Boston can boast plenty of legends in sports, music, politics, and theater. But fashion? That hasn’t always been a huge one for the city — with only a few exceptions. And one of those exceptions is also one of my favorite people: David Josef, known for his fashion talent and exquisite evening wear, his charismatic personality, and his support for the LGBTQ+ community. He’s dressed iconic women from Debbie Reynolds to Raquel Welch, and continues to jet all over to make gowns for Broadway stars, Tony Award winners, and everyday women alike.

This Monday, June 16, in celebration of Pride Month and in of support Boston’s only public high school for the visual and performing arts, The Boston Arts Academy Foundation (BAAF) will host Cocktails and Conversation with David. Catch him from 5:30 to 8 p.m. at Fenway Johnnie’s (https://www.fenwayjohnnies.com/) with WCVB TV’s Rhondella Richardson, among many others. If you miss that (seats are very close to being filled), don’t worry — there will be an even bigger splash on Oct. 23, when he’ll be honored at the annual BAAF Honors event, ”The Power of Art to Transform Well-Being,” at MGM Music Hall at Fenway. David will be the fashion honoree, alongside other local legends such as Donnie Wahlberg, Eliza Dushku Palandjian, and New Edition singer and songwriter Johnny Gill. (To learn more and to get tickets, visit baahonors.org.)

I’ve known David since I was 16, way back when I started my fashion career working at the high-end bridal boutique Yolanda’s in Waltham. When I called him to chat, he was with his husband, Danny, getting ready to head off to Manhattan for a client.

Q. I remember working with you when I was 16 and working at Yolanda’s. Do you have any memories from that time?

A. I do! I was always in the boutique doing shows back then. Yolanda was my mentor, and she was so supportive. And it’s been so amazing to follow your life since then. So much has happened.

Right now Danny and I are about to go to New York to dress singer-songwriter and actress Melissa Manchester — I get to dress her for concerts — and I have to tell you, I live in a state of gratitude. She’s the person who got me through all the bullying as a little gay kid. One of her songs gave me the strength to get through anything. And as I got to know her later as a fashion designer, one day she said congrats on an award I’d just won. And I played it down and she stopped me and said, “No, no. You will never feign humility with me. You earned it. You must know your value.” Now I love who I am. And I without being snobby, I can accept my value. Every night I lay my head on my pillow, and am so grateful looking back on my career of 50 years in this business. It’s remarkable.

Q. Will you share with readers how you first got your start in fashion?

A. I grew up as a kid gay kid in Providence, where my mother had an alteration shop that I made clothes in. Donahue Models offered to feature my clothes at a restaurant once a month, and mafiosos would buy them for their girlfriends! Eventually I got accepted to Parsons School of Design but I was afraid to go to New York City, so I went to Lexington instead in 1976 and I rented a space where I did four years of custom designs. When I was 23 I moved to Copley Square in Boston and started approaching local stores, and one day got accepted by Bonwit Teller in New York, and soon was selling to them and Neiman Marcus and many others all over the country.

But then I burnt out in 2000. I got tired of the rat race — and my mother got sick and passed away. I got depressed. Yolanda saw me and said, ‘I see what you’re going through. Come work at my store.’ I went back and worked one-on-one with her customers. Then I was found the space I’m in in Waltham and slowly got myself back together. Now my clients fly me all over the world for fittings, and I’m happier than ever. So you really can come back stronger than ever.

Q. And over those years, you’ve dressed some really big names. Is there any glamorous tea you want to spill?

A. Well, Debbie Reynolds was the funniest, naughtiest woman I’ve ever worked with. And Judith Light was the classiest. We have a a 40-year-friendship. And I’m loving working with Beth Leavel, a Tony-winning actress currently co-starring with Bernadette Peters. I get to dress these incredible women. It’s just astounding!

Q. What does Pride Month mean to you?

A. Well, Pride for Danny and me is not a one-month thing. Someone just told us that he was lucky enough to have us as role models, and that’s what we’ve been lucky enough to be. We know our place. We’ve had 45 wonderful years together. And we still look cute.