A casual date night is an important ritual for couples to maintain, even as life gets busy. Regular one-on-one time helps to reestablish the connection with your partnerโand you donโt always have to roll out the red carpet. Carving out quality time with your loved one can be as simple as pizza night or backyard picnic.
For any date, itโs important to be comfortable so you can focus on getting in some quality time instead of constantly adjusting your clothes or footwear. Plus, heels arenโt great for your health. Research has shown that high-heel-related injuries doubled between 2002 and 2012. In addition, more than 50 percent of women experienced foot pain due to high heels according to a survey. With that said, there are plenty of stylish flat options that will help elevate your date night outfit from basic to elegant, while significantly decreasing your chance of discomfort. Stylish and comfortable, a pair of Rothyโs might just be your perfect match.
Wondering what to wear on a casual date? Here are some of our favorite casual date ideas.

1. Scenic Night Stroll
If you can plan out a stroll at night, a walking date is one of the best activities you can enjoy with your loved one. Take your time while youโre walking and enjoy your natural surroundings. Maybe even consider bringing along a mug of something warm like hot chocolate or mulled wine if itโs chilly out. And remember, if itโs cold, plan accordingly by wearing a warm winter date night outfit.
What youโll need:
- Flashlight
- Reusable water bottle
- Lightweight towel
- Granola bars or other snacks
Outfit idea:
- Leggings, long tunic shirt, a zip-up fitted athletic jacket.
Rothyโs:
- The Sneaker in Sand will keep you comfortable and ready to take on anything in your way.

2. Beach Bonfire
The calming sound of the waves and the beauty of the beach helps make your casual date night fun and relaxing. Keep the fire going long into the night, use a stargazing app to find interesting constellations, or simply lounge by the beach and enjoy each otherโs company. When youโre choosing your outfit to wear with flats at the beach, donโt forget to bring layers so you stay toasty as the sun goes down.
What youโll need:
- Wood
- Sโmores materials
- Towel or picnic blanket
Outfit idea:
- Dark skinny jeans
- Loose blouse
- Medium-weight sweater
Rothyโs:
- The Flat in Cheetah provides wash-and-wear durability so you can sport them to the beach again and again.

3. Attend a Beer or Wine Festival
Do you and your partner like a cold one or a glass of red on the weekend? If thatโs the case, thereโs no better place to bond than a craft beer or wine festival. After you get home, you can talk about which beverages were your favorite or follow it up with dinner. Casual date night looks should be able to easily transition from day to night, so keep that in mind as you plan out your clothes.
What youโll need:
- Pretzel necklace
- Designated driver
- Festival tickets
Outfit idea:
- A bright sundress
- Sunhat
- Vegan leather jacket
Rothyโs:
- The Point in Lazuli is the perfect bright-colored flat to make your festival experience more comfortable than ever.

4. Nighttime Picnic at the Park
Grab an electric lantern for mood lighting, a big picnic blanket, a bottle of your favorite wine, and a cheese and meat plate. Pick somewhere with a view so you can relax and enjoy the sights and sounds of quieter cityscape or countryside.
What youโll need:
- Picnic basket
- Cheese and meat tray
- Red wine
- Reusable cups
- Lantern
Outfit idea:
- Jeans
- Sweater
- Light jacket
Rothyโs:
- The Chelsea in Fawn will keep your feet happy as you traipse through the park on the way to your picnic rendezvous.

5. Home Movie Night
Throw a themed movie night based on the movies you and your partner love. Fans of horror? Make your way through famous 80s B-horror movies. Love documentaries? Learn something new with your partner. Or if you arenโt sure what to pick, go for the classics with romantic comedies like When Harry Met Sally, 500 Days of Summer, Amelie, and Say Anything.
What youโll need:
- Popcorn
- Movies or Netflix
- Lots of blankets
Outfit idea:
- Jeans
- T-shirt
- Athleisure sweatshirt
Rothyโs:
- The Loafer in Navy will keep your feet comfy throughout your at-home date night.

6. Go to a Museum or Attraction
Go to a museum that is tailored to you and your partnerโs interests. Are both you and your partner fascinated by aviation? Go to an aerospace museum. Do both of you have a love for strange history? Visit a place like the Winchester Mystery House.
What youโll need:
- Museum passes
- Instant-film camera
Outfit idea:
- Solid jumpsuit
- Bright clutch
Rothyโs:
- The Point in Big Cat will ensure youโre focused on absorbing interesting information and not on your feet

7. Go to a Farmerโs Market
A nighttime farmerโs market is the perfect place to bond over fresh produce, samples, and a delicious variety of delectable offerings. Buy some fresh flowers, try something new like an exotic fruit, and donโt forget to get some artisan coffee to fuel your wanderings.
What youโll need:
- Reusable grocery bags
- Metal straw
Outfit idea:
- Jeans
- Long-line cardigan
- Lightweight sweater
Rothyโs:
- The Loafer in Mocha Spot will add a pop of fun to your date night outfit.

8. Cook at Home Together
Instead of relying on a restaurant to provide your food, itโs time to turn the tables and do it yourself. Decide how you want to divide up the labor. For example, someone can be in charge of the appetizer and dessert while the other takes care of creating the craft cocktail and the entree. Or, alternatively, you can turn it into a Chopped-style competition if you both love cooking. The best part is that at the end, you both win.
What youโll need:
- A recipe book
- Apron
Outfit idea:
- Skinny jeans
- Comfy blouse
Rothyโs:
- The Flat in Scooter Red adds some unexpected flavor to your home-cooked recipe.

9. Go Camping
Even if itโs just for one night, escaping for an intimate night away in nature can bring you and your partner closer together. What better way to end the night than sitting with each other around the campfire eating sโmores and star gazing?
What youโll need:
- Tent
- Sleeping bag
- Sโmores
- Matches
Outfit idea:
- Jeans
- Button-up flannel
- Woolen leg warmers
Rothyโs:
- Get in touch with nature with The Chelsea in Wildcat.

10. Take a Class Together
There are tons of classes you can take together. You can take a cooking class to bring your traditional Sunday night dinners to the next level, or take a wine and painting class for an introductory approach to art.
What youโll need:
- Groupon or Meetup class
Outfit idea:
- Casual date night dress
- Watch or bracelet
Rothyโs:
- The Point in Black Solid is the solid staple you didnโt know you needed.
Date Night Ideas and Outfits to Rekindle Your Relationship
Even if youโve been with your partner for ten years, going on dates never loses its importance. You may think that because you live together or see each other that there's plenty of one-on-one time. But if you live a busy life with jobs and a family, it may be hard to fit in some alone time. With a little effort and planningโand the right casual outfits for date nightโyouโll be on your way to reconnecting with your significant other.