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Cindy Conaway

1. When do you feel at your most attractive?

Naked, actually. But I love cashmere.

2. Do you notice women on the street? If so, what sort of women do you tend to notice or admire?

Most of the women I notice are super put together Asian women. I don't know where they get their clothes.

3. What are some things you admire about how other women present themselves?

I always have cat fur or chocolate on me somehow. I admire the effortlessly neat and clean.

4. Was there a moment in your life when something “clicked” for you about fashion or dressing or make-up or hair? What? Why did it happen then, do you think?

I read a book called "Simple isn't Easy" and immediately pruned a lot of stuff. My mom brought me up that if you had it, you wore it, even if you don't really feel good in it or if it's getting worn out. Now I try to prune better. Also I decided my work uniform would be a dark well, fitting, t-shirt and pants, and a cashmere cardigan. I always feel put together that way. Summers are a little tougher.

5. What are some shopping rules you wouldn’t necessarily recommend to others but which you follow?

Natural fabrics only (except maybe a little spandex for stretch). it's kind of exhausting to care about that when other people clearly don't care and find a ton they want to wear.

6. What are some rules about dressing you follow, but you wouldn't necessarily recommend to others?

Have a work uniform. Always earrings and either a necklace, ring, or bracelet, but not more than one unless it's for a fancy party.

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

A co-worker told me to wear cobalt blue every day because it was my best color. It got into my rotation and still is, although now that I live in NYC I'm more likely to stick to black or grey unless it's really sunny out.

8. Do you have a unified way of approaching your life, work, relationships, finances, chores, etc.? Please explain.

Not really.

9. Are there any clothing (or related) items that you have in multiple? Why do you think you keep buying this thing?

I have many of the same 2 styles of black Banana Republic t-shirts, and many cashmere cardigans. I feel put together and don't have to think too hard when I get dressed.

10. Have you ever successfully given someone a present of jewelry or clothing that you continue to feel good about?

I bought my boyfriend a great cashmere scarf. Now that we live together, I sometimes want to steal it back.

11. Is there any fashion trend you’ve refused to participate in and why? 

I stay classic. This means my clothes never really go out of style.

12. Can you say a bit about how your mother’s body and style has been passed down to you, or not?

My mom brought me up on "permanent press" and she was always dieting. I'm mostly pretty slender and like natural fabrics. She's the one who told me I was a winter, though, and I do stick to black and jewel tones, because she was right that I don't look right in most pastels.

13. Have you stolen, borrowed or adapted any dressing ideas or actual items from friends or family?

Most of my family has terrible taste. One of my grandmothers had great jewelry, though, and most of my necklaces and rings came from her.

14. Was there a point in your life when your style changed dramatically? What happened?

I transferred to a preppy private school in 11th grade and tried to dress like them without the money, quite unsuccessfully. Fortunately, I spend the summer at an arts camp and came back with some chartreuse socks and pink pinstriped jeans that made me feel more like myself and went back to being the artsy girl I'd been before.

15. Is there anything political about the way you dress?

No. My boyfriend teaches global business, though, so I sometimes check out where all the clothes I'm wearing were made, but I usually don't shop on that basis.

16. Please describe your body.

Slim for a 47 year old. I didn't actually start having breasts until I was in my 30s and gained some weight, but I'm a nice size now. Good hips.

17. Please describe your mind.

I'm smart, but pretty right brained and ADD. It's easy for me to forget my keys or to call a student back because my brain is full of stuff like everyone who ever guest-starred on Seinfeld or that Evelyn (Champagne) King did "Shame."

18. Please describe your emotions.

I'm easily frustrated but fairly even tempered. I used to cry a lot, but as an adult nearly never, even when bad stuff like my cat dying happens.

19. What are you wearing on your body and face, and how is your hair done, right at this moment?

I'm in PJs because I'm working at home as I do every Friday (and often Mondays or Wednesdays). My hair is in a ponytail. No makeup--when I go out I'll use moisturizer and a Chanel bronze lipstick. My fluffy white cat is lying on me. I won't get dressed in real clothes until it's time to go to the dinner party we've been invited to because his fur will just get on my clothes.

20. In what way is this stuff important, if at all?

Clothes are important in identity formation. I keep a blog where I talk about the media I'm consuming, but I start with 3 sections which I label Consuming/Producing/Anticipating. In Consuming I'll talk about TV, movies, or books but also food, museums, or clothes. It's all part of me and what I've experienced.

21. With whom do you talk about clothes?

My boyfriend mostly. He has no real style but was brought up to replace his stuff frequently (mostly with identical clothes from the Ralph Lauren outlet), and encourages me to get new things and dispose of things that are looking worn. He's moved up into administration, though, so I'm helping him shop for better suits and ties and a nice messenger bag instead of a collegiate backpack.

22. How do institutions affect the way you dress?

I think work deserves appropriate dress. When I worked in corporate life, I wore more suits or dresses and never do as a professor, but I don't wear jeans or sweatshirts/t-shirts with writing on them or tank tops to work. Many of my colleagues do, but I prefer not to.

23. Do you think you have taste or style? Which one is more important? What do these words mean to you?

I have taste, I think. I know what looks good on me and what doesn't, though I don't always dress to best effect. I don't have a lot of flair and sometimes I get bored and think I need to switch it up.

24. Do you remember the biggest waste of money you ever made on an item of clothing?

I am still carrying around, despite having lived in at least 20 houses or apartments since then, a silk Nipon coat dress I bought in 1989 for my first job. It's gorgeous and oddly still fits even though I'm 5 sizes bigger, but the styling is so 80s, with big multicolored lapels that I'll never wear it.

25. Are there any dressing tricks you’ve invented or learned that make you feel like you’re getting away with something?


26. Do you have style in any areas of your life aside from fashion?

I've accumulated a nice selection of vintage furniture I think. My apartments usually look pretty nice. After a year with my boyfriend in a NYC apartment, I'm not sure this place looks as nice, but I'm still happy looking at the furniture I brought plus the (new) couch we bought together.

27. Can you recall some times when you have dressed a particular way to calm yourself or gain a sense of control over a situation that scared you?

I was on Jeopardy! and wore my uniform of a nice pants and a cashmere sweater with what I thought of as my lucky earrings and my grandma's ring. I lost but I still wear those things.

28. Would you say you “know what you like” in the area of fashion and clothing? If so, do you also know what you like in other areas of life, that is, are you generally good at discernment? Can you say where your discernment comes from, if you have it? Or if you don’t have it, why or why not?

I'm a picky eater with a lot of dietary restrictions (quasi-Kosher, lactose-intolerant, allergies) so I can usually zero in on the 2-3 dishes on a menu I can have and will like, and make a decision fairly quickly. Friends who eat more are surprised I've decided before they've even zeroed in on a few choices.

29. Did your parents teach you things about clothing, care for your clothing, dressing or style? What lessons do you remember? Or did you just pick things up?

My mom didn't teach me to iron, so I don't. She did teach me to hang up my clothes promptly, which I don't always do, but she uses wire hangers and I won't.

30. What sorts of things do you do, clothing or make-up or hair- wise, to feel sexy or alluring?

Silk lingerie is nice, though not for every day.

31. Many people say they want to feel “comfortable,” or that they admire people who seem “confident.” What do these words really mean to you?

I find bras or tight pants are something I feel all day. I usually wear one of those tank tops with a shelf-bra in them instead of a real bra, even though I have plenty of those, and looser pants. People compliment me more in tighter pants and a real bra, though.

32. If dressing were the only thing you did, and you were considered an expert and asked to explain your style philosophy, what would you say?

Simple elegance, ease.

33. What is really beautiful, for you, in general?

Simplicity. Clarity--just a few well-chosen accessories.

34. What do you consider very ugly?

Bare midriffs on any but the very young. Abercrombie or Hollister t-shirts. I can't stand going to Times Square where everyone wears those.

35. Are you generally a good judge of whether what you buy will end up being worn? Have you figured out how to know in advance?

I keep it simple. Good fabrics, black, grey, or occasional jewel tones and it will end up in the regular rotation.

36. When you look at yourself before going out, and you are trying to see yourself from the outside, can you describe a bit about what this “other person” is like? What do they like, dislike, what sorts of judgments do they have? Is this “outer eye” based on someone you know or once knew?

I'd like to think I model myself on Coco Chanel and Audrey Hepburn.

37. What is your process getting dressed in the morning? What are you considering?

Weather. I'm not going to wear black or jeans if it's going to be super sunny out. Am I going to be in a meeting, or just hanging out in the office?

38. What are you trying to achieve when you dress?

To look good, but also be comfortable. As a younger person I wanted to stand out, but not that's not important to me.

39. What, for you, is the difference between dressing and dressing up?

I can dress up for a party or wedding and look very good. Mostly I stay simple, though.

40. If you had to wear a “uniform” what would it look like?

I do. Black or grey slacks, a black or grey t-shirt, and a cashmere cardigan. I have one in nearly every color, although now that I'm in NYC I mostly stick to black, grey or navy.

41. What would you say is “you” and what would you say is “not you”?

Trends are not me. Polyester is not me. High heels are mostly not me.

42. What is your cultural background and how has that influenced how you dress?

I'm Jewish, but I don't think I wear a lot that smacks of that.

43. Do you remember a time in your life when you dressed quite differently from how you do now? Can you describe it and what it was all about for you?

In high school and early college I wanted to stand out and to have people know I was an artsy actress type. Now I'm happier looking sophisticated and comfortable.

44. What sorts of things do you do, clothing, make-up or hair-wise, to feel professional?

I still have a suit, but mostly just for one of my nicer cashmere cardigans.

45. How do you conform to or rebel against the dress expectations at your workplace?

A lot of my colleagues are slobs because they're academics. I try to look nice.

46. Do you have a dress code, a school uniform, or a uniform that you wear for an extracurricular activity?

I wear jeans or tank tops on the weekends, but still with cashmere.

47. Are there ways in which you conform to or rebel against these uniforms?

Sometimes I get bored and wonder if I should buy something trendy or different. I did recently buy some more "fashion forward" pants at an expensive French boutique, but they're still grey. I get a lot of compliments on them but I don't think they look so different from my wardrobe.

48. Do you find it comforting or constraining to have a uniform?

Mostly comforting, but sometimes I wonder why I can't just get over myself and buy something made of mystery fabric sometimes.

49. What is an archetypal outfit for you; one that you could have happily worn at any point in your life? What do you like about it?

Wearing cashmere cardigans makes me feel like I'm part of the bon vivant lifestyle to which I wish I could become accustomed. They're expensive but I keep them forever.

50. Do you ever wish you were a man or could dress like a man or had a man’s body? Was there ever a time in the past?

No, except it would be nice to have the free tailoring at stores.

51. If there was one country or culture or era that you had to live in, fashion-wise, what would it be?

Paris in the 20s.

52. Do you consider yourself photogenic?

No, though I'm working on it.

53. When you see yourself in photographs, what do you think?

Looks goofy.

54. Are there any figures from culture, past or present, whose style you admire or have drawn from?

Coco Chanel and Audrey Hepburn plus Any Warhol.

55. Have you ever had a dream that involved clothes?


56. What would be a difficult or uncomfortable look for you to try and achieve?

Skinny jeans, platform shoes, a bare midriff.

57. If you were totally comfortable with your body, or your body was a bit closer to what you wish it was like, what would you wear?

If I were more hairless, and didn't have to shave my legs all the time, I would wear more dresses.

58. Is there anyone that you are trying to attract or repel when you dress?

Not really.

59. Are there any dressing rules you’d want to convey to other women?

I wouldn't presume to do that.

60. What do you think of perfume? Do you wear it?

I love Chanel #5, but have a fragrance allergy so mostly stick to unscented everything. Most perfumes smell like rotten eggs on me anyhow, and I have a terrible sense of smell.

61. What are some things you need to do to your body or clothes in order to feel presentable?

Shower, shave my legs and underarms. I don't iron but will often hang clothes in the bathroom to steam while I shower. Use a tape roller to get the cat fur off. I nearly never leave the house without lipstick and earrings.

62. How does makeup fit into all this for you?

I mostly just use lipstick, but I always wear it out of the house. They changed my L'oreal Lipfinity, so now I'm wearing Chanel long-last for the first time. I still havent forgotten it cost me $35.

63. Is there a certain look you feel you’re expected to like that you have absolutely no interest in? What is it? Why aren’t you interested?

Dressing sexy.

64. Can you describe in a basic way what you own, clothing and jewelry-wise?

Lots of good fabrics, mostly Banana or J. Crew. Many many cashmere sweaters. A few good Coach bags. Vintage necklaces and rings from older relatives. Dangly earrings, not vintage because my relatives didn't have pierced ears.

65. What is your favorite piece of clothing or jewelry that you own?

My grandma's topaz ring. It wasn't her birthstone, but it's mine.

67. Looking back at all your purchases over the past five to fifteen years, can you generalize about what sorts of things were the most valuable to buy?

A vintage Chanel jacket. My black Coach purse. They make me feel put together and well off.

68. Is there an item of clothing that you once owned, but no longer own, and still think about or wish you had back? What was it, what happened to it, and why do you want it back?

Just out of college I bought a purple linen Rebecca Moses shift to wear to my advertising job, which started in summer. It was gorgeous. I stained it a year later. There's no way it would fit now, but I still miss it.

69. If you had to throw out all your clothes but keep one thing, what would you keep?

My black cashmere cardigan.

70. Building up your wardrobe from nothing, what would you do differently this time?

But only the better cashmere. You do get what you pay for.

71. What’s the first “investment” item you bought? Do you still own or wear it?

I occasionally wear my vintage Chanel cardigan. I can't button it, but if I don't try, it looks nice enough.

72. Was there ever an important or paradigm-shifting purchase in your life?

The first cashmere sweater I bought was at The Limited for about $20 on sale, but it felt so great. I don't think I bought a second for many years.

73. What item of clothing are you still (or have you forever been) on the hunt for?

The perfect black pants. Something like Karen wears in the early seasons of Will and Grace.

74. What are your closet and drawers like? Do you keep things neat, etc?

I'm messy, but I keep my closet organized by type and then by spectrum. It's tough. I've just moved from having two closets of my own to sharing one with my boyfriend and I don't quite have space to do it the way I would.

75. Were you ever given a present of clothing or jewelry that especially touched you?

My boyfriend has bought me some perfect earrings.

76. Did you ever buy an article of clothing without giving it much thought, only to have it prove much more valuable as time went on? What was the item and what happened?

I bought Ecko shoes in Poland because the ones I bought weren't holding up to the Cobblestones. They're moderately ugly, but they are the most comfortable shoes I have for walking around NYC.

77. How and when do you shop for clothes?

I don't much. I've spent a lot of time looking at cashmere sales at J. but I have enough sweaters now. We go to outlets sometimes when we leave town.

78. Do you like to smell a certain way?

I have to stick to fragrance-free mostly.

79. How does how you dress play into your ambitions for yourself?

I don't want to be an administrator, and the Associate and Full professors I know don't dress better than I do so I don't have to change my style any. I'd like to be richer, though, so I do try to dress like I would if I could when I can find a good deal.

80. How does money fit into all this?

I was brought up basically to feel guilty for spending any money on new clothes, so I always do.

81. Is there an article of clothing, a piece of make-up, or an accessory that you carry with you or wear every day?

Always lipstick (bronze/chestnut). I have to have a purse because I need my sunglasses (prescription) and regular ones.

83. Do you remember the first time you were conscious of what you were wearing? Can you describe this moment and what it was about?

When I was a little girl I only wanted to wear dresses, never pants. I was afraid to go into the hardware store because I thought the sign was advertising Dutch Boy pants and that my dad was going to make me wear jeans.

What’s your birth date? 
Where were you born and where do you live now?

November 30, 1967. I was born in North Carolina. I live in NYC now.

Say anything you like about your cultural/ethnic/economic background.

I'm Jewish. My folks are academics, as am I.

What kind of work do you do?

I teach media studies. I've had several earlier careers, though, so I started my Ph.D./academic jobs fairly late.

Are you single, married, do you have kids, etc.?

I'm single. I live with a guy. He has stepkids who are almost my age (his ex is a lot older), but neither of us has children. We have a cat.

Please say anything you like about yourself that might put this survey into some sort of context.

I read the book and liked it. I was jealous of my colleague who was quoted.

How do you feel after filling out this survey?

Tired. It was longer than I thought. I thought I would watch Project Runway before I started my workday but this took almost as much time.


I teach media studies and write mostly about brainy and talented girls on teen television. I live in NYC with my boyfriend and our cat, Holden.

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