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

Beyond dapper and functional, this combination of a tan plaid wool blazer and a grey pocket square brings variety. Bump up your ensemble with a pair of dark brown leather chelsea boots.

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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

This casual pairing of a charcoal wool suit and a grey pocket square is very easy to put together in next to no time, helping you look sharp and ready for anything without spending too much time digging through your closet. For an on-trend hi/low mix, add black leather dress boots to the mix.

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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

Exhibit your chops in menswear styling in this modern casual combo of a grey houndstooth overcoat and a grey pocket square. And if you need to easily ramp up this ensemble with footwear, why not complement your getup with a pair of 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

This casual street style combination of a charcoal wool blazer and a grey pocket square can only be described as devastatingly dapper. Complement your getup with a pair of black leather dress boots to easily rev up the classy factor of any ensemble.

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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

Go for a simple but casually stylish choice by opting for a charcoal wool blazer and a grey pocket square. You could perhaps get a bit experimental with shoes and smarten up your ensemble by slipping into a pair of black suede chelsea boots.