How To!

How To Dress with Confidence

Fashion guru Leesa Evans, on returning to the office in style.


Episode Notes

Coming out of the worst of the pandemic, a lot of us need to relearn how to socialize, from what to say to what to wear. Our listener, Kristen, is headed back to the office and wants to feel like a boss. The only problem? She looks at her wardrobe and doesn’t know where to begin. On this episode of How To!, we bring in celebrity stylist Leesa Evans to give her a crash course in clothing. Leesa has helped some famous clients (i.e. Amy Schumer) discover fashion that is both functional and flattering. The key? Finding pieces that make you feel confident.

If you liked this episode, check out “How To Look Like a Superhero.”

Do you have a problem that needs solving? Send us a note at or leave us a voicemail at 646-495-4001 and we might have you on the show. Subscribe for free on Apple, Spotify or wherever you listen.

Podcast production by Derek John and Rosemary Belson with help from Katie Shepherd.


About the Show

What if Dear Abby were an investigative reporter? Each week, Amanda Ripley (bestselling author of High Conflict: Why We Get Trapped and How We Get Out) takes on listeners’ toughest problems and, with the help of experts, finds the answers to questions you’ve always wanted to ask but couldn’t. Until now.

Do you have a problem that needs solving? Have you found the advice on our podcast helpful? Send us a note at or leave us a voicemail at 646-495-4001 and we might play it on the air.

All episodes