Welcome to the blog of [company name], where we answer your questions about dating and relationships. We’re here to help you navigate the world of dating, so you can have more fun and less stress!
If you have a question about what to wear on a second date, send us an email at [email address].
When you’re trying to make a good impression, it can be hard to know what to wear. But the truth is, there’s no one-size-fits-all answer—the best outfits are those that feel right for you and your date! And if you’re not sure where to start, we’re here to help.
We’ve put together this guide of ten great outfits for your second date, so you’ll always have something stylish but also comfortable at the ready when you’re meeting up with someone new.
Whether it’s a casual coffee date or an eventful dinner party with friends, these looks will help ensure that your second date is just as fun as your first!
What to wear on the second date
There’s no question that a first date can be nerve-wracking. But a second date? That’s when you really have to bring your A-game—and we’re here to help.
The second date is usually the first time you get to see what your partner is like outside of the context of a restaurant or bar. It’s not just about having fun; it’s about getting to know each other as people and discovering whether or not you’re compatible enough to move forward with this relationship.
So how do you make sure you don’t mess this up? The key is dressing appropriately for the occasion, which means wearing clothes that are comfortable but still look good on you and make you feel confident in yourself. The last thing anyone wants on the second date is to feel self-conscious or out of place because their outfit didn’t fit right or made them feel awkward.
If there was one thing we could tell every single person who has ever gone on a second date (and everyone else too), it would be this: don’t wear jeans! Jeans are probably not going to be appropriate for most outings, but even if they were, we’d still advise against wearing them for this particular occasion because they make your legs look shorter than
Wearing the right outfit is important for any occasion, but in many ways it’s even more critical for a second date. After all, you want to look good for your partner, but you also want to make sure that what you’re wearing reflects who you are and makes sense with the venue or activity.
So how do you know what to wear? Here are some tips:
On a second date, you can really let your true colors shine, especially if you played it safe on date number one. If you are a T-shirt–and-pants kind of girl, wear that, but if you want to pull out all the stops and wear a bright floral dress and satin platforms, there’s no time like a second date to do it.
9 Second-Date Outfits That Will Get You a Third
by LAUREN EGGERTSEN
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Look up “what to wear on a first date” and surely you’ll find hundreds of outfit ideas to draw inspiration from. Thanks to your incredible first-date look (and your charming personality, of course), you scored a second date. Things are looking up until you remember you need an outfit for that too. Why does no one talk about second dates? They really are just as important as the first, if not more important, and we want to make sure you have the ensemble to prove it.
To help us out a bit, we gathered some second date-outfit inspiration from a handful of our beloved bloggers. Some of the ladies ahead are married, some are single, and we are here just to admire the quality of their outfits for being top-notch second date material. On a second date, you can really let your true colors shine, especially if you played it safe on date number one. If you are a T-shirt–and-pants kind of girl, wear that, but if you want to pull out all the stops and wear a bright floral dress and satin platforms, there’s no time like a second date to do it. At the end of the day, wearing what makes you the most comfortable and confident is the right choice, date number aside.
Ahead, shop the second-date outfit ideas straight from some of our favorite bloggers.
What to Wear on a Second Date: 11 Cute Outfit Ideas
Co-authored by Lisa Shield and Aly Rusciano
Last Updated: April 12, 2022 References Download Article
You’ve been asked out on a second date—how exciting! The scary first date is over, but now you’ve reached a whole new dilemma…What do you wear for the second date? Finding a flattering and flirtatious outfit that isn’t too over-the-top may seem daunting, but you’ve got this. To help, we’ve put together a list of our favorite second date outfits for any and all occasions. Keep reading to learn how you can dress to impress and score that third date.
1
Blazer and Boyfriend Jeans
Image titled What to Wear on a Second Date Step 1
This business casual duo is perfect for winter dates. It’s casual enough that you won’t be overdressed, yet shows you’ve put thought into your look. Wear a white tee underneath if the date is super chill, or go for a silk blouse for a fancier look.[1]
Up the chic factor by pairing your look with some heels. This is a great option if you didn’t wear heels on the first date—now it’s time to show your date what you’ve got!
You can also finish off your outfit with a nice pair of boots.[2]
2
Midi Dress and Leather Jacket
Image titled What to Wear on a Second Date Step 2
Layers are perfect for an outdoor date. This versatile look can show off all the wonderful sides of your personality! Pairing an edgy leather jacket with a flowy, flirtatious dress says, “I’m cute but mysterious.” Your date will be so curious to learn more about you and your style that they may just ask you out a third time.[3]
Pair this edgy and flirtatious look with a pair of Keds, Vans, or ankle-high boots.
Don’t have a leather jacket? Not to worry! Throwing a jean or khaki jacket over a dress is another chic and versatile combo perfect for a second date.[4]
You don’t need to wear a lot of makeup or jewelry with your outfit—a natural look is also great![5]
3
Pop of Red
Image titled What to Wear on a Second Date Step 3
This sexy, bright color is bound to capture your date’s attention. When it comes to the second date, you want to play it safe while also mixing things up a bit. Adding a pop of red to your outfit is a bold and courageous move that’ll spice up your look. Try pairing a white top with red shoes, using a red handbag, or wearing a red pair of sunglasses.[6]
Nothing red to wear? No problem! A pop of red lipstick can bring out the color of your eyes and enhance those beautiful lips.
4
Cardigan and Jeans
Image titled What to Wear on a Second Date Step 4
Keep things simple but flirtatious on the second date. Sometimes a cozy yet flattering outfit is all you need to capture their interest. If you’re going to the movies, out for pizza, or to grab coffee after class, stick to wearing a pair of jeans that show off your curves and a cardigan that makes your eyes pop.[7]
Cardigans come in all shapes and sizes, so pick one you absolutely adore! Your confidence will show if you wear something that makes you feel good.
Accessorize with knee-high boots, a purse or satchel, and maybe even a scarf. This will tie the look together and give your outfit that extra oomph.
5
Matching Set
Image titled What to Wear on a Second Date Step 5
Show your date you’re put together and stylish. Nowadays, there’s a matching set for every occasion. If you’re not exactly sure how to style a look for your second date, you can’t go wrong with a matching set! Try a matching pants or skirt suit when going to a restaurant, a matching leggings and sports bra for a rendezvous at the gym, or a form-fitting sweatsuit set if you bring the second date to your home.
Make sure you know the location of your second date ahead of time so you can plan your outfit accordingly. There’s no shame in knowing where you’re going, especially since this is only the second date.
6
Slip Dress and Heels
Image titled What to Wear on a Second Date Step 6
Show off your amazing body with this saucy number. The second date is all about showing off more of your style, so give your date something new by dressing up. A slip dress is sexy but elegant and perfect for candlelit restaurants dates. Choose a color you feel confident in and stride into your date knowing you’re hot stuff.[8]
Accessorize with dangling, sparkling earrings and a clutch for an extra bit of glam.
Layer an oversized T-shirt over your dress for a more relaxed look.
7
Ribbed Tee and High Waisted Jeans
Image titled What to Wear on a Second Date Step 7
This date look is casual and flattering. A textured shirt and mom jeans may not seem like much, but this outfit screams, “I’m put together, and you have to wait a little longer to see more.” This vintage-inspired look is perfect for a second date to the movies or a walk in the park. If your date wants to see you all dolled up, they’ll just have to ask you out for another date![9]
Pick a pair of jeans that hug your frame—you want to show off that booty!
Ribbed tees not your style? Go for a form-fitting tank top or henley for a fashionably vintage look.
8
Skater Dress and Pumps
Image titled What to Wear on a Second Date Step 8
Stay chic and comfortable at a fancy restaurant. If your date decides to take you out for your second date at an upscale restaurant, opt for an a-line or skater dress. The fitted top and flared skirt will flatter your figure before and after your meal.[10]
Steer clear of bodycon or tight-fitting dresses on the second date, especially if you bloat after you eat. Finding a dress that you feel comfortable and can move in is ideal.
If you tend to spill food while you eat, don’t sweat it—we’ve all been there! Avoid white and pastel dresses to keep any spills secret.
9
Retro Jumpsuit
Image titled What to Wear on a Second Date Step 9
This versatile and comfy clothing item is perfect for a second date. You never know where the night will take you. Maybe your night starts at a nice restaurant, but you later find yourself dancing with your date at a club. Jumpsuits are great because they can match almost every date style, allowing you to look and feel good in any setting.[11]
Find a style that speaks to you! Go for a silhouette with flared legs for a retro look, or be bold with a wild printed fabric.
Cinch your waist with a belt to draw more attention to your jaw-dropping curves.
Pair your jumpsuit with heels for extra glam, or stick to Converse or sandals for a more relaxed look.
10
Swimsuit and Cover Up
Image titled What to Wear on a Second Date Step 10
Try this fun and practical look if your second date is at the beach. Dress to the occasion if your date wants to take you to the boardwalk or plans a beach picnic. Even if you don’t know if you’ll be swimming, plan your beach look around a swimsuit just in case. Opt for a vibrant halter-top bikini and high-waisted shorts, a floral maxi dress and brimmed hat, or go for a patterned bikini top and colorful kimono wrap or oversized sweater.[12]
Be fashion-forward by pairing this look with heeled strappy sandals and large sunglasses.
11
T-Shirt and Jeans
Image titled What to Wear on a Second Date Step 11
Be comfortable all while showing off your personality. You’ve been asked on a second date, which means they like you and want to learn all about you! When it comes down to it, if you don’t know what to wear and can’t find anything that screams “you,” opt for the classic T-shirt and jeans combo. Go for a shirt with your favorite band, movie, or quote on it. A fun tee is the perfect icebreaker and will give you a chance to tell your date something new about yourself.
Try ripped jeans for an edgier look.
Toss on a jean jacket or your favorite cardigan just in case it’s chilly.
High tops and Vans are stylish and comfy shoes you can pair with this personalized look.
You can also pair your jeans with a button-up shirt, too.[13]
Casual second date outfit
What to Wear on a Second Date: 11 Cute Outfit Ideas
Co-authored by Lisa Shield and Aly Rusciano
Last Updated: April 12, 2022 References Download Article
You’ve been asked out on a second date—how exciting! The scary first date is over, but now you’ve reached a whole new dilemma…What do you wear for the second date? Finding a flattering and flirtatious outfit that isn’t too over-the-top may seem daunting, but you’ve got this. To help, we’ve put together a list of our favorite second date outfits for any and all occasions. Keep reading to learn how you can dress to impress and score that third date.
1
Blazer and Boyfriend Jeans
Image titled What to Wear on a Second Date Step 1
This business casual duo is perfect for winter dates. It’s casual enough that you won’t be overdressed, yet shows you’ve put thought into your look. Wear a white tee underneath if the date is super chill, or go for a silk blouse for a fancier look.[1]
Up the chic factor by pairing your look with some heels. This is a great option if you didn’t wear heels on the first date—now it’s time to show your date what you’ve got!
You can also finish off your outfit with a nice pair of boots.[2]
2
Midi Dress and Leather Jacket
Image titled What to Wear on a Second Date Step 2
Layers are perfect for an outdoor date. This versatile look can show off all the wonderful sides of your personality! Pairing an edgy leather jacket with a flowy, flirtatious dress says, “I’m cute but mysterious.” Your date will be so curious to learn more about you and your style that they may just ask you out a third time.[3]
Pair this edgy and flirtatious look with a pair of Keds, Vans, or ankle-high boots.
Don’t have a leather jacket? Not to worry! Throwing a jean or khaki jacket over a dress is another chic and versatile combo perfect for a second date.[4]
You don’t need to wear a lot of makeup or jewelry with your outfit—a natural look is also great![5]
3
Pop of Red
Image titled What to Wear on a Second Date Step 3
This sexy, bright color is bound to capture your date’s attention. When it comes to the second date, you want to play it safe while also mixing things up a bit. Adding a pop of red to your outfit is a bold and courageous move that’ll spice up your look. Try pairing a white top with red shoes, using a red handbag, or wearing a red pair of sunglasses.[6]
Nothing red to wear? No problem! A pop of red lipstick can bring out the color of your eyes and enhance those beautiful lips.
4
Cardigan and Jeans
Image titled What to Wear on a Second Date Step 4
Keep things simple but flirtatious on the second date. Sometimes a cozy yet flattering outfit is all you need to capture their interest. If you’re going to the movies, out for pizza, or to grab coffee after class, stick to wearing a pair of jeans that show off your curves and a cardigan that makes your eyes pop.[7]
Cardigans come in all shapes and sizes, so pick one you absolutely adore! Your confidence will show if you wear something that makes you feel good.
Accessorize with knee-high boots, a purse or satchel, and maybe even a scarf. This will tie the look together and give your outfit that extra oomph.
5
Matching Set
Image titled What to Wear on a Second Date Step 5
Show your date you’re put together and stylish. Nowadays, there’s a matching set for every occasion. If you’re not exactly sure how to style a look for your second date, you can’t go wrong with a matching set! Try a matching pants or skirt suit when going to a restaurant, a matching leggings and sports bra for a rendezvous at the gym, or a form-fitting sweatsuit set if you bring the second date to your home.
Make sure you know the location of your second date ahead of time so you can plan your outfit accordingly. There’s no shame in knowing where you’re going, especially since this is only the second date.
6
Slip Dress and Heels
Image titled What to Wear on a Second Date Step 6
Show off your amazing body with this saucy number. The second date is all about showing off more of your style, so give your date something new by dressing up. A slip dress is sexy but elegant and perfect for candlelit restaurants dates. Choose a color you feel confident in and stride into your date knowing you’re hot stuff.[8]
Accessorize with dangling, sparkling earrings and a clutch for an extra bit of glam.
Layer an oversized T-shirt over your dress for a more relaxed look.
7
Ribbed Tee and High Waisted Jeans
Image titled What to Wear on a Second Date Step 7
This date look is casual and flattering. A textured shirt and mom jeans may not seem like much, but this outfit screams, “I’m put together, and you have to wait a little longer to see more.” This vintage-inspired look is perfect for a second date to the movies or a walk in the park. If your date wants to see you all dolled up, they’ll just have to ask you out for another date![9]
Pick a pair of jeans that hug your frame—you want to show off that booty!
Ribbed tees not your style? Go for a form-fitting tank top or henley for a fashionably vintage look.
8
Skater Dress and Pumps
Image titled What to Wear on a Second Date Step 8
Stay chic and comfortable at a fancy restaurant. If your date decides to take you out for your second date at an upscale restaurant, opt for an a-line or skater dress. The fitted top and flared skirt will flatter your figure before and after your meal.[10]
Steer clear of bodycon or tight-fitting dresses on the second date, especially if you bloat after you eat. Finding a dress that you feel comfortable and can move in is ideal.
If you tend to spill food while you eat, don’t sweat it—we’ve all been there! Avoid white and pastel dresses to keep any spills secret.
9
Retro Jumpsuit
Image titled What to Wear on a Second Date Step 9
This versatile and comfy clothing item is perfect for a second date. You never know where the night will take you. Maybe your night starts at a nice restaurant, but you later find yourself dancing with your date at a club. Jumpsuits are great because they can match almost every date style, allowing you to look and feel good in any setting.[11]
Find a style that speaks to you! Go for a silhouette with flared legs for a retro look, or be bold with a wild printed fabric.
Cinch your waist with a belt to draw more attention to your jaw-dropping curves.
Pair your jumpsuit with heels for extra glam, or stick to Converse or sandals for a more relaxed look.
10
Swimsuit and Cover Up
Image titled What to Wear on a Second Date Step 10
Try this fun and practical look if your second date is at the beach. Dress to the occasion if your date wants to take you to the boardwalk or plans a beach picnic. Even if you don’t know if you’ll be swimming, plan your beach look around a swimsuit just in case. Opt for a vibrant halter-top bikini and high-waisted shorts, a floral maxi dress and brimmed hat, or go for a patterned bikini top and colorful kimono wrap or oversized sweater.[12]
Be fashion-forward by pairing this look with heeled strappy sandals and large sunglasses.
11
T-Shirt and Jeans
Image titled What to Wear on a Second Date Step 11
Be comfortable all while showing off your personality. You’ve been asked on a second date, which means they like you and want to learn all about you! When it comes down to it, if you don’t know what to wear and can’t find anything that screams “you,” opt for the classic T-shirt and jeans combo. Go for a shirt with your favorite band, movie, or quote on it. A fun tee is the perfect icebreaker and will give you a chance to tell your date something new about yourself.
Try ripped jeans for an edgier look.
Toss on a jean jacket or your favorite cardigan just in case it’s chilly.
High tops and Vans are stylish and comfy shoes you can pair with this personalized look.
You can also pair your jeans with a button-up shirt, too.[13]
