How should a man dress in his 40s? If you’ve searched for the answer online, you’ve probably already encountered endless lists of the ten things every man over 40 apparently needs to own, along with a few things you’ve presumably become too old to wear.

After more than 20 years as a bespoke tailor, I don’t think that’s particularly useful advice.

Two men can both be 45 and need completely different wardrobes because their careers, lifestyles, bodies, personalities and the way they spend their time have almost nothing in common. So rather than starting with your age, I think there’s a much better place to begin: your diary.

In this episode I talk about how my own style and the fit of my clothes have changed as I’ve got older, why jeans and trainers don’t suddenly become inappropriate when you turn 40, how our wardrobes need to evolve as our careers and lives change, and why today’s less formal working world has actually made dressing well more complicated rather than less.

I also explain why I’m not convinced by the idea that every man should aspire to own a tiny “capsule wardrobe”, why I regularly find thousands of pounds worth of perfectly good clothes in clients’ wardrobes that somehow don’t work together, and the question I’d ask before you buy anything else.

If you’re in your 40s and wondering whether you need to start dressing differently, perhaps the better question isn’t, “Am I too old for this?”

It’s simply: “Does this still work for me?”

Roberto Revilla is a London bespoke tailor who has spent more than two decades helping men build wardrobes around their bodies, careers, personalities and the lives they actually lead.

If your wardrobe still reflects the life you were living five or ten years ago rather than the one you’re living now, that’s something I can help you with. My work at Roberto Revilla London goes beyond making individual suits or jackets: I work with clients to understand what their weeks actually look like and gradually build a wardrobe around their body, personality, career and lifestyle, so the clothes they own work together rather than becoming another collection of expensive solutions to old problems.

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If you’ve ever stood in a shop wondering why clothes that used to work for you suddenly don’t, or ordered three different sizes online only to discover that none of them fit properly, this episode is for you.

Bespoke tailor Roberto Revilla explores why shopping becomes increasingly frustrating for many men after 40, from changing body shape and inconsistent sizing to the rise of smart casual and the simple fact that most successful men become far more protective of their time as they get older.

He also explains why his own approach to tailoring has changed, moving away from the much closer fits he wore in his forties towards straighter trousers and softer, more comfortable tailoring, and why understanding the life you live now is ultimately more useful than trying to dress the person you were twenty years ago.

The full written article is available on the ⁠Roberto Revilla London blog.

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Are flip‑flops appropriate for the office, what really counts as the coolest cars ever made, and is Apple’s upgrade programme a smart way to get your next iPhone? In this episode of Tailoring Talk Magazine, Roberto Revilla and Jon Evans test a new three‑hub format built for audio listeners.

In The Fitting Room, Roberto, a bespoke tailor at Roberto Revilla London, reacts to recent style articles claiming that men who wear shorts to the office can still be considered well dressed – and that flip‑flops are now acceptable in corporate work environments. He explains why he strongly disagrees, what good office dressing actually looks like, and why respect for your colleagues, clients and role matters more than chasing trends.

In The Lab, they move into tech to talk about Apple’s iPhone upgrade and finance options, including the newer UK upgrade programme and Flexible Finance Account that replace the old iPhone Upgrade Programme. They unpack who these subscription‑style deals are really for, how they can lock you deeper into the Apple ecosystem, and whether you’re better off buying outright or committing to a long‑term plan.

In The Garage, the conversation turns to TopGear’s “208 Coolest Cars Ever Made” list. Jon shares memories of growing up around prestige cars, Roberto talks about the ones he’s owned and loved, and together they pick out stand‑out entries and ask what truly makes a car “cool” beyond price or badge.

This is a pilot for a regular magazine‑style audio format on Tailoring Talk, blending office style, Apple tech and motoring into one show. Some listeners will be here for the dress code debate, some for the iPhone finance talk, and some for the TopGear car nostalgia – and that’s exactly how this episode is designed to work.

If you enjoy this structure, please follow Tailoring Talk Magazine in your podcast app, rate the show and leave a quick review telling us which segment you liked most and what you’d like us to go deeper on next time.

For all your bespoke tailoring needs – from office suits to summer trousers that keep you cool without resorting to shorts – visit Roberto Revilla London at robertorevillalondon.com

Timestamps (use these to go direct to your preferred section of the show!):

00:00 – Welcome back & new three‑hub format (Fitting Room, Lab, Garage)

01:00 – The Fitting Room: Office shorts, flip‑flops and respecting dress codes

22:00 – The Lab: Apple iPhone upgrade, Flexible Finance Account and subscription tech

38:40 – The Garage: TopGear’s 208 coolest cars ever made and our favourites

55:00 – Thank you, feedback on the format & outro

Key themes this episode:

•flip‑flops appropriate for the office

•office dress code

•shorts in the office

•mens office style

•workplace fashion

•bespoke tailoring

•Apple upgrade programme

•iPhone Upgrade Programme UK

•Apple Flexible Finance Account

•tech podcast

•iPhone finance

•coolest cars

•TopGear coolest cars ever made

•motoring podcast

•UK podcast

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