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Kay May

1. When do you feel at your most attractive?

When I'm happy.

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

I notice everyone, but the women I pay attention to are ones with their own style, who don't look like they're following trends; the ones whose style, or piece of jewelry, or shoes makes me smile.

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

The ease in which they wear their clothes as opposed to their clothes wearing the women.

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?

Gosh, I wish I had an answer to this, but no. No moments. Ok. Maybe one… I saw a pair of perforated leather shoes made in Spain. They were two-tone spectators with a Louis heel and looked like they landed straight from 1933. They were also more than I had ever spent on shoes, yet I knew I had to have them. That began the end of the made in-China, cheap shoes and the beginning of all shoes vintage styled, accurate from toe box to vamp to heel shape.

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

Well, I really would recommend this to others, even though store clerks hate it: scrunch the fabric in you hand and if it wrinkles like a prune, consider if that's something you and your iron can live with. If ordering online, go for the waist fit and the bust and hips will fall in place and if not, they're easier to alter than the waist.

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

Ok, this one I wouldn't recommend because it's my way of thinking and I'm not trying to make anyone else do things my way: I buy online vintage or handmade because I don't want to spend money on a dress and then see a thousand other people wearing the same thing.

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

Can't say that's ever happened.

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

Oh gawd no. I go by vibe on life and relationships and am a hurricane in need of taming for everything else.

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

Do you mean multiples of the same thing? LIke white t-shirts? Find one that fits, buy a couple of more? If you mean do I have lots of certain types of clothing, then dresses (!) is the answer. Love dresses and wear them 95% of the time.

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

Yes. I gave my friend at work something of mine I thought she'd like and she did. She loved it and wears it and I'm so happy it worked.

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

Platform stiletto pumps. They're ugly and they're everywhere.
Is fur a trend? No. Fur. Ever.
Bandage dresses - it's like layered Spanx in colors.
Animal print - I feel too costumey.
Flip flops - nasty.

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

My mom died when I was a teenager and I don't remember much about her style or body.

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

I wear my boyfriend's white button down shirt tucked into high-waisted tailored tweed palazzo pants. Cuter than it sounds.

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

No, it's all been gradual.

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

Maybe the "no fur" stance.

16. Please describe your body.

Petite, athletic; good legs; trim waist; bit of a belly; working to stave off government worker ass.

17. Please describe your mind.

Of course; just as soon as I find it.

18. Please describe your emotions.

My hormones are fluctuating and I would probably cry at a dessert menu if you handed me one, and if you didn't, I'd probably be mad at your for ignoring me. Other than that, I'm generally kind to people and friendly.

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

Face: Skinceuticals tinted sunblock.
Baby sunblock on my chest.
Colorstick blush
Burt's Bees tinted lip balm
Body: Biocell Oil; cream moisturizer on legs and arms
Hair: Mid-length bob, micro bangs, R&Co. styling creme.
Clothes: novelty print cotton dress, sweater, 1940's watch and bracelet.

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

Ask my dermatologist and she'll lecture you on the sunblocks. The makeup… sometimes I a piece of plain paper is lovely just as it is; other times I want to doodle on it, color it, draw shapes. Hair… since it frames my face or pokes out under a hat, I like it a certain length and want it to look healthy.

21. With whom do you talk about clothes?

Coworkers; strangers I meet who comment on my clothes or shoes; friends.

22. How do institutions affect the way you dress?

I work in government and we have a certain protocol. I wouldn't say "conservative," but certainly not as creative as say, a independent designer clothing boutique employee.

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

I'd like to think I have both, but if I had to pick one…. style? Seriously, I can't really define them to be inherently different.

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

If I really put my mind to it, but I tend to stuff those bad decisions in the way-back portion of my mind.

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

Sort of: I wear t-shirts backwards. Bateau necklines are flattering on me and it's difficult to find that in t-shirts that aren't on the floaty, baggy Eileen Fisher side of life (not to mention her ridiculous price tags). So I find basic tees, turn them around and have a bateau neckline and v-back or scoop back. Ta da!

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

My investigative skills are a force to be reckoned with. I've located missing persons, missing heirs and fugitive criminals with some incredible skill and creativity.

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?

Pockets - I wear a dress with pockets when I know I'll be in a spot that requires some control. I don't like that commonly female body stance of holding the fingers in front of the torso (you know the one - you see it in clothing catalogs, TV reporters, etc.). One hand goes in the pocket, the other can move around. Forget that the one in the pocket is picking at hangnails, no one sees that, and I feel better at the task at hand.

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?

Geez, these questions are getting tough! Yes, I know what I like (and don't) in fashion and clothing. Ditto with food - where it comes from, how it's made… That comes from a desire to eat more pure and cruelty foods. Something else that's gradually developed over earlier years of fast food and candy bars. I know cleaner food and exercise makes me feel happier, stronger and stand up straighter.

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 made my clothes for me. It was fun to pick patterns and fabric and I loved wearing what she made.

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

You know, I don't really do anything specific. It's either there or it isn't on some days.

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?

Depends on the circumstances in which those statements were made. To me, comfortable means I'm good with myself and not worried about what other people think of my clothes, hair or opinions.

Confident - I *know* my clothes, hair and opinions are mine and I'll gladly put them forward.

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?

Nothing. I'd change the subject.

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

There is beauty in nearly everyone and everything when I look with an open heart.

34. What do you consider very ugly?

Smokers. Abusers. Overgrowth on open spaces.

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?

Yes! I might take a couple of hours trying to decide if I really, really need it or do I just really, really want it, but I've learned to quell the urges and purchase what I'll actually wear more than once.

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'm going to pass on this question.

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

Work week: What time is it? Do I have time to iron this? Why didn't I decide last night what to wear today? Can I ride my bicycle in this dress?

Days off: What's the weather like? Where are we going? Will this look good at the cafe this morning?

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

Work week: I'll be wearing this all day and maybe doing some physical work, but I want to be fresh and stand out a bit from the crowd. And if I'll be riding far on my bicycle, am I wearing something that I won't sweat in too much.

Weekend: No real goal other than to be functional and fun.

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


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

Cotton day dress and heels.

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

Me: Crisp cotton, colors, simple lines, true vintage.
Not me: Fur, animal prints, rockabilly, cubicle wear.

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

On my own at a very young age, so anything that was trendy was appealing. I was very young and wanted to fit in with people. Don't know why it changed to almost a complete flip flop.

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?

Yes. After my folks died and I was on my own, there was some snark that I would spend my inheritance recklessly. To show these people that I wasn't like that, I didn't spend money. At all. I had a pair of denim and jute shoes that were literally falling apart. An older woman looked at me and said, "You can buy new shoes, you know." So I tentatively went out and bought cheap, trendy clothes that I thought were so sophisticated.

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

There really isn't anything. My professionalism comes from my skill at work. If I'm in court, I'll wear long sleeves or a jacket over a sleeveless dress though.

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

Ok. This goes NOWHERE but here… once in awhile I leave the undies at home. Ok. I said it. Next question!

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

Nope. I even wear my skirts and dresses when I ride my bicycle.

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


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


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?


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

As cliched as this sounds, Paris in the Jazz Age. The constraints of the Victorian Era were being loosened (to the shock of that generation) and the new generation was wearing clothing that was shorter and freer. Cloche hats looked good on everyone, the most shocking thing a girl could do was bob her hair and CoCo Chanel was designing some fantastic silhouettes.

52. Do you consider yourself photogenic?

No! I'm either very unphotogenic or that's how I really look, and I prefer to believe the first option.

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

Thought #1, directed orally to the person who took said photo: "This does not go on Facebook!"

Thought #2, "meh."

I actually think I look just fine, that is until I see a photograph of myself.

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

Norma Shearer.

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

Lack of, perhaps, but not clothing itself.

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

Strapless anything. I just don't like the look and don't think it's appealing on me.

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?

I actually like my body. What I'd wear if it looked better on me? Cigarette pants and a sweater that hit above the hips.

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

Attract? No. Repel? No.

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

Dress for the body you have.

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

Like it on sometimes on some women, but not on me so much. Absolutely hate it on a hot day. Absolutely hate the sent of vanilla. We have a woman in our office and I can tell where she was because her scent is so strong. The rare times I wear it are on sultry fall nights and I use only enough to smell it on myself, not so that others will smell it, unless they are very, very close to me.

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

Clean and iron. To be specific, the clothes get ironed, not me.

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

I live on the coast so a fully made up face isn't the norm. Makeup is sparse but usually lip color.

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?

Rockabilly. I think because I like vintage styles, people assume anything with polka dots, poodles and spiky heels is something I'd like. It's not.

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

Jewelry is mostly vintage, collected over the years - bracelets, dress clips, earrings and one watch.

Dresses are mostly vintage and handmade.

Pants - Levi 501s button fly; Calvin Klein boyfriend jeans.

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

My 1940's watch is really special. My boyfriend bought it for me and was quite proud, as he knew I'd been eyeballing it for over a year.

66. Tell us about something in your closet that you keep but never wear. What is it, why don’t you wear it, and why do you keep it?

Closet cleaning is a tough gig! If I haven't worn something in a year, I pull it out and box it. My excuse for keeping something in my closet longer is that I MIGHT wear it. Yeah, I know.

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?

Valuable? Do you mean what I wear over and over? That would be my vintage jewelry. Certainly have gotten my money's worth because I wear pieces all the time.

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?

It was a beautiful, purple silk shantung dress. I wore it till it fell apart! The color was beautiful - a red purple, it had boning and I felt so pretty in it. I guess I just liked how it made me feel and the time in my life that I was wearing it was fun, so maybe that's the real reason I'd like it back.

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

Brutal! I've run that thought by a few times in the past and I've never really had an answer.

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

Use more self control and not purchase so much.

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

Those perforated, two tone leather shoes! Yes I still own them and yes I wear them. And yes, the shjoe cobbler is my best friend.

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


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

Lili Ann princess coat. That doesn't cost an arm and a leg!

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

Drawers, neat. Closet… not so much. We have a walk in closet but between the mens suits and shirts and my dresses, it's crowded in there.

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

Yes. I box my unworn clothes for donations, but I like to give my clothes to friends and if they don't find things they like, then I donate the remainder.

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?


77. How and when do you shop for clothes?

Online mostly. Sometimes I buy when I need a boost (retail therapy) but mostly for a special occasion.

78. Do you like to smell a certain way?

Clean? I don't know if I like to smell a certain way or if it's more that I don't want to smell a certain way (stale perfume, general stink…).

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

It doesn't.

80. How does money fit into all this?

Well, it fits very neatly because there isn't a lot of it.

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 carry ip balm, always wear Skinceuticals sun block.

82. Did anyone ever say anything to you that made you see yourself differently, on a physical and especially sartorial level?

Maybe, but quite frankly this survey is really long!

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?

See above comment.

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

Born in May in a big city in CA and live on the coast in CA.

What kind of work do you do?

Government/law enforcement.

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

In a relationship; no kids; great pets.

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

I can't. I'm computered out!

How do you feel after filling out this survey?

I think I have carpal tunnel now!

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