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10 Stylish and Classy Outfits to Wear on a First Date

Make that first impression count!
10 Stylish and Classy Outfits to Wear on a First Date
IMAGE Instagram/sarahlahbati, ramonathornes
Make that first impression count!

If there was ever a time to bust out the all stars in your closet, it's for when you're going on a first date. Butterflies might be crowding in your tummy, but here's a tip from us: You'll feel your best when you look your best (and vice versa!) Picking out the right outfit for the big night is already half the battle, trust us.

Need some inspo to get you started? Scroll away for some chic and classy outfit ideas that'll for sure make your first impression the best one.

10 classy first date night outfits to try:

1. Black Midi Dress + Black Heels + Gold Jewelry

No article of clothing is as romantic and effortlessly sultry as a little black dress. It can instantly switch on your vixen mode depending on how you style it. We recommend slipping it on with some sleek heels in the same shade, and some gold bling to dust on even more sophistication to the look.

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classy first date outfits
PHOTO BY Instagram/sarahlahbati

2. Collared Shirt Dress + Sandals + Shoulder Bag

If your meetup is going to be a bit more on the casual side of things, a breezy collared shirt dress will be just what you need. You'll feel like you're wearing nothing but air with how relaxed its fit is, yet the collar makes it look spiffy and put-together. Depending on where you're headed, you can put on sandals or a sensible pair of heels with this look. Whatever shoes you go for, try matching your bag to them for added flair.

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classy first date outfits
PHOTO BY Instagram/whianwamos

3. Vest + Wide-Legged Trousers + Gold Earrings

Everyone grabs a blazer when the occasion's on the more dressed up side of things, but why not don the seldom-worn suit vest instead? Button it up and sport it as a top with some wide-legged trousers for a cool but still just as sophisticated evening look.

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classy first date outfits
PHOTO BY Instagram/irenadrezi

4. Oversized Suit and Trousers + Sneakers + Handbag

But of course, we can't deny the timeless stylishness of a blazer and pants ensemble. Hit the upgrade button on these go-to pieces and rock a more oversized, boxy set that's at once cool, comfy and chic. If your pants are on the longer side, and if your date's set outdoors anyway, we think you'd be able to get away with wearing your trusty sneakers.

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classy first date outfits
PHOTO BY Instagram/ramonathornes

5. Turtleneck Top + Blazer + Pleated Midi Skirt + Boots + Crossbody Bag

To add more spice to a blazer-helmed OOTD, throw it on over a simple turtleneck tucked into a pleated mini skirt in a fun, neutral hue. The lenght of the skirt gives you some leg room to rock a cool pair of ankle boots instead of the usual heels, too.

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classy first date outfits
PHOTO BY Instagram/iamsofiaandres

6. Floral Midi Dress + Mules + Shoulder Bag

For evening affairs held by the sea or under palm trees, bring out your favorite, body-hugging midi dress with the daintiest floral print. Who said dressing "fancy" has to exclude prints, right?

classy first date outfits
PHOTO BY Instagram/catriona_gray
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7. Floral Mini Dress with a Cut-Out + Strappy Heels

To show off your fun, easygoing side via your 'fit, you can don a cute little mini dress that may have some cutouts here and there. Teaming it with a pair of strappy heels sprinkles some flair to the girl-next-door ensemble.

classy first date outfits
PHOTO BY Instagram/angeldei_
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8. Baggy White Collared Shirt + Sweater Vest + Mini Skirt + Kitten Heels + Shoulder Bag

Give the preppy aesthetic a whirl on your date night and layer a neutral-toned sweater vest over a relaxed buttondown shirt. We usually see this combo with sporty tennis skirts and sneakers, but for a more mature take on it, try it on with a silk mini skirt and kitten heels.

classy first date outfits
PHOTO BY Instagram/elissejosonn
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9. Lace Cami Top + Flared Trousers + Heels

We all love our fail-safe tank top and jeans outfits. For a more classy take on that tried-and-true combo, take a dainty cami top, delightfully adorned with lace, and tuck it into tailored trousers for an easy but oh-so-chic date outfit. If your trousers flare out a la '70s fashion, make sure to slip into shoes that have some height to balance out the proportions.

classy first date outfits
PHOTO BY Instagram/charliedizon_
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10. Structured Jumpsuit + Heels + Fun Earrings

If there's one thing (and we literally mean one thing) you need to try sporting for your next date night, it's a structured jumpsuit. It eliminates the fuss of pairing a top with a bottom since it's an entire outfit in one piece, and is a great alternative if you don't feel like putting on a dress. Add your personal touch to it with some fun earrings.

classy first date outfits
PHOTO BY Instagram/apartment8clothing
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