Did your boss’ nondescript oxfords illicit yet another yawn from you this morning? Like the rest of your outfit, shoes are an extension of your personality, and etiquette coaches are quick to have you know that people often judge you from head to toe, the minute you walk through any door.

Unfortunately, unlike shoes from the fairer gender, men’s work shoes are often cookie-cutter and in some of the most neutral (read: boring) colours known to humankind. How often do you see a pair of red brogues? So we’ve gone on the hunt for some of the most interesting or unusual work shoes for you. Some are a bit over-the-top and some, subtly snazzy.

Either way, these shoes will have people do a double-take, earn you high-fives from your colleagues, and (maybe) a nod of approval from your boss.

1
Prada spazzolato leather and mesh wintgtip brogues

Prada has been big on reinvention this season and now, they’ve applied its leather expertise to some interesting design wizardry. Part classy and part sporty, these brogues are crafted from spazzolato leather, and look ordinary at first glance, until you notice the mesh panelling, ventilating grommets and grey rubber accents outlining the laces. Wear them with simple slim-fit trousers to keep the attention on these babies.

S$960, Prada

2
Berluti Blake polished-leather oxford shoes

It looks like an ordinary pair of work shoes — except it isn’t. Look carefully and you’ll notice its heel is a contrasting shade of navy, a contemporary detail to the otherwise classic pair of Venezia leather shoes. Perfect for showing your fun side, but only very subtly.

S$2,624, Mr. Porter

3
Thom Browne grosgrain strap brogues

Thom Browne adds a unique touch to the regular brogues with what else but his signature tri-coloured grosgrain ribbon. Epitomising the quirkiness and energy of New York, the pebbled leather shoes are punctuated by the iconic colours, which run all around the shoes and at the pull tab behind — great for finishing that preppy look with a distinct modern edge.

S$1,670, Thom Browne

4
Common Projects Cadet suede derby shoes

Though minimalist-looking, these Common Projects ‘Cadet’ derbies will pack lots of miles with their versatility. In a charming shade of navy, each pair is made in Italy from smooth suede, and finished with the brand’s trademark: Individualised gold serial numbers at the side. Substantial rubber-crepe soles form the foundation of the shoes, which, like the pull-up tab at the back, contrast with the shoe to help it stand out more. Easy to dress up or down with, these shoes will take you from work to after-dark activities effortlessly.

S$583, Mr. Porter

5
Burberry asymmetric leather wingtip brogues

Inspired by legendary British sculptor Henry Moore’s monumental and curvilinear depictions of the human form, Burberry’s classic brogues are reimagined with an asymmetrical throat line for a quirky disposition. The shoes’ pebble-grained leather — in a robust shade of burgundy — has been ever-so-lightly stonewashed for a lived-in finish. Guaranteed to make everyone do a double take.

S$960, Burberry

Shatricia Nair
Senior Writer
Shatricia Nair is a motoring, watches, and wellness writer who is perpetually knee-deep in the world of V8s, tourbillons, and the latest fitness trends. She is fuelled by peanut butter and three cups of coffee a day.