On Board
When it comes to board meetings, you’ll want a supremely tailored piece that makes you feel like a boss. This striped piece from Italian gentlemen’s outfitter Brioni, which is opening its standalone boutique at Marina Bay Sands in September, seals the deal with its refined cut and authoritative sensibility.
$950 from Uomo Collezioni

The Sharp End
Even if you’re not ripped or model-skinny, always choose a shirt that closely fits your torso to avoid billowy folds—they draw attention to your flaws and make you look frumpy. With its sharp, slim-fit silhouette and elegant, slightly shimmering blue hue, this sophisticated piece sets the right tone for a versatile work-to-bar look.

$89.90 from Benjamin Barker

Measure Up
Good for you if you can wear small, medium and large, but generic ready-to-wear never feels as good as a handcrafted, bespoke dress shirt. Get measured at Kevin Seah Bespoke for a traditional Savile Row standard, which feature fine 1/8” French seams, 23 stitches per inch stitching and mother pearl. All these mean you get a shirt for you and you alone, in terms of fit, hang, structure, comfort and the way it moves.

$350 upwards from Kevin Seah. By appointment only.

Casual Chic
Timeless, utilitarian and comfortable, chambray is a great alternative fabric to heavy denim, which doesn’t sit well with our sweat-inducing climate. High-street label Ben Sherman does one in a cool, indigo shade with brown buttons for contrast, which adds instant sartorial edge to dress-down weekends.

$189 from Ben Sherman

Made Man
Nothing looks classier than a crisp, immaculate Don Draper white shirt. And it goes with everything you put on, whether it’s a pair of jeans or a dark suit. If you already have plenty of these in high thread-count cotton, mix things up with one in Cambridge oxford fabric, like this classic button-down from American designer Thom Browne.

$290 from Surrender