I’m going to let you in on a secret – I’ve been afraid of cowboy boots for years. Thought they’d make me look a bit daft, like I was trying too hard. And then I saw my colleague Sarah wearing them with jeans and a blazer, and something clicked. She looked brilliant. Not the least bit costumey, not overstyled at all — just really put together.
Cut to today, and three pairs have accumulated by my front door. Apparently, cowboy boots are ridiculously easy to style once you stop overthinking it.
Why They’re Everywhere Right Now
Walk down any high street and you’ll spot them. My local Zara had an entire wall dedicated to Western boots last month. Even my mum asked me about them, which tells you they’ve gone properly mainstream.
Which boots are trending hardest? Anything in rust or forest green. Square toes are massive because they’re actually comfortable (your toes can breathe, thank god). But honestly, if you’ve got brown or black leather boots already, you’re golden. No need to buy into every trend.
Dresses Are Your Best Mate
This combination saved me so many times. Got a wedding? Floral midi dress with boots. Sunday roast with the in-laws? Same thing. Night out? Short dress, tights, boots, done.
My favourite trick is wearing a slip dress with chunky boots. Sounds weird, works perfectly. The dress keeps it feminine; the boots stop you from looking too delicate. I wore this to my friend’s birthday dinner and got more compliments than I knew what to do with.
What to wear with cowboy boots for females really comes down to balance. If your dress is quite girly, the boots add edge. If your dress is plain, decorative boots become the star. Simple as that.
The Blazer Thing Everyone’s Doing
Remember when Emily Ratajkowski did that Princess Di-inspired number? Blazer, jeans tucked into tall boots, plain white tee. It read as expensive without trying too hard.
I copied it for a work presentation last month. I tucked black jeans into knee-high boots and threw on my oversized navy blazer. My boss actually told me I looked “very professional but approachable”, which is certainly a win.
The trick is keeping everything slightly loose. Tight blazers with cowboy boots feel wrong somehow. You want that relaxed thing going on.
Jeans – But Make It Right
Skinny jeans tucked in? Great for winter, keeps you warm, looks neat. I put on this pair at least three times a week. Black skinnies, brown boots, oversized jumper. It’s my “can’t be bothered to think” outfit.
But the boots showing under high-waisted jeans? That’s when you want to give it a try. Tucking in your top, slipping on a belt and bam, you look way more put together than moments before.
My sister loves good wide-leg jeans with pointed-toe boots. You only see the tip of the boot, but it appears very polished. She wore this at a gallery opening and was completely one of the arty people.
How to Wear Cowboy Boots in Winter Without Looking Ridiculous
This is where boots prove their worth. I’ve been wearing it with midi skirts and thick tights. Chuck a chunky cardigan on top and you’re set for wintry days.
I did a long black dress last week that dragged along the floor with my boots underneath. Added a leather jacket. Seemed moody and cool without effort. I got stuck in the rain and my feet stayed dry, which is more than I can say for my trainers.
You can wear a maxi dress, but be sure there is a slit. Otherwise no one can see your boots so what’s the use?
Things I’ve Tried That Didn’t Work
Double denim with cowboy boots? Made me look like I was going to a line dancing class. Athleisure (leggings and a sports camisole) with decorative boots? Just looked confused.
Also learned the hard way that frilly, puffy dresses are too much with statement boots. You need one main character in your outfit, not two fighting for attention.
The Unexpected Combinations
Here’s something that surprised me. Tailored trousers and cowboy boots? Absolutely works. I wore camel-coloured trousers with black boots to a christening and felt properly chic.
My mate Emma does this thing where she wears her electric blue boots with the most basic outfit possible – black jeans, black top. The boots do all the talking and it looks ace. She’s braver than me with colour, but I rate it.
Making Them Actually Work For You
Start with one neutral pair. Brown or black. Nothing too fancy. Get comfortable wearing them before you buy those embroidered statement ones that cost a fortune.
I waterproofed mine before winter properly started, and it’s saved them from getting wrecked. Takes five minutes, costs about eight quid, and is absolutely worth it.
The thing about outfits to wear with cowboy boots is there’s no magic formula. What works for me might not work for you. I’m short and usually go for the tucked-in jeans look because it makes my legs look longer. My tall friend prefers the wide-leg jeans situation because she’s got legs for days anyway.
Try different combinations. Take photos if that helps. See what makes you feel good, not just what Instagram says you should wear.
Actually Wearing Them Out
When I wore mine to the pub for the first time, I was aware of feeling slightly self-conscious. Kept thinking everyone was staring. They weren’t. Nobody cared. The second time, I forgot I even had them on.
Now they’ve become a staple in my wardrobe rotation. Some days, I feel like wearing trainers; some days, I don’t want to wear anything but my boots. It depends on how I’m feeling and what I’m up to.
They also slot in for casual days (shops, errands, walking around town), smart-casual things (dinners out, drinks with friends, cinema) and properly dressed-up occasions if you style them right. You can’t really ask for more versatility than that.
The confidence thing is real, though. These boots speak, whether you wish it or not. But then, that’s sort of the point, isn’t it? If you were trying to disappear into the background, then there were ballet flats.
So here’s the deal: if you have a pair sitting in your closet that you’re afraid to put on, just wear them tomorrow. Style them with jeans and a jumper. Nothing fancy. Get used to them. Then start experimenting.
Because once you crack it, you’ll genuinely wonder why you waited so long. They are comfortable, they will last forever if you take care of them, and they make it that much easier to get dressed in the morning.
That’s pretty much it. No complicated rules, no fashion degree needed. Just boots and common sense.
