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

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

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]
X
Research source}
- 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]
  X
  Expert Source
  
  Lisa Shield
  Dating Coach
  Expert Interview. 13 December 2018.}

2

Midi Dress and Leather Jacket

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]
X
Research source}
- 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]
  X
  Research source}
- You don't need to wear a lot of makeup or jewelry with your outfit—a natural look is also great!^{[5]
  X
  Expert Source
  
  Lisa Shield
  Dating Coach
  Expert Interview. 13 December 2018.}

3

Pop of Red

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]
X
Research source}
- 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

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]
X
Research source}
- 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

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

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]
X
Research source}
- 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

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]
X
Research source}
- 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

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]
X
Research source}
- 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

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]
X
Research source}
- 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

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]
X
Research source}
- Be fashion-forward by pairing this look with heeled strappy sandals and large sunglasses.

11

T-Shirt and Jeans

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]
  X
  Expert Source
  
  Lisa Shield
  Dating Coach
  Expert Interview. 13 December 2018.}