White Dress Shirt with Chelsea Boots Cold Weather Outfits For Men After 40

Favorite

Unfavorite

Navy Paisley Silk Scarf White Dress Shirt Grey Herringbone Overcoat Black Leather Belt Black Suit Black Leather Chelsea Boots

This getup demonstrates it pays to invest in such smart menswear pieces as a white dress shirt and a grey herringbone overcoat. When in doubt about what to wear in the shoe department, add chelsea boots to the equation. So if you're on the lookout for outfit inspiration for dressing as you pass the big 4-0, this outfit is perfect.

Favorite

Unfavorite

Navy Sunglasses White Dress Shirt Navy Tie Dark Green Fur Collar Coat Charcoal Plaid Chinos Black Leather Chelsea Boots

For a casually classic look, rock a white dress shirt with charcoal plaid chinos — these two items fit really well together. Avoid looking too casual by rounding off with chelsea boots. Dressed like this, any 40-year-old gentleman is bound to put many a younger man to shame.

Favorite

Unfavorite

Dark Green Sunglasses White Dress Shirt Olive Print Tie Dark Brown Canvas Backpack Dark Brown Houndstooth Overcoat White Chinos Dark Brown Leather Chelsea Boots

Consider teaming a white dress shirt with white chinos to exude manly sophistication and polish. And if you need to instantly up the style ante of this ensemble with footwear, why not introduce a pair of chelsea boots to this look? So take cues and be the sharpest dressed gentleman in town.

Favorite

Unfavorite

Dark Brown Sunglasses White Check Dress Shirt Grey Wool Waistcoat Navy Plaid Overcoat Navy Jeans Brown Leather Chelsea Boots Black and White Print Bandana

This combo of a white dress shirt and navy jeans will add alpha male essence to your ensemble. If you need to easily class up your look with footwear, why not complement this getup with chelsea boots? And if we're talking dressing ideas for middle-aged gents, this combo looks good on most guys.

Favorite

Unfavorite

Dark Brown Wool Hat White and Blue Vertical Striped Dress Shirt Violet Tie Tobacco Print Scarf Navy Blazer Camel Overcoat Charcoal Dress Pants Dark Brown Suede Chelsea Boots

Teaming a white dress shirt with charcoal dress pants is a great choice for a stylish and refined look. A trendy pair of chelsea boots is a simple way to add a confident kick to the outfit. Outfit inspo like this will help you stay amazingly stylish well into your 40s.