Grey Pocket Square Dressy Chill Weather Outfits

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Dark Brown Herringbone Flat Cap Light Blue Dress Shirt Navy and White Horizontal Striped Tie Grey Pocket Square Black Leather Watch Tan Plaid Wool Blazer Tan Crew-neck Sweater Brown Dress Pants Dark Brown Leather Chelsea Boots

For a laid-back getup, make a tan plaid wool blazer and a grey pocket square your outfit choice — these pieces fit beautifully together. Introduce a pair of dark brown leather chelsea boots to the mix for an instant style boost.

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Light Blue Chambray Dress Shirt Grey Pocket Square Grey Knit Wool Turtleneck Charcoal Wool Suit Black Socks Black Leather Dress Boots

Consider wearing a charcoal wool suit and a grey pocket square to put together an everyday ensemble that's full of charm and character. Introduce a pair of black leather dress boots to the mix to avoid looking too casual.

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Charcoal Beanie Clear Sunglasses Charcoal Wool Turtleneck Grey Pocket Square Grey Houndstooth Overcoat Grey Houndstooth Wool Suit Black Leather Tassel Loafers

Perfect the casually stylish ensemble in a grey houndstooth overcoat and a grey pocket square. Up your whole ensemble by wearing black leather tassel loafers.

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Charcoal Flat Cap Clear Sunglasses White Dress Shirt Grey Pocket Square Charcoal Tie Black Leather Watch Silver Bracelet Charcoal Wool Waistcoat Charcoal Wool Blazer Charcoal Vertical Striped Chinos Black Socks Black Leather Dress Boots

To assemble a casual ensemble with an edgy spin, try teaming a charcoal wool blazer with a grey pocket square. Why not add black leather dress boots to the equation for a sense of elegance?

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Dark Brown Sunglasses White Dress Shirt Grey Pocket Square Burgundy Tie Charcoal Wool Waistcoat Silver Watch Grey Vertical Striped Chinos Charcoal Wool Blazer Charcoal Socks Black Suede Chelsea Boots

This casual pairing of a charcoal wool blazer and a grey pocket square couldn't possibly come across as anything other than incredibly stylish. Throw black suede chelsea boots into the mix to completely shake up the ensemble.