Marnie text a photo of herself wearing a floaty midi dress and some chunky ankle boots at 11pm on a Tuesday night. Her caption: “verdict?? ?” By 11.47, the girls group chat had irrevocably divided into two sides. Bea: it looked like she’d put a wedding dress on and changed her mind half way down the stairs. Priya: the boots were the whole point. Without them, she’d look like she was wearing a christening suit somebody dropped her at. Sister of person who isn’t even in our chats but got sent the screenshot anyway: “it’s giving Timberland at a barbecue.” If I think about it too hard, that last one still unsettles me.
I didn’t say anything for about twenty minutes, because the real, honest place to start here is me actively not knowing which side I was on. I’ve worn ankle boots with dresses literally four hundred times in my life and I STILL don’t know what the rule is. What I do know is that I have a dead zone of outfits in my brain that either worked spectacularly well or made me look like I was off to a fete and was regretting it, and buried inside that mess of failures and successes is the real answer: that we’re even having this argument about a RULE to begin with is the problem.
The actual controversy here isn’t boots, it’s line.
Beneath all those Timberland jibes, this is what I think was REALLY going on in that group chat. Nobody hated ankle boots as a style. They hated one photo of Marnie where the dress hit at an awkward length and the boots were bulky, creating a problem with proportion rather than the boot/Dress rule people think they’re fighting about.
This is where people get it wrong ALL THE TIME. Including myself, for YEARS. I thought – believed – with every fibre of my being that ankle boots and dresses simply either worked as a whole unit or they didn’t, like you would commit to being “team stripes” or not. I spent most of my twenties labouring under that belief and I was WRONG the entire time. Boots aren’t the problem. It’s not even dresses. It’s where your boot stops your leg and where your dress stops your leg, and whether those two lengths fight each other or play nicely side-by-side.
If you have a skirt that falls at your knee, and boots that fall at your ankle, you’re left with one long uninterrupted expanse of leg in the middle, and just as an A line skirt tends to flatter more figures than something pencil-slim due to the extra material gathering at the sides (it’s still ALL about the hips, sorry), that solid uninterrupted line looks intentional, and frankly quite nice. If your dress hits mid-calf, right where most boots “finish” visually because of their extra material at the ankle, you end up with two distinct halts in that line, close together, and it gives the illusion that your outfit was somehow…interrupted before it could reach its natural conclusion. THAT is what was wrong with Marnie’s outfit. It wasn’t about the boots. It was about that dress length meeting those boots at that exact spot on her leg, creating a sort of visual full stop right in the middle of her shin that our brains pick up on subconsciously but our Instincts react to VERY loudly.
Trust me, I learned this lesson after I destroyed my own cousin Deja’s engagement party three years ago in a khaki midi-dress with boots from Mango that hit almost exactly at that “wrong spot”. I still have a photo of myself standing against a pillar at the party, and honestly if you LOOK at it, I look SMALLER THAN THE PILLOWbase they’re standing next to. Winnie took one look at me the next day and said my whole outfit “looked like I was wading through something”, which was definitely not the vibe I was going for at my cousin’s engagement party. The boots were fine. The dress was fine. Together, they cancelled each other out at that bloody awkward length.
WAIT BUT CAN YOU REALLY wear ankle boots with a dress? ?
Yes. Yes you absolutely can. Let me address this right out of the gate, because I honestly think that after YEARS of boring wedding guest “etiquette” columns telling you boots were for boyfriend jeans and dresses were for heels, there’s probably somebody reading this right now who still believes that and we need to have a little chat. Put the firmly but politely, it’s 2019 and you are not allowed to listen to that voice telling you heels are the only acceptable dress footwear anymore. I lived my life assiduously avoiding that rule for YEARS, because a Boots with a dress “looks like you can’t find your other shoes” from my aunt when I was fourteen and believed her ever since. Aunt, if you’re out there: you were dead wrong. ALL the way dead wrong. My twenty-eight year old self looks at your boot/dress rule squarely in the eyes and REFUTES IT.
The question of “can I wear boots with a dress?” isn’t yes or no depending on some imaginary rule book. It’s yes or no on a case by case basis depending on where that boot falls on your leg vs where the dress falls. Which, I know, sucks because it doesn’t give you a hard and fast rule like you wanted. But that’s what I’ve noticed after trying and failing and trying this combo enough times. Slim ankle boots, ones with a slight pointed toe or sleek Chelsea style, under a floaty voluminous dress that doesn’t cling to your hip line feels like it works automatically. Chunkier heel boots can work too, but the dress usually needs to have a more laidback vibe to it to balance out that boot. Skinny jeans with a statement boot is the same sort of principle of fighting vs working together I see at play here. It’s not that one or the other is inherently wrong, it’s that they’re saying two different things at once and nobody’s quite translating between them.
Let me give you an example my colleague Ottoline rocked to our office Christmas party last year. She wore some biker boots with a sheer slip dress and it was honestly, bar none, THE BEST THING IN THE ROOM. And I hated her boots. Like went online and searched for the same pair before Christmas hated her boots. They undercut that dress in such a brilliant way. They told everyone walking into the room “yeah, I know this dress is maybe slightly too much for Wednesdays and a function centre above a pub but I also don’t care”. THAT is the secret you guys nobody talks about. Boots don’t HAVE to be the heels your dress forgot about. They can totally take on a personality of their own and when they do that, suddenly you’re telling a story as opposed to just wearing boots with a dress. And that, I think, is the whole goddamn point.
Okay but WHICH boots should you wear if you’re actually gonna do this?? ?
Look, I am NOT saying there’s some sort of magical boot out there that works with every dress I own because I hate that bloody “VERSATILE PIECE” crap as much as you do and tbh it doesn’t work that way. But I WILL say I’ve worn enough boot and dress combos in the last two years to notice a trend in the ones that work for me personally, triumphantly or otherwise. I even Googled “how many boot dresses do I own” so I could count them up just because I’m bored in my kitchen on a Sunday.
I WILL also say that every pair that’s worked for me, I’ve reached for more than once, which should give you some indication of what sorts of boots I’m talking about here. I’ve had successes and failures with roughly eleven or twelve different dress/boot combos in my entire closet over the past two years. Keep that number in mind.
My go-to boot for any mini or knee-length dress is a pointed or almond toe boot, in a soft leather with a low block heel or even no heel at all. They add to your line rather than chopping it in half. Paired with a slim boot like that, I wore my mini dress to a work lunch earlier this year and my boss, who has never complimented ANYTHING I’ve worn in our four years together sat down across from me and said “oh, I like that combo” as she poured me a coffee. From her, that’s rooftop anthem material.
Midi and maxi dresses are less tricky because your boot is kind of camouflaged underneath all that material, acting more like punctuation at the bottom of your outfit than anything else. THAT is where I’ll reach for a boot with a bit more personality. Something with stacked heels or top stitching or Western detail. Something with a flair because your boot no longer needs to balance out the shape of your dress like it does with something knee-length or shorter.
The ONE boot/dress combo I will say I still haven’t nailed is a bulky sock boot with a fitted knee length dress. I don’t know why that specific combo is so WRONG for me, but try. I have. Three separate times. Once on that bitch aunt’s sofa. Your mile high is probably not that. But also, don’t wear something that looks like you’re about to kick my ass if it doesn’t work for you.
Own the boots you’re in.
Marnie ended up wearing that same damn dress again about two months later, this time with a narrow pointed boot instead of the wider ones. She even posted the photo herself with the caption “redemption arc” and do you know who admitted she liked it? Fucking Bea. The dress didn’t change. Her boots did. And all it took was swapping out boots that interrupted her line for ones that complimented it to fix the whole mess. Two centimetres of ankle is all it took to end a months-long arguments about a debate that doesn’t even exist.
