Hey Joes,

Today I’d like to share some style ideas for men who are in their 50s or getting close to this number but still embrace their love for feminine women in their prime. Before moving forward we need to acknowledge and accept that presenting yourself in a sexy light past your 40s is a bit more difficult because social stereotyping starts working against you.

Let me explain,

When it comes to clothes and style most guys in this age bracket either end up “rocking” khakis, oversized short-sleeved buttoned shirts and sandals with socks just to end up looking like that weird uncle or go full-on formal with expensive suits and ties that look great but position them as straight-up sugar-daddy material. Neither really gets us to the Promised Land of looking sexy.

Even more so, unless you dedicated your life to fitness and healthy living, chances are your body is not as firm as it was in your 20s, so a popular strategy of going for skin-tight clothing also might not be the best option.

And yet, I honestly believe that men, like good alcohol, only get better with time. In your 50s you are much more likely you have your shit together, know what you want and how to get it and have a trick or two up your sleeve to get women hooked. Not to mention all the experiences, adventures and stories that would give the most interesting man in the world a run for his money.

So here’s our dilemma for today’s style inspiration: how can we present ourselves that is fun, exciting, adventurous to show that we have what it takes to make her go wild but also sophisticated and classy to show that we know what we’re doing and, very importantly, not end up looking like that weirdo who still dresses like a teenager or a sugar-daddy, who’s trying to buy his way into her panties.

How To Dress Sexy In Your 50s

Not surprisingly, for our inspiration we’ll turn to Italians.

I have to say, I love this look – it has everything we’re looking for and is not dependent on having a superb physique (though as in all cases, it definitely helps).

Source: TheSartorialist.com (click on the image to view original)

But let’s dig deeper and learn.

Why It Works

  • Shirt, vest & blazer combo visually makes the most out of the upper body. It’s also a very classy combo.
  • Extra open button on shirt – a great touch to look a bit more laidback, casual.
  • Denim vest breaks the standard semi-formal look and adds an exciting touch.
  • Because of great color management, even though denim vest does break the traditional look, it doesn’t look out of place.
  • White pants draw and grab attention, without looking try-hard.
  • Rugged grooming adds an edgy touch to an otherwise clean look (Yes, men in their 50s need to maintain the masculine look too.)
  • PAY ATTENTION: notice how the sunglasses frames match the jacket – little details like that differentiate you from the crowd and get best results.

I’d like to comment a bit further on the last point. Wearing clothes that fit you just right will help you look better than most guys. Adding a cool, interesting and matching color pallet to your look will upgrade you to about top 5 – 10% style-wise, really, most guys are terrible at this. But it’s the little details that raise you to the top 1% and as with most things in life, it’s the top 1% in the field that reap all the benefits – something to think about.

Other notes

  • Even though the title of this article is style inspiration for men in their 50s, this look would work just as great for men of all ages.
  • This combination would also work great for men of all physiques and heights. One thing shorter guys should consider though, the contrast between upper and lower body should be minimal, so you might want to pick a brighter brown blazer or swap white pants for sand brown.
  • Would work well for most occasions, except formal events.

Deconstructing the outfit


Source: Asos.com

Please note, this is a slim fit version. Guys with a fuller physique might want to look into modern or regular cuts.

Denim Vest

Source: Vested Interest

Make sure it doesn’t have unnecessary pockets and similar details (admittedly, this piece can be a pain in the ass to find )

Light Blue Shirt

Tommy Bahama - Island Modern Fit Isle Of Oxford L/S Shirt (Light Sky) - Apparel

Source: Zappos.com

White Trousers

Perry Ellis - Linen Cotton Herringbone Suit Pant (Bright White) - Apparel

Source: Zappos.com


Tommy Bahama - Alexander (Khaki Nubuck) - Footwear

Source: Zappos.com


Sunglasses should be chosen based on your face form. Ideally, the frames are similar color/shade as the blazer.

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