253 Bobby and Jon are back with another candid Tailoring Talk Magazine call, covering hot weather dressing, the return of office dress codes, Bobby’s Bentley factory visit, craftsmanship, AI fatigue, iPhone regrets, Apple rumours and why smartphones might be the root of all evil.
The conversation begins with the practical problem of dressing well when it’s hot, including summer shorts, espadrilles, sliders, Jesus creepers and why office dress codes are starting to make a comeback after going too far the other way.
That leads into a bigger discussion about dressing appropriately for your role, your environment and your audience, rather than simply defaulting to “wear a suit” or “wear whatever you like”. Bobby shares how he’s been helping companies think through modern dress codes in a more nuanced way, especially now that workplace expectations are shifting again.
The main thread of the episode is Bobby’s recent private visit to the Bentley factory, where he hosted VIP clients and came away deeply inspired by the craftsmanship, process, detail and human skill behind each car. That sparks a wider conversation about why people value handmade things more once they understand what goes into them, and why showing the process behind bespoke tailoring could completely change how clients experience the workroom.
From there, Bobby and Jon get into AI, authenticity and the likely return of appreciation for human-made work. They discuss whether AI is useful as a tool, where it becomes problematic, and why practical effects, handmade objects and real creative accidents still matter.
As always, it’s candid, chaotic and only loosely on the rails.
Timestamps
00:00 - Scorchio, Harry Enfield and the heatwave
00:48 - Jon’s difficult week and British stewardess behaviour
01:51 - Hot weather, dogs and summer dressing problems
02:32 - Jon’s heatwave outfit confession
03:50 - Bobby’s off-duty dog-walking outfit
04:23 - Shorts, trainers and espadrilles
05:20 - Jesus creepers and visible feet in summer
06:20 - Hot weather and office dress codes
06:46 - Why workplace dress codes are coming back
07:40 - Modern dress codes need nuance
08:16 - Dressing appropriately for your role
09:02 - Bentley factory visit and professional standards
10:10 - Rookery Hall and the Bentley trip
11:31 - The Bentley Bentayga and soft-close doors
12:09 - Meeting the people behind the cars
12:49 - Why Bentley’s craftsmanship moved Bobby
13:10 - Reworking the Roberto Revilla London workroom experience
14:08 - Showing clients the process behind the product
15:26 - Building a visual journey into the workroom
16:26 - AI, handmade work and the artisan resurgence
17:28 - Practical effects and why Project Hail Mary feels real
18:30 - Vinyl, cassettes and analogue nostalgia
18:51 - The Boys and practical effects
19:40 - Creative accidents versus perfect planning
20:33 - Where AI helps and where it becomes dangerous
21:00 - Jon’s AI workflow for teaching
22:32 - Google AI and the foothills of the singularity
22:58 - How seeing craft changes the client experience
24:44 - Lost signal and revisiting the Bentley headrest story
25:58 - Robots, Minis and mass production
26:50 - Bobby’s BMW M2 finally gets a proper run
28:14 - Why Bentley changed Bobby’s view of expensive cars
29:03 - Ferrari interiors and Jony Ive design philosophy
30:36 - iPhone 17 Pro Max damage and aluminium versus titanium
31:38 - Bobby’s iPhone 17 Pro and Pro Max usage
32:36 - Why the iPhone Air makes sense as a work phone
34:22 - Amazon deals and the MacBook Air bargain
35:07 - Folding iPhone rumours
35:42 - Would Bobby actually buy an iPhone Fold?
37:02 - Jon’s anti-phone existential crisis
37:37 - Phone fatigue and wanting to shut the curtains
38:04 - Reading nights, music and fewer screens
38:36 - Apple Watch Ultra and AirPods rumours
39:25 - AirPods cameras, gestures and accessibility
40:52 - What Jon wants from WWDC
42:04 - A better Siri and Apple Intelligence
43:40 - Washing up, domestic glamour and Bond First Light
45:28 - Wrapping up
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