Though the rules around what to wear to the office have been slowly and steadily relaxing for the last 30 years, getting dressed for business is still a relatively straightforward affair: Look sharp, sign deals, go home. But once you cross the threshold of your workplace, the rules can be confusing. What’s a guy to wear when he’s not in the boardroom, or pounding the pavement in pursuit of entrepreneurial ends?
A ribbed collar lends a note of refinement to the hardworking chore coat (ditto the Italian goat suede). Add some kick with clean white high-top sneakers, which will age with as much character as well-loved loafers.
Officine Générale Italian goat-suede jacket, $1,450; Loro Piana cotton-and-silk polo, $1,050; Drumohr wool pants, about $360; Delvaux Brillant L’XXL weekender in Dream Calf, $10,300; Hermès high-top sneakers in calfskin, $1,025; Saint Laurent recycled-acetate sunglasses, $460.
Casual, but make it business: A technical blazer, such as this zip-pocket cotton example in a rich carob brown, plays surprisingly straight when paired with tailored trousers and suede tassel loafers. A sleek leather case adds to the modern playboy-industrialist vibe.
Hermès cotton blazer, $3,150; Giuliva Heritage linen sweater, about $1,080; Canali linen-and-silk pants, $695; Santoni suede loafers, $890; Louis Vuitton cowhide Nomade Porte-Documents Voyage Moka, $4,400.
The current mood for relaxed dressing has room for more than just safari jackets. Elevated workwear, such as this rugged mechanic’s jacket from Tod’s, is a simple swap for your current favorite bomber or overshirt.
Tod’s washed short jacket, $1,375; Frame cotton T-shirt, $68.
A Touch of Gray
For running around town, nothing works harder than denim and some luxe trainers. Keep the rest equally comfortable (and decidedly polished) with a soft, monochrome mix of cashmere, suede and flannel.
Stòffa lamb-suede shirt jacket, $1,600; Louis Vuitton cashmere turtleneck, $1,260; Bally denim jeans, $640; Mark Cross classic tote in leather, $1,350; Celine by Hedi Slimane western belt in smooth calfskin, $520; Brunello Cucinelli wool-and-cashmere-flecked chevron flannel baseball cap, $595; Ralph Lauren Purple Label suede sneakers, $795.