I chose this featured image because it is ridiculous. I can just see the envision the photoshoot:

“Hmm, how are we going to make this floral dress look more autumnal, Bob?”

“Oh, I don’t know, Sally. Is a pumpkin too on the nose?”

“Maybe. Here, how about we put this stalk of wheat in her hands?”

“Great idea, Sally! Who wouldn’t hold a stalk of wheat while wearing a dress?”

Does anyone remember those old Wendy’s commercials depicting the Soviet fashion show? “Svimwear!” and the lady came out in the same dress only she was holding a beach ball? The eveningwear with the flashlight was probably my favorite. That model holding the wheat reminded me of that commercial.

Few think of florals in the autumn. Flowers are spring things when the world is blooming again after a long winter. Floral shades are rarely considered fall colors and during colder months, we’re often searching for deeper, more carnivorous, patterns and textures. Of course, any florist or landscape architect will tell you there are plenty of autumn and winter-blooming flowers but for all intents and purposes, people most commonly equate florals with spring and summer.

As if fashion isn’t confusing enough right now, the stores are stocking up on floral dresses as far as the eye can see, and when you shower any retail floor with a bunch of different florals it turns into a mishegoss of pattern that can be overwhelming to navigate. Add to the fact that many of these floral dresses have been cut into what looks like survivalist off-the-grid bunker clothes or something Laura Ingalls Wilder wore to pen her book series, there’s a lot of ugly to sift through.

But it isn’t all bad and some of it is quite nostalgic. If you remembered the commercial I referenced then you probably remember floral dresses of the ’90s. Those Blossom-esque styles that were free form and we styled with things like combat boots. I was scrolling through Rent the Runway looking for a dress recently and I was shocked by how many floral dresses I encountered that were very reminiscent of my younger years. It’s true, what is old is new again and I had to remind myself I’m nearly 30 years older than the last I wore dresses that looked like that. Needless to say, the dress I rented did not have a flower anywhere on it.


Beyond the survivalist bunker, prairie, 90’s-Blossom floral dresses, there are some gems out there and despite my often general distaste for floral prints, when they are in beautiful, rich, autumnal shades, even I don’t find some of them offensively ugly. I have put together five autumnal floral dresses that have been styled for work, depending on the workplace dress code, and have added more styles to shop at the end of this post.

Outfit #1

autumn fall floral dresses

You can call this autumn floral dress from Cara Cara boho or hippie or even something that looks like what your Holly Hobby doll wore. The print itself is stunning, the shape…I’m still wrapping my brain around. It’s relaxed and easy, which is nice but it also has a ruffled bottom. Of course, it’s all in the styling and edging it out with this pair of tall cognac boots, like this pair from Lucky Brand helps make the dress not look like you are a four-year-old dressing for a birthday party in the ’70s. I finished the outfit simply with a pair of hoop earrings.

Outfit #2

autumn fall floral dresses

You may want to add a floral dress for work to your wardrobe this fall but also don’t want to look like you just stepped out of a time machine back from Woodstock. This style from Reiss has a nice shape and a professional look while still being on-trend. I finished the outfit with chestnut block heel pumps from Marc Fisher and crystal-studded huggie hoop earrings.

Outfit #3

autumn fall floral dresses

A lot of the autumn floral dresses in the stores are super short and are a carry over from summer where we saw a lot of this profile. For fall, it’s being paired with opaque tights and usually flat boots or booties. I styled this floral dress from Cinq à Sept with navy opaque tights, navy booties from Aquatalia, and teal drop earrings from Kendra Scott.

Outfit #4

autumn fall floral dresses

This autumn floral is in a classic shirtdress style from Tory Burch that makes it an easier silhouette to wear. The shoes you select can vary from flats, and heels to tall boots. Booties also work well but they come with a caveat. First, speaking of Laura Ingalls Wilder, if you wear them with nylons, they can look very prairie and even tights can look a bit odd with a longer dress and booties. You’re best off wearing booties and a dress with bare legs unless the booties and tights match. I styled this dress with cognac flat booties and a chunky blue aluminum necklace.

Outfit #5

autumn fall floral dresses

Lastly, the most go to work-y looking autumn floral dress from Julia Jordan. It’s a classic silhouette simply cut in a beautiful autumnal floral print. I styled it with vicuna pumps from J.Crew and emerald earrings.

Shop for Fall Floral Dresses