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The prairie dress. It may conjure thoughts of Laura Ingalls Wilder, but the prairie dresses of 2020 are much more chic than the ones Ma sewed for her girls. Yes, the trend has been enjoying a moment this year, popping up everywhere from local and online boutiques to big-box retailers. It makes sense as the style can be worn by many and can even camouflage any COVID pounds we aren’t so proud of. (Just us?!)

As with most-things-fashion, though, there is an art to wearing the prairie dress trend so you look haute, not hokey.

We asked Southern stylist Milton White of The Fashion Office to style eight prairie dress looks and tell us more about this trend as we need all the pointers and styling tips we can get! Each of these looks was shot on location at the new Grand Hyatt Hotel in Nashville, TN.

Look #1:

Kendal wearing snakeskin chiffon tiered prairie dress

If you have a warmer weather dress, extend its wear by adding another layer. “We added a color block cardigan to this dress, which gives it a second life,” Milton says of the transition piece. On Kendal: Karlie snakeskin chiffon tiered prairie dress, $148; French Connection cognac color-block cardigan, $138; Lack of Color ivory hat, $132; Chinese Laundry beige croc-embossed boots, $90, all from e. Allen | Boho Girl gold ring, $14, from Vinnie Louise

First things first: What defines a prairie dress? “The prairie dress is probably one of the most misunderstood, often poorly styled silhouettes,” explains Milton. “It’s a retro-Western-meets-Victorian garment that has a few key features: ruffle accents, floral prints (though not always), puffed sleeves (a huge runway trend this season!), high necklines (though many we found did not), tiered panels and a breezy A-line silhouette.”

When worn properly, the look can be flattering. “It’s easy, comfortable and pretty, which is exactly what we need right now,” Milton says. “I would much rather see a prairie dress in a beautiful fabric at the grocery store or on a Zoom call than a pair of yoga pants. And when worn and styled properly, it can be quite fashionable and forward-looking.”

Look #2:

Brooklen wearing Faherty navy floral maxi dress

A bold statement necklace doesn’t overpower the look. Rather, it works together with the floral print and flat boot. On Brooklen: Faherty navy floral maxi dress, $258, from Oak Hall | Sam Edelman cognac boots, $58; silver and copper pendant necklace, $24, both from Designer Finds

Look #3:

Kendel wearing Lovestitch metallic floral maxi dress

This dress features several of the key prairie dress features, including ruffle detailing, puffy sleeves and a floral print. On Kendel: Lovestitch metallic floral maxi dress, $74, from Vinnie Louise | Moonstone Joile bar earrings, $138; smoky quartz mini rock Dominique cuff, $288; smoky quartz mini rock one-stone wrapped nest clasp, $158; smoky quartz Rondelle Dominique cuff, $238, all from Judith Bright

Now, for the actual styling part. Here are the three most important rules for styling a prairie dress:

Rule #1: Avoid heels. “One thing I probably wouldn’t do is wear pumps or high-heeled sandals,” Milton explains, adding it would lean too corporate and/or sexy. “There’s nothing wrong with either of those, but this [type of] dress needs a great flat shoe, sandal, espadrille or mule for spring/summer and a ballet flat or loafer for autumn/winter. If you must wear a heel, then it needs to be a boot, short (ankle) or tall (knee).

Rule #2: Opt for statement pieces. “The long, tiered silhouettes in pretty, dainty patterns benefit from being paired with large pieces of jewelry,” Milton says. In fact, he suggests mixing metals as well as using fabrics such as leather or suede and embracing multi-colored gemstones.

Rule #3: Go for an unstructured handbag. “I think unstructured clutches and crossbody bags are the way to go,” Milton explains. “While solids work, don’t be afraid of textures like knits, suede, wovens or fur.”

We can see these suggestions at work in these looks Milton styled today. It’s obvious the right selections and proper styling can make a big difference.

RELATED: The “Shacket” & 4 More Outerwear Trends to Try

Look #4: 

Brooklen wearing Sue Sartor meadow rose prairie dress

The high neck on this dress feels on-trend, not outdated. And notice the inconspicuous cross-body bag. On Brooklen: Sue Sartor meadow rose floral dress, $525, from Sue Sartor | Courtney hoop earrings, $148; rainbow 5-stone Mila ring, $158; wrapped Cleo clasp bracelet, $163, all from Judith Bright | Sam Edelman cognac boots, $58, from Designer Finds

Look #5: 

Kendel wearing Karlie leopard tiered boho midi dress

Not all prairie dresses feature floral print. Here, a feminine animal print is complemented by a bold but stylish clutch. On Kendel: Karlie leopard tiered boho midi dress, $175; glitter sunglasses, $15; suede feather earrings, $14, from Posh | Large stone cuff, $90; Wimberley grey clutch with stone flower, $198, from AshBlue

Look #6:

Brooklen wearing Marie Oliver animal print prairie dress

This perfectly feminine frock enjoys the edge that the white boots bring to the look. On Brooklen: Marie Oliver animal print maxi dress, $438; Qupid white boots, $88, from K. McCarthy | Black wrapped Cleo clasp bracelet, $163, from Judith Bright | Vinnie Louise black and gold fan earrings, $18, from Vinnie Louise

Looks #7 & 8:

Two models posing on a rooftop in downtown Nashville

No two prairie dresses are the same — or the same length. Here, two mini-dress styles have the trademark prairie dress look, just on a shorter scale. On Kendel: Loveriche wine floral mini dress, $44, from Vinnie Louise | On Brooklen: Misa floral mini dress, $348; beaded lips handbag, $60, from Posh


Fashion Editor: Milton White, The Fashion Office
Photographer: Preston Long
Photo Editor: Leila Grossman
Models: Brooklen Wilkes and Kendel Joy of Tribe Talent Management
Make-up Artist: Brianna Rice
Fashion Assistant: Nemo Renwick, The Fashion Office
Location: Grand Hyatt Hotel


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