Red Pocket Square Dressy Fall Outfits After 50

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Clear Sunglasses White Dress Shirt Red Pocket Square Red Cable Sweater Dark Brown Wool Blazer Silver Watch Dark Green Corduroy Dress Pants Dark Brown Leather Derby Shoes Navy Socks

Wear a dark brown wool blazer with a red pocket square for relaxed dressing with a street style spin. Complement your outfit with a pair of dark brown leather derby shoes to take things up a notch. Can you see how super easy it is to look on-trend and stay cozy come cooler days, thanks to this look? When it comes to fashion for middle-aged men, this outfit is ideal.

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Clear Sunglasses White Dress Shirt Red Print Pocket Square Light Blue Polka Dot Tie Grey Overcoat Black Leather Watch Navy Check Suit Brown Leather Double Monks White Socks

A grey overcoat and a red pocket square are a city casual pairing that every modern man should have in his casual collection. Go ahead and slip into brown leather double monks for an air of refinement. As you can see here, this getup is a really wonderful pick, especially for awkward transition weather, when the temperature is falling. This pairing illustrates how to look good as you get into your 50s.

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Clear Sunglasses White Dress Shirt Red Print Pocket Square Blue Polka Dot Tie Grey Overcoat Dark Brown Leather Watch Navy Check Suit White Print Socks Brown Leather Double Monks

Try teaming a grey overcoat with a red pocket square for an easy-to-achieve outfit. Feeling venturesome? Spice things up with a pair of brown leather double monks. When it's one of those dreary fall days, what better to spice it up than a seriously stylish look like this one? No doubt, a great choice if we're talking style for older men.

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Black Sunglasses Burgundy Turtleneck Red Print Pocket Square Black Bracelet Black Leather Watch Black Overcoat Navy Check Suit

Wear a black overcoat with a red pocket square for an unexpectedly cool menswear style. As you can see here, it's extremely easy to look seriously stylish and stay toasty come cooler weather, all thanks to ensembles like this one. Overall, a tested choice when it comes to style tips for 50-year-old gentlemen.

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Dark Green Knit Tie White and Blue Gingham Dress Shirt Red Polka Dot Pocket Square Dark Brown Wool Blazer Dark Brown Wool Dress Pants

One of the best ways for a man to style a dark brown wool blazer is to combine it with a red pocket square for a laid-back combo. When it's one of those dreary fall days, sometimes only a cool ensemble like this one can get you out the door in the morning. Wondering what you should wear as you head into your 50s? This ensemble is the perfect answer.