Flat Cap Dressy Cold Weather Outfits For Men After 50

Favorite

Unfavorite

Navy Flat Cap Navy Overcoat Navy Vertical Striped Dress Pants Black Leather Chelsea Boots Blue Scarf

If you’re a jeans-and-a-tee kind of dresser, you'll like this pared down combination of a navy overcoat and a flat cap. And if you want to effortlessly step up your ensemble with one item, why not throw black leather chelsea boots in the mix? And if we're talking style for mature gents, this combo is a good look on most gentlemen.

Favorite

Unfavorite

Tobacco Flat Cap Navy Knit Wool Turtleneck Charcoal Overcoat Charcoal Plaid Wool Dress Pants Black Socks Dark Brown Leather Loafers

This combo of a charcoal overcoat and a flat cap is super easy to replicate and so comfortable to work all day long as well! Add dark brown leather loafers to the equation for an element of class. So if you need style tips on what to wear in your 50s, this ensemble is perfect.

Favorite

Unfavorite

Brown Flat Cap Clear Sunglasses Light Blue Gingham Dress Shirt Dark Brown Leather Gloves Navy Tie Dark Brown Wool Blazer Brown Herringbone Overcoat White Corduroy Dress Pants Dark Brown Suede Tassel Loafers

Pair a brown herringbone overcoat with a flat cap to put together an interesting and city casual ensemble. Inject this outfit with an air of polish by rocking dark brown suede tassel loafers. This ensemble illustrates that even in your fifties your sartorial options are far from limited.

Favorite

Unfavorite

Grey Herringbone Flat Cap Black Print Silk Scarf White Dress Shirt Charcoal Wool Waistcoat Charcoal Wool Dress Pants Red and White Houndstooth Overcoat

A red and white houndstooth overcoat and a flat cap are a casual street style pairing that every modern gent should have in his casual styling routine. The ability to wear looks like this is one of the dividends of middle age.