How To Dress For Every Type Of Date In Your Diary

It wasn’t so long ago that advice on how to dress for a date came from one of two sources, each as unreliable as the other. When you’re young, it’s your parents, who tell you that the best accessory to wear is your heart on your sleeve (cheers, mum). Then, back in the noughties, it was pick-up artists with their origami pocket squares, who tried to convince everyone that a well-tailored suit is to women what lingerie is to men.

We think we can do better. The trick with date outfits is to turn heads without looking like you’ve overthought it. You want to be comfortable, but also a little bit adorable. A cashmere cardigan is no replacement for a personality, but something tactile is never a bad shout, either.

The rules change slightly for all the different date ideas out there, so here are some go-to date night outfit ideas that work like a sartorial wingman.

Making An Impression

First Date

There’s a school of thought that says having at least one interesting talking point on an outfit makes you memorable. It’s true in job interviews. It’s true at weddings. And it may well be true on a first date, when first impressions count for extra. What it doesn’t mean, however, is pairing your lemon-coloured blazer with a cerise shirt and plastic green Wayfarers.

Be subtle about it. Try checks on checks. Or a high-low combination like a biker jacket with tailored trousers. If your skin tone can carry brighter colours, give them a go, but only in a single piece.

Get the basics right, too. Pick out the best fitting clothes you have, not the loudest. Match your belt with your shoes. Grab a jacket with internal pockets so that your trousers aren’t bulging at the sides. All you have to do now is not spill the drinks.

Second Date

Like the second song on a mixtape, what you wear on a second date has to keep everyone interested after the banger you kicked off with. In some ways, it’s easier. Stick to the theme and it will hopefully confirm that good first impression. If you went preppy with a blazer and tailored trousers on the first date, try a shawl-neck cardigan or bomber jacket for a different take on the Ivy League look. If you went all black, do the same but maybe throw in a colourful accessory.

This is no time to get lazy, either. Leave your battered sneakers at home. If you’re meeting after work, lose the shirt and slip a T-shirt under your suit jacket for a casual take on tailoring. Your backpack can stay under your desk and switch your Oxfords for something lighter, like a loafer or Derby.

What Kind Of Date Are You Going On?

Dinner Date

Once upon a time, a dinner date was something to dress up for. To restore a sense of occasion to the world Tinder took over, go all out on the reservation and all out on the outfit to match. Tailored separates and dressed-down suits are top of the specials board here, and work just as well for an after-work cocktail as a three-course meal.

A change from your boardroom best isn’t always necessary. Plan ahead when getting dressed in the morning and opt for a suit that that’ll transition seamlessly from office to restaurant bar come clocking-off. A little texture or pattern wouldn’t go amiss, but as with all tailoring, fit comes first.

Just as important as a sharp suit is what you wear under it. If it’s a work shirt that’s been labouring harder than you have, swap it for a freshly laundered substitute. There’re pheromones, and then there’s downright offensive.

For a better option, dump the shirt for a roll neck or knitted polo instead. Inch perfect cocktail attire just in time for cocktail hour.

Drinks Dates

The simplest way to stand out in a bar full of other dudes: do a manual override on the reflex that tells you to wear jeans. Tailored trousers say you’ve made an effort when you really haven’t and give you the basis of a non-boring outfit.

What you pair then with might depend on whether you’re meeting after work and what the dress code is. If you work in a blazer, keep it on but swap the work shirt for one with a bold, dark pattern instead.

If possible, we’d recommend a statement jacket instead. A good biker, bomber or trucker torpedoes the old myth that your shoes are the first thing people notice about you and plays nicely against the smarter trousers below.

Your round.

The best outfits for drinks dates

Cinema Date

Yes, you’ll be sat in the dark for two hours, but don’t get dressed in the dark beforehand. Think practically. Skinny jeans won’t work while you’re cramped in an overheating theatre with a box of popcorn on your crotch. And there’s no elegant way to remove three layers of clothing in a narrow row of seats, so don’t go in with much more than a cool jacket or overcoat.

Beyond that, play it smart-casual. Think dark selvedge jeans, neutral chinos or tailored trousers teamed with a button-down shirt worn under a jumper or cable-knit cardigan. Finish with a blazer or bomber depending on when you’re going for the post-film analysis. You’ll arrive like a laid-back leading man rather than someone who’s taking The Lego Movie 2 way too seriously.

Don’t forget your feet. Unless you’re planning to Uber your date from A to B, there’ll be some walking involved, so steer comfy with your footwear choice and opt for a pair of unfussy trainers, worn-in slip-ons or trusty boots.

What to wear to a date

Home Dates

A time will come in all healthy relationships when you can encase yourselves in the softest jersey fabric you own and watch Netflix for four hours and hardly speak to each other. That won’t do for the early home dates, however. You have to keep up the pretence for at least six months.

In the meantime, you get to don your favourite knitwear as you do your best Gordon Ramsay impression (minus the potty mouth) and cook up a feast. You’re at home here, so you should feel at ease – even if it’s their home, not yours. Go for cable knit jumpers, merino cardigans or chunky waffle-knit pullovers, worn over loosely tailored trousers and your best, best, best socks.

Oh, and while we haven’t consulted any scientists on this, we’re pretty sure cashmere is an aphrodisiac.

The best outfits for home dates

Day & Outdoor Dates

Assuming you’re not hiking Kilimanjaro together, getting outdoors can (perhaps literally) be a walk in the park for your wardrobe. To make the best impression here, fall back on those items that were once designed for practicality and hard wearing but nowadays just look the business. Think trench coats, selvedge denim, hiking boots or wax jackets.

Layering is also advised, especially if you plan to be in and out of pubs or coffee shops. Try a roll neck, blouson and overcoat on colder days, while a tee or knit under a mac is a casual way to look tailored in the spring.

Your choice of footwear is dependent on how outdoorsy you’re feeling. Bear Grylls wannabes should check for heavy treads on their boots (and also double-check that your date is on board). For everyone else, something comfortable and durable will work. Anything from Chuck Taylors to a stomping pair of Dr Martens.

Outdoor date outfit ideas

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