Contrary to popular belief, a short girl CAN wear a long maxi dress. The term maxi has been used since the late 1960s to describe ankle-length, typically informal dresses.
The petite Nicole Richie is a testament to that. I am pretty tiny (standing only at 5 ft. and at 90 lbs.), but I have learned a few tricks that have allowed me to wear long dresses without being engulfed by them. All you have to do is follow certain guidelines:
Style Strategy #1: Embrace Solid Colors or Monochromatic Looks
Maxis with solid colors, especially darker ones, will definitely make a short person appear taller because they are slimming (thus elongating) and offer less distraction to the eyes.
If you’re plus-size petite, dark, solid colors are a must. But if you’re small and petite like Nicole Richie, you can afford to wear light, solid colors.
If you want to wear a color block maxi dress, make sure it’s monochromatic. Otherwise, choose maxi dresses with block orientations that will not cut you in half.
Recommended Choices:
Hayden Panettiere elegantly styled in a flowy, gray, strapless maxi dress for a lunch outing in Los Angeles, CA (Nov 12, 2008) / Pregnant Nicole Richie radiates in a white maxi dress at the House of Harlow Jewelry launch, Los Angeles, CA (Mar 7, 2009) / Lea Michele opts for a casual yet chic two-slit black maxi dress in West Hollywood, Los Angeles, CA (Oct 13, 2014) (Credit: WENN)
Styles to Avoid:

Style Strategy #2: Select Prints That Complement Your Size
Wearing printed maxi dresses is unavoidable because they are quite abundant. Make sure you pick prints that are proportionate to your size.
Believe me, it matters. If you’re thin and short, pick maxi dresses with small prints. Wearing a long dress with large prints will overwhelm your tiny frame.
If you’re medium-built and short, you can go for medium-sized prints. Now if you’re plus size and also petite, just go with medium prints instead of large ones (large prints are most ideal if you’re tall and plus size).
Avoid prints that are horizontally inclined because that will definitely shorten you.
Recommended Choices:

Styles to Avoid:

If you’re going to pick out a striped maxi, go for subtle, thin diagonal (45-degree angle) lines that are not as bold. Avoid wearing bold, repetitive horizontal or vertical lines.
Such will either cut across and make you look shorter or create the illusion that you are wider. Chevron prints can be just as bad as well.
Don’t get me wrong, vertical lines are good, but only when they’re not bold and repeating. For example, a single vertical line running through the center of a dress can make a person look slimmer and taller.
Styles to Avoid:

Style Strategy #3: Choose Flattering Cuts for Petite Figures
Generally, for petite women, maxi dresses cut closer to the body look flattering. Dresses made of soft and fluid jersey or silk fabrics cut on the bias are ideal. Avoid boxy, balloon, or tent-like dresses with extra stiff materials.
Pick maxis that accentuate the waist (whether it be the empire waist or your true waistline).
Empire-cut maxi dresses with soft flowy skirts work best in hiding tummy bulges and giving the illusion of longer legs (more height).
If you’re wearing a maxi that is belted on the true waist, make sure you wear heeled strappy shoes with the long dress to make your legs look longer (and you taller).
Recommended Choices:

Styles to Avoid:

Style Strategy #4: Opt for the Most Flattering Lengths
Again, contrary to popular belief, floor-length dresses will always work best for petite women compared to ankle-length ones, NOT the other way around.
Why? Well, once the hem of your dress touches your ankles, you will appear shorter whether or not you’re wearing heels because the hem is like a horizontal line cutting across. Do yourself a favor and avoid tea-length dresses as well (calf-length).
Recommended Choices:

Styles to Avoid:

Style Strategy #5: Select the Perfect Footwear
With the maxi dress already covering more than half of your body, it’s best to keep the feet open and sexy. Some people may tell you it’s okay to wear pumps with maxi dresses, but I’m afraid I have to disagree with that.
The best companion of a maxi dress is a pair of heeled strappy sandals. If you want to wear flat ones, go with thong sandals that show a lot of skin.
Recommended Choices:

Styles to Avoid:

Style Strategy #6: Elevate Your Look with Elongating Details
Vertical lines come in many forms. It can be a deep V neckline, a single vertical line running through a dress, detailing at the center, or even a long, deep V-shaped accessory around your neck. The idea is that a deep V neckline elongates.
V-necks are also perfect for plus-size or busty short women. One-shoulder (asymmetric) necklines are also flattering since they give the illusion of a slimmer silhouette.
Recommended Choices:

Halter necklines are also elongating. However, busty and plus-size petite women must stay away from them. Avoid maxi dresses with contrasting border details on the hem.
The borders will only make you look shorter than you already are. Also, don’t be tempted by dresses with horizontal panels.
Styles to Avoid:

Style Strategy #7: Accessorize Wisely
Avoid using belts in contrasting colors as much as possible because that would be like creating one horizontal line across your body and cutting it in half. However, this does not mean you can’t wear one.
If you want to wear a belt, wear heeled sandals (to compensate and balance out the loss in height). Also, pick a similar color (or almost the same) as the dress.

As long as you follow these simple rules, you’ll look maxi stylish for summer. Enjoy dressing up!