My guest this week is artist Phillip Toledano You might know him from his photography, the B/1 watch Toledano and Chan, ‘Geezer’ style, Viva Bastardo or his other endeavors. We get into it! Phillip talks his early career, designing watches, photography and AI art and revisits a book that changed Jeremy’s life. It’s all in there.

My guest this week is Tim Heidecker. Tim’s career contains multitudes—from his comedy career, Office Hours, to his acting to his music—it’s all in there, and it’s beautiful. Tim and I discuss family, Warren Zevon, Randy Newman, the Beatles, the difference between comedy and music, and his new album Slipping Away, releasing October 18th.

Mike and I discuss the origins of Manresa, big brother style,  sobriety, the recent GQ article declaring GORP is dead, making clothes for things you actually do, and what’s next for the brand.

If you follow Derek on Twitter, you've probably seen photos of David Lane. He's the stylish guy who keeps popping up in Derek's threads about how to dress for different body types. Along with being an art teacher, David runs a custom leather goods business, where he mainly focuses on making handsewn leather watch straps (he even got the co-sign from Hodinkee some years ago when the two did a collab). In this week's episode, Peter and Derek talk with David about building a wardrobe if you're a...

My guest this week is Robert Triefus, CEO of Stone Island. Many people know him for helping to turn Gucci into an absolute powerhouse, but he's been in the industry for a long time—beginning his career in the early 90s. Robert has worked at Calvin Klein and Giorgio Armani, but we dive right into Stone Island. Robert and I discuss his career in the industry, the brand's allure, the infamous arm badge, Oasis, the new Ghost Collection, and how Stone Island is evolving in today's landscape.

My guest this week is James Pumphrey After leaving Donut Media and turning the internet upside down, James is back with Speeed! James chats with us about why he left, the state of Car YouTube, getting into Good Art, why crying is great, big fits and what to expect from his new venture – Speeed.

Shopping All the Way to the Woods: How the Outdoor Industry Sold Nature to America isn't necessarily about men's style, but it explores an important theme that can be easily transposed to any discussion about menswear. It's a book about how people buy outdoor gear to create an idea of a more "authentic self" and connect with nature. Derek chats with the author and professor, Rachel Gross, about her research and how commercial culture is tied to creating identity.

We got Mr. Throwback! More specifically, the co-creator Daniel Libman (who was also a co-creator of Champaign Ill, another favorite of mine), Olivia Perdoch, costume designer, and even Adam Pally join in to chat. Before we get too deep, Mr. Throwback is a new show on Peacock/NBC featuring Adam Pally, Steph Curry and Ego Nwodim. We chat, working with Steph Curry, digging for good vintage, tailoring, the infamous white whale redwings, and more.

Antonio Ciongoli of 18 East is back. When he isn’t skating ledges, he’s riding big fits, and I was so glad he’s back to dig in with me. Antonio helped usher in the big-fit revolution (or evolution). I don’t care what you call it, but it’s been amazing to watch Antonio’s brand, 18 East, flourish over the years.  He’s such a talented designer and thankfully he joins me to check in on 18 East, Japan, LA pop ups and just being comfy.

Custom tailoring is fraught with potential problems. Maybe you chose a bad tailor or the wrong fabric, or a commission didn't come out as you hoped. Peter and Derek discuss some of the issues when wading into this territory and how to choose a good tailor.

My guest this week is Luke Fracher of Luke’s (NYC and now LA!) Luke is a legend in the fashion scene. He is known for his wild, hot takes on social media and for having some of the best gear you can find anywhere. His knowledge of brands is almost intimidating, but you would never feel it as he’s a simple, humble guy – with a strong opinion. Luke and I chat about his life coming from Virginia, co-founding Round Two in LA, going full on YouTube, his love of Balenciaga, and bringing Luke’s to...

Derek and Peter talk to her about what it's like to run a bespoke tailoring business in the US and how someone can enter this trade.

My guest this week is Tom Kay, founder of the outdoor brand Finisterre A brand born in 2003 from the needs of hardy British surfers, Finisterre designs functional and sustainable products for those who share a love of the sea. In this week's pod, Tom and I discuss what drives design, wetsuits, surfing, and how to make an outdoor brand. We also chat about repairs, collabs, and how to unwind.

My guest this week is bootmaker Graham Ebner. Graham has become one of the most talked about artisans of the past few years—a team of one, making bespoke boots by hand in his small workshop in Austin, Texas. Graham talks about bespoke bootmaking, working at the legendary Texas Traditions under Lee Miller, why he takes things slow, dealing with waiting lists, gatekeeping, and classic cowboy style.

Shoemaker Nicholas Templeman has been working with Derek for nearly ten years and is one of the best artisans he has ever used. So it was about time that Derek and Peter invited him to an episode for a chat. Nicholas shares his career as a bespoke shoemaker, his process, and more. Dig in!

The return of author W. David Marx!David and I get back into it! Our first pod was a year and a half ago, and you’re welcome to dig into it. Recorded in Tokyo, David and I discuss his upcoming book, indie music, craftsmanship, getting dressed, artists vs creators, and Tailor Caid. The ramble begins now!

My guest this week is Adam Brown, founder of Orlebar Brown Adam and I discuss how the brand was created organically, evolving past swimwear, holiday travel, retail, the perfect day, and what’s next for the brand.

Recently, Peter asked Derek to elaborate a bit more on the concept of path dependency in clothing and getting dressed. FWIW, path dependency is a concept from social science regarding why we do the things we do. e.g., Why do we wear jeans, and why are they blue? Derek admits it's a nerdy way of looking at clothes, but this is Die, Workwear! and the insight we all love!

This week's guest is Nicolas Gabard, founder of the Parisian brand and tailoring house Husbands. Founded in 2012, Husbands is one of the brands behind the new wave of tailoring. Their suits are cut with a strong silhouette, generous lapels, wider trousers and are incredibly chic. Nicolas and I discuss the origins of Husbands, style vs fashion, how to give directions to clients, how to wear black clothing,his philosophy on fashion, and how the brand continues to evolve.

My guest this week is Nathaniel Asseraf, co-founder of Casatlantic. Nathaniel and I discuss the legendary vintage store, Broadway & Sons, founding Casatlantic, Ralph Lauren University, vintage vs thrift, how to make a proper fit guide, seasons vs constants, and making clothes for a global audience. 

Since at least 2010, menswear writers have been predicting—perhaps secretly hoping for—the end of the slim-fit trend. But it wasn't until January 2016, when Raf Simons debuted his first collection after leaving his directorial role at Dior, that things started to change. Since then, big fits have cropped everywhere, from J. Crew's giant chinos to Jerry Lorenzo's Armani-sized tailoring. If you're just starting to dip your toes into these waters, Peter and Derek discuss how you can incorporate...

The fit-god and industry legend is on Blamo! As the co-founder of United Arrows in 1989, Kurino-san has been in front and behind the scenes of retail and men’s fashion for almost 50 years. He has seen countless changes and evolutions in the industry and remains as optimistic as ever. Kurino-san and I discuss growing up studying iconography, his love of music, his approach to getting dressed (take notes), the stores that inspired United Arrows, what makes Japanese retail different, what...

My guest this week is David Cho. David is almost always one of the people behind what you love, from podcasts, journalism, and media he’s been an intricate part of THE INTERNET. It's kind of wild to think about, tbh. David and I chat about media diets, getting introspective, why the internet is hungry for earnestness, his previous career at Grantland, The Awl, and his new project, Postcard.

WARNING – This may be the first and only menswear podcast episode on how to dress more like Mark Zuckerberg. In what feels like one of the biggest PR turns in the last year, Zuck’s style improvement has generated considerable online chatter and even a recent New York Times profile. Peter and Derek discuss how Zuck’s style has improved and—if you can believe it—what style lessons people can take away. Has Mark Zuckerberg undergone a makeover?