Everyone has a fashion blind spot. Mine, generally, is shoes (and bags, but I’ll save that for another post). The problem is that, like some Amish farmer, I believe that any shoes that I buy should go with everything in my closet, and they inevitably never do. So I don’t often buy them. I have friends that buy different shoes for almost every outfit. I admire that kind of commitment and attention to detail. But I don’t have the space, and I need that money for jeans. So I always try to find shoes that will work in lots of different contexts.
In the summer I wear one pair of shoes: my Birkenstock Gizehs (in Golden Brown). Go ahead and mock them, but understand this: this shoe goes with everything you could possibly wear when the weather is warm, with the exception of bridesmaid dresses. I buy a new pair every couple summers and call it a day. But during boot season, it’s a lot harder to get away with one pair, especially because boots come in so many tempting variations. I think I’ve worked it out, and have found four pairs of boots that I have been wearing with everything this season. Best part? The styles are relatively timeless, so I imagine I will be wearing them through this March, and the next.
The Clog Boot
The clog boot has been going strong for a few years, and given the monetary investment involved, it’s a good thing they’ve stuck around. The thing I like about them is that the wooden platform lengthens your leg but is way more comfortable than a traditional heel, which raises the back of your foot and puts all the pressure on your toes. That’s not to say that they are comfortable. If you want to approximate the sensation of walking in clog boots, I suggest tying your feet to a couple bricks. They also come with ridiculous instructions, including the suggestion that you not walk in them in the rain, and that you re-adhere (using superglue) any wood chips that you inadvertently knock out of the wooden soles. In other words, they are a stealthily high maintenance shoe. But I like wearing them a lot, especially with flowy skirts, for the contrast.
The Chukka Boot
My friend Jack does something related to basketball at Adidas–I’m still not sure what–but I know that whenever I see him, I like what he’s wearing, and even better, he looks like he hasn’t put too much thought into any of it. Most of that, I attribute to his shoes, because he, like me, lives in his Clarks desert boots.
I have two pairs of these, and they are beyond beat up because I wear one color or the other almost every day. They have single-handedly ruined my feet because they have zero arch support, but my feet are a small price to pay for a shoe that goes with every pair of jeans and cords that I own. If you believe that you only look good in heeled shoes, nothing I say here is going to change your mind. But I would urge you to give these a try. The cut of them is extremely flattering because they stop right below the skinniest part of your ankle. For some reason, these boots seem especially flattering if you wear your pants short, like me.
The Riding Boot
I am finicky about knee boots in two regards: I don’t like a lot of metal, and the shaft height has to be exactly right. The gold buckles on the pair here are not my favorite, but they do make it easier for me to dress them up for work. If you have any muscle in your calves, as I do, be careful that the shaft of the boot covers up the widest part of your calf. Otherwise, the boots may give the illusion that your legs are thicker than they are. The pair here have an 18″ shaft, which is about 4 inches taller than most knee boots. The red zipper is totally a bonus. I love them. I wear them with sweater dresses and minis, like the buffalo plaid one here.
The Shearling Boot
My impression about the Gap these days is that the less interesting their clothes become, the more interesting their shoes get. For years, the Gap produced ballet flats and other seasonal shoes that you wouldn’t expect to last more than a year. Recently, though, they’ve been coming out with cool boots in real leather. They are also priced like real leather, but I also feel like I’ve never been to the Gap when all their merchandise isn’t marked down 30%. My feet get cold in the winter, but I have resisted Uggs this long and have no intention of caving now. These are a good concession–they have the shearling but the silhouette is refined enough that I can wear them with my skinnies and skirts.
Take care of your boots and they will last you a long time. I cover mine in all-weather spray, and am religious about sticking boot shapers in my knee boots, to prevent folding of the leather. My favorite pair of Fryes are four years old and look pretty new, thanks to those boot shapers.