20 Cute And Preppy Date Night Outfit Ideas


There are three key ingredients for a successful date outfit: 1. Comfort 2. Personality and 3. Identity. If you don’t feel comfortable in your outfit, how are you supposed to feel comfortable with your date? Reduce the anxiety and wear something that makes you feel good. Don’t be afraid to share your personality, wearing a specific item of clothing that reminds you of a fond memory or is representative of you can make for a good conversation starter and gives your date an easy icebreaker. Make sure you are dressing for yourself and wearing clothing that makes you feel beautiful. If your outfit is fashionable or trendy but you don’t feel like yourself in it, then it’s not date-worthy. Your date is there to get to know YOU, so show ’em who you really are!

1. Coffee & Open Mic Night

A chunky knit sweater with a fit and flare plaid skirt shows off your figure and your flirty side. Pair it with some over the knee boots and you’ll look as sweet as the mocha you’ll be sippin’ on.

this is such a cute date night outfit!

2. New Year’s Eve Cocktails

A luxurious embellished romper thrown over some black tights will shine brightly on New Year’s Eve as you ring in the new year with your beau!

this is such a cute date night outfit!

3. Crepes for Breakfast

A light cardigan layered over a pressed collared shirt looks super put together. Adding a statement necklace or a string of pearls gives it a flirty and feminine touch and gives you something to play with if you get nervous.

this is such a cute date night outfit!

4. Movie Date

It often gets drafty in the theaters, so throw on your favorite down vest. This preppy staple will keep you warm as you snuggle up and watch the latest blockbuster.

this is such a cute date night outfit!

5. Farmer’s Market

Layering a collared shirt under a cozy sweater gives a polished vibe as you two stroll hand in hand through the market place. A pleated skirt and some sheer tights add a feminine touch and will move freely with you as you go.

this is such a cute date night outfit!

6. A Night at the Theater

A warm yet classic pea coat provides a cover from the cold, besides your date, and amps up the fanciness of a shift dress. Pair it with some over the knee socks to keep your legs warm on this uber romantic date.

this is such a cute date night outfit!7. Hockey Game

Going to see a sporting event like a hockey game with your guy can be a blast, and it’s a great excuse to break out some of your sporty chic clothes. Leggings and a warm fleece with a ball cap are casual enough for the game, but still cute enough for a date. Bonus, soft clothing is comfy for you, and your date.

this is such a cute date night outfit!

8. Spring Picnic

A beautiful sunny day calls for a picnic in the park, and what better time to don a bright shift dress. With a sweet hair bow, this look radiates spring and the romance that comes with it.

this is such a cute date night outfit!

9. Snow Ball Fight

Playing in the snow with your s/o can be a blast, but be sure to bundle up. A peacoat over a sweater over a collared shirt may seem like a lot, but it will keep you warm and you’ll still look put together. Add a hat, snow boots, and some mittens for extra warmth without the bulk.

this is such a cute date night outfit!

10. Study Date

A light collared shirt tucked into a belted wool skirt has a real scholarly feel as you two quiz each other and prepare for the next quiz in your Italian class or read side by side in the stately collegiate library.

this is such a cute date night outfit!

11. Night On the Town

Heading to a party or just out to a bar with your s/o can be as effortless as a one piece outfit. The benefit: you only really have to pick out one item of clothing!

this is such a cute date night outfit!

12. Brunch Date

Heading out to brunch? A pair of white jeans and a turtle neck sweater will keep you warm and cozy as you munch on scones and eggs benedict with your beau. A monogrammed necklace adds a luxe preppy flair to a modern look.

this is such a cute date night outfit!

13. Pillow Fort

Staying in can be just as fun as going out! Keep it comfy and casual in an oversized sweatshirt. This one features a monogram, a preppy touch, and it can be paired with leggings, jeans, or pajama pants (depending on how comfortable you are with your date!)

this is such a cute date night outfit!

14. Apple Picking

Roaming around the orchards on a misty afternoon can be such a romantic treat, wearing some sleek yet functional rain boots with some thick socks will keep your feet warm and allow you to stay out in the murky weather for hours. Layer on a patterned scarf to spice up an otherwise basic outfit.

this is such a cute date night outfit!

15. Christmas Light Looking

A pink peacoat with matching gloves and a statement necklace are a feminine twist on an old classic outfit. Perfect for wandering through neighborhoods after the sun goes down and taking in the beautiful lights.

this is such a cute date night outfit!

16. Baking With The Beau

Baking cookies or a cake is a fun way to get your s/o involved in something as sweet as they are! A plaid shirt layered under a neutral cardigan is an easy way to look put together and still stay cozy in the winter chill.

this is such a cute date night outfit!

17. School Spirit Event

Attend a school sponsored event and show off your colors! This can be done in school apparel or even in a corresponding 3/4 zip with a monogram. Add a baseball cap for a real flair of academia.

this is such a cute date night outfit!

18. Buddy’s Birthday Party

Accompanying your s/o to a party can be a fun excuse to class up your everyday look. Layering a collared shirt under a shift dress is a simple nod to a classic style and is festive enough for the occasion.

this is such a cute date night outfit!

19. Attend Church Together

Connecting with someone through faith can be really meaningful. A modest, yet bright colored frock is ideal for this event.

this is such a cute date night outfit!

20. Dinner Date

The all time classic date deserves an even more classic approach. A little black dress with a statement necklace and a swipe of red lipstick reads romance a la Audrey Hepburn.

this is such a cute date night outfit!

Can you think of any other cute and preppy date night outfit ideas? Share in the comments below!

*This is a sponsored post. All opinions are my own.

Featured Image Source: https://www.pinterest.com


Betsy Podsiadlo

Obsessed with organization, music, and feminism. A freshman Voice Performance major at Rider University's Westminster Choir College.

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