Black Waistcoat with Dress Shirt Smart Casual Chill Weather Outfits After 40

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White Dress Shirt Black Tie Black Blazer Dark Brown Field Jacket Dark Green Canvas Briefcase Beige Chinos Dark Brown Socks Dark Brown Suede Desert Boots Red Plaid Scarf Black Waistcoat

For sophisticated style with a twist, you can opt for a black waistcoat and a dress shirt. Finishing with a pair of dark brown suede desert boots is a guaranteed way to infuse a more laid-back aesthetic into your look. If you're worried about dressing your age, this pairing is perfect.

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White Dress Shirt Blue Denim Jacket Black Waistcoat Charcoal Check Overcoat Black Chinos White Canvas Low Top Sneakers

For a look that's refined and totally wow-worthy, wear a black waistcoat with a dress shirt. Put a more casual spin on this outfit with white canvas low top sneakers. This getup illustrates that dressing stylishly as a 40-year-old man is totally doable.