Jake Woolf, a seasoned voice in men’s fashion, has dedicated over ten years to shaping and reporting on style trends for major publications including GQ, Robb Report, Highsnobiety, and the now-defunct Four Pins. His deep understanding of emerging styles and what makes an outfit “cool” has made his Substack and social media accounts popular sources of fashion insight.
Currently, Woolf is juggling multiple creative projects, including a newsletter and an upcoming TikTok edit. At the time of the interview, he revealed that his latest newsletter—already released—focuses on a pair of pants he has chosen as his summer staple. In addition, he is working on a script for a paid partnership video set to be filmed in the coming weeks.
When asked about current items on his wishlist, Woolf named a vintage watch, specifically a Cartier Tank, as his top interest. Though he already owns a Rolex Datejust purchased new, his next timepiece will likely be a model crafted before his birth.
One of the most satisfying purchases under $20 he’s made recently was a bag of candy from BonBon, a splurge at $18. Among the sweets, he singled out rainbow-colored, sugar-coated, tape-like treats as a guilty pleasure—nutritionally questionable but irresistibly tasty.
Woolf also spoke about one of the most difficult style investments he has contemplated: a made-to-measure suit. Though he has long aspired to own one, he finally acquired a custom suit from J.Mueser while working on a video project about the tailoring process. The experience, from choosing fabrics to attending fittings, was transformative. He emphasized that the result made every off-the-rack suit in his wardrobe pale in comparison in terms of fit and comfort.
Regarding footwear, Woolf has been gravitating toward comfort and function over aesthetics—embracing styles often labeled as “grandpa shoes.” His rotation includes four pairs of Mephistos (including collaborations with 18East), orthopedic shoes from Danish brand Jacoform, and moc toe loafers from Banana Republic made with buttery-soft leather, ideal for all-day wear in summer without socks.
Despite creating a substantial amount of online product recommendation content, Woolf still prefers shopping in person. Living in New York City provides him with access to a wide range of brands and products, allowing him to try items before purchasing.
When asked about the best city for shopping, Woolf cited Tokyo as the top choice—even though he has yet to visit. For now, he considers New York City the best destination for shopping due to its wide range of options, from bespoke tailoring to rare sneakers and curated vintage collections.
As for what he considers a “necessary extravagance,” Woolf pointed to a good haircut. He sees it as a worthwhile investment given how often one has to live with the result.
Conversely, when it comes to socks, Woolf is much more frugal. He frequently loses them—either in his apartment or while traveling—so he typically sticks to inexpensive black Nike Dri-Fit socks.
Two clothing items he tends to buy in multiples are Abercrombie’s premium heavyweight cropped tees and Skims boxer briefs. The former are his go-to shirts for summer, while the latter have become his preferred choice for everyday comfort, leading him to recently stock up further.
Woolf’s fashion insights and practical approach reflect both his deep knowledge of the industry and his personal evolution in style—balancing aesthetics, comfort, and timeless quality.
Related Topics
