Pocket Square Smart Casual Chill Weather Outfits After 50

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Clear Sunglasses Grey Hoodie Navy Denim Shirt Dark Brown Pocket Square Tobacco Overcoat Dark Brown Chinos White and Black Leather Low Top Sneakers

This casual combo of a tobacco overcoat and a pocket square is a never-failing option when you need to look dapper but have zero time. When not sure as to the footwear, go with white and black leather low top sneakers. And if we're talking dressing ideas for 50-year-old gentlemen, this combo is ideal.

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Grey Horizontal Striped Beanie Clear Sunglasses Grey Crew-neck Sweater White Pocket Square Grey Leather Watch White Crew-neck T-shirt Grey Wool Suit Charcoal Socks White Canvas Low Top Sneakers

Why not wear a grey wool suit and a pocket square? As well as very functional, both items look good when paired together. White canvas low top sneakers tie the look together. A practical illustration of how to dress fashionably and look age-appropriate.

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Black Beanie Clear Sunglasses Black Turtleneck Grey Check Pocket Square Tan Blazer Charcoal Overcoat Burgundy Plaid Chinos Black Leather Tassel Loafers

Reach for a charcoal overcoat and a pocket square for equally stylish and easy-to-style getup. Rounding off with a pair of black leather tassel loafers is the most effective way to add an extra dimension to this outfit. More elegant getups like this go well with grey hair.

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Clear Sunglasses Blue Chambray Dress Shirt Purple Pocket Square Brown Print Tie Navy Sweater Vest Blue Leather Watch Brown Wool Blazer Khaki Chinos Navy Socks Brown Suede Desert Boots

Consider teaming a brown wool blazer with a pocket square to achieve an incredibly stylish and casual ensemble. Rounding off with a pair of brown suede desert boots is a fail-safe way to breathe a hint of elegance into this outfit. This pairing shows that as a man in his fifties, you still have a wide range of sartorial options.

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Clear Sunglasses Light Blue Chambray Dress Shirt Navy Pocket Square Red Cable Sweater Olive Wool Blazer Black Leather Watch Khaki Corduroy Dress Pants Brown Suede Desert Boots

An olive wool blazer and a pocket square are absolute must-haves if you're piecing together an off-duty wardrobe that holds to the highest menswear standards. Finishing off with brown suede desert boots is a fail-safe way to add some extra fanciness to your look. So pay attention and be the best dressed gent among your peers.