The Style Councillor

What to wear on a date

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The right clothes can make or break a date. Here’s our Style Director’s guide to hitting the right note with your look when it matters most

Deciding what to wear for any ‘date night’ is one of those style conundrums (along with casual Fridays and lounge suits) that often leave us scratching our heads. So many questions need answering before you dive head first into your wardrobe with any conviction. Where are you going? Is it swanky or low key? Are you entertaining at home? Going to the theatre? Has your other half alluded to an element of surprise..?

If your partner has gone to the trouble of booking a restaurant, or reserved a table at a suitably chic cocktail bar, then it goes without saying that some effort is required – this is no time to wear your ‘#Normcore’ get-up. Indeed, Valentine’s Day is one occasion where looking a little overdressed is no bad thing. So, whether you’re in the early throes of a blossoming romance or working comfortably through the marital long haul, here are five pieces to help pull that outfit together.

Cheaney Godfrey Suede Chelsea Boots1. The shoes: Cheaney suede Chelsea boots

Let’s start from the ground up; nothing says you’ve made an effort like a decent pair of shoes. Or, in this case a pair of well made suede boots. Trust me, after eyes and teeth, your partner will look down and take a look at your footwear. If it’s are not up to par, you’ll know about it.This pair by Northampton based shoemaker Cheaney will lend some gravitas to any outfit, from a slim dark denim jeans, tailored cotton chinos or trousers finished with cuffs. The boots show a bit more of your casual personality than your traditional black Oxford lace ups would and they’ll get noticed for all the right reasons.

£375, shop now

Barena Grey Blazer2. The jacket: Barena slim-fit unstructured Prince-of-Wales check blazer

Whether you live in a suit and work in the city or scoot to your tech start-up in Hackney in your sweat top and sneakers, a decent blazer should be in your wardrobe if it isn’t already. This fine example by Italian tailoring brand Barena crosses the divide between formal and informal, making it a very adaptable piece. Smarten it up with tailored wool trousers in navy, rich conker brown or a plain dark charcoal, to bring out the subtle check pattern. Finish with a pair of our aforementioned suede boots for a put-together look, with brogues for something more formal, or wear with simple white sneakers and jeans on the weekends.

£410, shop now

Incotex Batavia Chino3. The trousers: Incotex Batavia four season slim chino

Trousers worn without a tailored jacket can be a hard thing to get right. If they’re not denim (and they rarely should be), what do you wear? Slim tailored chinos are the ideal solution, and this well-cut pair will deliver a coherent look with a blazer and suede boots or polished monk-strap shoes. There’s a small percentage of elastane woven into the cotton fabric, so they maintain their slim shape, keeping saggy seats and knees from spoiling your date. Pair with crisp Sea Island cotton shirts, fine merino knits and unstructured tailored jackets and these will sit just on the right side of the smart-casual divide.

£220, shop now

L'estrange shirt4. The shirt: L’Estrange collarless evening shirt

A ‘special’ evening shirt can be hard to track down. If it’s not a traditional example with a bib or pleats, a regular poplin work shirt or your ‘lucky’ Friday night going out shirt, what are the options? We recommend this collarless shirt from L’Estrange, which combines all of the above into one neat design. In white, it’s understated and versatile, although the brand’s navy version is equally sharp. The cotton pique fabric adds textural interest without being too try-hard, and the collarless style is less uptight than your regular spread collar or cutaway alternatives. It’s perfect for hitting the right note, whether you’re in  a relaxed or dressed up environment.

£95, shop now

Hardy Amies Rollneck Sweater5. The knit: Hardy Amies slim-fit cashmere rollneck

Even if you work in a formal office environment, your date night look still requires effort to pull together. A little forward planning can save time and ensure that your work suit transitions to an evening out seamlessly. Cue this timely collaboration between Savile Row favourite Hardy Amies and retail powerhouse Mr Porter. Switch out your shirt and tie combo for a relaxed but no less chic look with this rich burgundy roll neck. It works with navy, brown and grey tailoring and the contemporary colour won’t have you looking like Milk Tray man – desperately clutching a box of chocolates.

£225, shop now