What Should You Wear on a First Date – 9 Outfit Ideas

Introduction

When it comes to getting dressed for a first date, it can be tough to know what to wear. On one hand, you want to make a good impression and look your best. On the other hand, you don’t want to come across as being too try-hard or looking like you’re trying too hard.

So, what’s a person to do?

Never fear! We’re here to help with 9 different outfit ideas for every kind of the first date. Whether you’re going for coffee, drinks, dinner, or something in between, we’ve got you covered.

Just remember: no matter what you wear, make sure you feel comfortable and confident in your own skin. That’s the most important thing of all!

Now, let’s get to the good stuff. Here are 9 first-date outfit ideas to help you make a great impression.

1. For a Casual First Date: Jeans and a Cute Top

This is a classic go-to for a reason: it’s both comfortable and stylish. Plus, it gives you the opportunity to show off your personal style. Opt for a pair of well-fitting jeans in a dark wash (no holes or rips, please!) and pair them with a cute top. A printed blouse or something with feminine details like ruffles or lace is always nice. Complete the look with some simple jewelry and shoes that are both comfortable and stylish—preferably a pair of low boots or ballet flats.

2. For a First Date Outdoors: A Cute Skirt and Cozy Sweater

If you’re going on a date that involves being outdoors, such as hiking or attending a sporting event, then you’ll want to dress in layers. Start with something comfortable like leggings or skinny jeans, and then layer a cozy sweater over top. Top it all off with your favorite skirt or dress—we love pieces that are slightly fitted at the waist for this look. Finish the outfit with cute ankle booties and some minimal jewelry, and you’re good to go!

3. For a Fancy First Date: A Little Black Dress and Heels

Fancy First Date
If you’re going on a first date to a fancy restaurant or some other upscale venue, then you’ll obviously want to step up your style game. The perfect outfit for this is a classic little black dress paired with elegant heels. Add in some sparkly jewelry and understated makeup, and you’ll look like a million bucks—without having to spend too much money!

4. For an Outdoor First Date: Casual Dress and Sneakers

Just because it’s an outdoor first date doesn’t mean you have to sacrifice style for comfort. A casual dress that hits just above the knee is both cute and comfortable, especially when paired with stylish sneakers or low boots. Complete the look with minimal jewelry—a dainty necklace and simple stud earrings should do the trick.

5. For a Coffee First Date: Skinny Jeans and a Blazer

A coffee date is a perfect opportunity to dress up your favorite pair of jeans. We love skinny jeans for this look, but any well-fitting pair will do. Pair them with a cute blouse or top, and then layer on a tailored blazer for an extra touch of style. Complete the outfit with heeled booties or pumps and some understated jewelry, and you’re good to go!

6. For a Brunch First Date: Midi Dress and Sandals

Brunch First Date
If you’re going on a first date for brunch, then you’ll want to dress in something both comfortable and chic. A midi dress is a perfect option, especially when paired with some cute sandals or flats. Add in a statement necklace and earrings for a touch of glamour, and you’re all set!

7. For a Drinks First Date: Little Black Dress and Heels

The first date for drinks is the perfect opportunity to dress up your favorite little black dress! Pair it with your highest heels and add in some sparkly jewelry to really stand out. Red lips are always sexy, so don’t be afraid to go bold with your makeup.

8. For a Dinner First Date: Jeans and a Blouse

For a dinner first date, you’ll want to dress somewhere between casual and fancy. A great way to do this is by pairing dark-wash jeans with a blouse or top that has some stylish details. We love blouses with ruffles or lace for this look. Complete the outfit with heeled booties or pumps and some understated jewelry, and you’re good to go!

9. For a Movie First Date: Jeans and a Cute Top

Movie First Date
A movie first date is a perfect opportunity to dress comfortably without looking too casual. We love the classic jeans and cute top combo for this—just make sure your top is something slightly more special than your average tee. A printed blouse or something with feminine details like ruffles or lace is always nice. Complete the look with low boots or ballet flats and some simple jewelry, and you’re all set!

Conclusion

Whether you’re headed out for a casual coffee date or getting dressed up for a fancy first date, you want to look your best. With these nine outfit ideas for every kind of date, you’ll have the perfect look no matter what!

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