Foolproof First Date Outfits To Ensure You Leave A Lasting Impression

Navigating the dating world is tricky enough, but toss in the question of what to wear to meet potential beaus and it can be downright stressful. But fret not, because we’re here to help. Whether you have dinner or a picnic planned, we’ve compiled five different outfits to keep you both comfortable and chic on a variety of dates.

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  • 1 of 25

    Get ready to kiss singledom goodbye with these knockout first impression looks.  

  • 2 of 25

    Mango

    Flower Print Chiffon Shirt ($40)

    Tight pieces are restrictive and uncomfortable, so let loose in this chiffon blouse by Mango.

     

  • 3 of 25

    Frame Denim

    Denim Le Garcon Slouch Jeans ($199)

    You don’t want to come off like you’re trying too hard on a first date, but you don’t want to sacrifice style, either. These rolled jeans by Frame Denim are the perfect compromise.

     

  • 4 of 25

    Coach

    Leela Heels ($228)

    Woven detailing lends a textural twist to these peep-toe heels.

     

  • 5 of 25

    Misela

    Liya at Anatolia Flap Front Bag ($395)

    This quilted chain-strap bag will add a dose of femininity to any outfit.  

     

  • 6 of 25

    Chan Luu

    Cashmere and Silk-Blend Scarf ($195) in Gray

    Ward off movie theater chills with this luxurious cashmere scarf by Chan Luu.

     

  • 7 of 25

    Topshop

    Floral Printed Playsuit ($96) in Red

    Whether you’ll be riding a bike or sitting on the grass, it’s wise to steer clear of short dresses or skirts. A printed romper is still feminine but much more practical.
     

  • 8 of 25

    J Brand

    Campbell Denim Jacket ($260) in Black

    Team an on-trend romper with this timeless dark denim jacket.
     

  • 9 of 25

    ASOS

    Format Leather Flat Sandals ($37) in Black

    Less casual than flip flops but just as comfortable, keep up with your guy in these flat leather sandals.
     

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    Angela Roi

    Mini Crossbody Bag ($79) in White

    A crossbody bag is essential for on-the-go, outdoor activities.
     

  • 11 of 25

    Illesteva

    Harrison Sunglasses ($220) in Tortoise

    Have these tortoise sunnies handy to shield the sun in style.
     

  • 12 of 25

    Topshop

    Boutique Silk Jumpsuit ($160) in Black

    The simple silhouette of this jumpsuit makes it perfect for showing off flirty accessories.  

     

  • 13 of 25

    Tome

    Sandals ($279)

    These snakeskin heels will add the perfect amount of sex appeal to your look.  

     

  • 14 of 25

    Anya Hindmarch

    Valorie Clutch ($650)

    Because you don’t want to be caught digging through your massive tote whenever you need a lipstick touch-up.

     

  • 15 of 25

    Club Monaco

    EB Statement Earrings ($170)

    A pair of elegant earrings are a sophisticated finishing touch.

     

  • 16 of 25

    Zara

    Dress with Hip Seam ($100)

    This easy, floaty dress is perfect for jamming out to your favorite band.

     

  • 17 of 25

    Chimala

    Camo Jacket ($529)

    Balance a girly white frock with this camo utility jacket.

     

  • 18 of 25

    Frye

    Pippa Chelsea Boots ($278) in Black

    Concerts call for comfortable, fuss-free footwear, and these Frye boots definitely fit the bill.

     

  • 19 of 25

    Opening Ceremony

    Pop Up Bucket Bag ($442)

    Keep your look casual with this simple bucket bag.

     

  • 20 of 25

    Virgin Saints and Angels

    Oval Magdalena Necklace ($248)

    This handmade, beaded medallion necklace is a stylishly unique choice.   
     

  • 21 of 25

    Topshop

    Lace Insert Cami ($56) in Black

    A hint of lace elevates this basic black cami.

     

  • 22 of 25

    American Vintage

    Hot Springs Twisted Jersey Mini Skirt ($85) in Gray

    Temper a metallic beaded jacket with a simple jersey skirt.

     

  • 23 of 25

    Mango

    Beaded Chiffon Jacket ($190) in Black

    An embellished jacket is a key piece to have in your after-dark arsenal.
     

  • 24 of 25

    Alexandre Birman

    Bailey Patent Sandals ($550) in Black

    These strappy sandals are definitely hot date-worthy.  

     

  • 25 of 25

    Illamasqua

    Lipstick ($23) in Eurydice

    Punctuate a barefaced look with bright pink lipstick.  
     

Shop this Story
Boutique Silk Jumpsuit

Boutique Silk Jumpsuit

Topshop, $160
SHOP
EB Statement Earrings

EB Statement Earrings

Club Monaco, $170
SHOP
Valorie Clutch

Valorie Clutch

Anya Hindmarch, $650
SHOP
Flower Print Chiffon Shirt

Flower Print Chiffon Shirt

Mango, $40
SHOP
Leela Heels

Leela Heels

Coach, $228
SHOP
Le Garcon Slouch Jeans

Le Garcon Slouch Jeans

Frame Denim, $199
SHOP
Cashmere and Silk-Blend Scarf

Cashmere and Silk-Blend Scarf

Chan Luu, $195
SHOP
Dress with Hip Seam

Dress with Hip Seam

Zara, $100
SHOP
Camo Jacket

Camo Jacket

Chimala, $529
SHOP
Pippa Chelsea Boots

Pippa Chelsea Boots

Frye, $278
SHOP
Oval Magdalena Necklace

Oval Magdalena Necklace

Virgin Saints and Angels, $248
SHOP
Campbell Denim Jacket

Campbell Denim Jacket

J Brand, $260
SHOP
Floral Printed Playsuit

Floral Printed Playsuit

Topshop, $96
SHOP
Format Leather Flat Sandals

Format Leather Flat Sandals

ASOS, $37
SHOP
Bailey Patent Sandals

Bailey Patent Sandals

Alexandre Birman, $550
SHOP
Beaded Chiffon Jacket

Beaded Chiffon Jacket

Mango, $190
SHOP
Hot Springs Twisted Jersey Mini Skirt

Hot Springs Twisted Jersey Mini Skirt

American Vintage, $85
SHOP
Lace Insert Cami

Lace Insert Cami

Topshop, $56
SHOP
Mini Crossbody Bag

Mini Crossbody Bag

Angela Roi, $79
SHOP
Harrison Sunglasses

Harrison Sunglasses

Illesteva, $220
SHOP
Lipstick

Lipstick

Illamasqua, $23
SHOP
EXPLORE: Shopping, First Date, Topshop, Zara, Frye, J Brand, ASOS, Mango, American Vintage, Club Monaco, Frame Denim, Coach, Chan Luu, Anya Hindmarch, Chimala, Virgin Saints and Angels, Alexandre Birman, Angela Roi, Illesteva, Illamasqua, Misela, Tome, Opening Ceremony
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