I never thought I’d be the person wearing cowboy hats. Grew up on the East Coast, lived in cities my whole life, wouldn’t know a ranch from a petting zoo. Then I visited Nashville three years ago, bought a hat on a whim, and suddenly I’m that girl who wears cowboy hats to brunch.
The tricky part wasn’t buying the hat – it was figuring out what the hell to wear with it. Pair it wrong and you look like you’re wearing a costume. Pair it right and somehow it pulls your whole outfit together in a way regular hats just don’t.
I’ve spent three years experimenting, making mistakes, getting compliments, and occasionally looking ridiculous. Learned what works through trial and error, mostly error. Here’s what actually pairs well with cowboy hats without looking like you’re headed to a themed party.
Denim Everything Actually Works
Denim and cowboy hats go together for good reason – the combination just works. Not groundbreaking advice, but there are ways to do it that feel current versus looking like a costume.
Fitted jeans with a simple white tee and a cowboy hat creates an effortless look that works for literally anything casual. I wear this combination running errands, meeting friends for coffee, weekend travel. The hat elevates what would otherwise be boring basics.
Denim jackets layer perfectly over dresses or skirts when you’re wearing a hat. The casual jacket balances the statement hat, keeping things from feeling too precious or styled. I throw a denim jacket over almost everything when wearing my hat.
Dark wash jeans feel more sophisticated than light wash when you’re trying to avoid full country vibes. Pair with ankle boots and a fitted blazer, add the cowboy hat, and suddenly you’ve got a look that works for dinner or casual Friday at work.
Denim skirts – midi length specifically – create interesting contrast with cowboy hats. The feminine skirt silhouette balances the masculine hat energy. I wear this combination constantly in summer with a tucked tank top and sandals.
Avoid head-to-toe denim unless you’re actually working a ranch. Canadian tuxedo plus cowboy hat is too much western in one outfit for urban settings.
Flowy Dresses Create Perfect Balance
Maxi dresses and cowboy hats became my summer uniform last year. The long, flowy silhouette balances the structured hat in a way that feels bohemian without trying too hard.
Floral patterns work surprisingly well despite seeming like they’d clash. Small floral prints on midi or maxi dresses paired with a neutral-colored hat create a romantic, vintage-inspired look. I wear this to outdoor concerts, farmers markets, casual weekend events.
Solid-colored slip dresses in earth tones – rust, olive, cream, tan – look effortlessly cool with cowboy hats. The simple dress keeps focus on the hat without competing. Add leather sandals and you’ve got an outfit that works from brunch to dinner.
Short dresses require more thought. Mini length can look costume-y with a cowboy hat unless you’re actually at a country music event. Midi and maxi lengths feel more intentional and less themed.
Avoid overly frilly or prairie-style dresses unless you’re deliberately going for that aesthetic. The cowboy hat already makes a statement – adding too many ruffles or lace creates visual chaos.
Leather Accents Tie Everything Together
Leather accessories create cohesion when wearing cowboy hats. Belts, bags, boots – these elements connect the hat to the rest of your outfit so it doesn’t look like an afterthought.
Wide leather belts worn over dresses or high-waisted jeans echo the western vibe without overdoing it. I use belts to cinch flowy dresses and create shape while tying into the hat aesthetic.
Leather crossbody bags or saddlebags (real ones, not costume-y fringe versions) add functionality while maintaining the western-influenced look. My brown leather crossbody gets worn with probably 80% of my cowboy hat outfits.
Ankle boots work better than tall cowboy boots in most urban settings. Full western boots plus western hat can feel like too much unless you’re somewhere that aesthetic is normal. Ankle boots or booties provide the leather element without full costume vibes.
Leather jackets – brown or tan specifically – layer beautifully over everything when wearing a hat. Black leather can work but feels less cohesive than browns that echo traditional western tones.
Monochrome Outfits Let The Hat Shine
All-neutral or monochrome outfits create the perfect backdrop for a statement hat. When everything else is simple, the hat becomes the focal point without overwhelming the look.
All-black outfits with a tan or cream cowboy hat create striking contrast. Black jeans, black tee, black boots – then the light-colored hat pops. I wear this combination constantly because it’s simple, flatters everyone, and always looks pulled together.
All-white or cream creates a softer, more feminine version. White jeans, cream sweater, tan hat – perfect for spring and summer. The tonal dressing feels sophisticated while the hat keeps it from being boring.
Beige and tan monochrome outfits blend with neutral hat colors to create a cohesive, earthy aesthetic. This works particularly well in fall with layered sweaters, relaxed trousers, and suede accessories.
Avoid matching your hat exactly to your outfit color. A little contrast creates visual interest. If you’re wearing all tan, choose a slightly darker or lighter hat rather than exact matching.
Unexpected Pairings That Actually Work
Cowboy hats with athleisure was accidental genius I discovered last year. Leggings, oversized sweatshirt, sneakers, cowboy hat – somehow it works for casual weekend wear. The hat dresses up what would otherwise be pure comfort clothes.
Tailored trousers and blazers create interesting juxtaposition with cowboy hats. The structured suiting feels urban and professional, while the hat adds personality and prevents the outfit from feeling too corporate. I wear this to casual business meetings or creative work events.
Leather pants or faux leather leggings paired with simple tops and cowboy hats create an edgy look that feels more rock-and-roll than country. Add a band tee and boots for concerts or nighttime events.
Long coats – especially dusters or trench styles – layer beautifully over everything when wearing a hat. The long lines create drama and the coat protects the hat from getting crushed in crowds.
Wrapping This Up
Cowboy hats work with way more outfits than you’d expect once you understand the basic principles. Keep the rest of your outfit relatively simple, incorporate leather accents, and don’t overthink it.
The hat becomes costume when every other element screams “western.” One statement piece – the hat – grounds the look. Everything else should feel like your normal style with slight nods to western aesthetics through materials and colors.
Start with combinations that feel comfortable and authentic to your existing style. Forcing an aesthetic that doesn’t match your personality shows. The best cowboy hat outfits feel like elevated versions of what you’d wear anyway.
Experiment in low-stakes situations before wearing bold combinations to important events. Grocery store runs and coffee shops are perfect testing grounds for new outfit pairings.
