Best Outfit Ideas on What to Wear on Your First Date
First dates are tricky. They’re a chance to meet someone new, but they require you to be your best self and show confidence. As we all know, first dates can be nerve-racking and a daunting experience, especially when deciding what to wear.
Experienced daters know that the right outfit choice is essential in creating an impression of confidence and style. Crafting an appropriate ensemble requires planning; selecting versatile pieces with flair will captivate your date while still expressing yourself authentically.
Picking essential items that reflect your personality while demonstrating sophistication will set you apart from the crowd. Learn how to choose and style your first date outfits that can work well with ease, polish, and style. Let’s get ready to dazzle! Keep scrolling!
1. Jeans and a Cute Top
An excellent option for your first date is to pair a pair of jeans with a cute top. Jeans are always comfortable, and you can always go right with them. Make sure you choose jeans that flatter your figure and tops that complement them. You can go for a dressier top like a blouse or a shirt, or a more casual one like a t-shirt. A great way to finish this look is to accessorize with jewelry, a belt, and shoes. With jeans and a cute top, you’ll look stylish and comfortable no matter where your date takes you.
Style Tip– If you want to go all out with your outfit, try pairing a cute top with some fun accessories (sunglasses, scarves) that complement each other well!
2. A Wrap Dress
A wrap dress is a fantastic option for meet-ups. It’s versatile and stylish, can be worn with a belt or without, and looks good on anyone! You can find wrap dresses in different fabrics and styles and one that best suits your body type and personal style. Wrap dresses come in long and short lengths so that you can choose the most appropriate for the occasion. If you want to wear heels with this dress on a date, go for it! But if you’re feeling more casual and want to break out into an old-school sneaker situation, no problem—a pair of sneakers will work just as well.
Style Tip– Accessorize with a belt, subtle jewelry such as a chain necklace, gold studs, or a clutch to complete the look.
3. A Flowy Skirt
Skirts are a great way to flaunt your legs and are easier to move in than pants. Choose one that falls above the knee and below the waist so it doesn’t ride up when you walk or sit down. A flowy skirt is a perfect way to look feminine and stylish for your date night.
Choose a color you feel comfortable in, but avoid anything too tight or too short. Whether you choose a midi or maxi length, this outfit option will make you feel confident and beautiful. You can dress it up with a blouse or dress it down with a T-shirt; either way, you’ll be sure to make an impression.
Style Tip– Pair it with a blazer or statement jacket to keep warm, and remember to accessorize with jewelry, a crossbody purse, and your favorite heels.
4. A Sheath Dress
Sheath dresses can be worn in almost any situation, from going out after work to dinner with friends to a fancy wedding. It’s stylish, sexy, and has enough drama to make you stand out without being too flashy. Sheath dresses come in all styles and colors—you’ll find everything from floral prints to neutral hues! They’re also flattering on most body types (even those curvier than average), so if you have an hourglass shape or other figure concerns, this style might be right up your alley!
Sheath dresses are available in various fabrics, ranging from lightweight cotton to luxurious silk, so you’ll be sure to find one that works for your date night look. Choose one that accentuates your curves and showcases your best features, such as a halter neckline or off-the-shoulder cut.
Style It Up – This classic look is versatile so that it can be dressed up with outer layers, a statement belt, an elegant necklace or pearls, and a pair of heels.
5. A Frilly Dress and Sneakers
If you’re looking for a playful but chic look, a frilly dress paired with sneakers is the perfect option for any date. The dress will give off a girly and fun vibe, while the sneakers will keep it casual and comfortable. For this look, opt for a pastel-colored or floral-print dress, and pair it with white or black sneakers. If you’re feeling frisky, sneakers are the perfect finishing touch. However, if you’re going for a casual date, make sure they match your dress! Mixing styles will help add interest to your look and keep things interesting. Embrace your inner boldness and mix and match different pieces together!
Style Tip– Add simple accessories such as a bracelet or small necklace, and you’ll be ready to hit the town with your special someone.
6. A Jumpsuit and Heels
Opt for a jumpsuit and heels to achieve comfort, style, and perfect balance. Jumpsuits are elegant and easy to wear and choose one with a waist-cinching belt to create an ultra-flattering look. For example, if you’re going out for dinner at an upscale restaurant, then wearing heels on your date would be appropriate because that’s what most people do when they go out in public. But whatever happens during those moments of relaxation between getting ready and leaving home should always involve high heels!
Style Tip– The key to this outfit’s success is ensuring your jumpsuit fits properly. Add a pair of statement heels in metallic hues.
7. A Printed Dress with Mules
A printed dress with mules is perfect for a chic and modern look. Not only does this outfit make a statement, but it also adds a touch of femininity to your look. You can pull off this look by choosing the right patterned dress – subtle enough to be noticed but not overpowering. You can wear a floral or geometric print dress with mules, creating an elegant and feminine look. Add some simple jewelry and a bright lip to complete the look!
Pro Tip– When it comes to shoes, pick a pair of mules with a medium heel for the best balance between comfort and style.
8. Black Dress
Did someone say black? Finally! Here’s what you need to know about classic black dresses:
The perfect dress for a first date makes you look thinner, taller, and more confident than usual. Black is the perfect color for this it shows off your best features while hiding flaws. You can wear it in many different ways. A basic black dress will work well with most wardrobes because it’s versatile enough to be worn, and they’re flattering.
Style Tip– You could opt for an edgier look by pairing your black dress with a leather jacket, boots, and a bold lip color. Opt for a chunky bracelet and dazzling earrings.
9. A Mini Dress and Blazer
A mini dress and blazer combo is a great look to rock on your first date. The mini dress gives you a flirty, feminine look, while the blazer adds an air of sophistication. Opt for a denim blazer or a lightweight, neutral-colored blazer for a casual date. To create a more casual look, try a pair of shorts as an alternative to pants or pants (yes!). Make sure you choose comfortable shoes, such as flats or low heels, so you can focus on your date instead of worrying about your feet!
Style Tip– Accessorize with statement earrings, delicate bracelets, and a sleek clutch to complete your outfit.
10. The Statement Coat
Nothing says “I’m ready for a date” like a statement coat. Make a bold statement by choosing an eye-catching jacket that stands out from the crowd. Look for bright colors, unique textures, and fun details like faux fur collars and lapels. Opt for an oversized boyfriend coat or a trench coat for a casual date. Try a structured blazer or cape jacket if you’re going for something a bit more formal. Just make sure that the coat you choose is both stylish and comfortable. A statement coat will keep you warm while also ensuring you look your best on your first date.
Style Tip– Think of donning satin or velvet to add a touch of glam to the evening in accessories or even your jacket.
11. All-white with a splash of color
Adding a pop of color to an all-white ensemble is an effortless way to stand out on your first date. Consider pairing a white blouse and white jeans with a colorful statement piece, such as a red belt or a vibrant scarf. For a more dressed-up look, pair a white jumpsuit with eye-catching earrings. A subtle hint of color can be just the thing to take your look from classic to wow.
Style Tip- Always break the whites with the second color; think of wearing fuchsia or teal for an extra dimension to your outfit.
12. A Bustier Top with Jacket and Slip Skirt
The bustier top is a great way to show off your curves, while the slip skirt is a playful and fun way to add some extra femininity. Make sure to pair it with high heels for an extra-glamorous look. Finish off the look with delicate jewelry and a clutch for an effortlessly stylish and romantic ensemble. With this combination, you’ll surely make an unforgettable entrance on your first date.
Style Tip– A sequin bustier with a satin or silk jacket paired with your skirt will give a refined look.
13. The Little Black Dress
LBD, for short, is a timeless fashion staple that has been around since the 1920s. It’s an all-time favorite piece around the world. The LBD is a classic, sophisticated, and stylish look for first dates. You can create a show-stopping ensemble with the right accessories and styling to make your date remember you! It’s also a great wardrobe essential in your closet as it’s an easy go-to outfit when you don’t know what to wear. Whether you choose a classic black dress with a subtle silhouette or an edgy dress with bold details, you can never go wrong with the LBD. The little black dress is a timeless choice for a first-date outfit, and this classic look never fails to turn heads. Whether you opt for a long-sleeve or short-sleeve option, the key to making this style work is to accessorize.
Style Tip– Add a bold statement necklace, chic earrings, or bright lip color to give your black dress a modern twist. Remember to do the muted eye makeup and heels.
14. The Sexy Jeans
Nothing says a night out like a great pair of jeans; go for sexy jeans that hug your curves and make you feel confident. Choose a light wash with subtle distressed detailing and pair it with a flowy top or dressy blouse for a chic, pulled-together look. Try accessorizing with a statement belt and chunky jewelry for a more casual vibe. For something edgier, pick leather leggings paired with a flirty off-the-shoulder top.
Pro Tip– If you want an effortless but glamorous ensemble, go for high-waisted skinny jeans with a cropped bodysuit. Complete the look with strappy sandals or heels, dangling earrings, and a pop of bold lipstick.
15. Denim on Denim
You can’t go wrong with a classic denim look if you want to keep it casual but still look put together. Pair a well-fitting pair of jeans with a nice denim button-down shirt or blouse, and add a fun accessory like a belt or necklace to complete the look. You’ll be sure to make a great first impression!
Style Tip- Pair your denim shirt or jacket with a denim skirt, and add a punch of color with a colorful bag and suede boots for an elevated look.
16. Yoga Pants and a Winsome Top
Yoga pants and a cute top are a great way to get your feet into the mood. Yoga pants are comfortable and flattering, and they’re easy to move in so you can be comfortable all night long. You can wear them with heels or sneakers—you can dress them up with different styles of tops.
Style Tip– Layer your outfit with a stylish jacket and a scarf for a more put-together look.
17. The Flowy Top
A flowy top is a great way to look stylish on a first date. With its flattering lines and lightweight material, a flowy top will show off your figure in all the right ways. For an extra touch of femininity, look for tops with cute details like ruffles, lace trim, or pleats. This type of top pairs well with various bottoms, so you can choose what best suits your style. Whether you opt for jeans, shorts, a skirt, or a jumpsuit, a flowy top will help complete your look and have you feeling confident and ready for a great date!
Style Tip– Wear bright lip color, a standout piece of jewelry, a gold necklace or statement earring, and a mini purse to keep the look sophisticated and feminine.
18. The Puff Sleeve Crop Top
The puff-sleeve top is an excellent choice for your first date! It’s a fun and flirty piece that will draw attention to your arms and shoulders. The puffed sleeves create a stylish and romantic look and can be dressed with statement jewelry or bold lip color. Pair the puff sleeve top with jeans and flats for a more casual look. With so many color and print options available, pick something that makes you feel feminine.
Style Tip– Opt for cigarette pants or skinny jeans with ankle boots for a fitted, put-together look.
19. Knit Dresses
Knit dresses are ideal for a first-date look that is both comfortable and chic. Opt for a shorter-length dress with a looser fit in a muted color for a casual yet put-together look. You can dress it up with heels, statement jewelry, and a clutch, or opt for flats, a light jacket, and a scarf to keep things casual. No matter what you choose, knit dresses provide the perfect balance of comfort and style for a successful date.
Style Tip– Pair your plain knit dresses with brown or neutral tall boots or even peep toe open booties for that different look.
20. The Stylish Sneakers
Yes! There is nothing wrong with slipping on a pair of stylish sneakers for a first-date look that is comfortable yet fashionable. Sneakers are a great way to stay comfortable on a long night out and still make you look chic. You can opt for a classic white sneaker or find one in an unexpected color or pattern. Whether you choose a slip-on style, a high-top, or even a trendy chunky silhouette, a pair of stylish sneakers can complete any look and add a touch of fun. Team your sneakers with jeans and a cute top or dress for the ultimate outfit, and you’re ready to go!
Choose Your Color: Psychology Behind Colors!
When it comes to colors, there’s much science behind them!
- Black is charming and enchanting. Wearing black clothes makes you appear thinner.
- White – The positive connotations include: peace, innocence, sterility, cleanliness, and empowerment. White may be paired with black to signify authority and truth.
- Red is considered a sign of love and passion.
- Blue symbolizes trust, loyalty, and wisdom and indicates confidence, faith, truth, and stability. It is also calming and soothing.
- Yellow symbolizes happiness, and orange shows friendship.
- Green means relaxation or calmness—and purple can be seen as creative!
Style Mistakes to Avoid!
- Avoid too many accessories.
- Don’t wear too many layers.
- Don’t overdo it with makeup and jewelry.
- Avoid wearing anything you feel uncomfortable in.
- Don’t wear something too revealing, which could be distracting for your date.
Things to Keep in Mind!
- Wear what makes you confident.
- Wear what makes you sexy and like yourself, not someone else or some idealized version of yourself that doesn’t exist in real life (or even exists at all).
- Always try a dress before the actual date.
- Find your style and stick to it.
- Keep the season, location, and weather in mind when choosing what to wear.
- If you’re wearing a skirt or dress, bring a jacket or shawl if you get chilly.
Remember your hair!
Remember your hair! Get it done professionally at least once every two weeks; otherwise, it will look dull and lifeless—not good when trying to make a first impression!
Make certain makeup products, hairspray/gel, etc., are applied correctly, so they appear natural rather than caked-on or heavy looking.
Click here to learn how to style your hair in a unique style.
Listen Up!
When you’re on a first date, it’s important to be ready. Ensure you have everything in order:
- Your wallet, phone, and keys.
- If you’re running late for your date, apologize immediately and explain why.
- If there’s no way around it, call ahead and let the person know what happened (and apologize).
And That’s a Wrap!
Be yourself. In the end, it’s all about you and your style. If you’re more of a casual person, wear jeans to your first date; if you prefer dresses and skirts, go for it! Just don’t worry about what others think—you’re going out with someone new! We hope this article gave you many helpful tips on what to wear on your first date. Remember, the most important thing is not to stress yourself out! The more comfortable and confident you feel when meeting someone new, the more fun it will be for everyone involved. While there are no hard-and-fast rules when it comes to fashion, following this advice should have you looking and feeling confident as you embark on your new romantic adventure! You may also like to read this excellent article on “How to look pretty to your crush – The unforgettable ways”
Get ready for your date, and wear a smile.
Watch our postings for new fashion inspiration, and let us know how you planned your first date outfit look in the comments area.
Written by: Varun Gupta
