A good rule for Western-style outfits outside of the American Southwest is one western-themed item per outfit, maximum!

So if you’re wearing a pair of cowboy boots, wear them with a sleek belt and a jacket rather than with a cowboy shirt and a bolo tie. You want to look like you’re making a calculated fashion statement, not trying to dress up in a costume.

Your cowboy boots are going to be social wear rather than business (unless you’re a Texan), so plan to wear them with relaxed jackets and trousers:

• Collared shirts are something of a must with cowboy boots, if you’re wearing them to look stylish. A T-shirt and blue jeans with cowboy boots will fit right in at a country music show, but unless that’s where you’re actually going, you should wear something else. A plain white dress shirt works remarkably well, as do more patterned, casual shirts. 
• Jeans should be dark and close-fitted, not the light blue of typical work jeans. You’ll want a boot-cut style for obvious reasons. Never tuck the jeans into the boots unless you’re doing actual work on horseback that requires it. 
• Dress trousers can go with cowboy boots as well, and so can casual suits. Just make sure they have enough room in the leg that the boot shaft isn’t making a bulge. 
• Jackets really help take you from “urban cowboy” to “snappy dresser.” I would almost tell you to never wear cowboy boots without a jacket, at least in a major metropolitan area. It just balances the casual boot style out in a way that a shirt on its own can’t.
•  Hats are pushing it, but if you really want to hammer the cowboy point home, a nice felt Western-style hat is an obvious complement to Western boots. Don’t do this unless you’re really dedicated to making people instantly think “cowboy” when they look at you, though. 
• Belts with decorative buckles or leather are always a good companion to cowboy boots. You don’t need a huge silver buckle with turquoise inlays, or a rattlesnake skin belt, but something a little more decorative than your average dress belt goes well.
•  Denim or leather jackets are a good alternative to the dressier sports jacket. Don’t overdo the casual styling, however — your boots are already pretty casual, so a jacket with lapels is going to be better than one without. Alternatively, a long trench coat is a very natural pairing for Western boots. Avoid billowing leather dusters unless you’re trying to make a costume out of it. 
• Spurs are for a few specific types of riding. If you’re not planning on hopping on a horse in the immediate future, please don’t wear spurs on your boots.

 The goal of all these specific details is to make an outfit that acknowledges your boots without being centered around them. You want to look comfortable, relaxed, and capable — all the things we associate with cowboys and Western culture. If you’re in a big city, you also want to look a little dressier than an actual rodeo-going cowboy.

For a fail-safe cowboy boot outfit, try a pair of dark jeans, a white shirt, and a brown or gray jacket with a soft, casual cut. Add a decorative belt and a paisley pocket square to evoke traditional bandanas and you’re looking both stylish and unique.

Where You Should and Shouldn’t Wear Cowboy Boots

If we haven’t made it clear by now, Western-style boots are casual clothing. They’re not business wear unless your business involves cattle or oil. Every once in a while you’ll see a businessman wearing a fancy suit with cowboy boots, but you don’t want to be that kind of eccentric.

For the most part we recommend keeping the cowboy boots to “fun” social events — things that are actively light-hearted, where a little machismo and a slightly more aggressive style isn’t out of place. Good places for cowboy boots include:

• Most kinds of step dancing — salsa, square, etc. Bars Casual restaurants
• County/state/grange/etc. fairs 
• Rock and country concerts 
• Romantic evening picnics with a loved one 
• Comedy shows (but if you sit in the front row they might say something) 
• Absolutely any activity done on horseback 

Questionable places to wear cowboy boots,

Unless they are a normal part of your personal style, include:

• First dates (might send the wrong impression) 

• Political functions of any kind (even just casual fundraisers) 
• Any presentation that you’re making personally 
• Long hikes or drives (not comfortable for either) 
• Upscale theater performances 
• Modern dance clubs (wrong style, and often hard on the dance floor) 

And of course there is some variance here depending on what your boots look like — a pair of white cowboy boots with bright red Texas stars on the toes are going to work in a lot less settings than a pair of deep, oxblood red boots with some decorative stitching in the same color thread. Exercise a little personal judgment, and if your boots are particularly gaudy, a little personal restraint as well.