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If you’re wondering what to wear to Toronto’s most fashionable summer event—The Greenwood Stakes 2025—we’ve got the ultimate men’s summer style guide to keep you cool, sharp, and event-ready from daylight drinks to late-night bets.

When it comes to men’s summer fashion, especially for high-style occasions like a racetrack event, it’s not about being flashy—it’s about nailing the fit, fabric, and finishing touches. This year’s race day blazers are all about lightweight construction, breathable materials, and standout colour combinations. From tailored jersey blazers to textured polos and soft stretch pants, these are the essential summer event outfits for men who want to stand out without sweating it out.

Whether you're posted up at the Turf Lounge or trackside near the Winner’s Circle, Gotstyle’s curated looks for the Greenwood Stakes will help you show up with purpose and polish.

Look 1: A Soft Pink-Olive Contrast That Hits Different

SHOP THE LOOK
 Shop the Soft Pink Jerry Key Blazer
 Shop the Army-Green Polo

DJ Darius is spinning at this year’s Greenwood Stakes in Toronto, and his outfit is the blueprint for what modern men’s race day fashion should look like—tailored but easy, sharp but a little unexpected.

He's stepping out in a soft pink double-breasted blazer by Jerry Key—crafted with precision tailoring but built with movement in mind. The pastel pink adds a soft, fashion-forward tone that works brilliantly in natural light and looks killer in photos.

Layered underneath is an army-green cotton stretch polo—a subtle yet confident contrast. The olive-green stretch trousers complete the colour story, giving the outfit earth-tone harmony while offering comfort and flexibility.

This look isn’t just race-ready—it’s effortless cool meets luxury menswear. If you’re aiming for that “I didn’t try too hard, but still crushed it” vibe at this year’s racetrack party, take notes from Darius.

Why It Works for Summer Events

• Lightweight blazer fabric stays breathable in the sun
• Color contrast makes a style-forward statement
• Stretch trousers allow comfort while walking the grounds or lounging at a VIP booth

Looking for men’s outfit inspiration for summer outdoor events? This is the one to bookmark.

Look 2: Summer Neutrals That Actually Work

SHOP THE LOOK
Shop the White Jersey Blazer by Distretto12
 Shop the Soft Blue Knit Polo by SAND

If bold colour combos aren’t your vibe, Andre’s look proves neutral tones can make just as strong a statement—especially at a style-centric event like the Greenwood Stakes.

His white jersey blazer from Distretto12 is a summer essential. It’s breathable, wrinkle-resistant, and features functional patch pockets—perfect for stashing sunglasses, betting slips, or your phone for those inevitable photo ops. The texture keeps the piece interesting, while the clean silhouette elevates the overall fit.Beneath the blazer, he’s layered a sky-blue knit polo from SAND Copenhagen—a nod to vintage styling with its ribbed texture and crisp collar. This soft blue adds dimension without overpowering the look.

The tailored cotton trousers from Jerry Key provide a streamlined finish, creating a sharp silhouette that works from brunch to cocktail hour. If you’re attending summer events where smart-casual is key, this neutral ensemble will have you dressed to impress.

Why It Works for Greenwood Stakes 2025

• White blazers reflect heat and stand out in the crowd
• Textured polos add visual interest and a touch of retro charm
• Tapered pants strike the balance between formal and relaxed

This look is ideal for men looking for breathable summer suiting options or stylish racetrack outfits in Toronto that go beyond basic navy and grey.

Join Us at the 2025 Greenwood Stakes – Toronto’s Most Stylish Race Day

🎟️ Pre-Sale Tickets: Only $35 for Gotstyle Clients
 📍 Location: Woodbine Racetrack, Toronto
 📅 Date: Saturday, June 21st, 2025
 👉 Grab Your Pre-Sale Tickets Now

The Greenwood Stakes is more than just a horse race—it’s Toronto’s most fashionable summer event. Hosted at the iconic Woodbine Racetrack, this day brings together the best in men’s style, art, music, cocktails, and fashion-forward experiences.

From fashion influencers to industry insiders and creatives, the crowd is always dressed to impress. Whether you're watching the races or hitting up the Turf Lounge, this is your opportunity to make a sartorial statement.

As a Gotstyle client, you get exclusive early access to $35 tickets (regularly $65). Gather your crew, claim your spot, and get ready to step into the summer style scene of the year.

Style Stakes Contest: $1000 Gotstyle Gift Card Up for Grabs

The annual Style Stakes Contest is back and bigger than ever. Come dressed for the spotlight—the best-dressed attendee will win a $1000 Gotstyle Gift Card.

We’re also setting up a photo booth to capture all the show-stopping fits throughout the day. So, whether you're rocking a floral dinner jacket, a monochrome linen look, or a pastel blazer with Cuban heels—make sure you’re camera-ready.

📸 Get noticed. Get photographed. And maybe even get crowned best dressed in Toronto.

Need a Race Day Look? Book Your Private Styling Session at Gotstyle

Whether your vibe is Trackside Glamour, Old Money Cool, or Rooftop Cocktail-Ready, our expert stylists will help you build a full look from blazer to brogue.

With a one-on-one appointment at Gotstyle’s Toronto menswear boutique, we’ll ensure your outfit fits flawlessly and feels event-appropriate without looking like everyone else.

👉 Book Your Private Styling Appointment Now

Our stylists specialize in:

• Blazer and trouser coordination for event dressing
• Breathable summer fabrics like jersey, seersucker, and cotton-linen blends
• Statement footwear to anchor your look
• Accessories like pocket squares, shades, and hats to seal the deal

Let us do the hard part—you just show up and show out.

Greenwood Stakes x Gotstyle – All the Details You Need

📍 Venue: Woodbine Racetrack, Toronto
 📅 Date: Saturday, June 21st, 2025
 🎟️ Tickets: $35 Pre-Sale for Gotstyle Clients
 👔 Full Race Day Styling Appointments Available at Gotstyle
 📸 Style Stakes Contest + Photo Booth
 🎶 Live Music, Cocktails, Fashion, Art, and Games of Chance

Follow @greenwoodstakes on Instagram for sneak peeks, outfit inspiration, and all the behind-the-scenes hype leading up to race day.

Why Gotstyle Is Your Go-To for Summer Event Menswear in Toronto

At Gotstyle, we specialize in helping men dress better to do better. From tailored pieces to statement summer blazers, we’ve got the tools, the team, and the taste to make sure you show up in style—whether it’s a racetrack, rooftop, or wedding reception.

Our selection of event-ready outfits for men in Toronto includes brands like:

• Jerry Key
• SAND Copenhagen
• Distretto12
• Benson
• ..and many more

Need help putting your race day wardrobe together? Stop by the store or book your appointment and let us help you win best dressed at the Greenwood Stakes 2025.

GOTSTYLE
Dress Better. Do Better.