Tailored Talks with OMJ

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.