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late summer outfits, male summer fashion
Photography via Launchmetrics/Spotlight
Style/Shopping

A Guide to Late Summer Dressing

Stylish takeaways from one of Canada’s biggest musical festivals.

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We’ve reached the point in late summer when the unrelenting heat can make getting dressed feel like a chore. To help you feel inspired again for the last stretch of scorching temps, we headed to Osheaga—Canada’s largest arts and music festival—to find heat- and humidity-tested summer outfit ideas that are as comfortable as they are stylish.

In the Osheaga lineup this year? Artists like Olivia Rodrigo, Doechii and Gracie Abrams. But great musical performances aside, the annual festival is also a reliably stellar spot for people-watching. After all, 142,000 people attended the festival this year—and while most of the crowd was dressed for comfort (and the mid-summer heat!), many attendees were also there to make a style statement. Think: coordinating outfits, sharp accessories and, in some cases, even full glam.

Ahead, some of the most fashionable ensembles we spotted at this year’s edition of Osheaga—and how to steal the look. Consider your late summer style inspiration, sorted.

Summer leather

A Guide to Late Summer Dressing
Photography courtesy of Osheaga

Who says you have to wait until fall to embrace leather weather? At Osheaga, showgoers wore boots and mid-rise leather shorts with statement pieces in sheer black lace. When temps drop in a few months, the same leather separates can be worn with cozy knits or velvet tops, but this combination of leather and lace is perfect for looking stylish in the late summer heat.

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Norma Kamali

Norma Kamali

Jort stuff

A Guide to Late Summer Dressing
Photography courtesy of Truc Nguyen

Tired of your cutoffs. ICYMI, the short of the summer is the humble jort, or jean short. Here, they are worn with the ubiquitous-at-Osheaga leather cowboy boots and a knit halter top, but you could also wear yours with a cropped, fitted t-shirt and heeled or platform flip-flops.

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Levi's

Levi's

More To Come

More To Come

Going wide

wide leg pants osheaga 2025
Photography courtesy of Truc Nguyen

Wide-leg pants are a fashionable pick, no matter the temp. But they key to taking this trend into the fashion stratosphere is to play with contrast. As seen here, the formal pinstripe gets the blokecore treatment with a sports jersey. Also, we love a tight fitted top paired with a more voluminous bottom. Add some chunky accessories for that extra spice factor.

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3.Paradis

3.Paradis

Ray Ban

Ray Ban

Urban Outfitters

Urban Outfitters

Shirt tales

shirt tails osheaga 2025
Photography courtesy of Truc Nguyen

A crisp white button-up can be a wardrobe hero year-round. Here, it’s worn almost fully unbuttoned over a stylish bra and on-trend jean shorts. The coordinating white socks also help balance out the look.

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Fleur Du Mal

Fleur Du Mal

T. Line

T. Line

Diesel

Diesel

Dark mode

dark mode osheaga 2025
Photography courtesy of Truc Nguyen

Even midsummer, it’s easy to stay cool in an all-black ensemble. Looser-fitting garments in breathable materials like linen and cotton will feel more comfortable in the sun, and you can always balance longer bottoms with a more skin-baring top and open-toe sandals.

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Massimo Dutti

Massimo Dutti

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Truc Nguyen is a freelance writer and whose work has appeared in The Globe and Mail, Teen Vogue, Elle Canada, CBC Life, Refinery29, Toronto Life and NUVO. She's a fashion school graduate, former celebrity stylist, and professional deal seeker.

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