There’s this moment every October—usually when I’m standing at the bus stop getting absolutely soaked because I thought a denim jacket would cut it for another week—when I finally admit defeat and dig out my winter coat. You know the one. It’s been hanging in the back of my closet since March, probably still smelling faintly like that cheap wine I spilled at my friend’s holiday party last year. And with that coat comes its faithful companion: the boots that have seen me through countless Portland winters, puddle splashes, and those mornings when I’m running late and can’t be bothered to check if it’s actually waterproof outside.
Last Tuesday was exactly that day for me. After three days of telling myself my thrifted blazer was “totally fine” for 45-degree weather (spoiler: it wasn’t), my weather app finally broke me with its wall of rain clouds and temperatures that made me want to crawl back into bed. I trudged to my closet, pushed past the optimistic summer dresses I’d been clinging to, and pulled out my trusty black wool coat—a lucky find from Crossroads Trading two years ago that cost me forty bucks and somehow still looks decent despite daily wear.
Right next to it were my go-to black Chelsea boots, the ones I saved up for from Everlane during their rare sale season because I’d learned the hard way that cheap boots in Portland are basically throwing money into puddles. As I walked to my bus stop that morning, properly bundled for the first time in weeks, I noticed something funny—I wasn’t alone in this ritual. At least six other women at the stop were wearing basically the same thing: some version of a dark wool coat paired with sturdy ankle boots. Different budgets, different stores, but the same survival formula.
That’s when it hit me—we’d all figured out the same equation without talking about it. One decent coat plus one pair of actually waterproof boots equals making it through winter without looking like you’ve completely given up on life. It’s not rocket science, but when you’re working with a limited budget and need clothes that can handle real weather, it becomes this unspoken rule that just makes sense.
I’ve been thinking about this formula a lot since then, especially after watching my coworker Emma nail it with her setup. She’s got this perfectly tailored navy coat that hits mid-thigh—I’m pretty sure it’s from Banana Republic during one of their 40% off sales—paired with these chunky black boots that should look clunky but somehow make her look like she stepped out of a cool European film. Meanwhile, my upstairs neighbor rocks a camel-colored coat (definitely thrifted, I’ve seen the same style at Buffalo Exchange) with these combat-style boots that give her whole vibe this effortless edge.
The thing about this coat-and-boots combination is that it’s basically foolproof once you crack the code. But here’s what took me years to figure out: it’s not just about having any coat and any boots. It’s about having the right coat and the right boots for your actual life, your actual budget, and your actual style. I learned this the hard way through a series of expensive mistakes in my early twenties.
My first “real” winter coat was this burgundy wool thing I bought at Nordstrom Rack for what felt like a fortune at the time—probably around $150, which was huge for me then. I thought I was being so smart, investing in quality. Except it was this weird cropped length that looked terrible with everything, and the color was so specific that it clashed with half my wardrobe. I wore it for exactly one season before it became my “I’m just running to the store” coat.
Then there was the boot disaster of 2019. I found these gorgeous tan leather ankle boots at Target for thirty bucks and convinced myself they’d be fine. They looked great for about three weeks, until the first real rainstorm hit and I discovered they were basically decorative. Water soaked right through, the sole started peeling, and by January they were held together with hope and determination. That’s when I learned that some things are actually worth saving up for, even when you’re broke.
Now my approach is way more strategic. I’ve got my everyday black wool coat that works with literally everything in my closet, cost me forty dollars, and has lasted two full winters so far. For boots, I saved up and bought one really good pair of waterproof Chelsea boots that were expensive upfront but have been worth every penny. That’s it—two items that handle 90% of my winter wardrobe needs.
But here’s where it gets interesting: having the basic formula down doesn’t mean it has to be boring. I’ve been experimenting with ways to make the same coat-and-boots combo feel fresh without spending money I don’t have, and it’s become this fun challenge that taps into the same problem-solving part of my brain I use at work.
Color is the easiest way to shake things up. While most of us default to black, navy, or camel coats (practical and versatile), I’ve started noticing women who go for unexpected shades that still work with everything. There’s this woman on my morning bus who wears the most beautiful forest green coat with brown boots, and it looks so much more interesting than the standard black uniform. When my current coat eventually dies, I’m definitely considering something in a rich burgundy or deep olive—colors that feel special but still go with my existing wardrobe.
The belt trick is another game-changer that costs zero dollars. Instead of using whatever sad belt came with the coat (if any), I’ve started using belts from my regular clothes to cinch and define the waist. My favorite is this wide black leather belt I got at a thrift store that completely transforms the silhouette of my coat and makes it look way more expensive and intentional.
I’ve also been playing with proportions lately, which sounds fancy but really just means wearing unexpected combinations. Instead of the obvious slim pants with my fitted coat, I’ve been wearing it with these wide-leg thrifted trousers and my chunky boots. It creates this more current, fashion-forward shape that makes the same old coat feel completely different. The trick is keeping everything in the same color family so it looks intentional rather than random.
Scarves are another area where you can get creative without spending much. I picked up this oversized rust-colored scarf at a vintage shop for eight dollars, and it completely changes how my black coat looks. Sometimes I wear it loose, sometimes I belt it as part of the coat rather than as a separate layer. It’s like having three different coats for the price of one accessory.
What’s really changed my thinking, though, is starting to consider my coat as part of the actual outfit, not just something I throw over clothes and immediately take off. I’ve started choosing what I wear underneath specifically thinking about how it’ll look with my coat partially open or buttoned up. That vintage band t-shirt that peeks out perfectly at the neckline, or the midi dress whose hem hits at exactly the right spot beneath the coat—these aren’t accidents anymore.
This shift makes total sense when you think about it. In Portland, I’m wearing my coat for like six months of the year. It’s actually how people see me most of the time, so why wouldn’t I want it to be part of my style rather than just weather protection? When you’re investing in fewer, better pieces because that’s what your budget allows, they might as well be pieces you genuinely love.
The boot situation has gotten more interesting too. I used to think you needed different boots for different occasions, but I’ve realized that one really good pair of boots can work in way more situations than you’d expect. My black Chelsea boots work with everything from jeans and sweaters to dresses and tights. They’re waterproof enough for actual weather but sleek enough that I don’t look like I’m dressed for a hiking trip when I wear them to work.
I’ve been watching how other women style the same basic formula, and there are these small details that make all the difference. The way someone knots their scarf, or chooses an unexpected pop of color in their accessories, or plays with mixing textures—wool coat, leather boots, maybe a chunky knit scarf—these tiny tweaks keep the practical uniform from feeling like, well, a uniform.
My friend Sarah does this thing where she wears really feminine dresses with her heavy-duty lace-up boots and structured coat. It shouldn’t work but it creates this cool tension between pretty and practical that looks completely deliberate. Meanwhile, my coworker Jake (yeah, this formula works for guys too) wears his wool coat with beat-up sneakers instead of dress shoes, and it gives his whole look this relaxed, creative vibe that fits his personality perfectly.
The best part about figuring out this formula is how much mental energy it frees up. Instead of standing in my closet every morning trying to figure out how to stay warm and look decent, I just reach for the coat and boots and focus on the smaller details that make it feel intentional. Which scarf today? Belt or no belt? What’s the one pop of color that’ll make this feel fresh?
It’s also been a lesson in buying better, not more. Instead of accumulating a bunch of mediocre winter clothes that don’t quite work, I’m slowly building a smaller collection of pieces that actually earn their space in my closet. That expensive coat becomes reasonable when you calculate the cost per wear over multiple seasons. Those good boots stop feeling like a splurge when you realize you’ll wear them almost daily for half the year.
As I’m writing this, it’s started raining again outside my apartment, and I can already see tomorrow morning’s routine in my head—reaching for the black coat and boots that have become as automatic as brushing my teeth. But instead of feeling like I’m putting on the same boring outfit, I’m actually looking forward to figuring out how to make it feel fresh. Maybe the rust scarf today, or that vintage belt, or the burgundy lipstick that makes everything look more intentional.
This whole coat-and-boots thing has become my version of a uniform, but in the best possible way—one that actually works with my lifestyle, my budget, and my personal style. It took me years of mistakes to figure out, but now that I have, getting dressed for winter feels less like a daily struggle and more like a creative challenge I can actually win.
Madison’s a Portland-based designer who treats thrift stores like treasure hunts. She writes about dressing well on a real salary—think smart buys, affordable finds, and brutal honesty about what’s worth it. Stylish, broke, and proud of it.
