Read Surveys (By Author)

Jennifer Leonard

1. When do you feel at your most attractive?

When I've taken that extra step to express myself uniquely - be it a lip color, a bold belt, a vintage purse or killer shoes. Even just one surprising - or humorous - element makes a world of difference for me.

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

God yes. I'm drawn to beauty, like most people, and have no problem recognizing it - and staring at it. I will absolutely stare. And appreciate. So there's that - that breathtaking kind of recognition.

But I get excited when I see a woman who stands out as an individual. I marvel at the effort, creativity and spunk. And I immediately want to be her best friend.

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

I admire the effort and thought that goes into an obviously awesome look. On the flip side, I admire the self-confidence in women when they present themselves exactly as is. Bare beauty is refreshing, especially when it's casual, comfortable, and with breezy laughter.

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?

Yeah, when I was in France for the summer, age 17. It was then that I questioned the "matchy matchy" I learned from my mom and wanted to jump out of the box and question every fashion rule I'd known. I wanted to break rules and be free to be me.

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

I do a lot of vintage and used clothes shopping - and I can do it really fast because I skim for fabric quality and authenticity. I try to avoid synthetic or poorly made as much as possible, but I can be a sucker for a good bargain - if I'm in a rush or frazzled. I can find myself shopping to "feel good" sometimes, as though the clothes are some magical elixir, but that doesn't usually end well.

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

Mix it up. Be surprising. Old with new. Formal with casual. Long with short. Buck the trend. Stand out. Be original and conversational with your clothes.

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

This one right now! And that time I had a phone call with a psychic and she suggested I use fashion as a metaphor for my work with others.

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

Playful irreverence.

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

Fruit of the Loom tanks and American Apparel leggings. I appreciate the consistent, flattering fit, and they're both multi-purpose.

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

The druzy quartz necklaces I gave my bridesmaids for my wedding day.

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

I'm game for anything but I usually like to spin a trend a bit and make it my own - never one to follow along just because.

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

Apple body! I need to NOT eat sugar because I'll be doomed with a top-heavy, big belly shape, and long thin legs beneath. (I'm grateful for the legs.)

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

Yes, there was this architect friend of mine who wore a workman onesie in navy blue with a gold calculator watch and I frickin' loved it. So Beastie Boys retro chic. I remember this look often and try to infuse the spirit of it in my fashion statements.

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

That time in France was pretty pivotal.

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

I once wore a slanderous Dick Cheney tank but other than that I keep my politics out of wardrobe.

16. Please describe your body.

Long lean and mushy in the center.

17. Please describe your mind.

Expansive, active, curious.

18. Please describe your emotions.

Deep, loving, quick to pour out on a page.

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

Peppermint oil on my body under sweat pants, polk dot tank and cardigan. Face is freshly washed and hair is pinned back in a bobby pin. (I just got up!)

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

In terms of creative self-expression it's very important. Thank you for starting the conversation!

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

Feb 15 1971. Born in Halifax, Nova Scotia. Live in San Francisco now.

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

10th generation Nova Scotian. Before that, lots of English, Scottish, Irish, French and German.

What kind of work do you do?

Writer, speaker, creative consultant

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

Married. No kids of my own. 1 teen step-daughter.

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

Aspiring to start my own business before end of this year! Oh, I have a radio show. You should totally subscribe to my podcast.

How do you feel after filling out this survey?

Liberated. And connected to other women who've participated like me.


Jen Leonard is a writer, speaker, design-thinker and yogi. She co-authored an award-winning book on the future of design (Massive Change) and hosts a radio show about change making and rule breaking. Sign up for her posts and shows at

Share This Page

Read more surveys (By Author) Read more surveys (By Question)