Waistcoat with Oxford Shoes Dressy Outfits After 50

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Yellow Sunglasses White Dress Shirt Grey Waistcoat Grey Blazer Dark Brown Woven Leather Belt Olive Chinos Brown Leather Briefcase Black Socks Burgundy Leather Oxford Shoes

This sophisticated combination of a waistcoat and olive chinos will be a good manifestation of your styling prowess. Serve a little outfit-mixing magic by rounding off with a pair of oxford shoes. This getup demonstrates that dressing well as a man in his 50s is not that daunting a task.

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Dark Brown Wool Hat White Dress Shirt Beige Tie Navy Waistcoat Black Leather Gloves Navy Dress Pants Black Leather Oxford Shoes Navy Overcoat

This combination of a waistcoat and navy dress pants is great for elegant situations. Oxford shoes are guaranteed to add a dose of stylish nonchalance to your ensemble. This combo illustrates how to stay stylish as you age into your 50s.

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Light Blue Vertical Striped Dress Shirt Charcoal Paisley Tie Grey Plaid Wool Waistcoat Grey Plaid Wool Blazer Black Watch Dark Brown Leather Belt Grey Wool Dress Pants Black Chunky Leather Oxford Shoes

This combination of a waistcoat and grey wool dress pants is a real life saver when you need to look extra stylish and elegant. Oxford shoes will bring a more dressed-down aesthetic to the look. As you can see here, even in your fifties your styling options are still rather broad.

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Dark Brown Sunglasses White Dress Shirt Charcoal Tie Charcoal Waistcoat White Pocket Square Charcoal Blazer Olive Camouflage Chinos Black Socks Orange Suede Oxford Shoes

Consider wearing a waistcoat and olive camouflage chinos to exude elegance and polish. Why not take a more elegant approach with shoes and complete your getup with a pair of oxford shoes? This is a good-looking but also age-appropriate combination for gents in their 50s.

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Navy Sunglasses White Dress Shirt Grey Tie Black Waistcoat Black Overcoat Black Vertical Striped Dress Pants Black Socks Black Leather Oxford Shoes

To look like a modern dandy with a great deal of class, marry a waistcoat with black vertical striped dress pants. Introduce oxford shoes to the equation to avoid looking too polished. This pairing illustrates that figuring out how to dress stylishly as a 50-something guy is easier than one might think.