How Dianna Winegarden Stays One Step Ahead

We interviewed Armoire member Dianna Winegarden. Read on to learn about her background, her style and what she’s wearing.

Female founders and CEO’s, we’d love to share our closet with you.


 What to wear as a female founder & CEO: Dianna Winegarden

Her Story

Past. A career path spanning large tech companies, rapidly growing startups, investor relations and a three-year stint in London.

Present. Co-Founder and CEO of HeyThrivy, a Seattle-based startup. Mama to two rambunctious teens and one schnauzer.

Future. A houseboat in Japan, ideally.


Her Style

Height… 5’0″
Go-to outfit… Admittedly, a lot of black. Black skinny pants, structured or modern tops, statement jewelry. I like things that are easy to travel with, easy to pack, and always look polished and professional.
Mostly dresses for… Conferences, running all over Seattle for client meetings, family time.
Based in… Seattle, WA

What’s Your Style?

Pretty modern, clean lines not a lot of floral prints or patterns. I’m pretty petite, so I like things that look pulled together easily. I love statement details, chunky necklaces, fun earrings, things that stand out without looking messy and are easy to travel with.


How does Armoire fit into your life?

My schedule changes a lot from week to week, I’m in a lot of meetings during the day and have a calendar full of evening events. Armoire gives the ability to sit down and think about what’s coming up in the week or the month ahead and plan for what I’ll need. I have a wide range of events, so Armoire also dramatically cuts down on my need to go shopping or go buy things that I’ll only wear once and then hang in my closet until the end of time.

What’s your favorite thing about Armoire?

Armoire pushes me to try new trend pieces that I normally wouldn’t look at. It’s low risk to try out new things because I don’t have to keep them, so when my stylist suggests it, I’m more likely to try something new than if I was out shopping.

 in French Connection Sleeveless Jumpsuit in French Connection Sleeveless Jumpsuit


What’s your get sh*t done mode?

Set priorities- monthly, weekly, daily. I set all my priorities and tasks for the next day the night before. Being able to execute and track those tasks frees up so much time that I would waste trying to decide what to take on and what to focus on that day. I’m obsessed with the Pomodoro Technique (work for 25 minutes, break for 5, repeat). Everything can be Pomodoro-ed.

Her Closet


Jill Jill Stewart Crocheted Cocktail Dress

Dianna says:

Great for a badass event! Crushed it!

Other women add:

So many compliments!


Tahari ASL High-Neck Short-Sleeve Woven Sheath Dress

Dianna says:

Wore this on stage for my keynote speech at a conference!

Other women say:

Great fit, cut, style for my body type.



Reiss Short-Sleeve Cuffed Blouse

Dianna says:

Nice shape!



Comments or questions?

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