Top 5 Date Outfits

Best Date Night Outfits

You’ve finally got a date. He’s cute, smart, funny, and he seems really interested in you. But now, it’s date day and you’re freaking out about what to wear. You’re wishing that you had been born 100 years ago when fashion was boring and it wasn’t difficult to decide on an outfit.

If you thought it would be easier dress for a date in the 1916, you would be surprised. While the dating scene and its rituals have changed over the years, fashion has always held center stage.

Your everyday clothing is an important topic, but there are few times when you care more about what you’re wearing as you do when getting ready for a date. Doesn’t matter where your date is taking you, for women, t-shirts, tanks, and other great basics from District make the perfect building blocks for a stunning date night look. To help you figure out what to wear tonight, let’s learn from old-school daters how they decided on their date night outfits.

Dating is a very personal process. People decide what level of commitment they’re looking for in a relationship and, with a bunch of new, modern ways to define your relationship comes a wide variety of date outfits to match. These days, for women, t-shirts and jeans are just as viable a date outfit as a nice dress – depending on the date, of course.

Racerback Dress

1st Date

A typical first date today often means grabbing a drink at a wine bar or nice restaurant. The atmosphere is romantic, flirty, and all about making a great first impression over the latest mixed drink. What you wear matters because it sets the tone. It tells your date what he can expect from you and shows your personality. You want to look nice, but feel comfortable, too.

Just wearing super casual clothes for a first date, like for  women, t-shirts and daisy dukes, might send the wrong message. Your date may think you’re not interested or that you’re not willing to put in some effort, so we recommend dressing up for the occasion in a classic little black dress. Don’t go overboard though: stick to ballet flats, booties, or low heels to keep it dressy and low-key. Whether you met on a dating app or through mutual friends, the focus of this date should be getting to know each other.

George Armstrong Custer

While you might be freaking out about your first date, remember that back in the day, people didn’t “date,” they “courted.” The first date was already time to decide whether a man and woman would be ready for marriage. What men and women wore on their first date back then, made an important first impression. The wrong outfit on a first date meant more than a bad first date, it could mean zero chance of marriage!

Women’s Mini Racerback Tank

2nd Date

Today, when you head to the movies on a second date, it’s fine to dress down a bit. If you’re still trying to impress, one of the best—and easiest—movie date outfits is a simple combination of your favorite jeans with a cute top. For women, t-shirts, especially those with a flattering, embellished cut can be a great look for a low key second date night.

If you want to be a little dressier, but still relaxed in your theater seat, go for a racerback tank with a simple mini-skirt and low boots. Your family might try and butt in to tell you what to wear, but you don’t have to worry about what they think; because they’re not coming on the date with you!

These days, we’re lucky that your mom isn’t coming on the date. During the 1910s, dates usually took place at home with the entire family. It wasn’t only a young woman or man who needed to think about their date outfit—the entire family did. Imagine the stress involved when four or more people needed to look presentable! For women, t-shirts and other casual clothes we might wear today were definitely unacceptable attire. Instead, women wore conservative long dresses, while men dressed in suits and ties.

Alice Joyce

3rd Date

Girls In Sundresses

When it’s time for you to head out for a daytime date, whether it’s to grab coffee or for a stroll in the park, you want to pull together an ensemble that’s flirty, feminine, and fun. It’s the perfect opportunity to try a relaxed look that shows off your personality. A flowy sundress is always a top-notch, daytime date choice, showcasing a flirtatious mood. If you’re more comfortable in pants, a pair of a capris and a nice blouse create a polished, easy-going look.

No matter which look you choose, be sure to pair it with your favorite sandals and a bright pedicure. A daytime date might be a quick lunch or it might evolve into a longer, spontaneous adventure. Set the tone with an outfit that shows you’re ready for anything.

Women During WWII

4th Date

Today, activity dates are extremely popular. While in the 1940s an activity date might have been a day at the malt shop, make-out hill, or a picnic at the park, these days it’s safe to bet you’re more likely going hiking or to the beach. When prepping for a date like this, it’s important to select an outfit that shows you’re ready for adventure.

Green Distressed Hat

An athleisure outfit will flatter your figure and feel good, while providing the perfect clothing for exploring nature, playing sports, or relaxing in the sunshine.

Of course, when it comes to outdoor looks for women, t-shirts, tanks, and other great basics from District are a good idea. In addition to clothing, we’ve got all the outdoor accessories you need. Whether it’s a cute hat to protect your skin from the sun or a backpack to hold all the water bottles and granola bars you need to fuel a long afternoon on the trail, we’ve got you covered from head to toe.

Womens 1960 Fashion

5th Date

The dating revolution in the 60s brings to mind a current trend: an at home date with Netflix. It has changed the dating scene and brought date night back to the home. When you’re staying in, it’s important to find a look that strikes exactly the right balance between casual and romantic. To keep things flirty, but not overly suggestive, start with basics. Layer your outfit over your favorite pair of leggings and a soft v-neck. We also love leggings with a cute, flowy tunic.

As you get ready for your relaxed night in, you’ll want your beauty look to be as effortlessly sexy as your outfit. Simple makeup, featuring lightly tinted moisturizer, nude lip, and a sexy eye created with a brown eyeshadow stick and mascara works perfectly. Wear your hair loose and wavy or put it up in a chic, simple topknot. Overall, keep it simple with comfortable clothing.

Final Tips

There are as many ways to approach dating as there are outfits to wear on a date. Whether you’re staying in and relaxing, hitting up the hiking trail, or heading out for a fancy dinner, there’s always an outfit that suits the occasion. The flexible styles District carries for women will fit any kind of date, so you can worry less about your date night look and focus more on being yourself.

Here, you’ll find everything to need to create a stunning date look. Our incredibly versatile basics make for great layering. There’s always something in our collection perfect for stylish women. T-shirts, tanks, and sundresses from District will enhance your look effortlessly, and we even have great accessories like hats and backpacks to keep you looking great on an adventure or activity date.

Best of all, District’s great date night clothes aren’t just for women; t-shirts, casual tops, and hoodies for men are all available for their date nights too. Shop at our online store today to get ready for your next night of romance.