Joanne Wilson - Executive Style Interview

This week Sociology of Style spoke with Joanne Wilson, a New York-based startup investor and advisor. (Find her at joanne wilson

The way you represent yourself says something about who you are and who your brand is. — Joanne Wilson

I’d love to know how you would generally describe your professional style, and if it differs at all from your personal style, and how that’s all changed over the years.

It’s funny, I can look back and say, “Wow, I’m wearing the same outfit and haircut that I did back then.” But my professional and personal style are the same, just a bit nicer.

How do you transition between the two?

If I’m going to go out that night to an event, I’ll wear the same outfit all day, I don’t care – unless it’s a fancy event. But in general, I’m a black pants/sweater or blouse/blazer girl, and stick to black/gray/white. Once in a while I wear a little color, but I’m basically a black-dresser.

Does that change at all, say when you’re on the West Coast? When I go from NY to LA, I feel compelled to change my style a bit.

It’s interesting – whenever I go out to the beach, even on the east coast, I’d have these ridiculous clothes from New York and put them on out there and be like “you look really stupid.”  So there’s definitely a more casual beach feeling out there. And you can wear the same thing every day and no one would really notice – I never, ever dress up out there. [In L.A.], it’s a little more casual. In NY, I feel like I dress nice every day. On the weekends, I’m more casual, but you put yourself together when you walk on the street [in New York].

Absolutely. So the West Coast is different in terms of dressing up/being casual; and I think it’s also different in terms of color palette – white/cream/gray/beige colors and a softer silhouette, not as much black.


What would you say is your biggest challenge when you’re getting dressed, if you have one?

The only challenge I ever have is when I feel a little overweight and nothing looks good, which I think happens to every woman. You feel like you’re not in your groove. Otherwise I figure out in the morning what I feel in the mood for during the day. I’m not a ponderer. I can get put on a new outfit, blow dry my hair, and get downstairs in 15 minutes.

Do you have a “go-to look”?

Not really. I mean, if you walk into my closet, you’ll go, “Wow, you really have that many black jackets?” But in NY, the key is having jackets and coats. It rains, it’s cold, it’s hot – constantly changing, even when it’s winter.

In your average day, what kind of audiences are you dressing for?

That’s very interesting. I’m in a casual industry. People don’t wear suits, no one does. Even my husband [Fred Wilson] only wears jeans. He had to wear black pants this weekend, and it was a stretch. I just think it’s really important to look good and pulled together every day. I hate to say it, but I think moreso for women than men. It represents who you feel you are.

How would you say you use your style to connect with whomever it is you’re trying to work with?

I don’t think I do that. I really just dress for my style, and what’s comfortable. I was in the garment center and I worked at Macy’s. I’ve got the last 25 years of September Vogue sitting on my shelf. It’s not that I don’t enjoy shopping as much as I used to; but I know what I like, I know what looks good on me – if I have an hour to kill, I can stop into a store. But I don’t ponder much.

Is that kind of confidence the thing that has helped you excel in the position you’re in now?

Yeah, for everyone, their style evolves. I don’t think my style is fundamentally different than it was 20 years ago, but I got better at knowing what looks good on you. When I was younger, I probably wore hellish things, but they were so cool that I had to wear them even though they didn’t work for me. As you get older, you get to know more of what makes sense to you. I remember going to college in New England, and thinking I was going to have a brand new “preppy” look. I bought button-downs, khaki pants, those brown shoes that everyone has worn forever – I wore them for a couple months, but after 3 weeks, I was like, “What was I thinking?!” But when you’re younger, your style changes more – it’s an extension of who you are, and you’re trying to figure yourself out. Clothes are a great way to express yourself.

Especially since you stick to a lot of black and neutral colors, what do you use as your “fashion weapon”?

Probably more jewelry than I used to. Sometimes it’s jewelry of the season that I love to death, then I don’t wear for another 10 years; or sometimes it’s really good stuff or handbags that I wear every day for months. It’s constantly changing. No doubt, I pay attention to what’s going on in fashion. I’m not a conservative dresser, and I’m not a trendy dresser, but I buy new clothes every season and wear those clothes.

What are some fashion blunders you’ve seen?

Younger women experiment more. At a certain point, you get to an age where your hair shouldn’t be to your ass. For some people, it’s their style and it works for them at any age, but for most, you need to dress yourself professionally. I hate to be so crass, but the way you represent yourself says something about who you are and who your brand is.

I think those are great words of wisdom for professional women. There are so many pitfalls and so many choices you can make.

Yeah, even men – it’s not okay to just wear a pair of fuckin’ ripped pants and a crappy t-shirt! I know that whole hoodie look is cute when you’re younger, but it’s not cute when you’re a 35 year-old person running your company. I think there’s something to be said about that always-always-casual atmosphere. You’re talking about work and money and dollars and your business, and you have to dress appropriately.

Do you read it as a sign of disrespect when they show up like that?

If you’re 22 years old and you dropped out of college and you’re running a company with 10 people, I really don’t – I get it. But if you’re 30, you should have a little more… polish. And I don’t mean “real polish,” I mean like a button-down shirt and a pair of jeans, and some nice sneakers. That’s not dressy, but it’s “what’s happening in the moment.” If we’re truly cutting-edge in the industry, we should be cutting-edge in how we put ourselves together.

That’s a great way of putting it.