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7. What is the most transformative conversation you have ever had on the subject of fashion or style?

I’ve never had a single transformative conversation; it’s a process. But I do remember the first weeks of getting to know my now best friend Sarah. She’s a damn sharp dresser with a lot of confidence. Hair hats, velvet, out of production colors. She dresses like a fantastic couch. But she’s generally a thoughtful, quiet introvert. She once said, “Everyone assumes if you dress ostentatiously, you’ll have a personality to match.” It really made me reflect on what we are expressing with our outward appearance. How accurate are these book covers?

At eighteen, I was newly back in the world after a bad illness. I’d lost a lot of weight and was learning how to take up space again. At the same time, a friend was beginning to transition, so we taught each other how to walk in heels and sit mostly gracefully in skirts. It was sweet and real and still really helpful.

I talk with my sister a lot about shape and color, too. She’s the one who convinced me that I'm a redhead so I can wear pink, and no it won't make me look like a little girl.

My husband and I often have conversations about style (and everything else for that matter). I think a great break-through for me was realizing that having an eye catching style is great for business. The more memorable the style is the better. Personal style can be an art form, it can help form first impressions and make an impact on the world just as any other art form can. It's amazing the effects style can have on people and how often style is controversial or the cause for (negative) judgement.

Probably the conversation I had with my mother about the relationship between the coat and the womb. She had given me a cashmere coat, and I tried it on and as I sat shrouded in the warm fabric, looking at her, I realized her womb was like the original coat. Maybe that seems like an odd leap of the imagination, but it felt right. Suffice to say it was the most unusual fashion conversation I’ve ever had.

My ex-husband said you could wear anything if you are in shape and your body is such that it looks good in anything. Although this likely gives some girls confidence to wear whatever they want, I wholeheartedly disagree with his lack of compassion for women who struggle with accepting their figure – whatever shape they are in.

Since then, my new husband has said that you should dress for the job you want, not the job you have. After adopting this philosophy, I have doubled my salary in the past 1.5 years.

I'm not sure. Maybe my mom telling me, as a teenager, that I wasn't allowed to wear skinny-strapped tank tops unless I owned a strapless bra because having straps showing was “tacky.” I don't think that's the case 100% of the time, but I suppose it did make me thinking about an outfit's underlying architecture from an earlier age.

I had a sort of heated argument with a friend once about what it means to follow popular trends in fashion. She looked down on trend-following as a sign of a lack of independent thought, or a sort of uncreative desire to fit in. I can't remember exactly. My friend probably doesn't even remember it. But I was very insistent that people should wear whatever they want, whether it's everywhere or nowhere, and be respected for making that choice. That fashion should be fun and personal, and that's it. That when people start censoring what they wear, or get that idea into their head that they should censor what they wear so they don't get judged or looked down on or labeled inaccurately, that something expressive and potentially joyful is squashed, and that's mean.

I know that the reality is that people judge you based on what you wear, often not consciously. And that I do that, too, without a doubt. And that's fine. It's unavoidable and okay. But I don't want to ever say anything about anyone's clothes out loud unless it's a compliment. Probably because I would like everyone else to do that, too. I just want getting dressed to be fun. It sucked so much in middle school, worrying about what people would think. It should just be fun from here on out.

I don't really know if that conversation was transformative for either one of us, but it did cement those beliefs in my head.

I was on an author book tour in Calgary and went into a bookshop to sign books, dressed very casually (probably jeans and leather jacket) and the owners kind of clapped their hands and said: 'You look exactly how an author should look!' I was taken aback, then realized it's true. People don't want artists to look the same as everyone else. We can get away with a lot. Phew.

I can’t say that I am very into fashion – I just don’t really know that much about it. But during college, I took a lot of courses on women and gender, and we often discussed the role fashion has in feminism and female confidence. I think it’s made me value fashion more. Now, as I get used to my place in the professional workplace, I am starting to reevaluate the importance of the type of outfit that makes me feel the most successful.

I always avoided them because it felt silly to parse style. I wanted it to just be, and not be discussed. It still feels somewhat gauche…but potentially interesting if I could get over my hangup about it.

It was more about style: An older wiser woman (who actually used to model in NYC the 70's) once told me that instead of down-playing compliments on my style or look, just say "thank you. You're so kind". I have done that ever since, and it has made for ease in conversation and changed my posture and outlook.

Most people in DC dress in such a boring way that when I see someone in something interesting, I go up to them and talk to them. I have met some of my best friends this way.

In 1997, when I was about thirteen, I created a fan website for this band I liked. The internet wasn’t what it is today, so the website was kind of a novelty for the band, and the drummer befriended me and was a great mentor. I wore really baggy jeans – like, really, really baggy – and oversized Nirvana t-shirts every day, because I thought only superficial people wore nice clothes. My clothes were supposed to signify my values and independent spirit, but I think all they really signified was that I was depressed and angry. Anyway, I remember being struck that the woman in this band that I liked dressed in a feminine way but was still really cool. They played at CBGB when I was fourteen or fifteen, and I had a conversation with her about clothes while sitting at the bar. She suggested that I might consider wearing more flattering clothes. It was a big turning point for me, realizing that my outer appearance didn’t have to reflect my inner angst, that I could take pride in how I looked, that I should probably look a little deeper than clothes when judging a person’s values… though I did (and still do) think that the clothes you buy or brands you display often do have at least some kind of association with your values.

My partner who is really into fashion and who writes about fashion has told me a lot about men’s fashion. I’ve gone shopping with him, for suits, before and it was fascinating to watch how much effort and knowledge had to go into finding a perfectly fitting suit. So, before I met my partner, I never paid a lot of attention to what men wore, or rather, to the parameters of men dressing fashionably but after meeting and talking with my partner I saw how complicated men’s fashion could be and how much fun. I always thought men had fewer options, fashion-wise, because of our gender-appropriate constructs, but being around my partner – who, for example, has worn a kilt, does wear a lot of bright colour and has no problem with flamboyance – had shown me that men’s clothing can be just as playful and sexy as women’s. Also, I’ve always been attracted to men in skirts so I’m happy to talk to any man in a skirt.

My family was in garment manufacturing when I was growing up, so I know what sort of hard work goes into clothing production. During some summers and weekends, I spent time clipping excess thread from clothing and folding it to be shipped. As a result, when I go to a shop and see clothing that is wrinkled and is covered in dangling threads, my first thought is that it was produced in a shoddy factory. Later I interned at a couple of fashion magazines, but none of the knowledge I had about clothing was applicable.

Also, my dad is always telling me that most things that say dry clean only can probably be handwashed—but only if it’s not synthetic.

I talk to my boyfriend a lot about clothes, as we live together and so he is there when I’m getting dressed, and vice versa. He has a really great, unique style, and believes that it’s important to spend money on clothes (something that I have a great deal of trouble doing). I also chat with my bestie a lot about what we wear. Her and I have almost opposite styles- she’s a lot more dark/ punky/ sexy, and I’d say I’m “grandma chic”. But we both dig the others’ style. In our conversations about clothes, we always end up really emphasizing that being sexy and feeling beautiful, is really just about illuminating who you are- and that both a sexy black dress, and what we lovingly refer to as “dumpers” ie. sweats/ housewear, can be equally sexy.

My friend Natasha and I were talking about what we wore to our school prom. I didn't actually go to mine but I was saying that I hated the idea that you had to spend hundreds of dollars on a dress. She looked at me and laughed and said "I wore a nightgown I bought at an op shop for $2 to mine". I've never since thought I needed to spend a lot of money on clothes, no matter the event.

My friend Cassy understands that fashion makes me feel very taken care of. She made me a silk blouse with a twist, from a complicated Rachel Comey pattern. Took me to Mood fabrics to pick out the fabric and everything. It made me feel very loved.

Cassy and I talk about fashion all the time. It's an ongoing transformative conversation.

Fashion makes me feel loved because it is about my mother, who was obese when I growing up. But she had been slim and beautiful as a young woman. She was a stewardess back in the days when they had to have specific measurements. Long story, she almost died from medication that was later taken off of the market, and was a part of a class action lawsuit and came into some money. She had raised 8 children in our small 4 bedroom house.

When she came into the money, I was in 7th grade. In 8th grade we moved into a bigger house. For a few months, almost every Friday she would take me shopping to LL Berger’s, the local fancy department store in Buffalo, NY. We shopped the sale racks, mostly. In the juniors department, I was all about Esprit. When I met my BFF Rachel in 7th grade, one of the first conversations we had we listed all of our Esprit clothes to each other.

My mom took me to the designer sale rack upstairs as well. Not just the regular grown up clothing, but serious designers, from the small room. Christian Dior, Norma Kamali, Flora Kung. This would have been maybe 1985. The rack was circular. Norma Kamali grey boxy sweatshirt fabric tops, with giant shoulder pads and tulip skirts in same fabric. A silk watermark Flora Kung dress, taupe and black wide stripes with red and blue patterns over that, and then the jacquard on the silk. A black wool Christian Dior circle skirt. Donna Karan wool bodysuits. This time with my mother was super important. She was reliving her lost beauty through me, I think.

And I can totally see doing this with my own daughter someday. I save clothes for her. A faded silk Diane Von Furstenberg from a sample sale that I was gorgeous in, in the 90's. I can't wait to see her in that someday. Maybe with combat boots or sneakers. I wore it for my 28th B-day party that I threw for myself at Galapagos in Williamsburg when I was first dating a writer/performer/cad that everyone in NY dated in the 90's and I remember sitting on his lap in that dress, his hands on my hip. “You’re not wearing any underwear.”

“Of course not,” I answered, thinking about panty lines. He thought it was for him.

On a tangent here.

My friend and colleague, the costume designer Melissa Schlachtmeyer, just died at 41, and I will miss the conversations we had about clothing. Tribalism, influences, politics, beauty, comfort, appropriateness- we saw everything through the lens of clothing. Those were really transformative conversations.

Judith Butler has been a huge influence on my style. Not that I've ever had a conversation with her, but reading Gender Trouble and thinking of gender as performance has been liberating in so many ways.

All my friends, male and female, talk about clothes sometimes. I think it's natural to be concerned with how you are perceived, and face, hair and clothing are the first things everybody sees. But transformative is not the word I'd use for these conversations. Mostly these conversations are soothing. Clothing is a part of life we can control to a greater extent than other parts (I can buy red pants if I want red pants, but I can't make someone like me if they don't already.) When a friend of mine was diagnosed with adult-onset epilepsy (not fatal, just really crappy), one of the first things she did was go through her clothes and bag things to give away. She couldn't clean out her brain so she cleaned out her closet.

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