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

2026 Men’s Style Trends: Straight Fits, Brown Suits, Vintage Watches & Ditching Athleisure | Tailored Talks

Brad and Will discuss lasting menswear trends for 2026 from a tailored, old-Hollywood perspective, starting with their vintage watches (a 1985 Rolex Day-Date and a 1980s Hamilton). They note a shift toward smaller, more elegant and often vintage timepieces and more originality beyond common Rolex “nickname” models. In clothing, they see the pendulum moving from skinny and ultra-baggy toward straight, tailored fits, including slightly longer pant lengths. They highlight brown and earth tones as versatile “quiet luxury” colors that pair well with navy and even black when balanced correctly. They also argue casualwear is elevating beyond heavy athleisure, emphasizing natural fibers (wool and cotton) and minimal, well-judged stretch for comfort and drape. They answer audience questions on go-to outfits, three wardrobe staples, and a versatile wedding suit suggestion (mid-gray or subtle olive with season-appropriate texture).

00:00 Welcome and Catch Up

00:57 Wrist Check Watches

01:17 2026 Trends Overview

02:24 Timeless Style Over Hype

03:44 Old Hollywood Fit Philosophy

05:56 Watch Trends Smaller Vintage

06:51 Stand Out Beyond Rolex

08:55 Vintage Value and Service

11:07 Pants Fit Swinging Middle

13:14 Brown and Earth Tones

16:29 Brown Takes Over

16:37 Beyond Athleisure

18:13 Natural Fibers Win

21:23 Brown With Black

22:44 Go To Outfits

25:59 Three Wardrobe Staples

27:45 Wedding Suit Picks

30:40 RIP James Van Der Beek

Hosts Brad and Will return for the first Tailored Talks episode of 2026 with a concise playbook for dressing better: a four-step plan to audit your closet, build a core wardrobe (navy suit, trousers, sport coats, crisp shirts and shoes), learn the basics, and stay consistent.

They stress intentionality, fit, and comfort and introduce the "one level up" rule — elevate slightly above your peers to boost confidence and open opportunities without overdoing it.

The Power of Branding: From Business Success to Personal Style

In this episode of Tailored Talks, hosts Brad and Will discuss the importance of branding and its impact on both personal and business levels. The conversation kicks off with a personal wrist check, highlighting their respective vintage Rolex and Omega watches, and evolves into a discussion about personal branding, quiet luxury, and the role of fashion in self-expression. They recount a recent break-in at their store, handling the situation with a positive mindset and community support. The episode delves into the journey and evolution of their brand, OMJ, emphasizing the significance of small details and intentional branding. It concludes with practical advice for personal branding and reflections on brands they admire for their authenticity and community focus.

00:00 Introduction and Birthday Celebration

00:54 Wrist Check: Special Watches

01:39 The Power of Branding

02:36 Store Break-In and Community Support

05:41 Defining a Brand

06:19 Fashion Brands and Their Impact

12:29 Personal Branding and Style

14:40 OMJ Branding Journey

23:11 Community and Relatability

27:34 The Rise of Nuanced Men's and Women's Wear

28:03 Effort and Advantage in a Casual World

28:54 The Value of Elevating Your Style

29:58 Transformative Style Stories

32:15 Consistency and the Two Steps Forward Method

33:52 Overcoming Peer Pressure in Fashion

35:43 The Power of Vintage and Unique Style

40:48 AI and Personal Branding

44:26 Lessons from Successful Brands

48:22 The Importance of Details in Branding

52:19 Quiet Luxury and Final Thoughts