“A lot of men feel there are two segments in their life: work wardrobe and weekend wardrobe. We’re encouraging people to see them as less divisive,” says Tom Riley, the Australian director of custom-tailoring service and lifestyle brand P Johnson Tailors.

Creating a solid wardrobe is one thing; making sure it’s worn well (and with the right attitude) is another skill entirely. Riley has mastered the art of both. His look is comfortable, elegant and “a little bit scruffy”, and draws on natural, soft materials. “It doesn’t suit me to be particularly tailored,” he says.

1. Retrosuperfuture round glasses – $406
For Riley, spectacles can’t be too heavy (or they’ll bite into the nose) but they have to be sturdy enough to avoid breaking. “Good prescription glasses are hard to find. I got these in Rome a few years ago. I wear several different types – they all have a different look and extend your character.”

2. Beard
Riley trims regularly with his trusty Wahl clippers. “My wife would leave me if I shaved completely; I look baby-faced.”

3. Off-White Honeycomb T-shirt – $225
“The textured weave and superfine pima cotton ensures you can wear it under a shirt and you won’t look like you’re having a mid-life crisis.”

4. White Oxford button-down shirt – $175
Riley’s not afraid of creased shirts. In fact, he likes his shirting to have a slightly dishevelled look. Once it’s been washed a few times and softened out, this partic- ular shirt doesn’t have to be pressed. “The collar can go up if you want to be more lush, or down if you’re off-duty.”

5. Custom navy linen shirt jacket – $595
Riley takes an “anti-tailoring” approach to outerwear, preferring unstructured “scruffy” jackets. In winter, he likes to pair this shirt with grey woollen trousers.

6. Custom beige cotton-linen trousers – $295
Riley doesn’t own jeans. Instead he rotates a collection of cotton-linen trousers with soft knitwear. “It’s not about wearing skinny-leg trousers. It’s not about being over tailored. It’s about being comfortable and therefore looking comfortable.”

7. Juan Suede espadrilles – $195
n a warm day, Riley chooses espadrilles. They can “calm down” a suit or be worn to the beach, and a padded insole makes them comfy for hours on end. “I don’t see espadrilles as informal, necessarily. There’s a difference between informality and a respectful elegance about the way you style them.”