Hilton Dresden Is A Literal Icon & We're Dead


This interview has been edited and condensed. Text and photographs Sean Santiago.


So I am actually a big fan.


I think you’re kind of amazing.
That’s so nice.


I feel like if I had had someone like you as a kid, my mind would’ve been blown. Your style is so good.
That’s so nice of you, thank you.


But it’s so true! Where did you move here from?
Milwaukee, Wisconsin.


Did you bring the clothes with you? Or did you start to amass once you got here?
Not really...I used to dress very badly. I showed up at college in Old Navy yellow shorts and a purple v-neck. Like, that level bad. And my hair was really short and I had acne. I was basically out because people assumed and I just didn't deny it, but over the course of college I started to make a shift and started to wear like, brooches. By the end of it I guess I was wearing things that were okay.

Women’s clothing typically fits me really well, which is kinda crazy because I have the body of a praying mantis, you know?

Did you go more Dandy-ish? Like a vintage, dandy-inspired thing?
Yeah, I guess junior into senior year of college. And then when I was in LA I started to get into ruffly shirts, and that seemed to be really working so I was like, I'm gonna keep doing this. And when I moved here, there's a vintage store right by where I live called Harold and Maude and I found some white ruffled shirts there that I really liked. And then I started buying cheap Victorian things from thrift stores and since then I've kinda figured it out more, how I want to dress.


Were you very conscious of trying to find a better way to be dressing, or the more you way of dressing? Or were you just like, I guess I'll go shopping now?
It didn't feel like I was expressing myself how I wanted to. I kept trying to dress how I thought would be fashionable and cool and it wasn't working. I had a friend who dressed in Victorian dandy stuff and I saw that and I was like, "Oh, that's interesting," and I started doing that and that felt so much more right. That's when I started wearing skirts and dresses and getting a lot more feminine. It just felt better, more comfortable, and strangers would see me for the first time how I wanted them to. And my conversations with strangers would be for the better. It's weird. So many times the first thing that someone says to you is, "Oh, I like your shirt" or whatever. It definitely felt more natural and I was meeting people I liked more because I was wearing things that I liked more.


Did you have any blockages like, I can’t or won’t and don’t wear XYZ because it feels like there’s some sort of restriction? Or was it more like, why didn’t I think of this before?
I'm very into trying out anything, nothing is really off limits. I don't wear heels that often because they hurt so much. I could buy some Syros. I have some heels that I wear that look great, but I can’t wear them for a long period of time because they hurt so bad. This one pair I wore out to a party a week ago and I had to take them off at this corporate party and walk barefoot because it hurt so badly. The toe was so narrow and my feet are wide.


You definitely have to take into account whether or not being hot is gonna kill you before the end of the night. During fashion week I wore these boots that really made my look, but after just a couple of hours I could barely stand, let alone walk.
You always think you can overcome it. I still haven't learned the lesson. I always buy pants that are too tight. I have so many pants that have ripped or the zipper has broken. I still haven't learned the lesson—don't buy something that doesn't fit!


Well with the outfits that are a part of 5 Things, what does that process of getting dressed for those look like?
It began with just my clothes. It was just me and my friend Talia writing these videos and she would shoot them with this camera I bought, with a microphone. It was just us. And it still is really just us. But as time went by I started to buy clothes to wear in the videos. Then, at a certain point, I was like—I can’t keep buying clothes. I can't do this. And so I started forming relationships with different thrift and vintage stores and they would just style them. So now it's sometimes my own clothes and sometimes vintage stores. At the end of the day it’s so simple, I'm just trying to have fun and not take anything seriously and dress how I want.


Your dress at the Out100 was a moment. I remember seeing that and being like "Oh, shit.”
The OUT100 look was maybe the best I’ve ever felt in my life. I wish I had better photos cause I only have iPhone photos and it’s sad. And I straightened my hair for that and my hair has been a big part of this whole style thing, too, because I basically haven't cut it for a year and I feel so much better the longer it gets. So, I don’t know, that could have something to do with it. Who knows what it means.


It often feels like there's no one who’s maybe more easily male-identified visibly articulating what it can be to be beyond just a “guy,” or to be moving back and forth and really pushing gender expression. I try to do that, but it’s new territory.
Well it makes people so much more uncomfortable than seeing you on one side of the spectrum or another, or if you're really in the middle. And who cares? Even an hour ago at the deli, this woman behind me was like, "Excuse me miss,” or something, which was great with me—call me miss, call me anything. And she looked at me and was like, "Oh, I'm so sorry" and freaked out and it was just crazy.

There always has to be an element of fuck this whole thing, I think.

I think about this a lot in stores where people approach me regardless of what I'm wearing, regardless of what I’m looking at, and they're like "Sir, can I help you?" or "Sir, here's our men's department," and I'm like, no.
Don't tell me where to go, and don't call me sir.


Don’t call me sir!! Or like, buddy.
Oh god, buddy...whenever I’m called buddy I die a little.


Right? And I feel like the thing that’s so weird about masculinity is that they see you and they think, "Oh, I don’t want to offend you,” because being a man and being offended is the worst thing. I guess?
That touchy masculinity, which is so not something that I feel anywhere near, but people will just put that on you. And I’m not even saying that I call myself a man cause I don't really. I don't really call myself anything so it's just....I don’t really know where I’m going with that. It’s just difficult. And for women to stick to what is in your department, that's so dumb.


I think shopping in gendered space makes you realize how many garments are made in spite of a person’s body most of the time.
Women's clothing typically fits me really well, which is kinda crazy because I have the body of a praying mantis, you know? It's like, there's nothing anywhere, and I don’t have any curves. I guess basically the main point is that everything is arbitrary and bullshit and you don't have to buy from anywhere, you're not obliged to.


How did you learn to internalize that? Was there a paradigm shift in how you thought about gender, or expressing gender, or talking about gender and how much that relates back to these externalized expressions of who you are? Or are they totally separate?
They’re definitely related, how I dress and how I feel about my gender. But in that I don’t really care. Or, obviously I care about how I look and I care about knowing who I am, but I don’t feel the need to define anything or decide anything. And I also don't feel the need to get offended if anyone decides something for me. You can think whatever you want, you can think I’m a boy or a girl or trans or not or whatever, and I don’t really know and I'm not really trying to find out. I'm happy with where I'm at with it, so that’s kinda how I feel about gender. And that comes out in how I'm dressing because I'm comfortable wearing a dress. I wore a dress to family Christmas. And I’m comfortable wearing pants and a shirt. It's still difficult to go out sometimes presenting super feminine because people, you know, the world isn't ready for it all. I guess I try not to take it seriously, I try not to take anything super seriously because at the end of the day everything is just bullshit. That's my main thesis.


I like the grayness. I feel like language fails us constantly, especially in the queer community where there's so much variation and the whole point is there’s not the one thing or the catchall term, so obviously the English language is going to fail and there are all these moments where we run up against the limits of language.
And that's where clothing, and maybe this is just cheesy and a reach but, that's where clothing is better than language sometimes. Because visually it’s more easy to communicate sometimes what you want to say about yourself than through words you know? I mean, maybe, it’s hard to find the right outfit a lot of the times. Communication is hard. And that's really what you’re doing when you’re dressing, you’re communicating who you are. I love the idea that you’re a character. And that’s not to say that when I get dressed I'm like, "Oooh, I'm a pilot today."


"I’m Little Bo Peep today."
Right! In an ideal world, I would be thinking of a character, but in reality I'm just usually pulling together whatever I can find. You know?


Well it’s interesting too how in the queer community, in the subset of gayness and maleness specifically, how so much of dressing is coded for a sex thing. And to turn your back on that and to actually dress to repel all the men. I had a guy approach me at a club and say "You look like a lady," but I think he was coming on to me kinda?
It’s so interesting with gay men because it’s so much about sex. For the longest time I was trying to dress because I wanted male attention and it wasn’t working at all. And as I said before, I looked bad for a long time—all through college—I really did not look good. And I would try and wear a tank top, the more skin you show it must help you, right? Just things to try to make myself look as male as I could. I don’t know. Or skinny jeans, to try to be sexy. And it looked terrible. And now I've really embraced dressing a lot more feminine and not caring about that as much anymore and I actually feel way more desirable and sexy. And I think men, or just people who are dressing in androgynous or feminine ways are hotter than a tank top. Clothing is such a factor in attraction to someone. I think the way I'm dressing is hot. I think it’s funny and stupid and....


Hot, yeah. Like, I feel hot when I'm wearing that hamburger skirt and it’s funny and it’s...fuck this. There always has to be an element of fuck this whole thing, I think. To have someone look at your outfit and be like, "Seriously? That’s what you chose to wear?" Yes, yes it was.


That's so good, just feeling that power and being in yourself and not looking for someone else's approval.
It's way hotter! The second it looks like you’re hungry for everyone to think you’re hot, it’s not hot, you know? I mean, unless you’re just a super hot person and you’re hot no matter what.

Sean Santiago