Tobacco Pocket Square Dressy Summer Outfits After 50

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Clear Sunglasses White Dress Shirt Brown Pocket Square Black Leather Belt Navy Plaid Suit Brown Leather Loafers

This pairing of a navy plaid suit and a tobacco pocket square is an appealing pick for when it's time to clock off. Go ahead and complement this look with a pair of brown leather loafers for a dose of refinement. This ensemble isn't a hard one to pull together and it's summer-appropriate, which is important when it's baking hot outside. This combination demonstrates that figuring out how to dress stylishly as a man over 50 is not particularly hard.

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Dark Brown Sunglasses White and Navy Vertical Striped Dress Shirt Navy Tie Dark Brown Pocket Square Beige Suit Navy Socks Dark Brown Leather Tassel Loafers

This combination of a beige suit and a tobacco pocket square combines comfort and functionality and helps you keep it low profile yet trendy. If you want to effortlessly step up your look with one single item, why not complete your ensemble with dark brown leather tassel loafers? If you're trying to figure out a summer-ready look, this one is a smart option. This one is a nice and age-appropriate getup for men over 50.

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Clear Sunglasses White and Navy Vertical Striped Dress Shirt Brown Print Pocket Square Navy Print Tie Navy Blazer Black Beaded Bracelet Grey Dress Pants Charcoal Socks Black Leather Tassel Loafers

This street style combo of a navy blazer and a tobacco pocket square is very easy to pull together in no time flat, helping you look stylish and ready for anything without spending a ton of time digging through your wardrobe. Break up your ensemble with a smarter kind of shoes, like these black leather tassel loafers. Naturally, it's easier to work through a boiling hot day in a cool look like this. Wondering what to wear as you slip into your 50s? This combo is the perfect answer.

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Clear Sunglasses Light Blue Dress Shirt White and Black Print Pocket Square Charcoal Print Tie Grey Plaid Blazer Beige Dress Pants Brown Pocket Square Brown Suede Loafers

Choose a grey plaid blazer and a tobacco pocket square for a killer and stylish outfit. Brown suede loafers are the simplest way to upgrade your outfit. So if it's an extremely hot hot weather afternoon and you want to look dapper without putting in too much work, this look will do the job in seconds time. All in all, a great option if we're talking dressing ideas for men in their fifties.

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Clear Sunglasses White Dress Shirt Dark Brown Pocket Square Burgundy Tie Brown Gingham Blazer Grey Dress Pants Brown Leather Oxford Shoes

For an outfit that's very simple but can be manipulated in a multitude of different ways, consider wearing a brown gingham blazer and a tobacco pocket square. Tap into some Ryan Gosling dapperness and add brown leather oxford shoes to the equation. As you can see here, this is a kick-ass option for summertime. Combos like this help welcome this next milestone that is your 50s with class and confidence.