Who Are the Dapper Boi Model Contest Winners?

Dapper Boi Contest Winners

Who are the Dapper Boi Model Contest Winners?

A brief conversation with three incredible people.

Penned By: The Dapper Boi

What does clothing mean to you? For some, it a form of personal expression. For others, it’s a means to an end. For us, clothing is a path towards confidence and authenticity.

Last month, when kicked off our model contest, we had no idea how big the response would be. We had no idea how many of you too, feel the same about clothes, so much so that you wanted to model ours. It is truly humbling.

Recently, we sat down with our three contest winners to learn more about their lives, their fashion inspirations, and when they started dressing how they wanted. Unfortunately, we had to drastically abbreviate these interviews for this article. But, let us know in the comments if you’d like to read the full versions. We hope you enjoy.

Kayla R. Dapper Boi 3rd Place Winner

 Kayla R. 

Third Place

INTERVIEWER: You’ve got an interesting job from the looks of your Insta. Can you describe what you do for work?

KAYLA: [Among other things] I photograph couples who come to me looking to rekindle their relationships. I photograph couples who are new and want to capture that new love… And singles... It’s a lot of me helping build them up and showing them how beautiful they are on the inside and outside. Because we live in a day and age now where there’s a standard that everybody has to follow and it’s just not how I run my life and business. So if you look through my feed there’s all types of bodies and all types of genders and I celebrate that. I help human beings see themselves the way they should see themselves.

I: Do you have any fashion inspirations? Either now or from earlier in your life?

K: I’m still learning and growing, but I have a friend Ciara, who actually works with you guys a lot, and she’s a stylist.

I: Oh! @thenewmixx?

K: Yeah yeah, that’s her. She’s a friend of mine. She’s local here… So, if I do have an inspiration for style, it would definitely be her. I love the way she dresses. Don’t tell her I said that. (Laughter). Just kidding. 

I: Can you remember the first time you dressed against gender norms, so to speak? How did it make you feel?

K: I was married to a man for six years and had always internally identified as a bisexual woman, but I was raised very traditionally. I was raised in a catholic household and went to a catholic high school… When I met my ex-husband I didn’t think I’d ever have to come out… Once it didn’t [work out] I just started dating women only. I just started to find myself and when I met my current fiancé, she helped me feel more confident. I wanted to wear something more masculine… and I started to wear things that made me feel like that and she would like it, it gave me that satisfaction and gratification that it was OK… That was in 2015. And at the time I was 25. Still hiding things from my parents. Dressing the way I wanted to dress, but not in front of them.

I: Did you notice a boost in confidence when you started dressing like that?

K: Absolutely. 100%. I even took pictures of myself,  which is not something I ever had done.

I: How did you discover Dapper Boi?

K: I’ve been following you guys for years... I did a google search cause I started looking for more— I hated always shopping in the men’s section and [the clothes] were never built for my body and so I started looking for androgynous clothing and a company owned by Queer people as well. That’s super important to me.

I: What’s your favorite DB product?

K: The Henley shirts. The short sleeve ones. I like the tightness around the bicep. Usually when I buy a men’s shirt I have to buy a large and the sleeves were always long so I’d have to roll them.  And I love not having to do that.


Darlene R. Dapper Boi 2nd Place Winner

Darlene R.

Second Place

Interviewer: Do you have any fashion inspirations? Either now or from earlier in your life?

Darlene: My fashion inspiration, ironically, is my father (laughs). I don’t necessarily wear clothes he wears, but he is always very proper. You’d be hard-pressed to find him without a starched button up shirt. Or polo shirts. He was and still is a man who would meticulously iron his shirts… He would take it to the extreme though. He would iron his jeans… It’s more so from the fact that he was always—well I guess dapper… matching belts, matching shoes. Nothing out of place.  

I: Do you remember early on noticing his outfits?

D: Oh yeah… My dad had two closets… My very first job growing up was working for a banana republic… And I’d always make fun because his closet looked like the store. All of the colors were aligned. Same types of shirts. He always wore his Ralph Lauren and Nautica. That’s the style I always knew him since I was born… He was the fashionista in the house by far.

I: Can you remember the first time you dressed against gender norms, so to speak? How did it make you feel?

D: I distinctly remember my 3rd or 4th grade school picture, where I pretty much dressed like my dad. I wore a button-up shirt. I think I ironed it myself. And it looked like a men’s shirt. I have it somewhere… It’s just a button-up but I think it went against norms because—and mind you, I don’t want to admit to this—but I wore it with khaki pants [laughs]. And I presented very masculine… But you’re so young that you don’t really even think about it. You’re just like “I want that shirt. I feel comfortable enough in it. That’s what I want for my school picture.”

I: Can you give me an idea of where you’d like to see fashion head in the future?

D: You know, whenever we envision things and—I think specifically for fashion, and this has been mentioned many times, but being able to walk into a store and just have clothes. That’s like the utopia. But I think more so than that, it’s having nice clothes that are sensible and lovely for anybody who wants to wear them. Sometimes you hear, especially for larger bodies, the fashion is always relegated to something your Nona would wear. [laughs] Sense and style shouldn’t be exclusive to a certain group of people. Everyone should have access to nice clothes. I think that’s the takeaway.

I: What’s your favorite DB product?

D: For me it’s been the t-shirts. I did one of those three packs. And it’s just the way they fit on my shoulders and the way they rest. That’s really what sold it. “Oh my gosh. Accurate measurements. That’s lovely!” And I just bought a blazer and a plaid shirt I’ll be wearing to a wedding in a week. It’s one of those things where you don’t realize how useful those snap buttons are until you put on the shirt and button it up and suddenly there’s no gap.

I: Any advice for people out there reading this that may feel uncomfortable with the clothes typically associated with their gender?

D: I think the biggest thing is, if possible, just find a friend… Take that leap together. Saying “you know what? We’re going to go out tonight together and you’re going to wear that brand new outfit that makes you feel comfortable." I think that really goes far. Knowing that you’re not the only one going through that awkward phase… clothes are really for you… People have lives to live. They’re not necessarily judging your every move so don’t necessarily do that to yourself.


Trish G. Dapper Boi 1st Place Winner

Trish G.

First Place

INTERVIEWER: Can you remember the first time you dressed against gender norms, so to speak? How did it make you feel?

TRISH: I actually remember being in 4th grade and being forced to wear dresses and skirts and I was miserable, so I'd sneak shorts into my backpack and change at school and then change back into the dress before getting on the bus to go home.  This was so miserable and I hated having to fight every single day about having to wear "girls" clothing. So, once I got out of high school and didn't have to wear prom dresses and fit that mold, I set myself free and wore whatever the fuck I wanted. It was a challenge to always hear comments from people who just didn't understand what it was like to struggle with clothing "norms," but now I'm so good about being myself that I feel better than I ever have. Once you truly decide not to care about what anyone else thinks of you, you'll reach a whole new level of confidence and sleep so well at night!

I: How did you discover Dapper Boi?

T: I found Dapper Boi in 2017 on a sponsored ad on Facebook.  My very first order was as mint button-down shirt for my firstborn's baby shower. Her colors were mint, black and gold and this shirt was perfect. Once I tried this shirt on, I was sold and have been addicted ever since.

I: What’s your favorite DB product and why? Also thanks for being an OG supporter!

T: My favorite is a strong tie between the jeans and short sleeve button down shirts. I love that I can put my phone, wallet, and keys in the pockets of my jeans without my wife having to hold everything and bothering her all night when I need one of those items. But then I love the button downs because that's all I wear to look "nice" for clients and I've finally found a brand that fits me just right. So, of course, when button downs come out, I'll almost buy every single one of them. Oops

I: You have a beautiful family. In your entry you said you and your wife are raising your children to be exactly who they’re meant to be. What does that mean to you?

T: Raising our children to be exactly who they're meant to be means LISTENING. My wife and I were never heard and we have zero relationships with our families. Imagine if my parents listened to me and what I felt and what I liked?  We may have been close today, who knows. So rather than cramming my ideas down my kids' throats, they get to form their own ideas about their own needs and happiness. Whatever that may mean.  They don't like onions? Cool, I'm not forcing them to eat onions in order to get dessert. They hate college? No problem, if art makes them happy and they go to bed at night full of joy, they have my support 100%. Because we will listen and hopefully build better relationships than we had with our parents. Our goal is to raise good humans at the core, the rest they'll hopefully discover on their own.


Dapper Boi

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