Canal Street Dreams – Jake Woolf on Canal Street Dreams

Podcast: Canal Street Dreams
Date: September 26, 2025
Hosts: Eddie Huang & Natashia Perrotti
Guest: Jake Woolf

Overview

This freewheeling episode of Canal Street Dreams features Eddie and Natashia sitting down with fashion writer/editor Jake Woolf for an unfiltered, nostalgic, and highly detailed conversation about fashion, personal style, the evolution of men’s and women’s wear, and the creative ecosystems of downtown New York. The trio shares stories from their childhood and early fashion adventures, discusses the significance of New York retail legends, debates authenticity versus curation in celebrity style, and gets candid about the internet’s role in shaping personal aesthetics. Expect vintage references, playful banter, and sharp cultural commentary.

Early Encounters & Fashion Roots

(00:00–12:30)

How They Met & Early Fashion Jobs

• Eddie and Jake reminisce about meeting in 2010 at a Wieden & Kennedy event where Jake was interning at Berkman Bros and Eddie was serving bao.
• The conversation includes nods to the scene, including Phil Chang and video collaborations, plus Eddie remembering buying shorts and getting put onto unknown brands by Jake.

First Steps into Fashion

• Jake describes his early love of fashion rooted in childhood roleplay:
  “As like a three year old ... I wore costumes every day, like superhero costumes and stuff. ... you put on clothes and you sort of assume a character.” (01:46)
• The hosts and guest swap stories about formative style choices—Natashia recalling dressing up as a cat, Christina Aguilera, and even stealing Victoria’s Secret thongs as a kid.

Memorable Moment:
Natashia, on discovering her sexuality via Aaron Hernandez:

“I think I like dick. I think I like men. ... Aaron Hernandez turned her out. ... It was a sexual awakening.” (02:45–02:59)

Nostalgia for Early 2000s Style

• Tall tees, Foot Locker, hip-hop influence (Cam’ron was the inspo for Jake's pink tall tee).
• Red rain boots and the iconic feeling of getting new basketball sneakers as the high point of a new sports season.

Parents, Class, and Sneaker Rules

• Contrasts between how Jake’s parents set aside specific shoes for basketball, while Eddie’s made him wear one pair for everything.
• Jake’s first prized pairs: Iverson's Answer Fours and TMacs; reminiscences about sneaker culture, team shoes, and the East Bay catalog.

Eddie on new sneakers:

“I used to think I had, like, super abilities with the new shoes. Like, I would read the specs, like, oh, I'm gonna be ill this year.” (07:20)

The Golden Age of Department Stores & NYC Retail

(11:55–18:30)

Barney's & Opening Ceremony

• Jake shares how shopping at Barney's Co-op in Philly inspired him and eventually led to his first fashion internship.
• The hosts mourn the loss of Barney’s and Opening Ceremony.
  • “We just want Barney’s back.” (12:03 – Eddie)

CHCM & Sweetu’s Boutique

• Deep admiration for independent menswear shop CHCM and its owner Sweetu, praised for introducing rare brands and maintaining a unique, uncompromising vision for over 17 years.
• Eddie describes Sweetu as “the record shop of menswear ... every other creative director buyer ... goes to see what Sweetu is buying.” (13:03)
• Natashia notes CHCM's welcoming, non-pretentious vibe, rare for menswear retail.

New York Retail Culture & Struggling to Fit In

(18:30–23:00)

Union NYC Stories

• Eddie recalls needing to befriend employees at Union to get access to certain styles—facing gatekeeping and "getting sunned" (denied or dismissed) by tastemakers if his style was deemed off.
• Anecdotes about Marianne, the legendary Union owner, and the Supreme crew illustrate NYC’s tightly-guarded fashion scene.

The “Tumblr Menswear” Era & Watch Talk

(22:37–26:10)

Jake’s Entry into the Menswear Movement

• Reflection on the heyday of #menswear Tumblr and early-2010s NYC, including the “Fuck Yeah Menswear” moment.
• Jake waxes on the tribal nerdiness of every subculture—whether cars, watches, or clothing.

Watch Flexes & Borrowed Elitism

• Jake and Eddie geek out on luxury watches, particularly the allure of the Vacheron Constantin 1921 and gold “222.”
• Eddie admits: "Like, my dick is gonna feel like 75 inches bigger…”
• Discussion on how these items are status symbols and exemplify a kind of insider validation in style and collecting.

Authenticity vs. Internet-Driven Style

(26:10–32:00)

Internet Communities & Fashion Forums

• How the internet allowed men’s style nerds to meet, roast, advise, and trade information in a way they wouldn’t in their own small towns.
• Stories of early nostalgia: AIM screen names, buying mixtapes online, and getting “cooked” on internet forums for bad fits.
• “If you out there and you listen to the show, it's okay to be sunned ... all of us are trash ... we're going to look back in a year and be like, that was trash.” (29:43 – Eddie)

Trend Cycles & Personal Commitment

• The crew debates the return of skinny jeans, “correct answer” fits, and Eddie’s lifelong loyalty to baggy silhouettes.
• Natashia describes her dual fashion identity: “the two wolves inside of me are stripper and ... boarding school.” (31:21)
• They lament the sameness of youth fashion today versus the more experimental “LG Chocolate”/“Limited Too” era of the 2000s.

Natashia on Limited Too:

“Like, that was so fun to just be able to like experiment with fashion at that age and not be like already trying to buy ... I don't know, cats are like I'm a 12 year old creative director. I'm like dog, go eat your own poop.” (32:45)

Making Mistakes & Forming Original Taste

(32:55–38:00)

The Importance of Getting Roasted

• Jake and Eddie tell stories about their most humiliating early fashion purchases—Jake’s mall Timberland sneakers and Eddie’s infamous Champ Sports employee polos.
• “I had copped five employee shirts. And he's like, you look like you work at Champs Sports.” (34:48 – Eddie)

Changing Technology & Personalization

• Remembering when your phone choice (Razor, LG Chocolate, Sidekick) was a key piece of your personal identity, compared to the monotony of today’s smartphones among teenagers.

Reflections on Fashion Eras & Forward Movement

(36:02–42:23)

2000s: The Last Great Original Era?

• Hosts and guest reflect on their nostalgia for dramatically varied mid-2000s fashion, asserting that today’s TikTok-driven “archival” revival lacks the experimental energy of their youth.
• Echoes of a larger point: imitation and reference can’t replace bold, individual risk-taking.

Jake on Gen Z copying Y2K:

“Now ... Gen Z TikTok kids are like, coming back to [Sean John, Fat Farm, Apple Bottoms, Juicy], you know.” (36:28)

Mood Board Culture & The Loss of Personal Style

• Jake: “there’s probably been no other time in history where there have been more good fits ... but good fits aren’t necessarily the highest level ... it’s gotta be good, different, and personal to that person.” (41:40)

Whose Style Is It Anyway? Authenticity vs. Styling

(42:23–52:30)

Who’s Really Inspiring Men’s Style Now?

• Jake lists Jacob Elordi, Austin Butler, and Jeremy Allen White as today's dominant male muses—but credits Shia LaBeouf as “the source” for modern menswear/fame-melding style.
• Discussion of style icons who actually dress themselves (e.g. Matty Matheson, Tyler, the Creator).
• Jake, on Matty Matheson:

  “Famously doesn’t have a stylist ... but he looks so, so cool all the time ... there is a sense with Matty of authenticity ...” (38:17–38:44)

“Correct Answer” Fits vs. Lived-In Style

• Everyone laments how current “good” fashion is over-curated, referencing mood boards and TikTok. They admire fits that seem natural or lived-in.
• Natashia appreciates Tyler, the Creator and says the realest fits look accidental or purely functional.
• Eddie’s critique of some celebrity fashion:

  “I don't want to feel like you're aware you're doing it. I want to feel like you're going to buy milk.” (46:15)

The Performative Trap & Influence Economy

• Debates over NBA tunnel fits, athletes’ “over-styling,” and how brand alignments and celebrity marketing teams drive nearly all celebrity style.
• Natashia:

  “There's an essence that comes out in something that either lets everybody know that you're being authentic or ... not. ... It's in the ether. You can feel it.” (51:05)

Closing Thoughts: Influence, Copying, and Why New York is Still King

(52:30–59:57)

Osmo Fakes and “Cosplay” Fashion

• The group acknowledges the internet’s double-edged sword—fashion is now democratic, but originality can be hard to spot.
• Jake describes seeing a guy doing head-to-toe Austin Butler “cosplay” at Apollo Bagels and knowing “99.9% of people have no idea what you’re doing, but I know what you’re doing ... cooked, bro.” (54:29–54:34)
• Natashia on fashion influencers:

  “I get it, and I respect that ... but I really like going outside ... and seeing people in New York City ... not doing the Austin Butler cosplay in Apollo bagels.” (54:53)

The Beauty of New York’s Street Scene

• Jake: “That's what's so great about New York ... you can see in real time trends happening ... you can see a girl in the West Village in these Dries Van Noten sneakers ... things go from Instagram feed to the West Village street almost live.” (55:36)

The Value of Structure in Writing and Art

• Eddie and Jake, as writers, discuss how editorial structure allows for personal flair and lasting impact. Eddie’s advice:

  “If you can just commit to structure, then it gives a stage for personal opinion and personal style. ... You can get freaky.” (58:25)

Heartfelt closing:
Jake thanks Eddie for early encouragement and advice about structure, remembering how formative it was to receive feedback and support from someone established.

Notable Quotes & Banter

• Natashia: “The two wolves inside of me are stripper and ... literally boarding school.” (31:21)
• Eddie: “I used to just, like, hump the couch looking at, like, Ralph Lauren purple ads with shorties on horses. ... but I needed. I need a sluttier one.” (31:40)
• Jake: “Good fits aren’t necessarily the highest level that you can achieve. ... It’s gotta be good and, like, different and cool and personal to that person.” (41:40)
• Eddie: “It’s okay to be sunned ... all of us are trash ... we’re going to look back in a year and be like, that was trash.” (29:43)
• Jake: “There’s probably been no other time in history where there have been more good fits in the world.” (41:40)
• Natashia: “More of that, please. ... She's just wearing that. That's her whole thing. She looks great. ... Sometimes you walk outside and you see somebody and I'm like, I know your whole algorithm.” (51:05–52:06)
• Eddie: “I should have been a copywriter for Lux. Like, for real.” (10:25)
• Jake: “Every other creative director buyer in the world in menswear goes to see what Sweetu is buying.” (13:04)

Key Segments & Timestamps

• Origin Story & Early Encounters: 00:00–01:37
• Fashion Upbringing & Childhood Style: 01:37–06:00
• Parental Rules & Sneaker Lore: 06:00–11:00
• Retail Nostalgia (Barney’s, CHCM): 11:55–14:38
• Union & New York Gatekeepers: 16:23–21:13
• Menswear Nerd Tribes & Watch Talk: 22:37–26:13
• Internet Style Era/Tumblr: 26:13–32:00
• Iconoclasts, Mistakes, and Influencers: 32:00–46:00
• Modern “Correct Answer” Style vs. True Originality: 46:00–55:00
• Writing, Influence, and New York’s Role: 55:00–end

Final Thoughts

A vibrant, layered discussion for anyone fascinated by the self-expression and identity wars of fashion, the rituals of becoming, the changing nature of style tribes, and the endless New York hustle to carve out something real. You’ll walk away nostalgic, inspired, and eager to rep your own unique fit—mistakes and all.