There are plenty of times that call for a bit of extra thought when getting dressed. However, few carry the pressure of a first date, even for the most self-assured dressers. Here at MR PORTER, we think that first-date dressing should reflect who you are and what you like, what you feel comfortable in – but don’t mind if we suggest a thing or two.

You’re looking, then, for pieces that are guaranteed to leave a good impression. Think of something smart like a double-breasted blazer from Dries Van Noten. Underneath, you won’t want to look like you’ve tried too hard – and a good pair of jeans never disappoints (bonus points if in a darker wash from Our Legacy). Add loafers and you’re flying.

This could be anything from a coffee run, a gallery visit, a night at the cinema or some after-hours drinks. This type of date calls for ease with intent. Think of pieces that look considered but not overdressed for the occasion. An excellent coat – this wool and cashmere one from Mr P., perhaps – goes with everything. And if you take that off, you need to maintain the same level of refinement with a printed shirt or a knitted polo.

Well-chosen shoes and accessories do the rest without shouting too much. Turn to loafers with a tactile pattern – like Manolo Blahnik’s lizard-effect pair – or tinted sunglasses from the likes of Cutler and Gross or Jacques Marie Mage.

Time to take things up a notch. Think tailoring, smart separates, leather shoes, a proper overcoat, etc. And if you do opt for a suit, keep it soft. This is a date, after all, not a business meeting.

Manhattan-based brand J. Mueser has created the perfect spezzato suit for it: a wide peak-lapelled, speckled virgin wool double-breasted jacket and neatly pressed trousers in green Prince of Wales check. Don’t make silly mistakes on the footwear front – definitely opt for a polished pair of Derby shoes – and if you’re feeling adventurous, smarten things up with a tie.

Heading into the great outdoors is a wonderful way to get to know someone better, whether you’re off on a city walk with beautiful views, a golf driving range or a river cruise. The only catch can be the weather, so just tool up on good garms. A warm coat – such as an easy-wearing shell jacket, such as ROA’s, or a shearling bomber jacket – and some sturdy boots or hiking-friendly sneakers, but a pair that look as good as they feel.

Then it’s about layering up with great texture and hard-wearing fabrics. A merino base T-shirt, for instance, or a slim jacket that will protect you from the elements – and that you can wear beneath your bulkier outerwear once the temperatures dip.