What to wear on a date

Whether it's your first date or your fiftieth, here’s our guide to hitting the perfect note with your look when it matters most

Deciding what to wear on a date can be a perplexing experience. After all, there’s a scary amount to consider: your date’s taste; your own taste; what you’ve got planned; where you’re going; how formal or informal to be. In short, it can be a bit of a menswear mind maze. However, we’re here to help. Whether this is a first date or a 50th, here are our suggestions for the outfits to suit. Just make sure your chat-up lines are as sharp as your look.

The low-key date

Whether a quiet afternoon coffee, a water-testing first drink, or a stroll in the park, you need to look put-together, but under no circumstances over-dressed. A combination like this will strike the right opening note.

Polo Ralph Lauren denim truckerPolo Ralph Lauren trucker

A well-worn dark denim or corduroy trucker jacket is an indispensable casual staple, and will look fashionable without looking fussy. You could also wear a dark suede trucker if you prefer – we rate Valstar’s. £175,

Officine Générale Shetland crewneckOfficine Generale knit

A simple grey knit is a safe foundation for a date; effortlessly stylish and understated. Officine Générale’s is knitted from soft Shetland wool with plenty of surface texture. Layer over a white T-shirt for failsafe style. £245,

J.Crew straight fit chinostan chinos, J Crew

The perfect thing to bring these two looks together is a pair of classic fit chinos – nothing too skinny, mind. J Crew’s straight fit chinos in beige are smart, but not too smart. Pair with clean white sneakers and roll up the hems for an easy look that’s sure to impress. £98,

The dressed-up date

If we’re talking dinner, cocktails or an evening’s theatre trip, it’s appropriate to look like you’ve made something of an effort. Nine times out of ten, a suit is going to look too stiff, but well-cut separates with a dark rollneck or open-collar shirt is a sure-fire winner. Men tend to drift towards the safest possibly territory when it comes to tailoring, but avoid a fusty navy blazer with brass buttons for a date. Instead, choose something that suggests you’ve at least some proficiency in putting-together a smart-ish look. Plain camel is an underrated colour for a blazer, as is RAF blue, or a modern take on a sports coat with a subtle check can work well too – see below.

Beams F sports coatBeams F blazer

Brand new to Mr Porter, this Japanese-made Beams F blazer ticks all of our ‘date appropriate’ style boxes. In a warm brown colour with a subtle blue check, it’s elegant and a little bit different. It’s softly tailored and slim fitting – so you’ll look suitably svelte. Best of all, the patch pockets and half-lining give it a relaxed feel – so you shouldn’t feel too trust up when you slip it on. £1,095,

Drake’s chambray button-downDrakes chambray shirt

The best thing about a button-down collar shirt is that the collar behaves itself – with or without a tie. Drake’s makes all its models in Somerset, to the highest possible standard, and in a mid-blue chambray this is a timeless choice that’ll look flattering and understated. £145,

Husbands serge trousersHusbands Serge trousers

There’s nothing wrong with a jacket and jeans, but a pair of crisp, tailored trousers in a sober colour will look considerably sharper. Husbands is a Parisian tailoring house, who cut their trousers with pleats and side-adjusters for a sleek look. Finish with dark brown suede or leather penny loafers. £380,

An evening in

If you’ve scored a romantic evening in with which to woo your inamorata, sharing a bottle of wine on the sofa and anxiously sweating over your finest home-made mushroom risotto, it is imperative to demonstrate that you’re not (as many might fear) a slob around the house. The complicating factor is of course that you can’t dress up for the date, so your look needs to sit across the fine line between looking polished, and yet completely at ease. The solution? Mix understated casualwear with sporty touches with a pair of reassuringly expensive slippers.

NN07 camel wool rollneckCamel rollneck

A fine merino rollneck (or lightweight crewneck during the warmer months) is as relaxed as can be, yet chic. This camel colour is warmer than a grey or charcoal, and will work well to flatter your complexion. £110,

Monitaly pleated drawstring trousersNavy drawstring trousers

These lightweight tapered navy trousers pull off a clever trick – mixing a tailored silhouette with a sporty drawstring waist. In cotton drill they’re super-versatile, designed by Monitaly, an independent Californian brand that oozes understated cool. £240,

G.J. Cleverley velvet slippers

Take note: whatever you do, do not wander about in knackered, whiffy old slippers, or heaven forfend bear footed with your hairy toes and mingin’ nails on show. Instead, slip into something suitably sophisticated that’ll work with your easy knit and pleated ‘athleisure’ trouser combo. GJ Cleverley’s quilted velvet slippers are a gentleman’s prerequisite, and will blend in effortlessly with your navy Monitaly trousers.

One last thought for you; If you’re going over to his or her place and taking your shoes off, wear the nicest socks you can possibly get your mitts on in a dark, plain colour – something like these are a safe bet. Nothing threadbare and no novelty patterns. Trust me, they’re a turn-off. £225,