Briefcase Dressy Outfits

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Black Flat Cap White Dress Shirt Dark Brown Wool Tie Charcoal Pocket Square Black Waistcoat Dark Green Check Wool Blazer Dark Brown Leather Double Monks Black Socks Black Chinos Dark Brown Leather Briefcase

For a casual look with a street style finish, consider wearing a dark green check wool blazer and a briefcase. Complete your ensemble with a pair of dark brown leather double monks to immediately amp up the classy factor of this outfit.

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Tobacco Turtleneck Dark Green Pocket Square Grey Check Wool Double Breasted Blazer Silver Watch Dark Brown Leather Briefcase Black Wool Dress Pants Brown Suede Oxford Shoes Navy Polka Dot Socks

Wear a grey check wool double breasted blazer with a briefcase if you're looking for a look idea for when you want to look casual and cool. If you need to immediately elevate this look with shoes, grab a pair of brown suede oxford shoes.

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Navy Dress Shirt Dark Brown Leather Belt Brown Leather Watch Navy Leather Briefcase Orange Chinos Navy Leather Oxford Shoes

This street style combo of a navy dress shirt and a briefcase is extremely easy to put together in next to no time, helping you look seriously stylish and prepared for anything without spending too much time searching through your closet. Ramp up the cool of your ensemble by rocking navy leather oxford shoes.

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Dark Brown Sunglasses White Dress Shirt Tobacco Tie Red Print Pocket Square Grey Wool Waistcoat Brown Lapel Pin Tan Wool Blazer Tobacco Overcoat Tobacco Gingham Dress Pants Tobacco Leather Briefcase Tobacco Leather Double Monks

A tobacco overcoat and a briefcase are a cool pairing worth integrating into your day-to-day off-duty rotation. Tobacco leather double monks are an effortless way to give an added dose of polish to this outfit.

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Olive Barn Jacket Brown Cardigan Olive Wool Waistcoat Navy and Green Plaid Tie Light Blue Dress Shirt Charcoal Wool Hat Tobacco Leather Gloves Brown Gingham Scarf Navy Wool Dress Pants Dark Brown Leather Briefcase Dark Brown Suede Desert Boots Black Socks

The combination of an olive barn jacket and a briefcase makes for a killer casual look. A pair of dark brown suede desert boots instantly dresses up any ensemble.