Square toe vs round toe cowboy boots

If you want one boot that will not be a mistake, this is the one most first-time buyers end up in. Ariat publishes a full-grain leather upper, Goodyear welt construction, a 12-inch shaft and a 2-inch western heel, with its Duratread outsole and a removable Pro Performance insole. The reason it suits a beginner is the combination: the welt means it can be resoled instead of thrown away, and the cushioned removable insole means it is wearable on day one rather than after a month of pain. It is sold in a square toe and in narrower shapes, so you can pick the toe that fits your foot rather than taking whatever the model comes in. At the usual street price it sits in the middle of the market - above the mall-brand boots that are glued together, below the handmade tier you do not need yet.

What you give up: You give up character. This is the Toyota Camry of cowboy boots - nobody in a boot shop will be impressed, and the leather will not develop the patina a $400 calfskin boot does.

A roper is the quiet entry point into western boots, and this is the one to start with. Ariat's Heritage Roper uses a round toe, a low walking heel and a shorter shaft than the Roughstock, which changes two things for a beginner: it is far easier to walk in on hard floors, and it disappears under a pair of jeans instead of announcing itself. If the thing stopping you buying cowboy boots is that you think you will look like you are in costume, buy a roper first. The same Ariat construction cues apply - full-grain upper, cushioned insole - and because the heel is low, the break-in period is shorter and the ankle rub most people complain about in week one is much milder.

What you give up: You give up the silhouette. A roper is not what people picture when they say cowboy boot, and it will not hold a stirrup the way a riding heel does.

If your first pair has to survive a concert, a fairground or a shift on your feet, buy a rubber sole and a low heel - and the Rebel is the clearest version of that. Durango publishes full-grain antiqued leather, a double-row welt stitch, a flexible dual-density outsole made with slip-, oil- and abrasion-resisting rubber, a 1.5-inch rocker heel, a tempered steel shank and a cushioned, ventilated footbed. The rocker heel is the detail beginners underrate: it rolls the step forward instead of dropping your weight onto a stacked heel, which is why this boot does not punish you at hour six. The 11-inch pull-on shaft with pull straps also makes it one of the easier boots to get on without a boot jack.

What you give up: You give up traditional looks and resoleability in the classic sense. The dual-density rubber sole is a cobbler job, not a simple leather resole, and purists will clock it instantly.

The Milwaukee is the Dan Post boot most people mean when they say Dan Post: classic western stitching on the shaft, a cowboy heel, and the brand's Soft Strike removable orthotic insole. The removable insole is the practical reason to care. If you wear your own orthotic or need more arch support than a boot comes with, a removable footbed is the difference between a boot that works and a boot that sits in the closet - and most boots in this price band are glued in. Dan Post's shapes run more traditional than Ariat's, so if you have been looking at square toes and finding them clumsy, this is the alternative to try.

What you give up: You give up modern cushioning technology. This is a conventional boot with a good insole, not an engineered comfort system.