Long Sleeve Shirt with Dress Pants Smart Casual Winter Outfits For Men After 50

Favorite

Unfavorite

Clear Sunglasses Orange Print Scarf Orange Crew-neck Sweater Navy Overcoat Blue Wool Dress Pants Dark Brown Suede Desert Boots White Long Sleeve Shirt

This combination of a long sleeve shirt and dress pants is the definition of refinement. Complement your ensemble with a pair of dark brown suede desert boots to effortlessly amp up the wow factor of your ensemble. During the colder months, when comfort is crucial, it can be easy to settle for a less-than-stylish outfit in the name of convenience. This outfit, however, is hard proof that you can actually stay warm and remain stylish at the same time during the colder months. As a guy over 50, you're guaranteed to like this getup.

Favorite

Unfavorite

Navy Sunglasses Light Blue Long Sleeve Shirt Orange Wool Turtleneck Camel Overcoat Beige Leather Zip Pouch Charcoal Dress Pants Burgundy Leather Casual Boots Brown Wool Gloves

This outfit clearly illustrates that it is totally worth investing in such timeless menswear pieces as a long sleeve shirt and dress pants. Add a pair of burgundy leather casual boots to the mix to instantly amp up the cool of this look. While it can be a bit challenging to dress stylish on extra cold days, it's getups like this that prove it's actually possible. Overall, a perfect example of over-50 fashion.

Favorite

Unfavorite

White Long Sleeve Shirt Dark Brown Shawl Cardigan Brown Fur Coat Black Leather Gloves Charcoal Wool Dress Pants Dark Brown Leather Desert Boots Dark Brown Sunglasses

Putting together a long sleeve shirt and dress pants is a fail-safe way to infuse your styling repertoire with some manly elegance. Clueless about how to finish off? Add dark brown leather desert boots to your look for a more laid-back twist. It's easy to see how this combination will keep you warm yet stylish throughout the season. This ensemble proves that figuring out how to dress stylishly as you slip into your 50s is totally doable.

Favorite

Unfavorite

Light Blue Vertical Striped Long Sleeve Shirt Dark Green Fair Isle Crew-neck Sweater Navy Parka Charcoal Wool Dress Pants Brown Leather Brogue Boots

This combo of a long sleeve shirt and dress pants couldn't possibly come across other than devastatingly sharp and classy. To bring an easy-going vibe to your look, introduce a pair of brown leather brogue boots to this look. During winter, when warmth is essential, it can be easy to surrender to a less-than-stylish look in the name of practicality. But this look is a striking illustration that you totally can stay comfortable and remain stylish at the same time during winter. The ability to rock outfits like this is one of the dividends of being middle-aged.