A good winter vibe: classy with a touch of ugly
A balance to strike when you're getting dressed
When you’re cleaning your closet, do you ever find that you’ll relegate one thing to a giveaway pile over and over only to pull it out right before you send off the discards because something about giving the thing away doesn’t feel right yet? Sometimes it only takes until the next time I’m cleaning to finally part from it — and that does feel really good because one emotional quality I have been thinking about lately is how hard it is (for me) to let go.
I think I hold grudges — like even though I’ll forgive people or never even mention I was upset in the first place, I hold on to the intensity of the feelings that probably want to pass through me thinking that if I don’t, I won’t be able to write my own story. Access the experiences that define my life, that teach me the most meaningful bits to pass on and put words to the sum of it. But this is what my teacher would call an “image,” the sleepy mistruths we walk through parts of our lives not realizing are lies that we live by.
Occasionally though, I will also find that waiting to part from a thing pays off. Recently there’s been this pair of brown Prada loafers, which I have almost sold every season for the last four years but have pulled back every time. I think the reason they keep returning to my closet is because they serve a purpose that most of my other shoes don’t — they’re a formal loafer on the top with a sole that is part espadrille, part foam, and that gives them a quizzically casual, decidedly rough edge.
This makes them a good foil to set up an ideal contrast to work clothes or an outfit that is classically pretty.
Last Thursday when I was getting dressed, I realized they were exactly the foil I was looking for — the thing sneakers (casual), clogs (pretty ugly but still not right) or a refined boot (too prim w the rest of it) could not accomplish. This got me thinking about a good vibe for the season. It feels fresh even though it’s not new — a page pulled directly from Miuccia Prada’s playbook defined by the pairing of something classically pretty with a good dose of ugly.
The melding of exaggerated masculinity on one hand and femininity on the other. Both are so exaggerated that the two entities almost cancel each other out.
Classy is a modifier that is subjective but the way I define it (possibly kind of cynical) is like a little stuck up and compulsively put-together. Cardigans, pearls, hair set back with a headband that erases one’s hairline.
There are plenty of ways to strike this balance — it’s an interpretation on the discord I always dissect, one way for your own yin and yangs to play out.
Or most casually imagined:
The details of how the styling plays out, at least as far as I’ve been able to make sense of it, seems to indicate that the shoes are where the most give can occur. Or maybe that’s not exactly right:
But I am fairly certain that shoes are the easiest area to play with — this might be a function of how my own wardrobe looks: the extent to which my clothes are quite classic (partially a product of where we have been within the trend paradigm for the past several years), but philosophically, too, if you think about what shoes bring to an outfit, it’s the literal direction of where you intend to go.
They’re an anchor that can either ground you or blow wind into the dust of whatever else you’ve got going on — challenging the expectations or “givens” about what you are trying to convey, delivering something less expected and new.
I have been citing Prada as a style reference for no longer than the last two or three years and have been wondering whether this uptick in my interest relates to the phase of life that I’m in, where and when my self-definition has changed, how I perceive myself as a woman.
Of course it has something to do with the newfound emphasis on how the culture reveres her work too but if I spent the whole of my twenties and possibly even the earliest days of my 30s trying to anchor into an identity: looking for absolutes to ground my character, I’m much more interested in play these days. Finding the spaces where I can create little surprises that give a sheen of youth to growth without discounting or worse, disrespecting it. A nod to meaningful risk taking that is less like what your 20s are about as you barrel through exploration with a mind that is open and eager to let new wisdom through.
In your 30s, this genre of curiosity becomes sport: a self-possessed act of intention and confidence. That seems to be the real magic of Prada, of Prada and of growing up.
So classy with a dose of ugly — try it.
Here is a visually satisfying breakdown that appraises 5 different pairs (all linked in some place above) of “ugly shoes” that I am particularly drawn to, and right below is the clunky version:
The clogs: best with flare-leg pants that graze the floor (though flares that expose the ankle can work too — my only caution here is that the shoes typically cut you off in a weird place on the top of the foot; also good with skirts — I’d recommend something above the knee for the same reason I prefer long flares to short flares: it’s better overall for how your legs will look).
If the wood sole is not your thing, implicit in this recommendation is the classic Birkenstock clog. The only thing I’d say there is that it’s def better with pants than skirts. These are also pretty good, actually.
The sneaker boot: Good for straight-leg pants, mid-length skirts or dresses with my preference coming in hot for like, a tailored suit.
Serves as a good foil, too, on account of the rubber sole for the unexpected pairing of boot and delicate necklace to hit you right around breast line (see: pearls, gold chain).
The chunky creepers: These serve a similar purpose to that of the clogs, so I’d recommend one or the other, not necessarily both. Best with flare-leg pants, skirts (or dresses) that end above the knee. Also nice with a tank top and tapered trousers a la:
The geriatric Velcro victors: The riskiest recommendation of the loot! These are good with skinny trousers, straight leg pants, refined jeans (think raw denim or a pair like these). I like the idea of wearing them with flared trousers, or on the weekend with knit trackpants/leggings and socks pulled over them too.
Can’t wrap my head around how to make them work with skirts or dresses yet, but can see a version of reality where I’m endorsing them with fine calf-length socks and mini skirts once the weather warms up a bit.
The tabis: The most specific/niche rec., and also the most subversive because we’re talking about a ballet flat, which is actually quite refined a shoe shape. But the toe is split and fairly wide, so you get a good dose of ugly from these in perhaps the least risky way of the whole range. (I do like these too…)
My preference is the satin because of what it does to a pair of wide-leg jeans or cotton gabardine trousers (like the khakis shown above, or something like a pair of green cargo pants). I like wearing them with loose, long jeans rolled at the hem (as demonstrated further above). Also nice for mid-length dresses, skirts, and styled with various jackets (like the kind you’d wear as part of an outfit, as opposed to just to keep you warm). Leather might be a better choice if you plan to wear more often with non-denim trousers and I would definitely size up half a size bigger than your normal size because they run a little small, and if you’re going to wear them with socks, which you should, you need the extra room.
Okay, that’s it from me this week. Long live l’aisle du céréale,