Prep season

The preppy look goes back to school this fall at Bally, Tory Burch, Polo Ralph Lauren and more. Varsity and collegiate-inspired fashion with “a polished edge” continue to be popular, says Julianne Costigan, the CEO and founder of Costigan Studio, a personal branding studio based in Toronto offering services such as professional wardrobe makeovers. Pieces such as a knit sweater vest, for example, can transition seamlessly from summer to fall; you can wear it solo now, and over a button-up shirt on cooler days, suggests Costigan.

Lacoste wool sweater vest
Lacoste wool sweater vest, $215 through lacoste.com.
Old Navy cable-knit vest
Old Navy cable-knit vest, $43 through oldnavy.gapcanada.ca.
NEW YORK, NEW YORK - FEBRUARY 10: A model walks the runway wearing Tory Burch Fall/Winter 2025 during New York Fashion Week at MOMA on February 10, 2025 in New York City.  (Photo by Slaven Vlasic/Getty Images for Tory Burch)
(Slaven Vlasic/Getty Images)

Utilitarian outerwear

If you don’t already have a barn jacket in your wardrobe, consider getting one for fall. You could go for a classic style from Barbour, which Costigan calls “the OG barn jacket,” or opt for something more seasonal – updated versions of the utilitarian topper were spotted on the runway at S.S.Daley, Max Mara and Missoni. “This season you can actually have a little bit more fun with it and … find it in different textures and colours and details,” says Costigan. An unlined version in a medium-weight fabric would work for late-summer nights, but you’ll want to save thicker or insulated styles for the cooler months. And consider sizing up if you plan to layer it over thick sweaters or down-filled mid-layers in late fall.

J. Crew Relaxed Barn Jacket
J. Crew Relaxed Barn Jacket, $291 through jcrew.com.
L.L.Bean Adirondack barn coat
L.L.Bean Adirondack barn coat, $239 through llbean.ca.
LONDON, ENGLAND - FEBRUARY 21: A model walks the runway during the SS Daley Ready to Wear Fall/Winter 2025-2026 fashion show as part of the London Fashion Week on February 21, 2025 in London, England. (Photo by Victor VIRGILE/Gamma-Rapho via Getty Images)
(Victor VIRGILE/Getty Images)

Vintage fits

There were retro references – particularly from the 1950s and ’60s – in many of the fall womenswear collections, including at Valentino, Miu Miu and Gucci. “Everything is a little bit more cropped and fitted,” says Isla Lynch, a buying director at Ssense. “Hem lines are just above the knee.” Whether you opt for a skirt suit or shift dress for the new season, the look this season is “very playful and quite girly, but not overtly sexy,” says Lynch. Accessorize with silk scarves, bandanas and brooches, and add novelty tights or socks for cooler days.

Veronica Beard Whistler mini dress
Veronica Beard Whistler mini dress, $648 through veronicabeard.ca.
MILAN, ITALY - FEBRUARY 25: A model walks the runway at the Gucci - Women's Fall/Winter 2025/2026 Fashion Show during the Milan Fashion Week Womenswear Fall/Winter 2025/2026 on February 25, 2025 in Milan, Italy. (Photo by Daniele Venturelli/Getty Images for Gucci)
(Daniele Venturelli/Getty Images)

Sharp suiting

While oversized, slouchy suiting is still on offer, the newest styles are more fitted and minimal. “There was a lot of suiting across all runways, but it really was so much more playful, directional, punk than seasons before,” says Lynch. Her favourites for fall 2025 include a collarless, gray pinstripe suit with boxy shoulders at Calvin Klein, and the “super exaggerated shoulders and sexy pencil skirts” at Matières Fécales, founded by Canadian designers Hannah Rose Dalton and Steven Raj Bhaskaran.

H&M long jacket
H&M long jacket, $70 through h&m.com.
H&M midi skirt
H&M midi skirt, $35 through hm.com.
Backstage at the Calvin Klein Collection Fall RTW 2025 fashion show as part of New York Fashion Week held at the Calvin Klein Headquarters on February 07, 2025 in New York, New York. (Photo by Kelly Taub/WWD via Getty Images)
(Kelly Taub/Getty Images)

Duffle bags

“People are still super obsessed with big duffle bags,” says Lynch. Their oversized scale catches the eye, whether you’re carrying one to the office or the gym, or as a weekender. Roomy, structured versions in leather and suede appeared at shows such as Louis Vuitton, Stella McCartney and Gucci for fall; some were big enough to be used as luggage bags for end-of-summer escapes or fall road trips. “We’re seeing so many new iterations each season,” says Lynch, adding that the bags are often seen as an investment purchase because of their practicality.

Longchamp medium Daylong leather bag
Longchamp medium Daylong leather bag, $1,330 through holtrenfrew.com.
Roots small Banff leather bag
Roots small Banff leather bag, $498 through roots.com.
PARIS, FRANCE - MARCH 10: (EDITORIAL USE ONLY - For Non-Editorial use please seek approval from Fashion House) A model walks the runway during the Louis Vuitton Womenswear Fall/Winter 2025-2026 show as part of Paris Fashion Week on March 10, 2025 in Paris, France. (Photo by Antoine Flament/Getty Images)
(Antoine Flament/Getty Images)

Tailored leather

Tailored leather jackets and blazers were plentiful on the runways at MM6 Maison Margiela, Dior, Lemaire and more, especially in black. A shorter, more fitted style will work well as a transitional weather topper, but you’ll want to avoid anything long or lined in suede or shearling this early on. Costigan suggests wearing a moto-inspired leather jacket with Bermuda shorts for late summer evenings, and layered over knitwear when it’s cooler out.

COS leather bomber
COS leather bomber, $590 through cos.com.
MILAN, ITALY - JANUARY 20: A model walks the runway at the Zegna fashion show during the Milan Menswear Fall/Winter 2025 - 2026 Fashion Week on January 20, 2025 in Milan, Italy. (Photo by Pietro D'Aprano/Getty Images)
(Pietro D'Aprano/Gamma-Rapho/Getty Images)

'70s suiting

There was “an ode to seventies tailoring” this season, says Costigan. Suits, featuring large lapels and baggier pants, were shown in jewel and autumnal tones at Giorgio Armani, Zegna and Sacai. “Whether it’s being done in a cord or a velvet, we’re seeing these fun shades for men that feel less obvious and less typical,” says Costigan. Not ready to commit to the full look? Take inspiration from the Amiri runway and try a richly textured blazer with dark-coloured trousers or indigo wash jeans.

Polo Ralph Lauren corduroy suit jacket
Polo Ralph Lauren corduroy suit jacket, $898 through ralphlauren.ca.
Kotn Cord Laureate jacket
Kotn Cord Laureate jacket, $225 through kotn.com.
PARIS, FRANCE - JANUARY 23: (EDITORIAL USE ONLY - For Non-Editorial use please seek approval from Fashion House) A model walks the runway during the Amiri Menswear Fall-Winter 2025/2026 show as part of Paris Fashion Week on January 23, 2025 in Paris, France. (Photo by Estrop/Getty Images)
(Estrop/Getty Images)

All about plaids

A rising trend this past spring for both men and women, plaid jackets and separates continue to be popular for the second half of 2025. A cool, vintagey plaid shirt can “take you through to the new season,” says Lynch. “It can be styled with shorts, but then it can also be styled with a pair of wool trousers.” She adds that you can find chic, minimalist options from brands such as the Row or something more exaggerated from a brand such as Willy Chavarria..

Outclass Hazel shadow plaid flannel shirt
Outclass Hazel shadow plaid flannel shirt, $220 through outclass.ca.
Uniqlo flannel checked shirt
Uniqlo flannel checked shirt, $50 through uniqlo.com.
PARIS, FRANCE - JANUARY 24: (EDITORIAL USE ONLY - For Non-Editorial use please seek approval from Fashion House) A model walks the runway during the Willy Chavarria Menswear Fall-Winter 2025/2026 show as part of Paris Fashion Week on January 24, 2025 in Paris, France. (Photo by Estrop/Getty Images)
(Estrop/Getty Images)

Slim-fit jeans

After many seasons of wide-leg pants dominating the catwalks, some designers such as Paul Smith and Miuccia Prada are starting to offer straight and slim-cut jeans in blue and dark denim this fall. Oversized jackets are very much in fashion, and that’s one reason why “we’re seeing that more tailored skinny jean on the bottom, because proportionately that just sort of makes more sense,” says Costigan. Wear yours now with a fitted T-shirt and leather sandals, and later with a chunky knit or oversized blazer.

Levi’s 514 straight fit jeans
Levi’s 514 straight fit jeans, $90 through levi.com.
PARIS, FRANCE - JANUARY 23: (EDITORIAL USE ONLY - For Non-Editorial use please seek approval from Fashion House) A model walks the runway during the System Menswear Fall-Winter 2025/2026 show as part of Paris Fashion Week on January 23, 2025 in Paris, France. (Photo by Peter White/Getty Images)
(Peter White/Getty Images)

Low-profile sneakers

Sneaker enthusiasts are “still super obsessed with low-pro sneakers,” says Lynch. These 1990s-inspired, slightly retro styles have “almost no sole” and are “a complete 180 to the Balenciaga chunky track sneakers from seasons before,” says Lynch. This minimalist, more refined sneaker is equally comfortable and versatile. “You can wear it with a suit and look really smart and go to a really nice restaurant maybe, but you can also wear it with sportswear and it doesn’t feel overdressed,” says Lynch.

Boss leather sneakers
Boss leather sneakers, $250 through ssense.com.
Reebok R400 nylon and suede sneakers
Reebok R400 nylon and suede sneakers, $110 through harryrosen.com.
MILAN, ITALY - JANUARY 19: A model walks the runway during the Prada Ready to Wear Fall/Winter 2025-2026 show as part of the Milan Men Fashion Week on January 19, 2025 in Milan, Italy. (Photo by Victor VIRGILE/Gamma-Rapho via Getty Images)
(Victor Virgile/Getty Images)