What To Wear On A First Date: 27 Best Outfit Ideas

10 mins read
Well organized wardrobe
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The first date outfit is a very important thing to get right, but it’s also intimidating! What you wear to meet your date for the first time can have a big impact on how things go. Here are some styling tips and ideas for what to wear on a first date. Find out what different outfits and styles you can attempt, for making a great impression!

27 Stunning Outfit Ideas And Styling Tips

Whether you’re going on a blind date or meeting someone for the first time after chatting online, nailing the perfect first date outfit is key to making a good impression.

1. A Fitted Blazer With A Statement Necklace

What to wear on a first date: woman in blazer
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A fitted blazer with a statement necklace is the perfect fashion-forward outfit for a first date. It shows that you are classy and modern, but also shows that you are fun and approachable. The key to pulling off this look is to make sure that the blazer fits well and that the necklace makes a statement without being too over-the-top.

2. Sundress With Sneakers

Smiling woman in sundress, caressing dog
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Sneakers with a sundress are great for daytime dates. The key to making this work is to keep the sundress simple and the sneakers clean and classic.

To start, pick out a cute sundress in a solid color or with a simple print. A sleeveless style or one with thin straps will keep you cool and relaxed in summer. Then, choose a pair of white sneakers to complete the outfit. Don’t forget to carry a cardigan or light jacket in case it gets cold later.

3. Midi Dress with Strappy Sandals

There are few things as chic and effortless as a midi dress paired with strappy sandals. This is a foolproof first-date outfit that will make you look cute and appealing. To keep the look from feeling too formal, choose a dress in a lightweight fabric and pair it with sandals. Then just add some simple jewelry, and you’re ready to go!

4. High-Waisted Jeans with A Crop Top and Blazer

Fashionably dressed woman in blazer and crop top
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If you are looking for a casual first date outfit, then a crop top with high-waisted jeans is always a good idea. You can never go wrong with denim, and the crop top will show off just enough skin to be flirty without being too revealing. Throw on a blazer to give the outfit some structure, and voila! You’re ready for your first date.

5. Leather Pants with One Shoulder Top

One-shoulder tops are both flirty and fun, while leather pants add a touch of edge. Put both together, and you’ve got a first-date outfit that’s sure to turn heads. To get the look, start with a pair of black leather pants. Look for ones that are fitted but not too tight, and that hit at the ankle. Then, add a one-shoulder top in a bold color. Finish the look with black heels and earrings, and you’re good to go on your date!

6. White Sleeveless Blouse with Printed Skirt for Evening Date

Woman in white blouse and printed skirt
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If you’re searching for a smart and elegant outfit to wear on a first date, you can’t go wrong with a white blouse and printed skirt. This classic combo is ideal for an evening date and can be dressed up or down based on the occasion. For a more casual look, pair your blouse and skirt with flats or sandals. If you’re dressing up for a nicer restaurant or bar, opt for heels and statement jewelry. You can style it however you want, this outfit will make a good first impression.

7. A Simple A-Line Dress with Bold Heels

Shallow focus photo of Woman in white dress
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A simple dress is perfect for a first date outfit. Choose a dress in a solid color for a classic and elegant look. Black, white, and navy are all great options. You can dress it up with bold heels and a statement necklace for evening dates, or keep it simple with a pair of high heels and understated jewelry. Just make sure you feel confident in your own skin.

8. Matching Top and Skirt Set

A matching set makes it easier to plan a first date outfit, plus it is trending. A matching top and skirt set is a great option for a daytime date. Opt for a playful print or a bold color to stand out from the crowd. Keep the rest of your look simple with nude heels and understated jewelry.

9. Midi Skirt with Casual T-Shirt or Tank Top

A midi skirt with a casual t-shirt or tank top is the perfect combination. The skirt will show that you put in some effort, but the relaxed top will keep things from feeling too serious. You can style it with a pair of strappy sandals or wedges. This outfit is comfortable enough that you’ll be able to relax and enjoy yourself on your date.

10. Skinny Jeans with Oversized Sweater

One of the best first-date outfit ideas is to pair skinny jeans with an oversize sweater and scarf. This look is both fashionable and comfortable, which is ideal for a casual date. To style this look, start by selecting skinny jeans in a dark color. Then, pair them with an oversize sweater in a light shade, like white or gray. You can also add a scarf to complete the look. Go with a pair of comfortable flats or boots for this outfit.

11. Wear Satin Dress

A dinner date is a perfect opportunity to break out your best satin dress. Whether you choose a slip dress or a more formal option, make sure your dress is well-fitting and super flattering. To style your satin dress for a date night, pair it with heels and a clutch for a classic look. You can even add some glimmer with jewelry or bold lip color.

12. Go for A Shirt Dress

When it comes to first-date outfit ideas, a shirt dress is always a good choice. It’s comfy, stylish, and easy to wear. And, it can also be dressed up or down based on where you are going for your date!

If you’re going for a more casual daytime date, try pairing your shirt dress with flats or sandals. For a more classy look, add heels and statement jewelry. And don’t fail to accessorize with a cute clutch or handbag!

13. Styling Pleated Skirt with T-Shirt

Pleated skirts are both stylish and flattering. To style a pleated skirt, start by choosing the right top. A fitted t-shirt or tank will balance out the fullness of the skirt and show off your figure. Next, add some fun accessories to give your look some personality. A statement necklace or earrings will dress up the outfit, while a printed scarf or belt can add some visual interest. Finally, don’t forget to pick the right shoes.

14. Distressed Jeans with An Off-The-Shoulder Top

Outfit planning for your first date can be difficult. You want to look your best, but you also don’t want to come off like you’re making too much effort. One way to strike the perfect balance is to wear a pair of distressed jeans with an off-the-shoulder top. This outfit is casual enough that it won’t make you look like you’re trying too hard, but it’s also stylish. Plus, it’s the perfect outfit for a summer date.

15. Leather Jacket with A Short Dress

Woman in black leather jacket
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A leather jacket with a dress is a great way to add a bit of edge to your outfit. It’s also an amazing way to stay warm on a cold day. Start with a fitted dress. A fitted dress will help to create a slimming silhouette. And then add a leather jacket.

16. White Dress with Denim Jacket

You can take the classic denim jacket and wear it with a white short dress to create a pleasing look. To style this look, simply pair your denim jacket with a white mini dress and add some playful accessories like your favorite pair of hoop earrings and sandals. If you want to switch up the feel of this outfit, try swapping out the denim jacket for a black leather moto jacket.

17. Ankle Boots with Mini Skirt or Dress

Woman lifting left foot in ankle boot
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One of the finest options for a first date outfit is a mini skirt or dress paired with ankle boots. This will make you look stylish and cute. To style this look, ensure that your skirt has the right length – you don’t want it to be very short or very long. Pair your skirt or dress with a pair of heeled ankle boots in a complementary color. If you’re wearing a black mini-skirt, for example, try pairing it with brown or tan boots.

18. Wide Leg Pants with Cropped Blouse

Wide-leg pants are a great pick for a first-date outfit. They are comfortable and trendy. To style them, pair them with a cropped blouse or top. This will show off your waist and create a balanced look.

19. Block Heels with A-Line Dress

Block heels are a wonderful choice for a first-date outfit, especially when paired with an A-line dress. Not only do they add a touch of sophistication to your look, but they also help to elongate your silhouette and make you look taller. Plus, they’re comfortable enough to wear all night long, so you can focus on having a good time.

20. An Off Shoulder Dress

An off-shoulder dress is a perfect choice for a dinner date. It’s elegant and stylish, but still shows a little bit of skin. To make sure you look your best, opt for a dress that fits well and flatters your figure. For a dinner date, you’ll want to choose a dress that’s slightly more formal than what you would wear for a casual outing. Consider pairing your off-shoulder dress with heels and simple jewelry for a polished look.

21. Sweater with Skirt

Woman in sweater and skirt
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A sweater and skirt combo is always a good choice for winter weather. Opt for a fitted sweater in a neutral color like black, white, or gray. This will look good on any body type and skin tone. Pair it with a printed skirt in a midi length for an elegant yet fun look. To keep things from looking too heavy, try pairing your ensemble with nude heels or ankle boots.

22. Wear Lace Camisole with Jeans

Lace camisoles are feminine and flirty, but still casual enough to not look like you’re trying too hard. Pairing a lace camisole with jeans is the perfect way to strike the balance between dressy and casual. Just make sure your camisole isn’t too sheer or see-through.

23. Wear A Floral Dress

For a daytime park date, go for a flowy floral dress. The print will add some personality to your look, and the loose silhouette will keep you comfortable as you walk and talk. Wear it with sneakers or sandals, and you’re good to go.

24. Frilly Dress with Sandals

If you want to dress up for your first date but still keep it casual, a frilly dress with sandals is the perfect outfit. A pretty sundress or maxi dress will show that you’re taking the date seriously, but you’re still relaxed and comfortable. And since sandals are always appropriate for summer weather, they’ll keep your feet cool and comfortable all night long. And don’t forget to accessorize! A statement necklace or earrings will be perfect to add some sparkle to your look.

25. Silk Cami with Shorts

If you’re confused about what to wear on a first date, jeans shorts with a silk cami is always a good choice.

Jeans shorts are comfortable and casual, but can still be stylish. Style them with a silk cami for a touch of classiness. Silk camisoles are versatile and can be dressed up or down. They’re also light and comfortable, making them perfect for the summer season. This outfit is perfect for a first date because it shows that you’re put together without being too formal.

26. Experiment with A Jumpsuit

There are few fashion items as versatile and stylish as a jumpsuit, which is why we think it’s the perfect choice for a first-date outfit. Go for a slim-fitting or tailored jumpsuit in a flattering color or print. Avoid anything too baggy or clingy. Pair your jumpsuit with low-heeled mules or sandals. Heels can be tricky to walk in, so stick to something comfortable and easy to walk in. If it’s cold, layer your jumpsuit with a cardigan or jacket.

27. Opt for Red or Black Color Clothes

Woman in red dress
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While there’s no hard rule about what to wear on a first date, there are certain colors that tend to be more appealing than others. If you’re confused about what to wear, opt for something in red or black. These colors are often seen as hot and classy, and they can make you look your best.

Remember, the most important thing is to be comfortable and enjoy the date. It doesn’t really matter what color you wear, as long as you’re comfortable with what you have chosen.

Outfits to Avoid on First Date

When it comes to what to wear on a first date, there are certain outfits that you should avoid. Wearing something too revealing, for example, can send the wrong message and make you feel uncomfortable.

  • Don’t wear anything too casual. First dates are usually pretty formal affairs, so jeans and a t-shirt probably won’t cut it. Rather, opt for something a little more dressed up, like slacks and a button-down shirt or a gown.
  • Avoid wearing anything overly flashy or attention-seeking. You want your date to concentrate on getting to know you, not on how you are dressed. Save the sequins and flashy jewelry for another time.
  • Avoid wearing gym clothes or track pants. There’s nothing wrong with being comfortable on a first date, but there’s a fine line between comfort and looking like you just rolled out of bed. Gym clothes and track pants may be comfortable, but they’re also casual to the point of being lazy. If you want to make a good impression, it’s important to dress like you care about your appearance. That doesn’t mean you need to break out the stilettos and designer duds, but you should at least put on some clean jeans and a cute top.
  • And finally, don’t wear anything that makes you feel uneasy. If you’re uncomfortable with what you’re wearing, your date will notice. Stick to clothes that make you feel confident and good about yourself – you’ll be sure to impress your date in the process!

Final Note

First dates can be nerve-wracking, but there’s no need to stress about what to wear on a first date. Just keep it simple and stylish, and you’ll definitely make a great impression. Don’t forget that, the important thing is to feel comfortable in your own skin. With the right outfit, you’ll be able to project confidence and show your date that you’re someone worth getting to know. From this list, you can mix and match pieces to create the perfect look of your own personal style.

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Khushi Chauhan

I'm currently persuing my b.tech degree in computer engineering. I am passionate for writing. Being a content writer interests me because I have keen attention to detail and thrive in a fast-paced environment.

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