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Pyjama dressing

Rachelle Simoneau

Out of the office, skip a more structured button-down in favour of a slouchy piece with a convertible collar.

Shirt, price on request, shorts, $425 at Boss. Monsieur watch, price on request at Chanel. Teva sandals, $110 through tevaonline.ca.

Match point

Rachelle Simoneau

A bandana pattern offers a more subtle take on a novelty print – unless you wear it from neck to knee, of course.

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Sacai shirt, $670, shorts, $685, boots, $1,165 at Ssense. Monsieur watch, price on request at Chanel. Tabio socks, US$20 through tabiousa.com.

Long game

Rachelle Simoneau/RACHELLE SIMONEAU

Size up when you make your own shirting buy. A larger piece channels a more relaxed feeling and can double as an extra layer on cooler days.

Kenzo jacket, price on request, shirt, $315, shorts, price on request, sandals, $610 through kenzo.com. Tabio socks, US$20 through tabiousa.com.

Top spin

Rachelle Simoneau

Phillip Lim mixes tropical motifs on an oversized tunic and cropped trousers.

3.1 Phillip Lim shirt, US$495, trousers, US$550 through 31philliplim.com. Undershirt, stylist’s own. Tabio socks, US$20 through tabiousa.com. Kenzo sandals, $610 through kenzo.com.

Flower power

Rachelle Simoneau

The Paul Smith collection regularly features a lineup of dapper tops. Spring 2019’s options include pop polka dots, classic stripes and exploding florals.

Paul Smith shirt, $399, AMI trousers, $377 through eastdane.com. Belt, $128 at Boss. Tabio socks, US$20 through tabiousa.com. Teva sandals, $110 through tevaonline.ca.

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See double

Rachelle Simoneau

To layer prints, mix short and long-sleeved oxfords to reveal different motifs within the same colour family, but at varying scales.

Kenzo short sleeve shirt, $270, long sleeve shirt, $285 through kenzo.com. Monsieur watch, price on request at Chanel.

Natural selection

Rachelle Simoneau

London-based Story MFG creates clothing, such as this jacket embroidered with palms, out of organic fibres dyed with natural elements including tree bark and fruit.

Story mfg jacket, £325 through storymfg.com. Undershirt, stylist’s own. Kenzo short, $260 through kenzo.com. Belt, $128 at Boss.

Bottle stop

Rachelle Simoneau

An array of beer graphics cover an Ovadia & Sons shirt jacket, which is part of a collection that combines psychedelic inspiration with sharp tailoring.

Ovadia & Sons jacket, US$595 through ovadiaandsons.com. Saturdays NYC shirt, $245 through eastdane.com.

New view

Rachelle Simoneau

Stocking up on short sleeve options lets you show off a statement timepiece, such as Chanel’s Monsieur model.

Saturdays NYC shirt, $245 through eastdane.com. Monsieur watch, price on request at Chanel.

Styling by Georgia Groom. Grooming by Mathieu Laudrel for La Frenchie Agency. Model: Chakshu Sharma at Elite Paris. Photo assistant: Loup Ka.

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