10 fashion mistakes midlife men must avoid

·5-min read
Prince Harry may have joined the Midlife Not Me club early, but there are some things he’s doing right
Prince Harry may have joined the Midlife Not Me club early, but there are some things he’s doing right

This is Prince Harry in a promotional video for eco firm Travalyst, doing what he currently does best, which is being “on message” while striving hard to look young and cool. As it happens this is also a recognised midlife stage (Harry is only 37 but no matter; you can join the Midlife Not Me club any time between the ages of 35 and 70ish, and Harry just happens to be an early adopter).

The “Girl Dad” T-shirt needs no explanation, surely? He’s the proud father of a girl! He’s a feminist! He wants the world to know that he’s the very opposite of an old-school, Henry VIII sort of dad – the kind who sobbed and railed at the birth of a daughter and then got divorced (or worse) – because there was a time when discovering you were the father of a girl was the worst day of your life. Harry’s T-shirt identifies him as a bloke who, in contrast, considers this role to be the greatest honour and privilege of his life. That’s the T-shirt message. Job done.

Meanwhile we’re also getting the message (not intentional) that Harry is the kind of bloke who likes to be associated with thinking up-to-the-minute, modern thoughts – eg, girl dads need to make this a better world for girls and people and each other.

MNM icons Rob Lowe and David Beckham, and ‘genuinely trendy’ Harry Styles, all have lessons for Prince Harry - Getty Images
MNM icons Rob Lowe and David Beckham, and ‘genuinely trendy’ Harry Styles, all have lessons for Prince Harry - Getty Images

This is different to wanting to look trendy and it’s taken more seriously, particularly by men who are for whatever reason (job, background, looks, especially hair) prevented from actually being properly trendy like Harry Styles. Prince Harry is a midlife man seeking to look young and cool with limited resources at his disposal – which is, let’s face it, the lot of many midlife men.


Not sure what’s the best bracelet combo to have right now, but the MNM needs something besides a watch and that might easily include a Fitbit or similar, a charity rubber band and/or a meaningful copper bracelet. Harry’s wrist candy includes a brass and string friendship bracelet variant (the ideal MNM bracelet hints at meaningful travel experiences) and something slim and black. Based on Harry’s showing we’d say two is a good number; you don’t want jangling armfuls.


No hats unless a baseball cap or a straw hat that is not a Panama (love a Panama, but it will place you in the retirement zone faster than you can say “Who’s for bowls?”). As for what to have on the front of your cap – because you might think that is a MNM opportunity waiting to happen – you’re probably best sticking with plain and washed-out. You certainly don’t want a camouflage one, or a pristine New York Mets one, or one that says Barbour, or a black one (you’ll look like your wife’s security).


Wisely, in his New Zealand promo film, Harry is not wearing shades because shades plus a baseball cap is modern code for celebrity travelling incognito who wouldn’t mind being recognised all that much. It’s one or the other really. As for the shades, if you’re going down the sunnies route, no mirrored lenses is all we’re saying. And nothing too fitted and Operation Desert Storm.

Facial Hair

A messy “holiday” beard signals that you are not some pomaded City type but an earthy freelance sort, in touch with the planet and kids and women. That’s the theory and once again we do not make the rules.

Air pods

No idea about the air pod rules, other than they suggest you might have an incoming Netflix conference call at any moment, and, if you’re nervous about going down the earring route, pods might be considered a good substitute.

One earring

Terrible mistake in our opinion, unless you have been doing the earring thing for a couple of decades (and Harry has so far resisted). The late-life earring is like midlife women getting into helix piercing, only worse.


Thirty is too late to start, we say (hard to say if Harry has gone for the late-starter tattoo – hope not). David Beckham has put us off tats for ever, though Brooklyn, certainly young enough to qualify, is helping with his penchant for see-through dress shirts worn over patchy ink bits.


Even Harry knows to draw the line here. No pukka shells for him. Not even a Paul Mescal silver chain. No doubt he has been tempted by a simple solid gold disc featuring his children’s names but, fortunately, so far, he has resisted.

Dental veneers

Tongue not in cheek, we commend Harry for avoiding the “wall of white” dental makeover and the hair transplant. We are kind of amazed (along with Rob Lowe who has been outspoken on royal hair loss and why Charles’s sons have not taken advantage of advances in hair surgery), but also relieved. The old Harry is still in there somewhere.

Slogan T-shirts

High-risk unless worn while mowing the lawn, in which case anything goes. Out and about, you can’t get away with much, certainly nothing amusing featuring arrows. Ironic dressing is hard to pull off in midlife unless you have a legacy of gold-plated cool in your younger days, and even then…