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

I can’t imagine having a more transformative conversation about style or fashion with anyone other than Malcolm. We used to talk about clothes all the time. Malcolm knew so much about fashion—from the historical to the practical. He knew everything about the great couturiers and the fashion movements in pop culture. But he could get his hands dirty too. He knew how things should be made, all the different techniques of fabrication, cloth, cut, etc. Looking at a pair of trousers flat, he could tell if it would suit you. Once, in Zurich, he took the bottle opener in the hotel and wedged it into a new pair of shoes (mine) to stretch it out. He knew exactly what he was doing.
We both loved clothes and were obsessed by them. We loved shopping and looking… at everything, not just clothes. I often joked that shopping was our favourite exercise—shopping for cheese, shopping for wine, shopping for nails, shopping for linens, shopping for books, shopping for objects and furniture, shopping for clothes… We always went shopping together. The only problem is, I would get bored more easily shopping for men’s clothes than he for women’s clothes. Men’s clothes are just not as interesting! He would insist always that I come into the dressing room with him while he tried things on and reproach me when I started to get bored.

I talked the most about clothes with my ex-boyfriend, who had dubious style, but understood fashion cuts and lines nonetheless. He is a painter, and so he appreciated my compositions of color, pattern and line. Dressing yourself can be like painting or any art form in that way.

I talk to everyone who is willing to talk to me about clothes. I like to see a wide range of styles. Everyone has their "character" of themselves that they dress, even if they try to tell me that the way that they dress is unconscious.

This is a very common answer, but Jeanne Becker and Fashion Television was something I watched when I was a kid. It showed fashion as an art and designers as artists. It showed Paris and New York and London. I had that before I had Vogue or Harper’s Bazaar or W Magazine.

At an artists colony another writer observed that I used a bubble mailer as a case for my laptop computer and asked, “Don’t you have a job? Can’t you afford better than that?” I was still thinking like a graduate student, operating from a place of deprivation. Basically, she pointed out that I was cheap and that it showed. I was embarrassed and later bought myself a computer case that I really liked. I think of that conversation sometimes when I’m trying to talk myself out of buying an article of clothing I really love.

my boss once told me never to have more than two crazy things going on on my head

I had some intense conversations about it with my husband when we first met. It first came up the first time he suggested we go shopping together, for fun. I had never gone shopping for fun in my life. I laughed and said I wasn't sure he was going to enjoy shopping with me, and he got really upset. It took a while for me to understand the way clothes were important for him, the buzz he got from wearing nice clothes and watching people move in nice clothes. Fashion had never been about pleasure for me. But seeing the way in which he feels particularly attracted to me when I'm wearing certain things sort of established the psychological link I hadn't had before, that wearing nice clothes is sexy. I like sexy clothes now, I like wearing something that makes me feel sexy, but it's a feeling very much indissociable from my relationship to my husband. I don't know what other guys consider sexy and I think I would have a really stressful time trying to figure it out.

When I was twenty, I did an internship at a women’s magazine. The conversations were mostly about celebrities, children (which most of the women working there had), and stuff you could buy – including fashion. I was a student, so I didn’t have much money. My style was also still developing. But one day, when the weather got colder, I wore a cashmere scarf that I had bought for 10 euros. It was awesome: deep green, so large I could use it as a blanket and so soft. When I walked into the office with it, the colleague I despised most told me: ‘What a nice scarf. This really is a statement piece.’ I thanked her, and then I realized: if I really love what I’m wearing, other people will notice that, too. Since then, I always ask myself when I’m considering buying something: could I love this? And I have indeed met many loves since.

I rarely talk about clothes, actually. Most of the conversations I recall about fashion and style were not quite friendly ones from adolescence, between my mother or older Southern-lady relatives pressuring me to wear something more formal or girly and me stoutly refusing.

At university, I had a brief conversation about how I rarely wear pants to work, but typically arrive in skirts, at which point I decided that I need to acquire a better selection of pants in my wardrobe, because wearing skirts too often to work can look horribly girly. Pants demand respect.

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.

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