Why My Pristine Country Wardrobe Screamed “City Faker” (And How I Fixed It)

I’ll never forget the mortification of stepping out of the car at my first proper countryside weekend, looking down at my spotless white Allbirds, then looking up at everyone else’s mud-caked boots. The silence was deafening. Well, except for Charlotte’s dad who took one look at my brand-new Barbour and asked if I was “off to meet the Queen later.” I wanted to disappear into the Cotswolds mud right there.

That was three years ago, and honestly? It was a wake-up call about how performative my approach to “countryside dressing” had become. I’d treated it like a costume party – buy all the “right” pieces, show up looking like a Ralph Lauren ad, job done. Except the job was definitely not done, and I looked like exactly what I was: a Seattle city girl who’d panic-shopped at REI the night before.

The thing is, I should have known better. Growing up in Boulder, I spent plenty of time outdoors, but somehow moving to the city had made me forget the basic rule of outdoor clothing: function over fashion, always. My mom would have taken one look at my pristine country getup and laughed herself silly. She raised me in secondhand hiking boots and hand-me-down fleeces that actually kept me warm, not Instagram-worthy pieces that looked good in photos but fell apart in real weather.

But here’s what I’ve learned since that humiliating weekend – dressing for the countryside when you’re fundamentally a city person isn’t about buying a whole new wardrobe of “country” clothes. It’s about being honest about what you’ll actually be doing and dressing accordingly. Revolutionary concept, I know.

Let’s start with the obvious: that Barbour jacket. Yes, they’re classics. Yes, they last forever. Yes, they’re worth the investment if you’re going to actually use one. But for God’s sake, if you buy one, at least make it look like you didn’t just take the tags off in the car. New Barbours are the sartorial equivalent of those people who buy vintage band t-shirts for bands they’ve never heard of – technically correct, but missing the point entirely.

I learned this from my friend Emma, who grew up in rural Yorkshire and has the patience of a saint when it comes to my urban awkwardness. She took one look at my stiff, waxy-smelling jacket and said, “Right, we need to fix this.” We spent twenty minutes deliberately scuffing it up, sitting on it, even rubbing a bit of dirt on the cuffs. “It needs to look like you’ve owned it since university,” she explained, “not like you bought it specifically for this weekend.”

The transformation was incredible. Suddenly my jacket looked… normal. Lived-in. Like something I might actually wear regularly rather than a costume piece I’d dragged out for the occasion.

If Barbour isn’t your thing – and honestly, they’re expensive enough that I totally get why they might not be – there are tons of alternatives that work just as well. My go-to now is actually a Patagonia rain jacket I bought for hiking that’s served me brilliantly at country house parties, music festivals, and dog walks through Seattle’s endless drizzle. It’s not traditionally “country” looking, but it’s practical, and practicality trumps aesthetics every time in rural settings.

The footwear situation is where most city people really mess up, myself very much included. After the Great White Shoe Disaster of 2021, I’ve become obsessive about appropriate countryside footwear. It basically comes down to three categories: wellies for proper mud, hiking boots for actual walking, and what I call “pub boots” – leather ankle boots that look normal but won’t disintegrate if you step in a puddle.

I bought my current wellies at a farm supply store in Washington state for thirty-five dollars, and they’ve outlasted every fancy pair I’ve ever owned. They’re unglamorous green rubber things that make my feet look enormous, but they’ve carried me through muddy fields, stream crossings, and one memorable incident involving a very enthusiastic golden retriever and a swamp. Sometimes function really is all that matters.

For actual hiking – because yes, that “gentle country walk” will inevitably turn into a forced march up terrain better suited to mountain goats – I invested in proper hiking boots. Not the fashion-forward ones that look cute with jeans, but actual technical hiking boots with ankle support and aggressive treads. I learned this lesson the hard way during a “quick stroll” in the Lake District that turned into a three-hour odyssey over rocks and streams. My feet have never forgiven me for that particular footwear choice.

The middle layer situation – everything between your jacket and boots – is where I see most city people make the same mistakes I did. We get so caught up in creating a “countryside aesthetic” that we forget about comfort and practicality. Those perfectly pressed riding pants you ordered online? They’re going to be wrinkled and muddy within an hour. That delicate cashmere sweater that looks so charmingly rural? It’s not going to keep you warm in a drafty farmhouse where heating is more suggestion than reality.

I’ve found my sweet spot with straight-leg jeans that I don’t mind getting dirty (key phrase there – jeans you don’t mind ruining), merino wool sweaters that actually provide warmth, and cotton long-sleeved shirts I can layer or remove depending on the wildly fluctuating temperatures you’ll encounter in old houses and outdoor activities.

The layering thing took me forever to figure out. Country houses are weird, temperature-wise. The kitchen might be tropical from the Aga, while the sitting room feels like a meat locker. You need to be able to adjust accordingly without looking like you’re doing a strip tease or bundling up for an Arctic expedition.

My most-used country accessory is honestly a huge wool scarf I bought at a thrift store in Capitol Hill five years ago. It’s served as a blanket during outdoor picnics, a pillow during long car rides, emergency dog towel, and once, memorably, a makeshift sling when someone twisted their ankle during a hike. It’s not particularly stylish anymore – it’s been through too much – but it’s infinitely practical.

Bags are another area where city instincts fail you completely. That cute little crossbody that holds your phone, keys, and lipstick? Utterly useless. You need capacity for water bottles, snacks, extra layers, first aid supplies, and whatever random objects you’ll inevitably be asked to carry. I now travel with a proper hiking daypack and a canvas tote bag that’s seen better days but can handle whatever gets thrown at it.

The evening wear situation is where things get really tricky. How do you dress for dinner at a country house when you’re not sure if it’s going to be “family supper in the kitchen” or “proper sit-down meal in the dining room”? I’ve learned to err on the side of casual – nice jeans and a good sweater will take you most places, and if you’re overdressed, you can always lose layers or change.

I made the mistake once of showing up to a weekend in Northumberland with what I thought was appropriate evening wear – a wrap dress and heels – only to discover everyone else was in fleeces and slippers for a kitchen supper. While nobody said anything, I felt ridiculous and uncomfortable the entire evening.

The real revelation for me has been understanding that countryside style should be invisible. When I’m properly dressed for a country weekend, I’m not thinking about my clothes at all. I’m focused on the conversation, the scenery, the temporary escape from urban stress. My clothes are just… there, doing their job quietly and efficiently.

It’s taken me years to get to this point, and honestly, I still sometimes misjudge things. Just last month I showed up to a farm stay in Oregon wearing what I thought were appropriate boots, only to discover they had zero tread and turned me into a liability on wet grass. But the difference now is that these mistakes don’t derail my entire weekend – I just adapt and move on.

The sustainability angle makes countryside dressing even more interesting, actually. The best country clothes are the ones that last forever, that get better with age and wear. That expensive ethical wool sweater I agonized over buying two years ago? It’s perfect for country weekends because it’s warm, durable, and looks better now than when I bought it. My secondhand hiking boots have broken in perfectly and show their history in a way that new ones never could.

There’s something refreshing about dressing for pure function rather than appearance, even if it took me embarrassingly long to figure that out. The countryside doesn’t care about your carefully curated aesthetic or whether your outfit would photograph well. It cares about whether you can walk five miles without complaining, sit by a bonfire without worrying about sparks, help carry firewood without fussing about your clothes.

So if you’re facing your first country weekend with the same terror I felt three years ago, here’s my advice: forget about looking like you belong and focus on being prepared for whatever activities are planned. Bring clothes you don’t mind getting dirty, shoes that can handle mud, and layers you can adjust as needed. The goal isn’t to convince people you’re secretly a country person – it’s to enjoy the experience without your wardrobe getting in the way.

And if all else fails, remember that everyone appreciates someone who’s willing to help out and laugh at themselves when things go wrong. Your pristine city person aesthetic might not fool anyone, but your willingness to embrace the chaos of countryside life definitely will.

Now excuse me while I go waterproof my boots again. Some things never change.