shit i bought and liked no. 57: the perfect boots

My sweet shitters,

I’ve been on a one-woman quest over the past year to find the PERFECT black Chelsea-ish boot, and after a number of failed online orders/attempts, I finally found a pair that fits every one of my extensive requirements.

Some of you might be thinking… ‘what are you saying, there are zillions of black boots out there, how could it POSSIBLY take you this long?’ Well, my inquisitive friends—there are many a variable that goes into a boot style, and I was simply unwilling to compromise on any of them. And lucky for all of us, I can now report back highly confident in my selection. What I had in mind was a simple, everyday black boot with a few non-negotiables:

First, they had to be a black leather or faux leather. No suede. No patent. None of that rubbery rain boot material that can look like a Chelsea boot at a distance. I wanted a low maintenance material/finish that would look good with my everyday wardrobe (mostly jeans). 

Two: I wanted a little block heel. Not too high! Still super walkable! But not a 100% flat boot, because I wanted these to work for both casual wear and going out. Speaking of which…

Three: They couldn’t be too expensive. About five years ago, I made my first big shoe purchase (aided immensely by Cyber Monday). It was this pair of black Rag & Bone boots (now mostly sold out) and they were amazing. They’re made of this gorgeous soft lamb leather and I LOVED wearing them, as evidenced by the very beat up state that my pair is currently in. But wearing a shoe that nice and that expensive out to a bar after work or on the weekends gave me major anxiety. So this time around I wanted a boot that I felt a little less precious about—that I could walk into a crowded bar or place in and feel totally ok, both in terms of durability and money I spent on them. 

Four: They couldn’t be too clunky. Obviously I have to walk around in them, so I didn’t want them to be heavy. But I also didn’t really want a chunky look. Super chunky boots are definitely in right now, and if I had an endless amount of money I would certainly be buying these amazing Prada boots, but because that is not my life at this point in time, I wanted something that could outlast a trend.  

Five: They needed a round-ish toe. The Rag & Bone boots had a gorgeous almond-shaped toe, and I spent a few years in these pointy Marc Fisher boots as well (comfy and definitely durable if you’re in the market for a pointy, flatter boot). But over the past couple years, especially as I started wearing more straight leg jeans, I’ve found myself liking a more rounded toe, so I didn’t want to compromise on that. 

And finally, six: They couldn’t look stupid around my calves/ankles. This might be the most individual of the concerns on my list, but my biggest gripe with most Chelsea boot variations is the “shaft” (that is literally the word, I don’t know how else to describe it—lets all move on without comment). I found that most boots I was trying either cut me off at right at the ankles, or that the opening around my legs was too wide, which made me look like I was wearing clown shoes. I wanted a pair that hit a little bit higher and had some kind of tapering so they didn’t look super clunky. 

Oh wait, I have a seventh—they obviously had to be comfortable, but that should be a nonnegotiable for pretty much every shoe you’re buying.

That is SEVEN big things that made this search COMPLICATED, but I finally found a boot I love that checks every single box—this pair by Steve Madden (additional sizes here).

Now, before you freak out about the strap, know that it’s REMOVABLE, which is great if you’re going for a more classic look. But I will say that the strap looks better on than I thought it would, and is a fun option to have even if it’s not your everyday style. 

I have to be honest—I didn’t find this pair on my own. I saw my friend Nikki wearing them last year and loved they way they looked on her, but I didn’t think they’d really be up my alley because of the strap. But when I came across them again this year and realized they were removable, it was a no brainer purchase. 

The boots are a classic black vegan leather, and lightweight with a clean silhouette. Again, the strap is totally removable, so you have options. They give you a little boost with a two inch block heel, but are still comfortable to walk around in or wear for long periods of time. They work with my normal outfits and nicer ones, and they’re not wildly expensive or too delicate to wear in a crowd. AND they taper slightly at the ankles, so they look great with cropped jeans and hemlines. What more could you ask for?! (They are a very good dupe for this pair by Gucci, which you can definitely buy if you feel the need to spend an extra grand for the logo, but just trying to save you a few bucks.) 

This is a relatively new purchase, but the break-in period hasn’t been bad. You can add your own insole if you’re looking for something more cushy, but they’re not uncomfortable on their own and run true to size. 

While you’re out shopping, I did want to put Neiman Marcus’s very good spend more/save more sale on your radar. Normally I wouldn’t care too much about a Neiman’s sale, but this one includes some very high-end beauty brands that don’t normally get discounted (Jo MaloneLa MerAesopNarsDiorBarbara Sturm, and more). I’m on still on the hunt for a new signature scent after the powers that be reformulated my beloved Si, but if you already have a go-to, it’s worth using this sale to restock (and send me some suggestions while you’re at it—currently back in the exploratory “I must sniff everything” phase). Linking some other sale picks for you right here.

As always, if someone sent you this newsletter or if you’re reading on the site, you can sign up for real at! Also, check out the archives! We are 50+ emails in, and from straight leg jeans to back massagers there are lotssss of good things in there. 

Hope you love the boots as much as I do!


This search took a whole year—ofc these are affiliate links!!! It is always very appreciated when you use them! 

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