In this episode of Tailored Talks, Brad and Will explore 250 years of American fashion — from homespun Revolutionary garments and Brooks Brothers’ ready-to-wear revolution to Hollywood influence, the rise of American designers, streetwear, and the recent return to craftsmanship and custom clothing.

They discuss how clothing served as political expression and social identity, the democratization of style, OMJ’s path into made-to-measure tailoring, and why American fashion keeps reinventing itself.

Join Brad, Will and Cullen for a mailbag episode of Tailored Talks where they answer listener questions about OMJ’s origin, what sets their custom clothing apart, tailoring tips for summer, community giving, and pop-culture style favorites.

They share practical advice for first-time custom clients, wardrobe essentials, and invite listeners to visit their South End showroom or submit more questions for future episodes.

Most Stylish Movies Draft (No Bond Allowed) | Tailored Talks w/ Noah Williams

Brad and Will welcome returning guest Noah Williams, creative director at Windsor Jewelers in Charlotte, to Tailored Talks for a draft of the most stylish movies (with James Bond movies banned). They open with a “wrist check,” discussing Noah’s Patek Philippe Aquanaut tied to major life milestones, Will’s 1989 two-tone Rolex Datejust, and Brad’s vintage 1970 Omega Seamaster, plus reflections on buying watches for intrinsic meaning. The group then drafts and explains their picks: Crazy Rich Asians, To Catch a Thief, The Great Gatsby (2013), Kingsman, North by Northwest, Ocean’s 11, The Talented Mr. Ripley (with a critique of the term “old money style”), Wall Street, Crazy, Stupid, Love, Top Gun, American Psycho, and The Thomas Crown Affair (1999), followed by honorable mentions and plans for future interactive episodes.

00:00 Welcome Noah Williams

02:22 Style Roots in Charlotte

04:32 Wrist Check and Wedding Suit

07:54 Vintage Watches and Meaning

11:38 Draft Rules No Bond

12:09 Pick Crazy Rich Asians

15:42 Pick To Catch a Thief

17:08 Pick Great Gatsby

20:22 Pick Kingsman Franchise

23:31 Pick North by Northwest

25:07 What Happened to Brooks Brothers

27:51 Brooks Brothers Legacy

28:17 Ocean’s Eleven Cool

29:51 Ripley Prep Debate

32:18 Wall Street Power Suits

33:51 Crazy Stupid Glow Up

39:22 Top Gun Vibes

41:21 American Psycho Satire

44:07 Thomas Crown Style

45:58 Honorable Mentions Roundup

49:33 Wrap Up and Next Plans

50:54 Post Credits Banter

🧵 Noah’s Picks

Crazy Rich Asians (2018)

→ Streaming on Max (HBO Max)

Kingsman: The Secret Service (2014)

→ Streaming on Disney+

The Talented Mr. Ripley (1999)

→ Streaming on Paramount+ (often rotates)

Top Gun (1986)

→ Streaming on Paramount+

🧥 Will’s Picks

To Catch a Thief (1955)

→ Streaming on Paramount+ / Prime add-ons (rotates)

North by Northwest (1959)

→ Streaming on Max (HBO Max)

Wall Street (1987)

→ Streaming on Starz

American Psycho (1999)

→ Streaming on Hulu

👔 Brad’s Picks

The Great Gatsby (2013)

→ Streaming on Max (HBO Max)

Ocean’s Eleven (2001)

→ Streaming on Max (HBO Max)

Crazy, Stupid, Love (2011)

→ Streaming on Netflix

The Thomas Crown Affair (1999)

→ Streaming on Amazon Prime Video