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15 Adorably Retro Day Dresses you'll want to Wear all Summer Long... with Sneakers

There’s something about the simple cotton 1950’s shirt dresses with a full skirt that seems so fresh right now! Like Taylor Swift’s ad campaign with Keds, when worn with a classic pair of light-weight sneakers, this combo may be the perfect Summer look that spans generations, i.e. is cute and appropriate for all ages.

With a nod to the 1950’s and to the 1990’s, finding these adorable and whimsical house dresses shouldn’t be too difficult, but they do come at a price. If you’re lucky to find one at a local thrift shop that’s in great condition {no stains or holes} and fits like a glove, pick it up because the vintage 1950’s and new shirt dresses don’t come cheap.

But for that one-of-a-kind piece that will make you feel carefree and comfy this Summer, it may be worth the splurge. From original 50’s vintage finds to brand new items, here are 15 adorably appropriate day dresses you’ll want to wear all Summer long… with sneakers. {links to buy below}

  • Day Dresses with Sneakers 1 of 16
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    Because everyone should be able to look fancy and feel comfortable at the same time!

    * Taylor Swift for Keds $50
    * Superga 2750's Classic Sneakers  $69-$70 {my favorite for cuteness and support}
    * Converse All Stars $40-$60

  • Adorably Sweet and New 2 of 16
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    I love this modern sleeveless take on the classic shape. This print is perfect for Summer and can take you into Fall with a cute cardigan, tights, and boots

    French Connection Floral Shirt Dress $144.25 via Asos

  • 1950s Shirtwaist Dress in Olive Green 3 of 16
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    A perfectly retro piece in a hue that doesn't scream "I'm so girly" I love this dress so much I may just buy it right now!

    Vintage I.MAGNIN 1950s Shirtwaist Dress in Olive Green $44 via Etsy

  • With a Modern A Lolita Flair 4 of 16
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    With a higher waist and a younger feel, this shirtdress is borderline babydoll, but I love it just the same. Pair it with white sneakers for a cute/preppy look and darker shades with some spikes to add an edge and a hint of punky grunge.

    ASOS Shirt Dress In Fluoro Jacquard Spot $93.34 via Asos

  • 50’s Vintage Shirt Dress 5 of 16
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    Another one of my favorites for the really gorgeous vintage print.  I love that the darker colors will work into the Fall as well.

    Vintage 1950's pink and black floral print shirt dress $148 at Etsy

  • Crisp, Modern, Timeless, New 6 of 16
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    This classic black DKNY shirtdress is a timeless piece that could really be in any woman's closet.  It's a bit expensive but think about how many years, if not decades you can wear this dress if you take care of it.

    DKNY Trapunto Stitch Shirtdress in black $395 via Shopbop

  • Vintage 1950’s pale lilac dress 7 of 16
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    It just looks so light and airy, with a cute floral or striped canvas sneaker, this look is perfectly whimsical.

    Vintage 50's Shirtdress in Lilac $124 via Etsy

  • Vintage 50’s Shirtdress 8 of 16
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    The print on this dress and the mixed greens really screams Summer to me and I just love it!

    Green Motif Oriental Print 50's Shirt Dress $45 via Etsy

  • Original 50’s Shirtdress 9 of 16
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    I love the mixed prints on this darker hued vintage frock.  Lighten it up with whites, soft pinks, and light blues.

    Vintage 50's Floral Print Shirt Dress $135 via Etsy

  • Vintage 50’s Light Blue Day Dress 10 of 16
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    "Look at Me, I'm Sandra Dee"

    Vintage 50's shirt dress $55 via Etsy

  • Pretty In 50’s Pink 11 of 16
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    Pretty In Pink!

    1950's dress - pink cotton 50's dress $124 via Etsy

  • The Large Button Makes it Super Retro 12 of 16
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    I can't tell if I love the large button or if I'd swap it out for a few smaller ones or even with a big brooch, but I love the large plaid print on this vintage dress.

    Vintage 50's Plaid Shirt Dress $110 via Etsy

  • 50s Summer Housewife Shirtwaist Full Skirt ShirtDress 13 of 16
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    I just can't see this cute little polka dotted dress with anything but a bright white pair of sneakers.

    Polka Dot 50's Day Dress $98 via Etsy

  • Sleeveless in White 14 of 16
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    Another classic and timeless dress that spans decades and has so much versatility. I'd swap the belt out for something a little lighter and pair it with a navy polka dotted sneaker. So cute!

    Antipodium Interface Shirt Dress With Contrast Collar $371 via Asos

  • Gold Striped 50’s Shirtdress 15 of 16
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    This gold metallic striped dress would look adorable with the gold tiny floral Keds.  Mixing prints will make this more modern and lighter for Summer!

    Gold metallic striped classic 1950s shirtdress $62 via Etsy

  • Sweet Vintage Perfection 16 of 16
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    This may be my favorite silhouette of all so I had to include it, even though it's wool and should never be worn in the Summer months... but breezy Fall weather will do it justice.

    Vintage 50's Wool Cobalt blue Shirtdress $148 via Etsy

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