Seven Days of Shoes

This foolproof footwear plan takes you from work to the weekend.

By: JACLYN LAWDate: 2018-07-31

Most men wouldn’t wear the same outfit to the office two days in a row, yet many are in the habit of wearing the same pair of black or brown dress shoes most days of the week. If you care about the impression you make with your attire, change up your footwear frequently (and besides, your shoes will last longer if they get a breather between outings).

Expanding your shoe wardrobe is both easy and pleasurable. Well-dressed men often have enough options for an entire week, with a variety of styles, colours, leathers and details. Here we offer inspiration for your new footwear lineup: seven handsome, high-quality shoes that will last for years.


BARKER Falsgrave Black Leather Oxfords

Step confidently into your work week with this elegant dress shoe, hand-crafted in England from high-quality European calf leather. It’s Goodyear-welted, which means it can easily be resoled. Exclusive to Harry Rosen.

Wear it with: A light grey or charcoal grey suit.


ANTONIO MAURIZI Burnished Brown Leather Oxfords

This beautiful brown oxford adds a little joy to a man’s morning routine. Made in Italy from gorgeous, cocoa-hued calfskin, this shoe has a subtle burnished effect on the cap-toe. Exclusive to Harry Rosen. \Available Online Soon.*

Wear it with: A gentleman’s power suit in navy or mid-blue with a peak lapel.


TO BOOT NEW YORK Cognac Cap-Toe Derby

This sleek and stylish choice is made in Italy from premium calfskin. The rubber sole ensures a comfortable stride. Exclusive to Harry Rosen.

Wear it with: A navy suit or, for a smart-casual look, a white oxford shirt (no tie) tucked into a pair of tan trousers.


HARRY ROSEN Brown Saffiano Monk-Strap

This double monk strap with brogue details and eye-catching buckles adds panache to a tailored look. It looks equally polished with a suit or casual trousers, so you’ve already doubled your investment. Exclusive to Harry Rosen.

Wear it with: Tailored dark jeans and a sharp blazer, or a slimmer suit with a bold pattern in blue, navy or grey.


BONTONI Brown Pebble-Grained Leather Penny Loafer

This lustrous, versatile calfskin loafer – handmade by Bontoni’s master cobblers – is the perfect pick for Friday. It looks good at the office but also fits the vibe for after-work drinks.

Wear it with: An unlined, deconstructed suit over a long-sleeved merino knit, or a pair of jeans and a crisp shirt.


MONCLER Emilien Sock Sneakers

These sock-style sneakers from Moncler are crafted with a textured mix of leather and neoprene with ultra-lightweight soles that are designed to support your stride no matter the terrain.

Wear it with: Moncler joggers and a piece from their iconic outerwear lineup.



Esteemed Canadian designer Christopher Bates has crafted this timeless style exclusively for Harry Rosen. Masterfully handmade in Italy, they're fashioned from supple suede dyed a versatile black hue. Their streamlined soles provide a sleek stride that's sure to complement a variety of casually refined looks.

Wear it with: a black pair of faded jeans for a casual Saturday night out.


TOD’S Suede Desert Boots

Desert boots lend a relaxed yet refined touch to a weekend outfit. This sophisticated example from Tod’s is crafted in Italy. It features a classic round-toe silhouette, and the rubber sole is pebbled for traction.

Wear it with: Navy or dark brown corduroy trousers and a sweater-jacket.