How to dress for a date (when you’re over 30)

Your ultimate guide to dressing for a romantic rendezvous

As an avid reader of Gentleman’s Journal, you already know how to dress for the boardroom and out-of-office life. But for a romantic rendezvous? Well, that’s a tricky sartorial minefield to master in itself. After all, you’ve spent the past decade experimenting with your ensembles (and even more time experimenting with your relationships), but now that you’re in your 30s, you can no longer impress a potential courter with those garish limited edition jackets or ripped drainpipe jeans.

But fret not, because we’re here to help. From the bar to the brunch spot, these are the timeless items that’ll help you dress to impress and hopefully snag that second date.

The drinks date

If you’re heading to the bar after working hours (but don’t want to show up looking like Mr Linkedin complete with a Windsor knot), then dial down every part of your ensemble. Lose the tie, swap out your two-piece for a luxe jacket and wool trousers, replace the cutaway collar for a relaxed button-down and switch the corporate lace-ups for some off-duty chukka boots. It’s the ideal outfit that straddles the line between formal and informal.

How to dress for a date (when you’re over 30)

Oxford shirt by Ralph Lauren

£95

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The fine-dining date you can’t afford (but still want to show off with)

So, you’ve snagged a table for two at the new ‘it’ eatery in town and want to look the part (even if your credit card is feeling the strain). To help you stand out from the dining room full of badly-fitted two-pieces, wear something understated yet high-end. A roll-neck with a pair of chunky chelsea boots will give you an air of Steve McQueen while a pocket square will add a subtle dash of swoon-worthy finesse.

How to dress for a date (when you’re over 30)

Blazer by Paul Smith

£585

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How to dress for a date (when you’re over 30)

Roll-neck by Sunspel

£145

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How to dress for a date (when you’re over 30)

Chelsea boots by Church’s

£630

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How to dress for a date (when you’re over 30)

Pocket square by Drake’s

£60

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The brunch date

If you’ve pencilled in a one-on-one over a plate of smashed avocados on toast, then you’ll need to dress accordingly – something easy, yet still shows you’ve made an effort to impress. To this end, opt for timeless and masculine off-duty pieces that are as easy-going as the Sunday morning that you’re meeting up on. This jumper by Thom Browne and these stripped-back sneakers by Common Projects are the perfect weekend getups, while these slim jeans by Ami add a rugged touch. As for the wallet? Well, you are paying for the meal, right?

How to dress for a date (when you’re over 30)

Jumper by Thom Browne

£750

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How to dress for a date (when you’re over 30)

Sneakers by Common Projects

£280

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Need somewhere to go for your date? Here are the most romantic restaurants in London

Further Reading