Tailored Talks #15: 2026 Summer Mailbag Edition

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 Deep Passion Behind Tailored Clothing and Finding Your Own In this episode of Tailored Talks, Brad and Will discuss their deep passion for the tailored clothing industry, detailing their personal journeys and the elements that make their work at OMJ so fulfilling. They share personal anecdotes about their introductions to fashion, the importance of authenticity, and how their diverse interests outside of fashion, such as music and whiskey, enrich their professional lives. The discussion extends to encouraging others to explore their own passions, providing practical advice on identifying signs that one might not be doing what they love, and sharing insightful resources for personal growth. The hosts emphasize the importance of curiosity, continuous learning, and balancing multiple passions to enhance both personal and professional fulfillment.   00:00 Introduction and Wrist Check 01:07 Why We Love What We Do 03:16 Finding Passion During COVID 04:57 The Power of Passion 06:57 Personal Journeys into Fashion 14:41 The Importance of Style and Fit 18:56 Exploring Passion Projects 20:36 Music as a Passion 21:43 The Journey of Creating Music 22:33 Building Relationships at OMJ 24:38 Finding and Following Your Passion 26:08 The F1 Rabbit Hole 28:11 The Importance of Deep Research 32:12 The Value of Passion in Business 35:18 Advice for Aspiring Entrepreneurs 37:51 Resources for Finding Your Passion 39:36 Final Thoughts and Encouragement  

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

The Future of Experiential Retail: Why It Matters in 2025 | Tailored Talks   Welcome back to Tailored Talks with Brad and Will! In this episode, we dive into why experiential retail will be crucial for survival in 2025. We discuss how small businesses can lead in creating unique, engaging customer experiences and why remaining adaptable is key. Explore the concept of the 'experiential retail pyramid' and how OMJ Marketing is evolving to provide ultimate customer satisfaction. Plus, hear insights on community engagement, successful and failing retail strategies, and the future impact of AI on retail.   00:51 The Importance of Experiential Retail in 2025 01:22 Wrist Check: Showcasing Vintage Watches 02:01 Evolving Retail Strategies 04:19 The Experiential Retail Pyramid 08:01 Creating a Lifestyle Brand 10:15 Challenges and Strategies for Small Businesses 11:50 Unconventional Marketing and Community Engagement 13:56 Examples of Experiential Retail 18:28 Local Small Business Highlights 22:14 Charlotte's Small Business Community 22:57 Brands That Missed the Mark 25:39 Challenges in Big Box Retail 31:27 The Power of Community in Retail 35:22 Innovative Marketing Strategies 40:44 The Purpose of the Podcast 42:55 Concluding Remarks and Future Plans  

In this episode of Tailored Talks, hosts Brad and Will discuss the impact of economic uncertainties such as the COVID-19 pandemic and ongoing tariffs on small businesses. They delve into the importance of optimism, adaptability, and transparency in maintaining business resilience. They share personal experiences and strategies from both the fashion and real estate sectors, emphasizing relationship-building, diversifying supply chains, and the need for community support. The episode also highlights the potential for businesses to pivot and focus on core strengths during challenging times. With insights from both hosts, the talk aims to provide practical advice for entrepreneurs and small business owners on how to thrive amidst economic turbulence.  

In this episode, Legendary Coach Matt Doherty interviews Brad, co-founder of OMJ, to explore the origins and evolution of his fashion business. Brad discusses how his college friendship with Filipe inspired their journey into the clothing industry, the challenges of finding the right professional attire, and the importance of timeless, well-fitted clothing. We dive into the ethos behind OMJ, the significance of their brand name, and their mission to make fashion both simple and significant. Brad shares his experiences working with NBA draftees, the role of community in their Charlotte-based business, and the future expansion plans for OMJ. Along the way, we also touch on fashion trends, wardrobe essentials, and the impact of looking good on personal confidence and success.