The temperatures may still be hovering around t-shirt and shorts levels for most of us, but any minute now all sorts of cool weather gear will be dropping into stores and online all across the country. Call it premature or call it good old fashioned forward planning, starting to think about your fall boots choice early just makes plain good sense.

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Astorflex Greenflex Chukka Boot

A name new to us, Astorflex are one of the best kept secrets in the men’s footwear game. The brand was originally founded back in the 1800s and are currently in their sixth generation of shoe makers, yet we’ve only started to see them appear in stores these few past seasons. The Greenlex Desert boot is one of their standout styles; the silky-looking suede is achieved by treating premium Italian leather to a unique 30-day ageing process, which leaves the boots with both a super soft appearance and low environmental impact. Handmade in Italy, with a price tag that won’t stretch the paycheck too far.

$145
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Thorogoods Roofer

Lace-To-Toe Boots

In the early 1950s, Thorogood produced the very first lace-to-toe workman boot, specially designed with roofer layers in mind. Build for comfort and flexibility, the Roofer – also commonly know as a Monkey boot – features a unique toe box and lacing system, which was originally designed to minimize the leather rubbing against your foot when in the kneeling position. With a slight hiking boot-feel, the US-made Roofer fits in perfectly in the modern day footwear market and features a Goodyear welt, lightweight rubber mid-sole, and water-resistant upper.

$190
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New England Outerwear

Fieldsman Boots

This self-labelled rugged boot by New England Outerwear has all the tools. Inspired by a traditional mid-19th century hunting boot, the Fieldsman is as robust and practical as it is stylish. The use of an authentic moccasin construction helps the leather to mold and adjust to the foot after a very short time. The result is one of the most comfortable winter boots on the market. Every part of these beauties has been handcrafted in the USA and will only get better with age.

$380
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Red Wing Iron Ranger Boots

A list about winter boots wouldn’t be complete without adding the name Red Wing into the mix. The Iron Ranger 6-inch boot is as hard as nails, originally built for tough-as-they-make-‘em Minnesotan iron miners. The added protection on the toe cap comes from miners covering their boots with an extra layer of leather to avoid hospital visits. Eventually Red Wing phased in this inventive modification as a permanent fixture, which has become somewhat of a trademark to the company’s footwear. Ain’t no elements seeping through these rugged bad boys.

$320
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Grenson Grover Boots

Footwear has always been at the industrial forefront in the small British working town of Northampton. The Grenson brand were one of the key footwear manufacturers to capitalize of the growing trend for well-made goods aimed at a younger market. This season sees their much loved Grover boot take a slightly different direction, with the move to a rugged commando sole for extra durability. Grover is a smarter take on a hard-wearing winter boot, featuring a snuff suede upper with traditional apron construction and hiking lacing system.

$370
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GH Bass Brigg Boots

A brand more commonly recognized for their much-loved “Dirty Bucks” and Weejuns loafers, GH has been quietly dropping a few interesting offerings into this year’s footwear market. The Brigg Boot is the brand’s smarter take on the iconic Duck Boot, with a distinctive molded front stitching design and contrast leather upper vamp. The thick rubber sole provides a decent amount of traction in the damper months.

$150
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Yuketen Johnson Boots

Some would say the combination of meticulous Japanese design and trusted North American construction is a match which is unrivaled. With one look at Yuketen’s Johnson boot it would be hard for us to disagree. The Johnson is the California-based brand’s reinterpretation of the classic military boot – otherwise know as the Boondocker. The heavy sole has been replaced with a lightweight, shock-absorbing Vibram Christy sole, and cotton laces have been ditched for leather laces for a more premium appearance. A pair of these guys doesn’t come cheap, but Yuketen’s method of construction, choice of materials and design reputation is rarely matched.

$484
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Tricker’s Stow Country Boots

This 7-eyelet Derby brogue boot by Tricker’s is indeed packing a little more extra sizzle than the rest of this bunch. Brown suede upper with contrasting green sole, purple heel tab and navy interior – it’s all sounding a little Willy Wonka, but we think it works perfectly. Sure, the Stow Country Boot is available in a more conservative selection of colors, but sometimes our lists benefit from a rogue within the pack. Tricker’s reputation as one of British’s premium shoemakers is firmly justified by boot made entirely in the UK the same way since 1829.

$509
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Fracap Scarponcino Boots

With their unique looking silhouette, the Scaponcino boot by Fracap is as recognizable it is durable. These Italians really are the go-to folk when it comes to hiking boots, and up until recently Fracas’s collection of hefty mountain climbers were only available to the Japanese market. Handmade in Monteroni, Italy, using locally sourced leather, a traditional D-eyelet lacing system and natural Vibram sole.

$249
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Chippewa General Utility Boots

“Footwear for every purpose” is what Chippewa does best, and while Red Wing may be known for creating one of the most popular Moc Toe boots on the market, these guys have taken the style one step further with a premium leather Cordovan shell. With its versatile, slim silhouette, flexible sole and slightly smarter appearance, the General Utility 6-inch boot is one of those staple footwear styles that’ll see you right for most everyday conditions. A US-made boot that comes in a just under $260.

$250