Nobody Puts Babydoll in a Corner

A babydoll dress and boots go a long way, especially in the summer. The airy ease of this short, voluminous dress will keep you chic and cool during a heatwave.

Sleeper Shop it: The Babydoll Dress

Sleeper Shop it: The Babydoll Dress

Wear it lounging around your bedroom or outside with a cool pair of cowboy boots. 

Anine Bing Shop it: The Babydoll Dress

Anine Bing Shop it: The Babydoll Dress

Anine Bing's babydoll iteration comes in a crisp white seersucker with a girly tiered silhouette to show off your legs, and your most coveted boots. 

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Belted And Cinched

A belted or cinched-waist dress paired with luxe patent leather boots works in both the summer and the fall.

Le Kasha Shop it: The Waist Cincher

Le Kasha Shop it: The Waist Cincher

Now 37% Off

An instantly snatched waist, accentuated legs, and subtle nod to Parisian dressing. 

Love Shack Fancy Shop it: The Waist Cincher

Love Shack Fancy Shop it: The Waist Cincher

The fitted waist on this mini dress makes adding a belt unnecessary. Just imagine looking down at a pair of croc-embossed boots while wearing this romantic dress. 

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Prairie, Please

The best prairie dresses of the season come in sheer, chiffon, and flower-child prints that can carry you into cooler temperatures. Whether at the office or a party, the midi prairie dress looks appropriate and admirable with black mid-height leather boots.

Les Rêveries Shop it: The Prairie Dress

Les Rêveries Shop it: The Prairie Dress

Now 20% Off

A statement floral print for every season. 

Get It Gingham

Gingham dresses work well in all seasons—especially when paired with contrasting white boots. Use this formula to create a plethora of different outfits.

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Ganni Shop it: The Gingham Dress

Ganni Shop it: The Gingham Dress

A gingham silk mini dress that is both business casual and organic grocery store run appropriate. 

Slip Into It

Slip dresses are a fashion-girl favorite because they can be layered, worn under winter jackets, and paired with boots, sneakers, and sandals alike. Opt for a pointed toe leather option this season. And don't forget to play with prints.

Dannijo Shop it: The Slip Dress

Dannijo Shop it: The Slip Dress

Now 30% Off

This will add the pop of color you need in your wardrobe. 

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H&M Shop it: The Layering Blouse

H&M Shop it: The Layering Blouse

An affordable trendy blouse that adds an updated element to a slip dress look. 

The Bigger, The Better

Wearing an oversized white dress with rain boots = pure sartorial perfection. You can't go wrong.

Closed Shop it: The White Midi

Closed Shop it: The White Midi

Closed version of the white midi features long white sleeves, and embroidered, pleated details. 

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Toss On A Blazer

Blazers work as the perfect transitional wardrobe item. Go for a wool style in the early spring, or a linen option at the end of summer. Either way, when thrown over a dress and worn with boots, the results are incredibly sophisticated.

Madewell Shop it: The Essential Blazer

Madewell Shop it: The Essential Blazer

Now 40% Off

For all your dress layering, work-wear, and evening needs. 

Play With A Structured Silhouette

When a structured, A-line dress is worn with knee-high boots it takes the look from busy midtown to relaxed downtown.

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Rhode Shop it: Structured Midi

Rhode Shop it: Structured Midi

A structured dress is an easy way to bring your sophistication level up a notch. 

Shirt Notice

Never underestimate the visual power of a long, white shirt dress. No matter what year it is, the staple continues to be redone and modernized. Pair yours with a low leather Chelsea boot.

Cortne Bonilla is freelance writer who occasionally dabbles in party reporting. When she’s not writing, you can find her vintage shopping, sipping iced lattes, reading on the train, and indulging in Pilates. 

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