Special Feature by guest columnist: Bonnie Bennett

The Fashion Police Is Here: 4 Styling Mistakes to Avoid When Wearing Maxi Dresses

Every year, maxi dresses come back into shops with more styles, colors, and fits than the year before. Once a trendsetting item, maxi dresses have found their place firmly as a spring, summer—and even fall—staple. Before the popularization of the maxi dress, it would have been downright odd to go for a stroll wearing a full-length dress, but those days are long gone. You’ll now see maxi dresses everywhere from beer gardens to first dates, to nights on the town.

What we love about maxi dresses is how accessible they are. They can be dressed up or down, they work in almost any setting, and for almost any body type, and they come in such an incredible array of cuts, shapes, fabrics, and sizes that it’s downright impossible not to find one that works for you.

Unfortunately, that doesn’t mean you can’t make fashion mistakes while wearing a maxi dress. Like any item of clothing, there are still plenty of ways to wear maxi dresses that won’t be flattering.

Here are the four most common styling mistakes we see when wearing maxi dresses:

No waist definition

We love how comfortable maxi dresses are, but that doesn’t mean you should wear them like an oversized bag. Having waist definition is still key to looking put together and stylish, and not like you just threw on a potato sack. If your maxi dress is looser than you’d like, belt it to add definition.

The wrong length

Maxi dresses are called that for a reason, so don’t wear one that looks like you’re getting ready for a flood. It’s fine if your maxi dresses aren’t grazing the floor, but if it’s at your ankles or higher, you’re committing a fashion faux pas. This odd, in-between length will make it look like you outgrew your clothes. This also goes for short girls dragging their dress hem in the dirt. If it’s too long, get a tailor to hem it. It’s cheap and will prevent you from looking like you stole from mom’s closet. If you can’t seem to find the right length, contact Filly Flair to find the perfect choice.

The wrong bra

The right underwear is key for any almost any outfit to work. When it comes to maxi dresses, the fabric and fit are going to dictate what you’re wearing underneath. Body-hugging jersey needs seamless underwear for no bulges or bumps, while spaghetti-strap dresses should be paired with a supportive, strapless bra. If you’re larger in the chest and can’t find a strapless bra that works, opt for maxi dresses with cap sleeves or wider straps to conceal bra straps. Also, it’s best to always go for nude underwear or black with black if the fabric might have a tendency to be sheer.


Maxi dresses may be great for all occasions, but they are still pretty attention-grabbing. For this reason, you want to avoid loading on the accessories. If you are wearing accessories, opt for a maxi dress with no patterns, in one color. For spring, we like to layer ours with a jean jacket and an infinity scarf for a pop of color.