First dates can be overwhelming. Whether you’re taking your first official date with a situationship, leaning into a budding romance with a friend, or meeting up with someone from a dating app, there’s a lot of potential for discomfort and awkwardness on a first date.
One of the best ways to feel like your cool and confident self when the time comes to meet someone new is by picking out the perfect outfit. When we wear clothes that feel good on our bodies, we feel good, and we present a great picture to the world around us, including the person we’re meeting for our first date.
That’s why our team at 10PM Curfew is here to share first-date outfit ideas and a closer look at what some of our favorite influencers and content creators are wearing on their first dates.
What Are Some of the Best Outfit Ideas for First Dates?
When it comes to the perfect first date outfit, there are a few things you’ll want to keep in mind. Most importantly, you want to figure out where the date is taking place and what the activity is.
The casual or formal nature of the date is going to have a huge impact on what you wear and how you style your hair and makeup. These are just a few of our favorite first-date outfits for a wide range of date ideas and activities.
Sundresses are a warm-weather staple that will never steer you wrong. They’re effortlessly feminine and can be dressed up or down with your favorite accessories and hairstyle, depending on the occasion. If the date transitions from daytime to nighttime activities, like a boat ride in the afternoon and dinner in the evening, a sundress can be the versatile piece that does it all.
You can find sundresses in a wide range of patterns, lengths, and styles, so it’s easy to put together a look that really feels like your own. Pair your sundress with cute white sneakers, sandals, or heels for comfort or elevation.
If you know you’re headed somewhere fancy for your first date, don’t hold back. Cocktail attire is a lot of fun, and there are many different ways to make cocktail clothes really work for your personality. Cocktail dresses are a way to feel feminine and elegant, and you can dress them up or down, depending on the formality of the event or occasion.
One of the easiest ways to change up the fanciness of your outfit is with shoes, so if you’re aiming for casual, consider classy sandals or swap for high heels for those more special events.
High-Waisted Jeans and Peasant Top
Another versatile option for your first date idea is a pair of high-quality high-waisted jeans paired with a puff-sleeve or peasant top. The right pair of jeans can be elevated and classy, and this can’t-miss duo is appropriate for a wide range of events and activities, so you’ll be covered even if your date doesn’t tell you the plan in advance.
It’s also easy to adjust this look for the weather, with long or short sleeves, and you can accessorize with your favorite jewelry and hair clips for an elegant and adaptable look.
Jeans and a Sweater
The peasant top is perfect for warm summer nights, but what do you wear on your date when it’s chilly outside? Consider swapping out your favorite peasant skirt for an elegant sweater. Depending on how oversized or bulky the sweater is, you may want to wear more form-fitting pants, but a curve-hugging sweater can look really cute with high-waisted jeans.
This is the perfect outfit for a coffee date or picnic at the park, and you can add a touch of elegance with dainty earrings or a minimalist necklace.
If you want to come across as the cool girl, then adding a leather or faux leather jacket to your lineup is the way to go. It can be paired with a wide range of styles, from simple jeans and a t-shirt to your favorite maxi dress.
This is a fun and accessible way to dress for dates during the in-between months and to add a little edge to any outfit. It even looks unique and cool when balanced with feminine styles for a little contrast.
Turtleneck Tank Top and Long Skirt
Another way to get that cool and edgy look is by balancing long and short pieces. Start with your favorite maxi skirt in a color or pattern that is appropriate for the night or event ahead. Then layer it with a turtleneck tank top that leaves the arms bare.
The balance of different lengths and styles can be really cool, and you can even use different textiles to make this outfit stand out. If you’re having a more casual first date, consider pairing this look with your favorite white sneakers or adding in the black heels for seeing a show together. And, of course, one way to really put it all together is with a leather jacket.
Maxi skirts aren’t your only option when it comes to first-date skirts. If you’re just not into pants, or you want to create a style that’s a little more feminine, a mini skirt can be the perfect piece for the job. They look especially cute when paired with pieces of a different size or shape. If your skirt is short and form-fitting, consider an oversized sweater. For loose and flowy miniskirts, a form-fitting tank top is best.
It’s especially important to ask about the activities of the day if you’re going to be wearing a skirt since you want to make sure you can engage in those activities without worry. Adjust your outfit so you feel cool and comfortable on every minute of your first date.
White Button Down
For a more casual date, like coffee at the local café, high-waisted, light-wash jeans and a white button-down top can be a really cool way to go. This look steals inspiration from French girl vibes, which is why it pairs well with minimal makeup and loose hair, but it’s cute, comfortable, and perfect for getting to know each other over an oat milk latte.
You can pair this outfit with white low-top sneakers or woven brown sandals, and you can even swap out the white button-down for one in blue or pink. Make this more cute and casual style really work for your needs and your next date.
Leggings and a Crop Top
If jeans and a white button-down shirt are casual, leggings are very casual. It’s typically not recommended to wear leggings on a first date, but the most important thing is that you feel comfortable throughout the day or night, and these are a good way to achieve that comfort level when you’re nervous.
The important thing to keep in mind when it comes to leggings is that they’re not appropriate for every type of activity and event. After all, you don’t want to walk into a fancy restaurant in your leggings and low-top sneakers. But if you guys are planning to go to the movies together or out to a ball game, leggings can be a good choice. They pair well with crop tops and hoodies for a cozy look. Just make sure you’re not wearing the pair with the holes.
The Bottom Line
Picking out the perfect outfit for a first date doesn’t have to feel scary. What’s important is that you like the outfit and how it makes you feel. If the person you’re meeting likes you for you, well, that’s really what matters most.
That said, you do have lots of different ideas to pick from when it comes to putting together that ideal first date style. It’s useful to account for the event and activity ahead, to make sure you’re dressing appropriately, and that you’ll be comfortable all night long.
Explore different outfit and style ideas, from sun dresses and cocktail dresses to turtleneck tank tops and leather jackets. You may even be able to pull off leggings and crop tops, depending on the formality of the date. And, of course, you can always adjust the style depending on your hair, accessories, and the shoes you wear.
For all your fashion, style, and trend needs, look no further than 10PM Curfew. We’ve got our ear to the ground on the latest looks your favorite creators are putting out, and we’ll help you to complete the perfect styles right at home. Find first-date outfit inspiration and learn about how you can begin working with our team today.