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10 Outfits to Wear in a City that Never Sleeps

They say traveling is a gift because it inspires creativity, breaks down cultural barriers, and fuels innovation. Enriching your perspective is one of the most important investments you can make for yourself. Even though pandemic restrictions have loosened, and the world is gradually returning to the norm, globetrotting might not be a viable option for you yet. The good news is that you don’t have to venture far to gain new experiences. Instead, make the best of what is within your city – but in a different way.

We’ve narrowed down the top ten ideas to get you started on what to do, where to go, and of course, what to wear.

1. Play Tourist

A great way to get to know your city is to play tourist yourself. Your favorite spots in town look different while hanging out on the top of a double-decker bus. Rally your friends and ride on the hop-on-hop-off to rediscover your city from a different point of view. You might even want to throw in a theme to make the day extra memorable, like dressing up in 70’s inspired fashion or your favorite action hero.

2. Join a Walking Tour

Spend an afternoon at the Giant Corn Maze in Ormstown, only an hour away from Montreal, for an adventure ideal for the whole family. If you were looking for something more informative, try a guided walking tour like Beyond the Basilica, which goes through Old Montreal, China Town, and the borough of Plateau to learn more about the architecture and influences that make your city. It’s a great way to meet people too. If you’re coming from out of town, don’t forget to grab poutine while in the city, or it’s like you’ve never visited. Have you seen the view from Mount Royal Lookout? It’s breathtaking! Make sure you have super comfy shoes and a stretchy pair of sweats for this activity.

Giant Corn Maze
Beyond the Basilica

3. Shop at Local Markets

Who doesn’t love a flea and street market to get their hands on authentic items, crafts, and spices from around the world? Head over to the market closest to you and let the inspiration begin. You’ll need breathable and comfy attire while bargaining down the vendors. On the other hand, did you know that four boroughs in Montreal will be giving away free plants on a first-come, first-served basis as part of a sustainability initiative? Make a trip out of it with friends and pick up your new house plant to join the circular movement.

Free Plants

4. Explore Nature

Escape the hustle and bustle of the big city and enjoy scenic views of water, mountains, and greenery to realign your energy. Vancouver has some of the best spots to quench your nature craving, with places like Stanely Park offering water views, awesome trails, gorgeous gardens, and Canada’s largest aquarium. Granville Island is another green oasis you don’t want to miss, with lots to do, like restaurants, artisans, craft shops, breweries, and an all-over good time. Vancouver is known for drizzly weather conditions, so don’t forget your water-resistant outerwear or hoodie when visiting these spots.

Stanley Park
Granville Island

5. Visit Urban Spots

You’ll have to dress extra funky and vibrant for this part. The skate scenes across Canada are bursting with diversity, culture, talent, and fun. Each offers unique landscapes and features to allow you to learn street or park-style skateboarding. Skateparks are the perfect place to practice and build your skills if you're a beginner. Learn how to pump on transitions, carve bowls, grind ledges, slide on rails, and so much more. Take it from us; nobody cares that you’re a newbie at the park, either. The skater scene is known for its friendly vibes and good times. Take a few minutes to observe the flow and where skateboarders start their “lines” to join the fun. You’ll get the hang of it eventually. And let’s be honest, this activity requires a cap.

6. Try a New Restaurant

In a city that never sleeps, you don’t want to miss out on the deliciously multi-cultural culinary flavors of Toronto. From hole-in-the-wall joints to luxurious menus, Toronto is every foodie’s dream and the perfect place to visit on a short staycation. With brand new hotels, restaurants, and a revived live-performance scene, dress to meet the sparkling vibe of this city. Go for matching tracksuits in sport-chic feels or monochrome ensembles to achieve effortless sophistication.

7. Visit an Obstacle Course

Plan a workout and a vacation at the same time. Obstacle courses offer fun, engagement, and team bonding activities for the whole family or your friend group. From races to mud and aquatic tracks, Canada has some of the best kiddie and adult obstacle courses to challenge yourself and endurance train. For a less rigorous workout and more bonding time, you can always head to the closest escape room available in your city to solve mysterious crimes and unlock hidden treasures. Choose sweat-wicking fabrics and jerseys to compete like a pro.

8. Music

The epitome of culture, music festivals blend sound, fashion, dance, and even camping to bring people from all over the world together. There are tons of fantastic festivals and concerts happening around our cities, don’t forget to dress for both style and comfort when attending these events.

9. Take Pictures

Disclaimer: Your TikTok will love this. Create an amazing photo or video mashup of urban landmarks and wildlife around your city. Think CN Tower, Orange Julep, or the Vancouver Seawall. If you’re in NYC, check out the new 750-mile bicycle path on the Greenway overpass. Make an event out of it by coordinating colors and ‘fits with your friends or family. Don’t forget to tag #Bench and #Lovemyhood for a chance to be featured on our website and socials.

Bench calls it “Lovemyhood” because nurturing local communities impacts the world.

CN Tower

Vancouver Seawall

10. Support Orange

Learn about the origins of Orange T-shirt Day and share the story with friends and family.

The orange shirt symbolizes the stripping of culture, freedom, and self-esteem experienced by indigenous children over generations. Learn more about Phyllis Webstad’s story and how her struggle inspired Orange Shirt Day in the link.

National Day for Truth and Reconciliation

Orange Shirt Day

Phyllis Webstad's Story

Seek adventure and find creativity in the mundane to shake up your perspective. You are your greatest investment, so treat yourself to a good time while you’re at it. And take it from Bench, people who wear athleisure have more fun.

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