
Many of you are probably wondering what all the fuss is about. After all, have midi dresses ever really gone out of style? Well, yes. And no.
Like bootcut jeans and mockneck sweaters, they had moved out of trend category and were in classic category, where they have remained for years. And women continued to wear them, undeterred by the whims of fashion. And now they’re all back.
And many of them look suspiciously like the “tea length” Laura Ashley dresses I wore to sorority rush back in the late 1980s. They feature the same ditsy florals, oversized collars, and lace embellishments as before, but with a twist.
Many of the current iterations of this look are faded. Worn.
These latest dresses look like they’ve experienced one too many braid-tossing jaunts across a prairie.
I’m pretty sure fashion brands do this just so we can’t pull out our vintage pieces and pass them off as new. There is always going to be a detail that dates the previous version of a trend.
If you’re not into the whole cottagecore, prairie-esque vibe, don’t dismay. The other crop of current midi dresses looks like they were swiped from Jane Fonda’s character in 9 to 5.

Little House on the Prairie or 80s secretary. That’s it. Those are your options. 🙂
Fortunately, somewhere between these two extremes is a whole category of dresses that are modest yet chic, flattering yet practical. And here’s how to find them.
Show Some Skin
The mididress is hardest to wear, and least flattering, when it covers you from collar to calf, and shoulder to wrist. Since these dresses are, by definition, midi length, you’ll want to add flattery with an open neckline or a shorter sleeve.
Both of these dresses are in faded, potentially frumpy brown prints.
The details make the difference between a dress you wear and one that wears you.
NM
Find a Good Length
When you’re eying dresses that hover treacherously around the mid-calf area, you need to choose wisely. A dress that ends at the widest spot on your calf will make you look shorter and wider, so shoot for a hem that hits above or below that spot. Looking for the exact best length for dresses, tops, etc? Check out the Fashion Fit Formula.

Choose Flowy Over Stiff
A dress in a stiff and structured style will be more tent-like and harder to wear, while one in a gauzy, silky, or otherwise flowy fabric that drapes over the body will be much more flattering.
Even though it has an uneven hem and a lot of fabric, the fluid nature of this dress, along with the flattering neckline, short sleeves, and waist definition, make it a flattering choice. The stiff fabric of this dress creates a tentlike effect, especially when paired with a high neckline and boxy sleeve.
Keep it Consistent
The most flattering midi dress is one that features a consistent color or pattern from top to bottom. This style is hard enough to wear without breaking up the eye further.

Wear Flattering Shoes
The ugly shoe trend is still going strong, but the midi dress isn’t your best bet to pair with it. A challenging dress requires very flattering, leg-lengthening, and contemporary shoes to look its best.
The choice of shoe makes a huge difference in these outfits.
A clunky sandal with a mididress creates a heavy, unflattering leg line Skip the dad sneaker with the mididress A sleek streamlined sandal is a flattering choice for a mididress
Keep it Modern
The best mididresses look fresh and contemporary, so skip styles that are overly classic/timeless, or those that have a strong retro feel. Both will look off and potentially frumpy.
This print and silhouette of this dress make it classic and a little stodgy. The details and silhouette of this dress make it quite retro, and a little too costumey for everyday life. A simple midi in a contemporary cut and color is going to be the most flattering choice.
Show Some Shape
Many of the trendiest midi dresses are shapeless, making them even harder to wear in a flattering way. Instead, choose a silhouette that flatters yours, with a defined waist and fitted bodice.
This dress is boxy through the torso, with a high neck, making it harder to wear. The V-neck, fitted bodice and short sleeve of this dress make it very flattering.
As always, you can shop my favorite versions of this trend (and many other trends!) in my 2021 Trends Catalog.
Nada Manley says
Thank you so much Carolyn! I really enjoy doing it so I am so glad you like it as well! I appreciate the comment!
Carolyn Caylor says
Nada, I’m so glad you include a print version of your blog! I don’t have a handy way to listen to audio now but can read your blog quickly and it’s always helpful! Thank you, Carolyn