Grey Chinos with Shoes Chill Weather Outfits After 50

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Navy Sunglasses White Henley Shirt Black Leather Biker Jacket Grey Chinos White Print Canvas Tote Bag White Canvas Low Top Sneakers

For a casually stylish outfit, try teaming a black leather biker jacket with grey chinos — these pieces play pretty good together. Complement this outfit with white canvas low top sneakers and the whole outfit will come together. If you frequently wonder how to dress your age, this pairing is a winning option.

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Grey Wool Turtleneck Beige Bomber Jacket Grey Chinos Dark Brown Suede Desert Boots

Combining a beige bomber jacket with grey chinos is an amazing choice for an off-duty outfit. Dark brown suede desert boots finish off this ensemble very well. As you can see here, as a 50-something gentleman, you still have a wide range of styling options.

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Clear Sunglasses Grey Wool Turtleneck White Bomber Jacket Grey Chinos Dark Brown Suede Desert Boots

For a casual look, try pairing a white bomber jacket with grey chinos — these pieces go really well together. Complete your look with a pair of dark brown suede desert boots et voila, your ensemble is complete. And if we're talking style tips for gentlemen in their fifties, this combination is ideal.

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Pink Baseball Cap Clear Sunglasses Brown Bandana Dark Brown Crew-neck Sweater Camel Overcoat Black Leather Gloves Grey Chinos Tan Canvas Briefcase Dark Brown Suede Oxford Shoes

Consider wearing a camel overcoat and grey chinos and you'll be the picture of manly refinement. Ramp up the cool of this getup by finishing off with a pair of dark brown suede oxford shoes. Wondering what to wear as you go into your 50s? This pairing is a great example.

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Blue Beanie Navy Sunglasses Navy Lightweight Puffer Jacket Grey Chinos Navy Canvas Duffle Bag Beige Suede Desert Boots

For laid-back elegance with a rugged spin, team a navy lightweight puffer jacket with grey chinos. Add a pair of beige suede desert boots to the equation and the whole ensemble will come together perfectly. As a guy in his 50s, you're sure to appreciate this ensemble.