How a midlife men’s fashion expert restored my confidence from rock-bottom

“When it comes to life’s big transitions – fatherhood, hitting 50, or finding yourself back in the dating pool – style is often an overlooked part of how men adapt and rebuild confidence,” says stylist Nick Hems. Men, he says, “don’t get much support in an area that goes deeper than just clothes.”

Hems, 45, has for the past five years been offering wardrobe edits and personal shopping to clients, most of whom are aged between 30 and 55. He says there are two key issues facing men buying clothes: getting the wrong size, which is “the worst thing you can do from an aesthetic point of view.” The other is buying an outfit for a particular occasion, which works for its intended use – then gets relegated to the back of the wardrobe forever more.

Hems believes that each piece in your wardrobe should work styled with various others, and offers all of his clients a visual mixing and matching service via an app, Hue & Stripe, where they can upload each garment from their wardrobe and try pairing different looks accordingly. More and more he is being called by midlife men, who have never paid any interest to their wardrobes before (or relied on their wives to do it), and have found themselves in the throes of a style crisis. His role is not just assisting them to pick out a few shirts, but to “help them to find an identity for themselves so they can feel good, feel confident and feel comfortable with themselves again.”

Among them is Julian Fleming, 49. “I went through a really difficult divorce and moved to a new country on the back of being a single parent to two boys, one of whom is quite severely disabled, and I was in a really, really bad spot,” says Fleming, a healthcare executive. “My confidence was at an all-time low. I’d put on loads of weight, [and was] feeling very sorry for myself.”

Meeting a work coach helped Fleming to reframe his mindset, and trigger a new fitness regime. He has lost around 30kg over the past six months – “but I needed some guidance on how to pull myself together with clothes and style, which I’ve never done in my life before.”

Before, his look was “extreme dad” – leading him to enlist Hems three months ago. First came a home visit including a colour test and wardrobe assessment, a shop together, and 10 or so phone conversations since. They started from the ground up, literally, first changing Fleming’s footwear from his usual uniform of trainers, to differing colours and styles of shoe, including a tan pair of suede boots and brogues from Loake.

They went to shops around Bath that Hems had already scoped out, allowing him to pull suitable looks ahead of his client’s visit. Fleming went from having little truck with cardigans and jumpers to buying both, along with high-quality suits from Ralph Lauren and Hackett, dress shirts and chinos from Charles Tyrwhitt, primarily in cooler whites and blues to better complement his colouring, along with venturing into camel tones.

“It really was striking,” Fleming says – both the change to his wardrobe, and the reaction, where “people at work and even people on the street [were] commenting, which was phenomenal for my confidence. It was actually the first time in my life that people were looking twice, which was not an ego thing, but it just felt really good.”

One of his most-complimented pieces is a camel coat, which he wears over a suit or dark jeans; he’s also switched from high-rise Levi 501s to 511s, which are low-rise, and closer cut to the leg. “Never in my life did I think I would do a slim fit, but actually they do work significantly better,” he says.

Inevitably, his shopping budget has changed. “If I spent £50 a month on clothes before that was a lot”; he has since spent around £3,000 rebuilding his wardrobe, but notes that this has involved investment in key pieces (such as suits), and that the weight loss required a total replacement in any case. His confidence has shifted radically – and there has been a marked effect on others close to him, too.

Fleming’s 17-year-old son – along with teasing that his dad is now “like Hugh Hefner” – has embarked on his own weight loss path, as “he’s seen it can be done and that in itself has inspired him.” Three of his colleagues have done the same. His rebuilt confidence has also led him to begin dating again for the first time since his marriage ended.

Fleming has been struck by the world of difference between women’s and men’s midlife overhauls; both the pressure piled on the former to stay looking young, and the disparagement heaped on men who so much as consider their appearance.

There is a misconception “that it’s not manly perhaps to really take care of yourself” - especially because transformations like the one he has begun requires “being vulnerable in the beginning. And that’s not something that men have traditionally been allowed to do,” Fleming says. He is hopeful, however, that things are shifting. “Men now [are] realising that they need to invest in themselves as much as women have done in the past,” the results of which can be life-changing. “The clothes and the style [are] the external manifestation of what is going on inside,” he says. For the first time in a long while, “I look in the mirror and think, yeah, actually I’m proud of where I’ve got to.”

Hems’ tips for men rebuilding their wardrobe:

Master layering

A lot of men sweat, but complain that they don’t like layers. I’ll ask them if they have merino wool or cashmere jumpers - and they say no. Jumpers made of those materials mean you can add a layer or two as the look requires, without getting overheated. Uniqlo’s HEATTECH and AIRism ranges are great starting points.

Inject colour

Not everything has to be blue, navy or grey. Or black, which for many is a default, but actually doesn’t suit most people. If you don’t have a stylist, you can use online colour matching tools to determine your palette, and the kinds of shades that work best with your skin tone.

Boost convenience

The number one thing that men trip up on is waking up and worrying about how to put an outfit together, which often leads to them wearing the same thing all the time - even though they don’t feel great in it. A wardrobe-matching app can solve that, as you can put together looks ahead of time, making for a quick, stylish exit in the morning.

Double your denim

The thing that most men are missing in their wardrobe is jeans. A lot of men have just got chinos, yet no denim, which can work really well for smart or casual looks. Paige is one of the best brands I have ever found for the ultimate comfort in jeans and trousers, no matter your physique.

Focus on quality, not quantity

Men often spend the most time thinking about workwear, but a solid arsenal of casual clothing is important. My favourite brands are Sandro (you can build a great capsule wardrobe from their clothing); Luca Faloni, and Sunspel. Their T-shirts may be pricey at £90, but pound for pound, you’ll find their quiet British luxury among the best quality you can find.