Pocket Square Dressy Chill Weather Outfits After 50

Favorite

Unfavorite

Clear Sunglasses White Dress Shirt Red Print Pocket Square Blue Polka Dot Tie Grey Overcoat Dark Brown Leather Watch Navy Check Suit White Print Socks Brown Leather Double Monks

A grey overcoat and a pocket square are a wonderful combination to add to your casual wardrobe. Turn up the dressiness of your getup a bit by finishing off with brown leather double monks. This one is a stylish and age-appropriate pairing for middle-aged gents.

Favorite

Unfavorite

Clear Sunglasses White Dress Shirt Navy Tie Navy Pocket Square Tobacco Overcoat Grey Check Suit Dark Brown Leather Briefcase Brown Leather Brogues

This combination of a tobacco overcoat and a pocket square is extremely easy to achieve and so comfortable to work over the course of the day as well! Add brown leather brogues to your outfit for an added touch of style. This combo illustrates that even after fifty your dressing options are still looking great.

Favorite

Unfavorite

Dark Green Sunglasses White Dress Shirt Black Tie Light Blue Pocket Square Dark Brown Leather Gloves Multi colored Print Scarf Navy Overcoat Navy Socks Dark Brown Suede Desert Boots Dark Brown Wool Suit

To pull together a casual outfit with an urban twist, consider wearing a navy overcoat and a pocket square. Complete your outfit with dark brown suede desert boots for an extra dose of style. On a mission for style tips for older gents? This combo definitely goes to your inspiration folder.

Favorite

Unfavorite

Black and White Polka Dot Silk Scarf Grey Wool Turtleneck White Pocket Square Grey Wool Suit White and Black Houndstooth Overcoat Black Suede Derby Shoes

One of the best ways for a man to style out a white and black houndstooth overcoat is to team it with a pocket square for a laid-back combination. Black suede derby shoes will bring a different twist to this ensemble. This is a combination you, as a gentleman in his fifties, can always count on.

Favorite

Unfavorite

Light Blue Dress Shirt Burgundy Vertical Striped Tie White Pocket Square Brown Trenchcoat Navy Suit Dark Brown Leather Desert Boots

Marry a brown trenchcoat with a pocket square to achieve an incredibly dapper and casual ensemble. Kick up the wow factor of your getup by finishing off with a pair of dark brown leather desert boots. This getup is a bright example over-50 men can still very well draw compliments.