Briefcase Smart Casual Outfits After 50

Favorite

Unfavorite

Clear Sunglasses Navy Check Long Sleeve Shirt Red Cardigan Olive Shirt Jacket Light Blue Jeans Tan Canvas Briefcase Burgundy Leather Derby Shoes

To achieve a laid-back look with a modern finish, you can easily dress in an olive shirt jacket and a briefcase. If you need to immediately dress up your ensemble with footwear, why not complete this ensemble with burgundy leather derby shoes? Wondering what you should wear as you slip into your 50s? This getup is a practical example.

Favorite

Unfavorite

Navy Baseball Cap Navy Sunglasses Blue Chambray Short Sleeve Shirt Navy Shirt Jacket Beige Chinos Navy Canvas Briefcase Dark Brown Leather Desert Boots Red Print Sweater Vest

If you enjoy a more relaxed approach to styling, why not pair a navy shirt jacket with a briefcase? A good pair of dark brown leather desert boots is an effortless way to upgrade your look. Now that's how you do smart casual as a 50-year-old guy.

Favorite

Unfavorite

Clear Sunglasses Red Dress Shirt Burgundy Horizontal Striped Tie Tan Check Blazer Olive Barn Jacket Silver Bracelet Tan Canvas Briefcase Blue Jeans Beige Suede Desert Boots

This combo of an olive barn jacket and a briefcase is extremely easy to do and so comfortable to wear a variation of as well! Let your outfit coordination credentials really shine by rounding off this look with beige suede desert boots. Like this idea for your styling routine as a middle-aged man?

Favorite

Unfavorite

Beige Baseball Cap Clear Sunglasses Blue Chambray Dress Shirt Dark Brown Tie Dark Brown Houndstooth Blazer Black Leather Watch White Chinos Tan Canvas Briefcase Black Suede Oxford Shoes

A dark brown houndstooth blazer and a briefcase are worth being on your list of menswear must-haves. For maximum style, add a pair of black suede oxford shoes to the mix. If you often wonder how to dress your age without giving up on fashion, this pairing is a wonderful example.

Favorite

Unfavorite

Clear Sunglasses Light Blue Chambray Dress Shirt White and Red and Navy Horizontal Striped Tie Navy Hoodie Navy Blazer Beige Chinos Tan Canvas Briefcase Navy Leather Loafers

Consider teaming a navy blazer with a briefcase to assemble an extra sharp and street style outfit. To introduce a little classiness to your ensemble, add a pair of navy leather loafers to your ensemble. So if you need fashion inspiration for dressing as you move into your 50s, this combination is perfect.