Welcome to The Who What Wear Podcast. Think of it as your direct line to the designers, stylists, beauty experts, editors, and tastemakers who are shaping the fashion-and-beauty world. Subscribe to The Who What Wear Podcast on Apple Podcasts and Spotify.
Becky Malinsky is all about curation. Her popular Substack, 5 Things You Should Buy, delivers insightful, straightforward advice and fashion analysis—and now has over 65,000 subscribers. She began her fashion career at publications like Cosmopolitan, Glamour, and GQ, and most recently she was the fashion market director at The Wall Street Journal.
After seeing how much fashion and work attire had changed from the pandemic, she decided to quit her job and start her own consulting business, offering professional styling, consulting, trend reporting, and more. We talked to her on the podcast about her journey in the industry, how she created her devoted Substack following, and how she parlayed her fashion experience into an exciting holiday collab with Alex Mill, which happens to drop today.
For excerpts from the conversation, scroll below.
I’m curious how you first fell in love with fashion and got started on this path.
I don’t remember a time that I was not opinionated about fashion, and I think my mother would tell you the same thing. I wanted to wear something specific, and I would save my allowance to buy specific things, like Gap Kids and Limited Too, and it was just always a part of me. I never knew that it was a potential career path until I was a little bit older. It was my mom who said, “Maybe you should pursue fashion,” and she was the one who opened my eyes that you could live a more creative life.
During college, I came to New York for an internship. My cousin was at Brooklyn Law School, and I went for the weekend to visit him. I had met someone who met someone who he was friends with, who was a fashion editor at Cosmopolitan, and she said, “Why don’t you apply to be my intern this summer? “And I did, and I’ve never looked back.
In 2022, you decided to start your own consulting business. Tell me about going freelance, working for yourself, and how that shifted things for you.
I was at The Wall Street Journal for many years, and I was really happy there when I decided to leave. Everyone was talking about this new working world [post-COVID] and how to get dressed for it, and no one could quite figure out how to get dressed. People didn’t want to feel overdressed. A suit and tie was totally dead, but people still have jobs, and they didn’t want to wear sweatpants anymore, and they weren’t wearing crop tops, and everyone was talking about this, and I just had this light-bulb moment.
This sounds like a job. This sounds like a service. This is a path, and it has to be right now because this is the moment everyone’s talking about it. It was definitely a risk, and that is scary. So when I was leaving to start this, I also recognized I was leaving a very creative job, and I needed something for myself to keep my ear to the ground to pay attention to what was still happening in fashion. I started the newsletter as a passion project for myself to keep me creative and keep me on a schedule going into this unknown world.
Can you share and tell us how the “five things you should buy” idea came about, and why you thought that would be the right way to anchor the newsletter?
When I was leaving my job, one of my closest friends was starting a new job, and she had been laid off during the pandemic and had a newborn at home. This happened on her maternity leave. It was her first time going back into an office post-pandemic and post-baby. Her body had changed, office wardrobes had changed, and she called me and was like, “I have been shopping for jeans for three days. I am exhausted. I have not bought any jeans. Can you just send me five things I should buy for this new job, and I will buy them?”
I sent her the jean. I thought she should buy a cool sneaker, a fun top, and a great blazer. I forget what the other thing was. I mean, I think it’s the first newsletter. And she called me. She’s like, “Oh, my god, this is it. It’s perfect. I don’t know how you did this, but I’m buying them, and I am done.” The idea truly came from a need.
Tell me about your Alex Mill collaboration that drops today. How did you partner up and what was the concept?
It’s called Holiday Things, and I am so grateful to the Alex Mill team for having me and for indulging me, and we’ve been working on it for a year. I first had the conversation with their team about potentially coming together to work on something in January, and I had done a newsletter partnership with them in December, and it did really well. And Mickey Drexler, who is obviously an owner of the company, he mentioned it seemed like, Why does it have to be this one thing?
We decided, What if we could collaborate on a small collection of pieces, and what would that look like? So I came in to look at their holiday delivery, and it was very sweater-heavy. And, obviously, Alex Mill has your everyday uniform down. When I was looking at all of it, I was thinking about the time of year. I thought, What about when she’s gonna go out at night to dinner, and what about when she wants to dress up or she’s taking family photos? Where are those pieces?
This is the first time I’ve ever done a collaboration. I’ve obviously worked with brands for many years and given my advice—whether they want it or not—on things that should be in the line, but this was the first time I’ve worked from start to finish.
I really wanted to create something that felt like me, but also still felt really part of the Alex Mill brand identity.
I’m curious about what pieces you’re personally going to be wearing and re-wearing throughout the season, and if you have any styling tips for them.
I’m obviously going to be wearing all of them, but my favorite piece from the collection is this pair of purple velvet pants. They have a double-pleat front, and they pool perfectly at the ankle in a way that feels like there’s the right amount of weight, so it’s not baggy when it pools.
Shop Holiday Things at Alex Mill
Alex Mill
Walker Pleated Pant in Velvet
Alex Mill
Claes Anorak in Taffeta
Alex Mill
Walker Pleated Pant
Alex Mill
Holiday Things Harriet Dress
This interview has been edited and condensed for clarity.
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