The second instalment of our sartorial problem-solving series sees us tackle tailoring and trainers.

Our PR Manager Mr Michael Dale is rarely seen out of a suit. Some have said it is a stipulation of his contract, others claim it’s a time-saving exercise. The truth, however, is far simpler. He does not moonlight as a lawyer, and he is not an opportunistic wedding crasher. He just, well, enjoys it. And, as you’d expect from a man with practice, he wears tailoring rather well. 

On entering the MR PORTER HQ recently, instead of teaming his suit with a pair of, say, John Lobb monk-straps, he wore Stan Smith sneakers. Nothing hugely shocking there, we know. Ever since high-fashion brands started finessing their sneaker game, and style icons such as Messrs Mark Ronson and Kanye West showed us how to dress them up, men have enjoyed experimenting in this way. And one look at this year’s collections tells us tailoring and trainers remain in a healthy relationship.

Runway trends aside, this combination says one simple yet powerful thing. It says you are wearing a suit not because a job or lack of imagination require it, but because you want to. And you feel very comfortable doing so. It is, therefore, an extremely assured look, but one that can be tricky to pull off.

Below, we have put together five ensembles fit for any occasion. Perhaps you’d like to start wearing more suits in your downtime, but worry you’ll seem a little stuffy. Maybe you are required to wear tailoring in the office but want to be more playful at the weekend. However you want to make suits and sneakers work, tread with confidence, and try to stick to a few ground rules…

When dressing for an important meeting, the first thought is usually: brogues or Oxfords? However, especially if the brainstorming begins fresh from a flight, you might consider an appropriate sneaker-and-suit combination (unless you tread the formal floors of law or banking firms). The key here is classic kicks such as Stan Smiths and fitted trousers. Don chunky high tops, and you run the risk of resembling a rebellious sixth-former. Go for a formally structured suit and it might seem as if you left your Oxfords in the luggage rack. This Burberry suit will travel well, and should avoid any puddling – while the grandad-collar shirt brings authority to proceedings. Here is a man who wears tailoring for the sheer fun of it, and walks, not hobbles, from flight to appointment.

Whether it be at fashion week or in our local bar, we’ve noticed some guys in the office are pulling off the contemporary sneakers and suit combination with increasing aplomb – aided and abetted by the increased offering from high-end designers, and some more creatively minded men showing us how it’s done. With a camouflage pattern, the last thing you want to do with these sneakers is blend in – but teamed with a simple dark Paul Smith suit, and tie-free white shirt, this should provide an appropriate palette for going from, say, a gallery opening to a party – and the approaching Art Basel in June might be the perfect place to try it out.

Some men who are required to wear tailoring for work also feel comfortable doing so during downtime. Ditching leather shoes at the weekend is a welcome way to remind your friends you’re wearing a suit to dinner out of choice, not because you can’t differentiate between socialising and networking. Patent Lanvin sneakers retain some of the finesse of a formal shoe, and, when worn with an understated shirt and tie, can be dressed up in a refined and contemporary manner. Make sure your suit is mat, and free of business-like patterns such as pinstripes. Instead, opt for something a little more casual than you might be used to, such as this one from J.Crew. And however many compliments you receive, remember not to get too comfortable. Sauntering in to your Monday morning client meeting in a pair of sneakers is never a good idea.

Your coast-bound train leaves at 7pm. You finish work at 6pm (the boss refused to let you out early). You want to be smart for the office (to appease said difficult boss) and look the part to kick-start a long weekend. Unless you intend on changing at 120mph in a train lavatory, you’ll need to think on your feet. This Oliver Spencer suit is lightweight and relaxed enough for a spring evening drink, but also offers enough sophistication for honouring Friday office etiquette. The easy slip-ons from Common Projects will alleviate any stuffiness from your look (keep them box-fresh, of course), as will the striped linen T-shirt. And you can always dress things up with a shirt should your plans require it.

For the modern professional, time is not in abundance. We brush our teeth in the shower, eat breakfast in front of computer screens and skip lunch to go to the gym. Until recently, Nikes such as these would have been seen only during a work-out, or with a pair of black jeans, but – inspired by the runway (and those who dwell in the trendier parts of town) – more men are leaving them on post-work-out and injecting a youthful pop to their tailoring. Some pointers: try to keep the suit slim and contemporary like this one from Calvin Klein, don’t stray too far towards the “performance” style of sneakers, and keep your kicks clean. You don’t want to channel those men who replace their “work shoes” with sorry old sports sneakers for the commute home.