said. What’s your answer?

“I feel prettiest when I’ve just washed my face and I’m wearing my silk robe and my bathroom is clean and my room is clean and my sheets are clean and I put on just a little bit of moisturizer and lip balm. It’s very simple, but it makes me feel put-together and in control of my whole life when all those things come together.”

“I feel the prettiest when I’m in a gross seedy bar, but that’s probably the wrong answer … Climbing mountains in the rain, or other feats of strength always make me feel real hot too. Feats of strength.”

“I don’t ever feel ‘pretty,’ exactly. I like myself and I like how I look, but I’ve never sat back and thought, ‘Wow, I’m so pretty right now.’ But that’s OK, because I feel other ways instead: proud when I finish a difficult article, strong and capable after working out, accomplished (and a little impressed) when I get my makeup exactly right. Pretty is great, but for me, these things are even better.”

“Whenever I get my eyes dilated at the doctor, I think I look pretty. But that might be a David Bowie fetish.”

“I feel prettiest when I have a tan, because I can wear less makeup and still look glowing.”

“Summertime when it’s hot and I have a little summer dewy glow. Getting ready is so easy. It’s hot, so you can’t wear much and you don’t need much makeup because you already look great.”

“[I feel prettiest] when I wear high heels!”

“I feel best about myself after I do something I’m good at, like finish a half marathon or have an art show. I feel pretty after I can really get a good cleansing cry out of myself.”

“I feel the prettiest when I’m on vacation somewhere tropical. My skin never looks better. It gets that kind of bronze glow that you can’t emulate with a spray tan or tanning bed. Another awesome thing that happens on vacation is the sexy beachy waves I get going on in my hair. A little bronzer, lipgloss and my fake eyelashes and I’m on fire.”

“I feel best about myself when I get out of bed naked and covered in a thin film of summertime sweat.”

“I feel the prettiest when I spend a lot of time getting ready to go out. I know everyone wants to hear, ‘I feel prettiest with my natural face,’ but nope! I feel prettiest with black smoky eyes, fake lashes, contoured cheekbones and MAC Snob on my lips. Black leather leggings and a sequin tank. I like attention, not gonna lie. I put a lot of effort into my look. I might be a little unconventional looking, but when random people stop me on the street and tell me I’m pretty, I know I did a good job.”

“I feel prettiest in a concert tee and skinny jeans and heels or knee boots!”

“Even though I love wearing a lot of makeup, I feel prettiest without much on. I feel the most like myself after a long day in the sun, with my hair all crazy from the lake and my skin warm and smelling like faded tanning oil and water. I feel prettiest when I’m driving barefoot with the windows open or wearing an old slip and no shoes sitting on the porch with people I enjoy.”

“I feel prettiest in the summer! It’s amazing what Vitamin D does for your skin and mood. I love getting a little color on my pale, porcelain skin. My eyes and teeth are brighter, my skin glows and I can get away with wearing less makeup – huge plus! I’m always in a better mood in summer too – more outdoor activities and more cocktails by the pool!”

“I feel prettiest when I’m singing, even though I know for a fact I make the most awkward faces. It’s just something I know I’m good at, so I feel attractive doing it.”

“I feel prettiest when I’m out of the shower, oily as fuck with fresh hair, makeup and perfume and my silk kimono. This is also when I get jumped most often.”

“Dripping sweat, beet-faced, post-run. Not because I’m anything good to look at, but because I feel so connected to my body that I know I’m a beautiful fucking work of nature.”

“I feel prettiest when I put on a dress and heels, a pretty red lip with a full face of makeup and get my hair blown out for a night on the town with my fiance. Or lying on the beach with no makeup on, wild windblown/sandstrewn hair covered in ocean salt, my skin tanned and glowing.”

“I feel beautiful when I go to weddings. I plan my outfit for weeks and make a point to shave my legs the morning of so they’re extra smooth. I do my hair all big and wear hot pink lipstick. Singles always be scoping out the other singles. And most of the time, the boys aren’t jerks because they’re connected to people you know and love. So it feels classy!”

“I feel prettiest after having kayaked and swam a river all day. My body feels rejuvenated and happy and I feel like I glow.”

“I feel pretty when I’m walking out to my car on my way to work. Empowered. Or when I catch a glimpse of myself in the rear-view mirror and give myself a ‘look.’ Aaaaand bust into song. Or just out of the shower, an in the moment natural beauty feeling and a fresh start.”

“I feel prettiest in a well made tailored column dress and pumps. I wish I looked good in jeans and a T, but I don’t!”

“After I’ve worked out before work and manage to do my makeup and blowdry my hair and everything. It’s the combination of the endorphins, looking like a grown-up and feeling capable to take on the day that makes me feel like I’m gonna be at my best that day.”

“I feel prettiest when I wake up in the morning with no makeup and the perfect film of oil on my skin. It doesn’t last long enough. I also feel beautiful in lace-top stockings and lingerie.”

“I feel prettiest when I’ve taken at least two hours to get ready. There’s something so glamorous about taking the time to take a long shower, put on my face and get my makeup just the way I like it. I always wear perfume on these special occasions. I love to do my eye makeup and spend forever getting every highlight and contour JUST right. After all my hard work, I feel so pretty and confident. I always show off to my husband and point out my perfect cat-eye or red lips. Invariably, he’ll take a long look and get this regretful little smile on his face and tell me, ‘Babe, you look great, but I think you looked best without all that … just the way you are.’ And THEN I feel beautiful.”