What I'm Wearing

The holiday winter edition

We have reached the point in the year where I do not know what day it is. That is simply not my problem. I will show up to work when needed, and otherwise, the days don’t count. I ate a Twix bar for dinner and Hostess Donettes (plural, like half a bag) for breakfast. And yes, I ate said breakfast in bed. (I have a green juice in the fridge, mom.)

Breakfast of champions.

I have watched a hell of a lot of TV (Heated Rivalry, great. Stranger Things, bad.) I have spent a hell of a lot of money (mostly on 1960s Christmas ornaments. Obviously.) And I have done what I do best - played dress up in my living room to an audience of one - my sister. She thinks I am ridiculous; I think I am fabulous. The jury is out on who is correct. But regardless, fabulous or not, I have put on some outfits. And here I am, in your inbox, to share said outfits with you. No, I do not have occasions for all these outfits. I wish I did. But I am also lame and spend most of my New Years Eves at home in bed. (I do have plans this year. I will likely be wearing sequin booty shorts. Outfit included below for those with curious minds and open hearts.) But I have a few days off this week, a whole lot of looks, and a plan to actually leave my apartment. I may go to the theater. I might even go to Rockefeller Center to witness the tree, and inevitable traffic jam, even though I know I will hate every second. The world is my oyster. And I have prepared enough outfits to also make it my runway. Also - apologies for the low quality photos. It’s been cloudy in Brooklyn, and my living room lighting has been abysmal. I tried my best. And additional apologies for the sheer level of unhinged this dispatch entails. Like I said, it’s the end of the year. And I am nothing if not a comedian.

So let’s dive in.

Starting off on an unexpected note - Kendall in a mini skirt? Alert the presses. I picked up this Alexander Wang skirt at Goodwill last year, and never wore it. I’m not a mini skirt girl. But, I bought these Jimmy Choo boots on an angsty walk home, and wanted to show them off. So we needed leg. No, I didn’t just stumble into a Jimmy Choo. I was having a not-so-good day, and stopped in at 2nd Street on my walk home from work. I know we aren’t supposed to buy things when we are emotional, for self-regulation purposes and what not, but every once in a while, I fall victim to dramatics. I have never claimed to be a saint. So, in about three minutes, I spent just under $150. And I stand by the fact that it was a good idea. And apologies, I cannot find these boots anywhere on God’s green internet. I swear I tried. This is the closest I was able to find.

The old Kendall would have paired her grey skirt with a grey jacket and black shoes. But, I am evolving. I am embracing new color combinations. So, I opted for grey and brown. Shocking, I know. I threw on my vintage leather bomber and some brown tights. I have been really leaning into the not-black tights of it all. I buttoned that jacket all the way to the top (reference below) for maximum funnel neck function.

Buttoned to the TOP.

I did not stop there. My grandma passed down this mink hat to me a few winters ago, and again, I had never worn it. This is the year of wearing things, I guess. I am a baseball hat girl until I die, but this winter I have really been trying to branch out to other silhouettes. I’ve worn a pillbox. Now, I am wearing this mink thing with a built in scarf? I think? I do not know the name for this type of hat. I do love this option, and this with a matching collar. To top it off, I added my Halston dupe belt - this time in gold. I actually got this for my mom for Hanukkah after she expressed her love for my silver version, but I obviously had to take it for a test run first. (If I find another on my eBay dives, you guys will be the first to know. For my Brooklynites, Consignment Brooklyn has a red & silver version in the store for $98.) And then I topped it all off with my vintage Ferragamo bag.

This, while a simple enough look, may be one of my greatest successes to date. I had this Givenchy jacket saved on my eBay watchlist for probably a year. No joke. I was going to treat myself one day, and then one day came, and tariffs had been put into place. And this jacket was coming from Japan. So, I left it in my watchlist, hoping that one day this hurdle to my dream would simply go away. To no avail, international trade wars stop for no eBay aficionados. And then, one day, after checking in on this supple leather delight, it was sold. I had a brief mourning period, like seven seconds, and moved on with my day. We were simply not meant to be. And then, maybe because I had been a good sport about it all, the universe turned in my favor. Blue Greene posted in a Substack chat that she was selling said jacket. I, not one to typically read all my Substack notifications with immediate urgency, slid into those DMs with the exigency and level of speed typically reserved for F1 racetracks and children running up basement stairs after turning off the lights. I would not miss out on this opportunity again. And so, with my fur coat on and Moon Boots laced up, I braved the first snow of the season, hauled myself down to Soho, and acquired my dream. (Everyone say thank you, Blue Greene.) I wanted to let the jacket speak for itself - I kept the rest of the look cool, calm, and casual (if you consider 7” platforms casual). The Solmar jeans make a repeat appearance (these aren’t the exact pair, but I like this option) - and as a 5’1” gal, I needed a bit of extra height. Enter, the loafers. I don’t think they sell this exact style anymore, but this is a pretty good alt. And I kept the accessories minimal - my saffiano leather top handle bag and my leopard pillbox hat. I wrote about both of them below, for anyone interested.

Moving right along - deep in my bones there is something that pulls me to menswear. Suiting, tailoring, wools. I like pleats, and I love box pleats. I especially love box pleats in wool. If you’ve been following along for long enough, you’ll know I also love Unearth Vintage. And so, I did my bi-weekly drop in to browse (and bother my sister. She works there now. I have a man on the inside.) This skirt spoke to me in a way that only my fellow vintage lovers will understand. It is perfect. It also only has one pocket because the closure is on the wearer’s right hip. I think that’s charming. Plus, it was $30. So I bought it. Here is a stunning option, a classic Liz Clairbore option, and a perfect Celine brown version (shop on eBay). I also recently acquired this satin fringe belt from eBay. It is in fact falling apart. It will not survive another wear. Which is rude, but also, it’s from eBay. So I guess that’s on me. I’ll see if I can revive it, but it’s tearing along the grain. And then, simply because I could not figure out how to get it to stay in place (it has a hook and no eye. I guess I could have added a chain loop, but I’m lazy) I added my Halston-esque belt (yes, this one is mine) to hold everything together.

This outfit is more in line with my traditional grey styling - grey on grey on black on white on grey on black. Ya know? This sweater is an old acquisition - I have no idea where or when I got it. (Here is the exact option, a great alt here (shop on eBay), and I’m kind of in love with this option.) But I liked the sporty undertones paired with the crisp tailoring of the skirt. And then to make the horizontal stripe feel intentional, I added some sporty striped socks. Again, I don’t remember where I got these. I wanted a chunky sole, but wasn’t feeling my lug sole Prada loafers. I then remembered my Stuart Weitzman Jesper oxfords. I have had these tucked into my shoe rack for years - I bought about seven pairs for my senior year runway show, and they are still in my mom’s basement. (She keeps reminding me. If anyone wants a pair, I have many.) These shoes felt more elevated than the chunky Prada loafers. And I finished it off with the same leather bag.

A quick departure from the full looks to show off my new jeans. I hemmed and hawed over these Still Here jeans for months. Was $300 a sound financial decision? In this case, yes. I live in jeans. I love in jeans. I laugh in jeans. And so it made sense to invest in good jeans. And these are really fucking good. They are already stretched out, but the fact that I prefer to sit like a pretzel may be a contributing factor in this development. If you saw me on Metro North this weekend, legs folded up like Shane in Heated Rivalry, no you didn’t. Mind your business. Carry on.

Never let them know your next move.

As much as I love dressing up for Christmas dinner, I simply did not have it in me this year. So this is what I wore to eat steak and potatoes. Also, my dad thinks my holiday outfits are dramatic anyway. So casual it was. The loafers are JCrew from last year, and they have finally molded to my feet and no longer set my soles on fire. (Get it? Because I have flat arches.) I think something more along these lines would have been a better purchase.

I was going for a vampire Lestat meets grandpa meets 70s dive bar, however, I’m open to criticism on that description. These pants were one of my most anticipated fall purchases - unfortunately, ordering vintage online doesn’t always work out. I double checked the measurements, and yet, upon arrival, they did not fit. They may or may not be clipped to the gods in this photo. (I have many, many clamp clips in my arsenal.) But I still wanted to make a look because they need their moment to shine. (Feel free to message me for these pants, I literally cannot wear them.) Don’t worry, I did find another pair. I’ve posted about them, and I love them. But back to the topic at hand. As we know, oxblood and grey pair well together. And I never wear this blazer. It’s cut slightly too narrow and long for how I like my blazers to fit, but like many of us on Substack, I am leaning into new ways to style jackets. Meaning: brooches. So I pinned my singular silver brooch onto the waist, cinched that baby in, and called it a day. It felt boring still, so I threw on my vintage fringe shawl. A true hero piece if I’ve ever seen one. And to keep the rockstar of it all, I of course had to include a bit of animal and a lot of platform. The Guiseppes have yet to let me down. And that’s about it for this look.

This is looking like it will be my New Year’s Eve outfit. Nothing says Lower East Side bar like hot pants and a barely-there shirt. I just bought this top from Consignment Brooklyn. (Writing this post has made me realize that I need to be stopped. Budgeting will be so in for me in 2026.) But shirts, specifically of the warmer weather variety, are something I lack. So I feel justified in this purchase. I’m starting to think this Substack might just be a place for me to defend my poor money-management skills. But that’s a discussion for another day. I didn’t want to go with plain black tights, and I didn’t want to go with pants either. I just bought (again, help!) these Calzedonia tights (this was justified, they were for a shoot). And, although hard to see, I put on my sequin booty shorts. I am 100% sure these are a circus costume given the fact that they came with matching fingerless opera-length sleeves. May I propose these shorts if anyone is interested? And these gloves?

These are the shorts, for those wondering. I bought them for this shoot. And if you want to see the whole shoot, I’m still very proud of it. And then, because I ran out of ideas, I threw on my trusty black boots. Luciano Padovan forever. I finished the look off with my vintage silver lily & pearl statement necklace. It takes a lot of work to look like you didn’t try. I think this also reminds me of the time I was obsessed with Effie from Skins.

This outfit was everything to fifteen year old me, and genuinely shifted my perspective on fashion. I did in fact wear an outfit very similar to this to see the Foo Fighters when I was in high school. I don’t know what I thought I was doing, but it’s nice to know there is still somewhere deep inside me that never moved on.

I am slightly more practical than Effie, however, so I would be insane not to include outerwear in this ensemble. It is New York in the winter. Which can only mean one thing - I will be wearing fur. This is another Unearth Vintage find. If you saw me on the subway with this coat would you think I had sequin hot pants underneath? Day to night, amirite? This is an insane alt, and I also love this and this (shop on eBay).

We are nearing the end, I promise. On to the final look.

I imagine this is something I would wear if I worked a corporate job. Which I do, but in a fashion sense. I guess I could still wear this to work, but I have no boardrooms to strut around in, no client lunches to endure. I was inspired by my own Substack in putting this look together - if you missed it, here are all my holiday styling ideas, for your browsing pleasure:

This skirt, another recent eBay purchase, is going triple platinum in my closet at the moment. Have you ever seen anything so perfect? I nearly put it in the linked newsletter, but thought better of it (there are additional similar options to shop). I bought it instead. It was $20, I had to. And thank god I did. I know this will be a lifetime piece - leopard never goes out of style. Catch me at brunch in my leopard pencil skirt. Maybe I’ll even try it with my leopard heels and leopard pillbox hat next time. Or, maybe not. Only time will tell.

I’ve been loving cornflower blue and maroon at the moment (original, I know), so I started with these Calzedonia tights. And, as luck would have it, I happen to have a calf hair belt in the exact same shade of red. So, on that went. I still wanted a little extra detail at the waist, so I let the very top of my sequin shorts peek above the skirt. Still not sure if it works, but I had fun, and that’s what matters. To keep the look from getting too out of hand, I threw on my favorite button down - a striped Chaps shirt from Goodwill. I love this one and this one (shop on eBay). All the blues and reds were accounted for, but I still needed shoes. I needed to bring the white back into the look somehow, and like I always say, animal prints are a neutral. So, I slipped on my Guiseppe Zanotti zebra platform heels. This is the exact pair (shop on eBay), but I also love these, these, and these (shop on eBay). I think there is enough going on that the random combination of pieces actually makes sense. Kind of an in for a penny, in for a pound mentality on this one.

A moment for the details. Look at those textures. The colors. I personally love it, and as my own #1 fan, am very impressed with myself.

And now I’ve rambled long enough. I hope you enjoyed this journey as much as I did. I am hoping to send out more outfit roundups in the new year - less quarterly, more monthly. So please, feel free to give your two cents (or a nickel, because RIP) on these looks. And with that, I’m signing off.

Until next time,

K

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