Dress Shirt Fall Outfits For Men After 50

Favorite

Unfavorite

Dark Brown Sunglasses Black Dress Shirt Charcoal Waistcoat Olive Military Jacket Black Leather Belt Navy Skinny Jeans Black Suede Tassel Loafers

A dress shirt and navy skinny jeans are the perfect way to infuse some cool into your current collection. Complement this outfit with a pair of black suede tassel loafers to completely shake up the ensemble. There's no better way to brighten up a dreary fall day than a sharp look like this one. This outfit looks great on middle-aged gentlemen.

Favorite

Unfavorite

Olive Beanie White Dress Shirt Olive Knit Tie Dark Brown Wool Waistcoat Olive Raincoat Dark Brown Canvas Briefcase Dark Brown Wool Suit Tobacco Suede Desert Boots

For a casually stylish outfit, pair a dress shirt with an olive raincoat — these two items play really nice together. Feeling transgressive today? Tone down this look by rounding off with a pair of tobacco suede desert boots. So when summer is fading away and autumn is taking its place, you may find this outfit your uniform. An exciting choice for a 50-something man!

Favorite

Unfavorite

Olive Flat Cap Purple Pocket Square Brown Corduroy Chinos Red Wool Waistcoat Olive Herringbone Wool Blazer Grey Wool Tie White and Red and Navy Gingham Dress Shirt

A dress shirt and brown corduroy chinos are among the unshakeable foundations of any versatile menswear collection. When leaves turn yellow and red and fall is at its best, you'll love this outfit as your go-to for transeasonal weather. This combo is something guys in their 50s can wear with confidence.

Favorite

Unfavorite

White Vertical Striped Dress Shirt Olive Print Scarf Brown Herringbone Wool Blazer Olive Quilted Barn Jacket

For a casually stylish ensemble, pair a dress shirt with an olive quilted barn jacket — these items go really nice together. Can you see how super easy it is to look stylish and stay snug when chillier days are here, thanks to this getup? Wondering what clothing is appropriate as you age into your 50s? This getup is the perfect answer.

Favorite

Unfavorite

Black Wool Hat Black Dress Shirt Black Leather Bomber Jacket Black Skinny Jeans Black Leather Watch Black Leather Chelsea Boots

Team a dress shirt with black skinny jeans for a simple look that's also put together nicely. If you want to feel a bit fancier now, complement this ensemble with black leather chelsea boots. As you can see, this combination is a really savvy idea, especially for summer-to-fall weather, when the temperature is dipping. Wondering how to dress age-appropriately as you move into your 50s? This getup is a good illustration.