What were you thinking: The emotional mechanics of getting dressed

An interview series

This is a public post from What were you thinking, a new franchise that breaks down the emotional mechanics of getting dressed through interviews about style. This is the first of its kind, featuring Cole Habersham, a communications director and writer who lives in Brooklyn.

“My name is Cole Habersham. I'm from Teaneck, New Jersey.

I came to New York 6 years ago, after college, moved to Harlem, then Hell's Kitchen, and now I live in Bed-Stuy. I guess I’m making my way further south as I go.

I went to a tiny liberal arts school in Mahwah and I studied design interactive media. I wanted to be a creative director and ended up in advertising. I'm a freelance writer on the side for Brookyln Magazine and other boutique publications. Mostly I write about my life, or fashion, or my neighborhood. I have my own Substack, Cashmere Tote.

The vest I’m wearing is vintage, from Rose Bowl Flea in Pasadena. I got it in LA in August, as I was leaving. The cargo pants are [J. Crew’s brand] Wallace & Barnes. The boots are pre-loved by Lucchesse. I got them a few months from eBay of all places. The sweater is also J. Crew.

Thinking and dressing

When I’m getting dressed, I usually start somewhere structured and traditional. I appreciate a traditional menswear aesthetic and then I layer some fun over. So I guess the menswear part is the cargo pants and sweater, but then I lighten it up — make it a little more playful — with the Don’t Let Disco jewelry and fringe vest.

I worked at J. Crew when I was in college (and actually think these pants go back to then); they (J. Crew) have a [dressing] formula. Top, bottom, third piece. My top/bottom are usually more traditional pieces, then my third is more interesting, whether it's a fun boot or a personality vest or a statement necklace, or all.

J. Crew has been [a seminal brand] in the foundation of my style. That's where I was first introduced to clothing and menswear in general.

I also love a blazer. That's often my “third piece.” Now though, instead of wearing being a 38 regular, I wear a 44 regular. Super oversized and boxy. And that's how I have some fun with it.

Yeah, the foundational lessons are still there for sure.

A local missionary in J. Crew

What attracted me to the aesthetic? Well, back then, it felt very clean and tailored. And controlled also. That’s what I was trying to project — at that time, this is so different from where I am now — but I was in a pretty religious environment and climate. I was a local missionary.

And so that put-together, clean aesthetic worked within that setting. My parents raised me as a Jehovah’s Witness but I haven't identified for the past several years.

When I came to New York, I realized I was gay. I am gay. And that's not, I guess, possible in that religion, which teaches…how do I say this tactfully…that "one cannot stay in God's favor when practicing — their words, not mine — homosexuality." And so my relationship with God, religion, and sexuality transformed after I realized I was gay.

My mom still practices, my dad does not — he is very supportive, mom not so much.

It was more difficult initially but it’s something that I've learned to accept and actually lean into with my writing. My newsletter is called Mom Hasn't Called, But. It's very much about finding joy and filling that void through everyday experiences, which are often [channeled through] friends, work, writing, fashion, good meals…all of that.

And a hundred percent I found [solace] in clothes. Clothing was one way I began to understand and project my sexuality, too.

I could only dress a certain way for a long time. And that was very clean, very straight, very rigid, very structured. And then as I realized my sexuality, how I could dress, and how I could project myself to the world — the possibilities became unlimited. So something as simple as mixing costume jewelry with beaded jewelry and colors, which wasn't possible seven years ago with the lifestyle I was raised in, became very possible. It's a small thing, but so freeing.

I still believe in God. That's recent — that's something I've been thinking about recently. What is my relationship with God today separate from that former understanding? I'm still figuring it out.

I don't think about it too often, to be honest. What I tell my friends is that there was a point in my life where every thought I had throughout the day, every day was wrapped in God. I have enjoyed not having to think about it, or Him/Her, so often.

But I’m eager to reintroduce myself to that being in the future.

It's a homecoming in some ways.

Coming out

And it is almost like J. Crew started to help me find [this advanced version] of myself?

I wrote about this a while ago, but some of the first men I was attracted to [before becoming aware of my sexuality] were J. Crew clients at Columbus Circle. And so that attraction started at J. Crew in many ways. And that, I guess, was the very early beginning of my understanding. Like okay wait, I am attracted to men. I don't think I understood that back then, but when I look back now, I do.

It [coming out] happened quite suddenly. The moment I realized, Oh, I'm attracted to men... I'm trying to think about how to articulate this. It wasn't as gradual as you’d think, I guess. It was more of a sudden realization. I think on a subconscious level, I was beginning to understand, and it reflected in my style — gradually and then eventually beginning to play with femininity.

I dyed my hair blonde at one point, love a French manicure. My walk changed!

These are cowboy boots, but I have heeled boots that I wear from time to time and I feel…powerful in them.

Very powerful. I think that’s how my walk changed. And this is even an example of how we limit ourselves based on the environment that we're in, what's expected of us.

I tried to walk as straight as possible and dress as straight. When I say straight, I don't mean heterosexual. More like a line.

Yeah [formulaically], exactly that.

And so what I was trying to project myself as was straight. I walked straight. But as I came out, I started to become comfortable with my sexuality, and comfortable with people knowing by looking at me how I identified in some ways. That was a change.

Style and self

I didn't even realize how much of my personal style is rooted in my upbringing and that transition from being a missionary to now a proud man with a strong religious background. A sort of reverence and respect for what was and also an acknowledgment of strength and power in what currently is.” As told to LMC

This Week’s Thing of Note:

Sarah Mower’s Vogue review from the Loewe show in Paris last week, which captures the designer Jonathan Anderson’s interpretations of this moment of reset, between two worlds — pre-pandemic and post, which is a bit “hysterical,” and tense.

Why’s it a thing of note? The juxtaposition of Sarah Mower’s willingness to interpret Jonathan Anderson’s Loewe, and his Loewe representing an extraction from the past, but “hysterical” loiter-period before the future reminded me that fashion is a tool — a way so many of the hopefuls among us try to make sense of two worlds that are always unfolding: the one inside of us and the one outside of us.

I love it — I love it so much.

Signing off,


And oh! Do yourself a solid and follow Cole.