The best way to update the rectangle headdress is to simplify it. Think of it not so much an extra place to add some more lace to a coordinate and more of a fancy headband. Whether you are making one yourself, or in search of the perfect one, make sure it's a relatively simple one. Avoid any gathered lace or ruffles around the hem or any extra large bows on it. If your headdress has ribbon ties consider tying it behind your neck instead of under your chin, or even stitching it onto a stiff headband. Try to find a very thin headdress, no more than about 2 inches wide, nothing that takes up your whole head! Below are some good examples of very up-to-date rectangular headdress.
Victorian Maiden is very simple. It's merely a thin strip of matching fabric with a tiny lace trim and a small ribbon. It's also on a headband base so you don't have to worry about tying it.
This velvet headdress from Innocent world is a bit wider, but since it doesn't have any lace or a ruffle around the end it can easily get away with it. It has a pretty strip of matching lace across it to give it some elegant details. It's also on a stiff headband.
Antique Beast made this headdress, and while it is extra lacy and even has bows on it, the lace lays flat against the head so it doesn't end up looking like a maid headdress.
Ebay shop, on the right is a Mary Magdalene headdress worn by this particular Japanese blogger. It's hardly a fair comparison! The Ebay headdress is awkward and goofy looking, while the Mary Magdalene one is simple and classy. These two headdresses are worlds apart in terms of style and quality, so it's not very hard to simply avoid the headdresses of questionable taste and find (or make!) something that is much nicer. While I don't know if the headdress is going to be coming back in style, it's certainly not something you should write off completely. I think that the right rectangle headdress can make the perfect finishing touch to a Classic or Gothic Lolita outfit.
These are a whole bunch of Mary Magdalene headdresses and hair accessories. I think these are pretty much the perfect rectangle headdresses! They are slim, simple, and yet still elegant and pretty.
One of my favorite things about these thinner, less ruffle covered headdresses is that you don't really need to style your hair around them! The thin and flat headdresses look just as nice with nicely brushed hair as they do with an up-do. Which is great for the everyday (or nearly everyday) Lolita, because sometimes you just don't feel like doing much with your hair besides running a brush through it! The extra ruffly headdress, on the other hand, usually needs at least pigtails to make it look a little less awkward.
What do you think about the rectangle headdress? Do you pretty much hate it no matter what it looks like? Or are you willing to make an exception for certain styles. Back when I first got into Lolita I had a couple rectangle headdresses and they always felt very awkward to wear, so I simply nixed the head accessories altogether for a few years until head bows became more prevalent. But, back then, many headdresses were much rufflier than these delicate head accessories that Victorian Maiden and the likes are offering up for sale, and I can definitely see myself getting more into this style of headdress, especially if it comes on a headband so I don't have to worry about accidentally tying my hair into the bow! Now that I have a shiny new sewing machine (that actually works for more than a couple inches of stitches at a time!) I plan on trying to make a couple slim rectangle headdresses. I'd like to try to make one in maroon with cream lace, and an all black one, because I think these would go very well with my wardrobe.