Lilly Brooklyn — Madeline K Barry Fine Art

"My internet footprint is very small. I like it that way" - LB

Who is Lilly Brooklyn?

Lilly Brooklyn is my newest muse. She is full of spunk, laughter, and willingness to offer her whole self to the people she meets.

I met Lilly years ago through my mother, another amazing and inspiring woman. Lilly is a captivating character in the second half of her life, and she has created a lifestyle that I believe we all should take notes on. For starters, Lilly has done almost every cool profession you can think of, shops only thrift, wears purple lipstick daily, and has over a dozen pairs of leather boots.

She gets it.

I was ecstatic to interview Lilly because of her unique perspective on fashion and on womanhood. Quite frankly, she has been through a lot, and through it all she has discovered new and beautiful parts of herself. She has let things meant for evil sharpen her character rather than becoming a victim. She’s chosen forgiveness for herself and for others. She has allowed these beautiful facets of her personality to shine through the outfits she creates, and the way she professionally and artistically presents herself. She has some amazing words of advice to offer to all of us in this same pursuit- to truly love who we are, even the parts of us that don't make sense.

I won’t spoil anymore of this goodness, I’d rather you read the words straight from her glittering mind. Lilly is an incredible woman and I’m excited to see how her perspectives on life fill their potential to change those who have the privilege of hearing them.

Fashion with Lilly

Where do you shop and why?

I only buy second hand… except for shoes. Shoes are worth spending money on, they’re part of the soul. But I love the hunt! Even when I had the money to shop luxuriously, I still had that desire to hunt. But now, I found, I can pull off shopping totally thrift. Anyone can buy good fashion full price! Anyone can say to an associate “here’s my money, put together an outfit for me,” That’s easy. But to put it together yourself and not pay full price? The other thing is that anyone can put together a Goodwill outfit and have it totally look like ‘yes you got that all from Goodwill’… Often, I’ll go somewhere and they’ll say “where do you shop?!" They don't believe me when I say it's Goodwill, but it really is. It’s all about knowing. It’s knowing what you’ve got, knowing what you want the final outcome to be. It’s not like walking into J. Crew where all the things go together and you just mix and match and pick your size. With thrifting, you have to know what you have and what you want so that you come out with outfits, not just pieces.

Is it not super time consuming? How do you not get overwhelmed by thrift stores and actually find what you want?

I think of it like a puzzle. I think about all of these pieces I have that can contribute to a "look", and I just try to find the one piece I need to make it exactly what I want. So, my first move when I go to Goodwill is to not even look at the clothes. I walk down an aisle and feel the fabric, feel the fabric, feel the fabric… Fabric is important to me. If I feel something I like, I pull it out and take a look. Keep in mind, if it’s not worth it to you to pay full price for an item, it’s not worth paying a dollar for. You have to find the clothes that fit your lifestyle, or you risk cluttering your closet. And if it’s not worth the trouble to take care of it, then don’t take it home. Like dry clean? I’m not willing to do that anymore, which is why fabrics are important to me. I used to have a couple dozen cashmere sweaters, but when I moved into this phase of life, I only kept 5. I just knew dry cleaning was not going to be a part of my life anymore, and I couldn’t bring myself to machine wash and dry a fabric like that. Let that be someone else’s problem.

How would you describe your style? Are you a minimalist?

*Shakes head emphatically* I’m not a minimalist. I do have specific styles I know I like, but I will buy those style in every possible color and pattern that I can. Usually not all in one fell swoop. Say there’s a type of shirt that I find, because it fits the description of what I like. Over time, I will accumulate lots of them. Like, I really really like button down shirts with button down collars, especially the Oxford print. At one point, I had probably 10 of those shirts in that specific print, just different colours. I’m the same way with white shirts, I think I have 50! I’m sure people wonder if I’m colour blind…but I know exactly what I want! So, I guess I’m a minimalist in stye. I won’t have 50 different styles of shirts, I stick with my little window of what I like. But I buy every single thing I can find that fits in that window.

Do you have a favourite colour to wear?

I think navy is my favourite, it’s a softer form of black. All neutrals are totally go-to.

Are you a jewellery person?

Yes. But I have less jewellery than clothes, percentage wise. I like to have jewellery that is incredibly meaningful. Clothing won’t necessarily remind me of a certain person or trip or experience, but jewellery is exceedingly personal.

Why do you think fashion is an important part of life, specifically as a woman?

It’s important because everything starts with presentation. Style is cool because it’s a way of presenting ourselves that is easy to change. But it’s important to present yourself as you really are. If you’re presenting yourself as how you wish people saw you, and it’s not really you, you’ll eventually catch yourself trying be that person you’re not. After a little bit of that, you’ll wonder, "what have I been doing?” For example, I used to wear stilettos quite often, mainly for the compliments that accompanied them. And now, don’t get me wrong, I love fun shoes but I got so tired of wearing them, they didn’t feel like me. We have to choose honest ways to present who we really are, in a way we feel most comfortable. That doesn’t mean I have to wear flip flops everyday with an 'I don’t care’ attitude, because that’s not me either. But even the teenage boy that grabbed dirty laundry from the bin made a choice on how to present himself. Everyone makes that choice everyday. There’s a freedom in being yourself that will automatically come out through what you wear, if you let it.

How have you figured out how to balance presenting yourself honestly and creatively?

I think it comes from age and experience, as well as those around you giving you open hands to present yourself. Growing up for years, someone else dresses you. As you get older, someone else is giving you the money so you can dress you, and they still have an opinion on what you can bring home and leave the house in. For years, if someone wasn’t excited about what you had on, you would choose something else. So you have a couple decades of opinions to work through that all have mattered more than yours. You have to get to a point where responses outside of yourself don't necessarily matter, as long as you feel good about going out the door. I can look back to college, high school, and younger and see my choices were more topsy turvy. I chose what would make other people happy, or because it was something on trend. Trends are tricky. Now, if I do a trend, it’s something small because they always come and go. I like the majority of my things to stand the test of time, and to represent who I really am- you can always be trendy through accessorising! But I think accepting yourself comes with time. However, working in fashion, I would come across people my age that still had no clue what to pair with black pants, so It’s not just time... It’s age, and it’s knowing yourself. And frankly, the fashion part of it is a process that some people will never get. Which is why we have sales associates! 😃

Influence

How have you used your passion and knowledge of style to help other women?

Well I worked at Talbots for 10 years, so I helped a lot of women there. But I would often have friends come to me with their entire closets and no clue what to do with them! We’d spend a day and throw it all over my bedroom, and I’d help them style things that go together. When we were finished, I would encourage them to get rid of whatever was left on the floor. Try as they might, they didn't have anything that works with those items, so I’d encourage them to hold space and potential in their closet instead. That was very time consuming, so I don’t do it anymore.

Paradox

Do you feel you’ve gotten to the place of truly being comfortable with who you are?

Well, it's a rare day that I leave the house and say “ohhh no why did I wear this?” and feel insecure as a result. If I do, I usually knew what I was getting into by experimenting with something new. I don' think it's about being being comfortable, like a sweat-pants-kind-of-comfortable. It’s about being comfortable in all different aspects of your life, just like you won't wear the same kind clothes to a girls night out that you would to work. You have be okay with being different moment-to-moment, but still being yourself in those different situations.

"Anything can be a costume if you don’t feel comfortable in it, personalities included,"

It’s a learning process to find who you are, and even more how to present it. Like personally, I can’t do ruffles. I tried for years to like ruffles, but I just can’t. And because of that, I sometimes struggle with feeling feminine. It seems silly, but I feel that if I don’t wear ultra feminine clothes, I may not be presenting myself as feminine as I really am inside.

"But I’m not a ballerina, I’m a cowgirl. And I’m okay with that.”

So my inside ruffly personality will come out through jewellery or hats or my purple lipstick. Sometimes I’ll wear so much jewellery they can’t help but see how girly I am because only a girl could drip with that much jewelry. So I find ways to feel feminine and feel like me. I want to wear my clothes, I don’t want them to wear me.

I think it’s also important to not feel a slave to whatever you see in magazines or on TV. There will be things that will jump out at you and you find yourself saying, "Yes! I could do that!” Grab those things, use the magazines as inspiration. Find those types of pieces to put together because you can see yourself in an outfit like it. The past 5 years, I think I've only found 2 things worth tearing out of magazines that are really me, but when I do find something, I tear it out so it can be a reminder to stay true to myself. I recently had a friend that gave me an oversized wool men’s vest. She knows how much I love oversized vests over button down shirt, it’s a look for me. So she gave it to me because it just didn’t work for her. She knew she wasn’t herself in it. Wear what you feel "yourself” in, be yourself. I just can’t think of a better way to say it.

Speaking of femininity, do you feel there is external pressure from our society to define femininity for us, to be that ruffly kind of feminine?

Remember Barbie clothes? When I was young, I had Barbies with all different outfits. Barbie had her “go-to-the-market outfit”, her “theatre outfit”, her “adventure outfit”. It seemed to me all of those outfits were designed so Barbie could find Ken.
"I don’t think femininity is like Barbie marketing herself to find Ken. But I think a lot of people will tell you that it is."
Do you have a defining moment that changed or aided this self acceptance? Did that play out in your fashion in any way?
My “aha!” moment came when I realised I was done trying to find Ken, and I was ready to just be me. We change and we filter everything we do and wear through this idea of being what people want. Being a single adult in the later phases of my life, it’s easy to feel irrelevant and invisible, I think that’s part of the reason I sing when I walk my dogs, and I wear bright orange dresses. I’m okay that my solid orange dress is a little unusual. Now that I’ve accepted my unusualness, I’m free to be exactly who I am without feeling the need to placate to what a man, or anyone else, wants me to be.
I used to constantly wonder “what about me kept that guy from noticing me? What could I have worn or done differently?” Let’s say you change that thing about yourself and he does decide to want you, then what? You have to keep it up the rest of your life. I want Ken to want who I am.
"At this point in my life, I am done trying to become what Ken wants,"
Do you have anything you wish you could tell women my age as they discover themselves?
Be you. They're either going to love you or not, but you can't control what people that come into your life, when they come, or how they feel about you. Your Ken will find you and love you if he's supposed to, and nothing you do, nowhere you move, no job change can affect that. Live your life freely as you truly as you can.
Being yourself doesn’t come completely effortlessly, you sometimes have to push yourself to live unrestricted, to live free from trying to please others.
The paradox is you. It’s who you are, and fashion should simply be a natural extension of your living as yourself.
The paradox is making an effort to be effortlessly you.