Toronto's Guide to First Dates: Top Spots & Outfit Ideas
Toronto is a city full of charm and endless possibilities when it comes to planning the perfect first date. Whether you're strolling through historic districts, enjoying a sunset picnic, or diving into the city's rich arts and culture scene, there’s no shortage of ways to connect and get to know someone better.
As menswear experts at Carpe Diem Men, we understand that feeling confident in what you wear plays a huge role in making that all-important first impression. That’s why we’ve curated our expert styling advice to ensure you look your best and feel great, no matter where your Toronto adventure takes you.
Here's our guide to some of the city's best first-date spots and first-date outfit ideas for each occasion.
Distillery District: Casual Chic
Photo credit: www.thedistillerydistrict.com/
The Distillery District is rich with history, art, and culinary treats. Take a stroll through the Victorian-era architecture, enjoy a coffee at Balzac’s, or sample craft beer at a local brewery.
A Rustic look would suit Distillery district well
What to Wear: Opt for a smart casual outfit that balances comfort and style. Consider wearing dark-wash jeans that fit well, paired with a crisp, button-down shirt for a clean, polished look. Layer with a lightweight sweater in a neutral color or a light jacket in the cooler seasons for added warmth and style. Complete the outfit with comfortable, stylish leather sneakers or boots for a relaxed vibe.
Art Gallery of Ontario (AGO): Cultured and Refined
Photo credit: https://ago.ca/
The Art Gallery of Ontario (AGO) is a romantic setting to explore stunning artworks and captivating architecture, perfect for sparking meaningful conversations. With free admission for those under 26, it’s an affordable and enriching way to connect with your date over shared artistic experiences.
Wear something comfortable for walking around the exhibition
What to Wear: Choose a polished, relaxed outfit. A pair of tailored chinos in a muted color is a great choice. Pair them with a fine-knit polo shirt for a touch of class and comfort. Add a structured blazer in a complementary shade to complete the overall look. Finish with dress shoes to give a refined touch that’s perfect for a gallery setting.
Snakes and Lattes: Fun and Interactive
Photo credit: https://www.snakesandlattes.com/
Snakes and Lattes is a cozy board game café that creates a fun and relaxed atmosphere, making it easy to break the ice while enjoying some friendly competition. With an extensive selection of games to choose from, you and your date can bond over classic favorites or discover new ones together, all while sipping on delicious coffee and snacks.
Wear something relaxed and polished to enjoy a night of boardgames
What to Wear: Go for a smart-casual look that's comfortable for sitting and playing games. Consider a casual button-up shirt with a fun pattern to keep the vibe light and playful, paired with stretch chinos for easy movement. Stylish, clean sneakers will keep the outfit looking fresh while ensuring comfort throughout your gaming session.
Storm Crow Manor: Themed Fun
Photo Credit: https://www.stormcrow.com/
For a unique experience, visit Storm Crow Manor, a geek-themed restaurant featuring various themed rooms inspired by popular movies and fantasy lore. The fun menu includes creatively named dishes like "D20 Nachos" and "Dragon Slayer Wings," while their imaginative cocktail menu lists playful concoctions like the “Elven Elixir.” It's the perfect place to enjoy delicious food and drinks in an adventurous atmosphere, making it ideal for a fun first date!
Stormcrow is a relaxed setting where your outfit can be more laid back.
What to Wear: Lean into the fun vibes and creative cocktails by opting for a laid-back and casual outfit. Consider pairing dark jeans with a quirky, themed t-shirt that adds a playful touch, though a polo or crewneck sweater will work great too. Complete the look with stylish sneakers for a fun and approachable style that's ready for a night of laughter and good company.
Riverdale Park East: Laid Back and Scenic
One of the most delightful ways to enjoy a first date in Toronto is with a picnic at Riverdale Park East. This expansive park offers stunning views of the downtown skyline and features beautiful green spaces perfect for spreading out a blanket and enjoying a meal together.
Toronto skyline from Riverdale Park, image by Craig White
Bonus tip, if you time your picnic right, you can plan to stay for a breathtaking sunset view across the skyline!
Polo and shorts work well for a casual look that's still stylish for a first date.
What to Wear: For a picnic date, comfort is key while still looking stylish. Go for tailored shorts or chinos in a light color, paired with a breathable linen shirt or a casual polo for a casual, but put-together look. You can keep cool and comfortable while looking great. Complete your outfit with comfortable loafers or stylish sneakers that are easy to walk in as you navigate the park's paths.
Extra Tips: First Date Outfit Ideas
Dress for the Location: Always consider where you’ll be going and dress appropriately. This shows thoughtfulness and respect for your date.
Fit is Key: Ensure your clothes fit well-tailored pieces can enhance your silhouette and boost your confidence.
Accessorize Wisely: A nice watch or simple bracelet can elevate your outfit without being overpowering. Keep accessories subtle yet stylish.
Be Yourself: Choose outfits that reflect your personal style. Authenticity can be more attractive than simply following trends.
Conclusion
At the end of the day, Toronto offers an incredible variety of date spots to help you connect, have fun, and create lasting memories. No matter where your first date takes you, feeling confident and comfortable in your outfit is key to making the right impression.
At Carpe Diem Men, we’re passionate about helping you look your best with expert styling tailored to every occasion. From casual strolls to refined evenings out, we’re here to ensure you’re dressed to impress—because when you feel good, it shows.
Visit Carpe Diem Men at 569 Danforth Ave to experience personalized styling, high-quality menswear, and complimentary in-house alterations with every purchase. As our customer, you’ll enjoy the benefit of one-on-one attention from our expert stylist Eddie, ensuring every piece you wear fits perfectly and reflects your unique style.
Let us help you feel confident and ready for any date.
