Privilege Blog

What Should You Wear To Speak On A Panel About Two Of Your Great Life Interests?

As you may remember, back before Christmas, I was asked to participate in a panel about the Apple Watch. Wristly, the sponsoring firm, had found me via my review, here. As you can imagine, deciding what to wear that day required serious deconstruction.

I considered my options across several axes, as one does. Modern vs. classic, fashion vs. business, and those beloved High WASP superordinates, effort vs. nonchalance.

I considered the outskirts of my axes. Not actual skirts, mind you. First up, I Really Don’t Give A Damn And Am In  Fact A Street Artist. Imagine this, but with a long-sleeved UNIQLO Moomin-print tee and my Vince sneakers from this outfit, or this one.

Long-Untrammeled-Gray-Hair Fourth

Nah. Felt like I was trying too hard in not trying, if that makes sense. The extreme physical comfort would have been completely negated by social discomfort, by a sense of pretending to be something I’m not. I veer Artsy but only a little bit.

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On the other hand, I thought about wearing this. We’ll call it, Yes I Was At The New York Stock Exchange On The Day The Market Crashed And I’m Still Here. And I mean the 2008 crash, not 1928, in case you wondered.


A gray Italian suit (which everyone who might show up on Wall Street ought to own), pointy-toe Manolo Blahnik flats, pearls, man’s watch, and a t-shirt. But the watch event was held in San Francisco, and I’m retired, and I think this suit will remain in my closet against the highly unlikely chance I ever go back to the NYSE.

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I considered two other outfits more seriously. First, Oh, Are The Seventies A Trend? I’m Too Cool To Care. A variant of my most reliable date night getup. Even when it’s a date with two young women friends in New York’s Koreatown.

Untitled #208


  • Vintage DKNY ankle boots with squared heels
  • 7FAM flared jeans
  • UNIQLO Basquiat tee
  • Gold dangly earrings (Those Catbird chain earrings are so nice!)
  • All-Saints biker jacket
  • Hair in a low ponytail

This might have worked, but my real-life Basquiat tee is a little too high-contrast for perfection, and I don’t like to wear a biker jacket unless the rest of my outfit is impeccable. See, nonchalance.

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And finally, Simply The Best I’ve Got. Which, as you can see, is where I wound up. On the first panel.


And the second one.


All da shoes.

I wore:

Of course, I hadn’t realized that we’d perch on canvas counter-height canvas directors’ chairs, bringing my legs truly front and center in a way I hadn’t foreseen.

One of those moments when the universe gives back. I spent my young career trying to camouflage my figure. Working for a chemical company, selling to the semiconductor industry, not a lot of women. And in the mid-80s the idea that unwanted attention might constitute sexual harassment was pretty new.

So at almost 60, there I sat, ankles and knees on parade. And then one of the moderators asked me what had it been like to be a woman in tech. “Do you really want me to talk about that? I said. “Yes,” she did. I said, as I have before, “I like men. I married two of them, I gave birth to one.” (I joke to make sure any defenses are down.) “But,” I said, “I can’t tell you how many meetings I sat in where business development discussions used ‘dating the pretty girl’ as a metaphor. And,” I continued, “Even today so many of you have used the example of  “Even my wife likes the watch,” as a ways to talk about the technically unsophisticated.”

“We women in midlife, we have the financial resources,” I said. “Ignore us at your peril.”

Everybody clapped. I suppose I put my best foot forward. Thanks, Wristly, for the do-over, and Dries, for the fabric courage. Sometimes the universe is a good pal.

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Glance Conference photos from Twitter (#glanceconf). Shoes by Philip Elmer-DeWitt.


Links may generate commissions. You will notice that several of these links go to The RealReal or Vestiare, sites for high-end pre-owned clothes. I’ve never used them, but seeing the price and purported quality of their goods I just might give it a try and report back.

71 Responses

  1. The high director’s chair! Wow! You looked great–your hair, your dress, your legs–all of you!

    And I like what you had to say.

  2. Long time reader but my first comment…
    Well done for the outfit and the speech, very inspirational. Are we allowed to use(part of)it ? Just in case of…

  3. You totally nailed your outfit and the hair is as they say your crowning glory! Your comment ignore us at your peril….well said.
    Hope the experience was enjoyable.

  4. I like your final choice, but that lovely suit doesn’t need to languish in the closet. Save the pearls and fancy shoes for other ensembles, unbutton the blazer to show off an insouciant tshirt underneath (here in France we use printed and even word-emblazoned Ts for this style) and your favorite casual shoes (sneakers are fine!) and give that suit a second life.

    1. @ParisGrrl, I hadn’t thought of that, but what an interesting idea. I’ll have to fool around with my current set of sneakers and tees to see what I can come up with. Thank you!

  5. Brava for your smart, smart words! I wish I could have been there to give you a feminist high-five. ;-)
    As for the outfits, pre-decisive choice, I laughed out loud at numbers one and two…your sense of humor is wicked….and breathed a sigh of relief at the third. “Ahh, now this is the Lisa we know and love.” But when I got to number 4, you took my breath away! The flash of red from the Louboutins, the modern but professional dress, and your glorious hair! Everything about your ensemble said, “I’m successful, so listen up!” (At the risk of undermining everything I just said in the name of feminism, “Damned, Lisa! Those gams!!”)

    1. @Mamavalveeta03, Oh thank you ever so much. And maybe in fully realized feminism great gams don’t have any impact one way or the other on one’s professionalism and authority, and can therefore be complimented if the time and company is congenial. xox.

  6. It seems to me that you made the right choices. The men in the photos have collared shirts and I don’t see anyone else i n flip-flops.

    I’m going to take the moral of the story to be that one should inquire what the seating will be like at potential focus groups. I dislike sitting places where I have to watch that my skirt doesn’t creep up above my Jockey slip shorts.

  7. Good stuff, Ms. Lisa! Smart, interesting AND well turned out. The trifecta!

    Interesting point about gray hair, that it should be clean and architectural. I agree.

    1. @Patsy, Why thank you ma’am. And I think wild gray curls can be great too, if that’s what you’ve got to work with. But I do believe in working with your natural hair, if you go gray.

  8. Perfect outfit and absolutely wonderful comments to the group! Many thanks and appreciation for Representing so well.

    1. @Susan, Thank you and my pleasure. I did feel in a way that I was given a chance to represent those of us in midlife, and I did want to do it as well as we deserve.

  9. What an interesting event! I love your message!

    I think you ended up choosing the perfect outfit! You look amazing and comfortable on the panel. And your blown out hair looks stunning! I always joke with my hairdresser that I wish I could afford to have her move in with me… It makes such a difference…

  10. Ok, I hope this doesn’t come across as too creepy, but man you have gorgeous legs. There, I said it. I apologize in advance if this creeps you out.

    Also, your comments were spot on. Grey power!

    1. @Mary anne, Ha! No, my uncle who told me when I was 15 that I had my mother’s legs was kind of creepy but you are my friend so it’s a very nice compliment.

    1. In a way I think it’s even more important that you spoke your truth, regardless of the effect or outcome.

  11. What a perfect outfit for this event and your legs looked fantastic, you were shining on your own but the dress and shoes just showed you off further.
    Love your answer to that question, well said Lisa! xo

    1. @DaniBP, Thank you! I guess what I hope for is that all the aspects of a woman can be melded in support of the goals that she and she alone decides. So, if good ankles and shoes allows someone to stand up for old ladies, booyah:). Right?

  12. Your hair is gorgeous.

    Your comments were very good. I read somewhere that car dealers have found out that the majority of family car buying decisions are made by women. That explains why they no longer treat me like a good little girl.

  13. LEGS!! You rocked that chair. In the best way!!
    And at first I thought the woman in the grey suit wasn’t you. But do you really pull that vibe. And the hair!! It’s just amazing. But those legs & shoes – sweet

    1. @JB, Thank you. If I pull a vibe, it’s earned. The legs and shoes, well, I’ll take what the universe dropped on my head;).

  14. Great look Lisa! Very modern, slightly naughty, but quite deliberate (although it looked effortless). Very Apple.

    And your legs looked fantastic!

  15. Great experience. Seems like you enjoyed the discussion. Loved your outfit and accessories. Perfect for the occasion. I will not be surprised if this brings more invites. Susan

    1. @Susan, Thank you. I did enjoy the discussion – the way in which industries shift, and product cause deconstruction, is my favorite part of business. I’d be happy to speak in other venues.

  16. Fabulous! I would think the even my wife comment implies that the watch is not very attractive and women in general care more about fashion (as evidenced by this blog) not that we are less technically inclined. What do you think?

  17. Loved the way you looked, loved what you said. Having had a career in a male-dominated industry, I get exactly what you went through in the 80s. As for the clothing, the dress was a perfect choice. I especially like your fishnets solution to the tights issue – I often wonder what I am supposed to do in between seasons.

  18. You looked great and spoke well. I agree that the suit would be fabulous with sneakers and a fun tee.

  19. As a woman of about the same age who worked in a manufacturing tech field that was approx. 10 percent female, I think your comment is spot-on. I worked in production with mechanics & engineers &, to their credit, sometimes they seemed a bit surprised to be working with women, but I was treated fairly & had the same advancement opportunities the men did.

  20. What a wonderful post, and it looks like you had a lot of fun doing it. I chuckled at the first outfit, laughed delightedly at the second (you look great, embodying this type so well it could be a stock photo).

    Seeing the outfits you ultimately chose, I said “wow LEGS” and “Yes!”. Your words were eloquent, but your visual presentation had already conveyed the same message quite clearly.

    At 50+ I think a lot about what I want my style and clothing to say. It’s fraught, but also so much fun as your post shows.

  21. Well said dear. Hope someone is listening. Tired of the sad old stereotype of the middle-aged dowdy woman. I recently answered a survey to a large upmarket women’s clothing brand here in Australia, I spend a lot of money on their brand each year. Not so much anymore. They seem to think that the young skinny 20 somethings are the ones with money. I told them they need to rethink their demographic. And ignore us middle aged women at. their. peril. Doubt anyone will listen. Eejits. #grumpymenopausalandannoyed. Ps your legs looked amazing. Just as well you did the tights at the last minute.

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