White and Red Pocket Square Chill Weather Outfits After 50

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White Dress Shirt Dark Green Tie Black Leather Watch White and Red Plaid Pocket Square Tan Corduroy Suit Grey Herringbone Overcoat

For a fail-safe casual option, you can't go wrong with this combination of a grey herringbone overcoat and a white and red pocket square. Wondering what you should wear as you pass the big five-oh? This combination is the perfect answer.

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White Dress Shirt Black and White Horizontal Striped Tie White Pocket Square Black Overcoat Black Double Breasted Blazer Dark Brown Leather Briefcase Blue Wool Dress Pants Dark Brown Suede Chelsea Boots

Flaunt your expertise in menswear styling by teaming a black overcoat and a white and red pocket square for a casual street style outfit. Feeling brave today? Dress up your outfit by finishing off with a pair of dark brown suede chelsea boots. In this, any guy in his 50s is bound to put the younger generation to shame.

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Clear Sunglasses White Dress Shirt White Pocket Square Grey Waistcoat Grey Check Blazer Beige Overcoat Beige Chinos Dark Brown Horizontal Striped Socks Dark Brown Leather Derby Shoes Dark Brown Leather Briefcase

A beige overcoat and a white and red pocket square make for the ultimate relaxed casual style for any modern gentleman. Dark brown leather derby shoes will give an added dose of elegance to an otherwise straightforward look. Rest assured this outfit is something you can totally wear as a gent in his 50s.

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Dark Green Sunglasses White Dress Shirt Burgundy Paisley Tie White Pocket Square White and Black Houndstooth Overcoat Dark Brown Socks Brown Leather Loafers Dark Green Check Three Piece Suit

Parade your expertise in men's fashion by wearing this laid-back combo of a white and black houndstooth overcoat and a white and red pocket square. If you feel like dialing it up, introduce a pair of brown leather loafers to this ensemble. A proper outfit for any gentleman over 50.

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Beige Baseball Cap White Dress Shirt Grey Long Sleeve T-Shirt White Pocket Square Brown Check Wool Blazer Dark Brown Suede Belt Khaki Corduroy Dress Pants Brown Leather Casual Boots

This combination of a brown check wool blazer and a white and red pocket square makes for the perfect base for a casually cool look. Amp up the classiness of your outfit a bit by rocking brown leather casual boots. Those who are curious how to dress fashionably as you slip into your 50s, you have your answer.