Style Stories

A good winter vibe: classy with a touch of ugly

A balance to strike when you're getting dressed
by Leandra Medine Cohen
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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.

A few good pairs of corduroy flares. And here are some Prada creepers from Poshmark in silver if you wear a size 7 and woah, another pair here for $94 if you’re a sz.10

This makes them a good foil to set up an ideal contrast to work clothes or an outfit that is classically pretty.

And Daughter cardigan, BITE grey t-shirt (this is the same one in white; and as an aside, I love these jeans too), Vince black sleeveless turtleneck (on sale here for $84), Pallas pants (but I defer to the above close-up for alternative options), and these ($990) loafers from Tod’s recently landed…

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.

A great Paco Rabanne chain bracelet, and here are some good pearls for you from Etsy

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.

Khaite dress, Delarge sunglasses, The Row boots (these scuba style ones work too but I actually think it’s these Toteme ones that accomplish the same thing as the pictured ones because they’re wide in the front with a durable but refined sole)

Sophie Bille Brahe earring (these from Etsy are smaller, but a similar vibe), Caro Editions hair clip

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.

Here is a great Prada coat I got from The Real Real for under $350 in November. Wearing a knit polo with it and a very dramatic confetti skirt — here are a few fun alternatives to it, and some brown lace-up boots to boot boot boot.

Here are some black Oliver Peoples sunglasses for $95. Green lenses, vague cat eye, hard recommend!

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.

Chanel jacket (or), La Ligne striped shirt (but just got and rec this one if you’re looking for a rigid standalone), Emi Mess pants (like these from Sandro with an elastic waistband or these for a straighter fit), Loewe lace-up loafers but any pair of geriatric-ish shoes do the trick here. Like even these. Maybe especially these.


Carlota Cahis hat, Delarge sunglasses, more pearls 4 u, Patou skirt and I still do really like these groovy Khaite clogs (and these suede Paco Rabanne ones for $262 would be better with tights on account of the suede)

Toteme sweater, New Arrivals skirt (this one’s a dead ringer, and I like the shape of this one for under a big sweater for $67 too), Khaite bag

Siedres sequined shirt (surprisingly into this one from Elie Tahari), New Arrivals jacket (this one’s alert the media good), Soeur Paris khaki pants, The Row brogues (another very good Real Real find, the interior says “Fall 2014,” they must be from one of the first shoe launches)

Jenny Walton hat, Delarge sunglasses, the gold chain I’m wearing is actually a necklace and a bracelet clipped together, this is more a cardigan than a jacket but I like it for the same purpose; then this guy is not black but it is FUN), the pants are Giuliva Heritage and the clogs are Fabrizio Vitti — love the black patent band separating the brown suede from the wood but not nuts about the floral appliques that you can’t see. I rec these for a suede clog

Or most casually imagined:

Delarge sunglasses, Tory Sport dickie (here’s a tamer version), Toteme quilted jacket (any iteration on a quilted collarless number works, but the above one is on sale for $377 in brown here), Frame jeans (the shape is called Le Jane), Margiela tabi flats

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:

Jenny Walton hat, Ciao Lucia jacket, this is a good red turtleneck, Nagnata red pants, The Row navy blue loafers (if you like them and are a size 8, get this color; it’s basically denim blue so will work well with red, army green, striped, white — basically color you wear your true blue jeans with)

Big weird slacks! (Similar vibe.) Fun shoes and a mens v-neck by Maryam Nassir Zadeh (the long sleeve one looks great too)/shirt from Commes des Garcons. Very easy to replicate with a plain button down (peter pan collar or not) and some velvet string (like from wrapping or whatever)

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 directionality 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 breakdown that appraises 5 different pairs (all linked in some place above) of “ugly shoes” that I am particularly drawn to.


Lucca Studded Leather Clogs
$464 USD
Best with flare-leg pants that graze the floor. Also good with skirts that hit above the knee.
Boston Leather Clogs
$200 USD
If the wood sole is not your thing, implicit in this recommendation *is* the classic Birkenstock clog, too.
The Row
Town Leather Clogs
$285 USD
These are good too.


The Row
Rubber-Trimmed Scuba Ankle Boots
$387 USD
Good for straight leg pants, mid-length skirts or dresses with my preference coming in hot for like, a tailored suit.


Leather Platform Loafers
$995 USD
These serve a similar purpose to that of the clogs, so I’d recommend one or the other, not both. Best with flare-leg pants, skirts (or dresses) that end above the knee. Also nice with a tank top and tapered trousers.


New Balance
WW577 Hook and Loop
$85 USD
The riskiest recommendation of the loot! These are good with skinny trousers, straight leg pants, refined jeans...
Blue London Pintuck Jeans
$330 USD
Think raw denim or a pair like these. I like the idea of wearing the sneakers with flared trousers, or on the weekend with knit trackpants/leggings and socks pulled over them too.


Maison Margiela
Brown Tabi Ballerina Flats
$331 USD
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.
Maison Margiela
Green Tabi Mary Jane Oxfords
$890 USD
I do like these too…
Maison Margiela
Green Tabi Ballerina Flats
$366 USD
My preference is the satin because of what it does to a pair of wide-leg jeans or cotton gabardine trousers. 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).
Maison Margiela
Green Tabi Ballerina Flats
$436 USD
Leather might be a better choice if you plan to wear 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,