Leather Boots Smart Casual Chill Weather Outfits For Men After 50

Favorite

Unfavorite

Charcoal Flat Cap Clear Sunglasses Navy Knit Wool Turtleneck Black Shearling Jacket Silver Watch Navy Jeans Black Socks Black Leather Casual Boots

If you feel more confident in functional clothes, you'll appreciate this off-duty combo of a black shearling jacket and navy jeans. Balance this ensemble with a dressier kind of shoes, like these leather boots. When it comes to style tips for gents in their fifties, this combination looks good on most.

Favorite

Unfavorite

Dark Brown Sunglasses White Crew-neck T-shirt Black Crew-neck Sweater Black Overcoat White Canvas Belt White Cargo Pants Black Leather Chelsea Boots

Try pairing a black overcoat with white cargo pants to look classy but not particularly formal. When in doubt about what to wear on the shoe front, go with leather boots. This combo demonstrates that as a man in his 50s, you still have a vast array of style options.

Favorite

Unfavorite

Beige Baseball Cap White Dress Shirt Grey Long Sleeve T-Shirt White Pocket Square Brown Check Wool Blazer Dark Brown Suede Belt Khaki Corduroy Dress Pants Brown Leather Casual Boots

This combination of a brown check wool blazer and khaki corduroy dress pants comes in handy when you need to look seriously stylish and elegant. Why not introduce leather boots to the mix for a more relaxed spin? So if you need outfit inspo for dressing as you age into your 50s, this combo is definitely worth saving for later.

Favorite

Unfavorite

Tan Flat Cap Tobacco Sunglasses Brown Wool Turtleneck Beige Leather Watch Camel Overcoat Dark Brown Beaded Bracelet Khaki Jeans Tobacco Leather Casual Boots

If the dress code calls for an effortlessly classic getup, try pairing a camel overcoat with khaki jeans. A pair of leather boots finishes off this ensemble very well. When it comes to fashion tips for gents in their 50s, this getup suits almost any gentleman.

Favorite

Unfavorite

White and Navy Gingham Long Sleeve Shirt Dark Green Zip Sweater Olive Overcoat Black Chinos Dark Brown Leather Chelsea Boots

This look suggests that it is totally worth investing in such menswear items as an olive overcoat and black chinos. Let your styling credentials really shine by rounding off your ensemble with a pair of leather boots. This is a stylish and age-appropriate getup for mature guys.