5 Date Night Outfits For Men Over 50

Updated: Jul 14

Whether you’re happily married and want to remind your other half that you’ve still got it, or you’re single and ready to mingle, these date night outfits for men over 50 are destined to get pulses racing.

Following on from our guide on how to dress sharp, we thought it was important to show you some prime examples of what men over 50 should wear on all-important date night.

At the end of the day, older men should be able to dress stylishly and stay in fashion.

The key to getting this right is remembering that less is more. Keeping your outfit simple and smart will tell your love interest that you aren’t desperately trying to stay “down with the kids” and haven’t yet conformed to old man, loose-fitting sweaters and bootleg jeans.

Dress appropriately on a date night and it’ll reignite some of that honeymoon magic back in the day – ooh la la! With this in mind, here are some examples to inspire your selection.

Men's date night outfits for over 50s

Tweed grey

If you have grey hair, then wearing an all-grey outfit for date night oozes sex appeal. Complement a stylish three-button grey tweed blazer with a lighter or darker great sweatshirt (if cold) and a crisp white shirt.

Finish the look off with a rich blue pocket square, patterned pair of grey trousers and a pair of smart Derby or Oxford shoes.

Waistcoat wonders

The next date night outfit for men over 50 involves a waistcoat. You only have to cast your mind back to the 2018 FIFA World Cup to remember the power of Gareth Southgate’s waistcoat attire.

The problem with a statement coat alone is that you’ll have to take it off as soon as you arrive. But with a waistcoat, you can maintain your smart appearance as you sit and enjoy the company of your other half.

Ideally, pair a muted-coloured waistcoat with a brighter/softer blue shirt – like the examples provided.

The statement

As we mentioned in our previous fashion over 50 article, investing in a statement piece of clothing such as a coat or scarf can elevate any outfit.

For example, adding a smart trench coat, pea coat or overcoat to a pair of dark blue jeans, white shirt and black or brown pair of Oxfords will ensure you make a perfect first impression on your date. For extra brownie points, include a statement scarf which matches with the coat – just like Mr Bond.

Summer vibes

When the sun is shining, you’re going to need a date outfit that doesn’t make you feel the heat. Channel beautiful Italia and long exotic sandy beaches with a white shirt (rolled-up sleeves), khaki chinos/trousers, a light brown belt and matching loafers.

Full marks if you have a stunning brown-strapped watch.

Turtleneck triumph

Turtlenecks are a prime example of how younger trends can work in men’s fashion over 50 too. Buy yourself a smart brown one and wear it with a brown tweed blazer/beige/khaki chino combination.

Or if it’s a more casual date, wear a white turtleneck with dark blue or black jeans and a pair of Oxfords or chukka boots.

Pay close attention to the shoes

You can spend all the money in the world on a date night outfit, but if you opt for an old tired pair of shoes, you’re going to undo all of your hard work. In fact, an article in Cosmopolitan revealed that women can tell what kind of partner you’ll be by simply looking at your footwear choice!

Picking a smart pair of Oxford shoes from our collection will tell your date that you’re a smart person and that you take care of your appearance. It also indicates that you’re taking your date seriously, as you’re clearly making an effort.

Simply start with a pair of Percy Strides and the rest of your date night outfit will fall into place.

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