Blue Pocket Square Smart Casual Chill Weather Outfits After 50

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Clear Sunglasses White Crew-neck T-shirt Blue Pocket Square Navy Sweater Vest Blue Blazer Black Leather Belt Navy and Green Plaid Overcoat Khaki Chinos Grey Athletic Shoes

When the situation permits a casual menswear style, you can always rely on a navy and green plaid overcoat and a blue pocket square. To bring out the fun side of you, introduce grey athletic shoes to your outfit. This is a combination you, as an older guy, can always rely on.

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Clear Sunglasses Light Blue Chambray Dress Shirt Navy Pocket Square Red Cable Sweater Olive Wool Blazer Black Leather Watch Khaki Corduroy Dress Pants Brown Suede Desert Boots

For comfort dressing with a twist, go for an olive wool blazer and a blue pocket square. Brown suede desert boots will breathe a touch of sophistication into an otherwise mostly casual ensemble. This pairing shows that figuring out fashion at age 50 is not that daunting a task.

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Grey Tie White Long Sleeve Shirt Navy Pocket Square Grey Wool Waistcoat Navy Wool Blazer Khaki Cargo Pants Navy Leather Tote Bag Burgundy Leather Work Boots

Dress in a navy wool blazer and a blue pocket square to create an incredibly dapper and casual outfit. For extra style points, introduce a pair of burgundy leather work boots to the mix. A no-brainer ensemble proper for over-50 men.