Selecting the right pair of ankle boots for your lifestyle is a hefty decision considering how many winters they will accompany you for. 

Google "men's boots" and the options feel endless, but most are cut in low-quality fabrications and have too many bells and whistles or sub-par design lines. 

Personally, I find heritage brands and classic cuts work best with menswear. Forget anything too on the zeitgeist and opt for the best-quality pair of leather ankle boots within your budget. 

The two things I look for are a thick leather or suede upper and a lightweight sole designed with comfort in mind.  

To make your life easier and speed you on the way to meeting your new favourite footwear, I’ve done the groundwork for you and curated the best of the bunch. Here you’ll find 10 pairs on the market this season. Happy and comfortable stomping! 

Crane Brothers leather chukkas, $595

An elegant and relaxed option, the tactile nature of suede makes the laced chukka boots from Crane Brothers a perfect pairing for indigo denim and heavy woollen overcoats. 

Working Style brogue boots, $699

Modelled on the traditional English lace-up street boots and handmade in Spain, these are perfectly matched to raw denim or chinos. Their rubberised sole adds extreme comfort, so long days or nights on your feet become a breeze. 

Camper Brutus boots, $255

A Camper original since 1986, the "Brutus" is an urban style with lightweight technology and durable 360-degree stitching. Fashioned in black organic cotton and leather, these boots feature Camper's extra-lightweight outsole, great for men who find lugging around a heavy boot a chore. 

Hudson London Battle Hi Shine boot, $298 from Workshop

The Battle Hi Shine boot from Hudson is classic with a twist. The secure ski hook and lace fastening are nods to the hiking trend seen for the past few winters, and the elegant narrow fit means they’ll comfortably take you from the office to the restaurant. 

RM Williams Craftsman boots, $645

Let's face it, a pair of RM Williams Craftsman boots are a rite of passage for a large proportion of Antipodean men. Handmade in Adelaide, they scream tasteful and understated Everyman and pair wonderfully with both a suit or casual wear. The black suede will be less forgiving in the elements than the hard leather, so I suggest investing in a can of waterproofing spray to protect them. 

George Cleverley Toby suede brogue boots, $890 from Mr Porter 

George Cleverley's Toby design mixes the elegance of brogues with the practicality of winter boots. They've been handmade in England from roughout suede, lined in leather and set on high-quality soles for longevity. Pair with raw denim or cords in a classic fit. 

Church’s Coalport soft grain derby boots in walnut, $1656

Perfect for out-of-town meanderings but sophisticated enough for the city, the Coalport derby style embraces its rugged silhouette and adds tough accents. These boots are crafted from soft grain calf leather with a natural finish and detailed with equally casual metal eyelets and cotton laces. Should you wear them on rambling strolls, they will live up to their robust aesthetic, thanks to their fully lined, durable construction and water-resistant storm welt. At over $1500, they're an investment, but remember they're made to last. 

Country Road suede chukka boots, $229

A soft blond suede boot with a lugged sole, this cheap and cheerful option will work well next to lighter colours such as taupe, sage and beige. The chukka cut finishes lower on the leg than a traditional chelsea or dress boot, so this is a great style for men on the shorter side. 

Paul Smith Tufnel boots, $585 from Smith & Caughey's 

Super lightweight and made for walking, the Paul Smith Tufnel could be the perfect pair of boots to take on your next sojourn overseas. They feature a moccasin toe and cow-hide leather panelling and are handmade in Portugal. 

Marsèll lace-up boots, $1074 from Farfetch 

I’ve saved the best pair for last. These boots from Marsèll are Italian made and deliciously high cut on the shin. The chestnut brown suede leather will play well with navy and earthy neutrals and looks fantastic with blue denim. 

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