4 Looks You’re Never Too Old (Or Young) To Wear

Dressing for our age is a game that's rigged: Try as we might, the outcome is fixed and not often in our favor. One moment women are told they’re dressing too old, too provocative. The next, why so matronly? Live a little, will ya? So, thanks but no thanks. We're not playing. The thing is: We've always been firm on the fact that an amazing sense of style doesn’t have an expiration date and isn’t reserved for a particular age group. Which is why we turned to the tried-and-true pieces in Coach's fall collection — varsity jackets, little black dresses, and playful sweaters, for starters — and the women who wholly embody their agelessly awesome appeal. We not only came away with four forever-cool outfits anyone can emulate, but also four unique perspectives — from a high school senior to an almost-senior citizen — on the power behind clothing that transcends generations and is unique to you. Ahead, get their take on what it really means to be stylish beyond your years — no rules attached.
Alexis Jae, 17
Model and student Is there anything you wear that's surprising for your age?
"I dress kind of provocative and I like to show my skin and figure, which some may have a problem with. But I don't care — I'm comfortable in my body and I feel good about what I'm wearing." Are there any trends you’d never wear, regardless of age?
"All of them. I define a trend as something that once was cool and then became mainstream. I don’t have a problem with trends — I used to be a trendy girl myself — but now I’m striving to be an individual. I don’t really want to blend in with everyone else; I want to stand out in the way I dress or the way I talk. I just don’t want to be categorized." So for a piece of clothing as enduring as a leather jacket, how would you have worn one when you considered yourself “trendy” as opposed to now?
"Well I’d just wear a leather jacket with anything back then but now I wear a leather jacket to create a look. Like a 'French motorcycle girl' or something really strange. I don’t just go out in an outfit — I always have a specific look and aesthetic in mind."

When did you start thinking about style this way?

"[It was my] friends that got me out of my shell. I was always into dressing up, but now I use it as an opportunity to create myself and give myself a reputation without even having to speak." What do you find most exciting about getting older?
"I’m always changing my mind and I’m always willing to grow and try new styles, as well as come up with my own. I feel like I’m going to dress so cool when I’m older because I feel really comfortable with how I dress now, and I know that the older I get the more I’m going to discover myself."
Bee Walker, 33
Creative producer and photographer What are some of the first "rules" you ever heard about dressing for your age?
"As a young girl, I was always told that grown women are to be well dressed, put together, and ladylike. I looked forward to (getting older) because it meant I could wear makeup, paint my nails, and have jewelry. As a kid, that really appealed to me." Does that idea still appeal to you now?
"Yes and no. I think refining your style and getting comfortable with who you are is a really big part of growing up. On the other hand, the idea of dressing up that I had when I was younger is not realistic. I don’t have a manicure every day, I don’t always leave the house with mascara on. I realized I just love so many things more than getting dressed and doing my hair."

Are there any pieces in your wardrobe that you still turn to time and time again?
"I’ve always kept a black cocktail dress in my closet for every situation since I was 16."

This dress is kind of the quirky, modern take on the LBD.
"It’s definitely something that’s versatile and figure-flattering — it looks great on me and lots of people. It’s also feminine, which I like. I used to always add masculine pieces to anything feminine, but as I get older I get more comfortable claiming I’m a strong, creative woman. I know now that I don’t need to be different."

What do you mean by "being different?"
"Because I’m in a man’s field, I used to downplay my femininity. When I was younger, I didn’t want to be known as the ‘girl photographer.’ I just wanted to be known for what I do well. And now, I’m more comfortable. I am a female photographer and I don’t feel any need to hide it or mask it."

What do you think has been the most exciting thing about getting older?
"It’s so exciting to get more and more comfortable with who you are as a person. Everything feels less produced. I can just be myself, I show up as me and I’m not afraid of anything. I remember being a teenager and being so anxious about things. I thought things like what I wore on the first day of school were the biggest deal. Putting all those things into perspective is so great."
Lyn Slater, 63
Professor of Social Work at Fordham University, Lincoln Center, New York and fashion blogger at Accidental Icon

Of all the dressing-for-your-age pieces of advice you've heard, which do you prefer to ignore?
"All of them! Don’t wear mini skirts, don’t wear crop tops, don’t expose your cleavage, don’t wear low-rise jeans — I ignore them. Age is never a variable I use to make decisions about what I wear."

So, which variables
do dictate your decision?
"It’s really about my identity, or what I want to convey to the world that particular day. I’ve seen a lot of these stories like, ‘what not to wear’ and ‘what to wear’ in your 50s or 60s, and, as a rebellious person, I’m automatically not going to do what I'm told. Anything can be transformed into your personal style. To me, the bottom line is: What am I comfortable in?"

The varsity jacket you’re wearing today makes a pretty specific reference to a point in one's life. Have you ever worn anything like this before?
"I did when I was in high school and it was my boyfriend’s varsity jacket. The size of the piece brings back the memory of having that kind of weight and feeling from when I was in high school. It gives me some moments of good memories."

Are there any difficult style lessons you've learned over the years?
"Whenever I was in a position where I felt like I had to conform, I never presented myself authentically. The lesson that I’ve learned is that, depending on the situation that you’re going into, it may be more important for you to be authentic than to look a certain part. People will detect that you are not being yourself, and it impacts your confidence and anxiety level."

It's amazing to know that you have the power to make yourself feel different just by adjusting how you're presenting yourself to the world.
"There’s actual science that shows how [what you're wearing] impacts your ability to perform and your emotions. It’s called enclothed cognition. And for me, the way that I’ve been embracing clothing and reinventing myself at this time in my life is making me young."
Diana Gordon, 28
Artist, singer, songwriter, and creative director

What's the problem with dressing-for-your-age advice?

"I think everyone has heard the age-old saying, 'dress age-appropriate,' but I have always felt like style and dress are more a reflection of how you feel as opposed to how old you are. The beauty of fashion as far as I see it is there are no hard-and-fast rules." Have you ever been advised to dress a specific way because of the industry you're in?
"Not really. I think you dress for who you are as an artist and who are you as a person."

What are some of the longest-enduring pieces that have been in your wardrobe forever?
"I have never had a uniform. My clothes are always a reflection of my art or a benchmark of a significant period of time in my life, like the mood of a song or album, a movie with great costumes, etc. Denim has always been a constant, though."

It's safe to say that nearly every child has worn a playful sweater at some point in their lives. Is this one nostalgic in any way?
"It brings up holiday vibes at my grandma’s house. We’d get a sweater and a Mickey Mouse watch, and I remember the first time I got the Mickey watch I broke it the same day. Also, it makes me feel like a '60s schoolgirl."

What’s the biggest lesson in style you have learned as you’ve grown older?
"I’ve decided to show less skin. I used to show my belly button a lot when I was younger but I finally realized that sexy doesn’t have to mean showing your belly button. As I get older, I've started to find other parts of my body sexy — my shoulders and my neck, for example. I want to show more than what’s traditionally sexy, if you were to Google 'sexy.'"

More from Styling Tips

R29 Original Series