Honestly, I just don't think anyone cares that they look like a big balloon in Facebook photos. The trade-off is a chic, breezy and extremely comfortable summer ensemble, which allows one to put aside the obvious lack of shape that is part and parcel of most maxi dresses.
However, for a population that wears maxi dresses so enthusiastically, we rarely don maxi skirts, which are equally ubiquitous with "fashion people" this summer. They're one of those trends that just hasn't made it to the general population yet. Why?
For me, they are a reminder of the long, denim skirts with buttons down the front that my teachers used to wear when I was in, say, second grade. The early '90s weren't really fashion's best years, so I steer clear of this trend because the way I've seen it worn is much too "Little House on the Prairie" for my taste. (I also hated reading "farm books" in second grade, so I think it's safe to conclude that maxi skirts caused my first and only B grade in reading.)
It's a different time now, and I must say that the few maxi skirts I've encountered in real life have been pulled off swimmingly by their owners. They provide the same relaxed, "it's-summer-so-I-just-threw-this-on" look you get from maxi dresses, with a little more shape in the waist to make you look less like a blob.
1. If an elastic waist is necessary, it must be subtle.
A lot of maxi skirts come with an elastic waist. There are two types I can get on board with: a paper bag waist and a drawstring waist. A paper bag waist has a slight ruffle atop the elastic, like a paper bag when you scrunch it together. This is very in right now, so it helps the whole issue of looking like you tucked a shirt into sweatpants. I like a drawstring waist because, unlike plain old elastic, it is adjustable. It gives you a better shot at hiding the stomach pooch that will inevitably show if you go with pure elastic.
2. Flowy fabric is ideal.
What is the point of wearing a long skirt if you can't twirl in it or wave it around? Jersey fabric is okay, but if you want a skirt that is snug all the way down, a midi skirt is the better choice for most body types. A maxi skirt, on the other hand, is great in a fabric like silk-chiffon, which can be voluminous without being bulky.
You may also want a look that's not as flowy, and for that I'd suggest a thicker fabric like linen or heavy cotton ... something that is not super tight but will keep its shape.
3. Make sure you can walk.
Your legs are not going to have a lot of wiggle room if the skirt isn't flowy or it has a constricting slip underneath. Side slits may be necessary as long as they're not too high.
4. Style with a casual top and possibly a belt.
Long skirts are inherently formal, especially in fabrics that are nicer than your average cotton. It's the perfect time to wear a chambray shirt, or even a plain, solid-colored T-shirt. All should be tucked in, lest you disguise your waist and end up as a blob despite all your extra work of finding the perfect maxi skirt. A belt is a nice accessory here, especially in the case of an elastic waist.
5. Be careful with heels.
Again, this can look too formal if you're not careful, so wedges or very chunky heels are the best choice if you need some elevation (which you likely will if you're short). Otherwise, a flat sandal is the way to go.
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