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Preston Konrad

Professional Fashion Expert

Best Mens Boots & Mens Leather Boots

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Leaves and temperatures are going to start taking a plunge in the coming months, and it’s time to start making that checklist of those things you should most likely have before you find yourself up to your knees in snow. A great pair of boots is a must when the weather is cold. Not only will a sturdy pair of boots prove to be functional in the fall, you’ll also look insanely cool with the options I’ve found for you guys. Here are my picks for the best boots to march down the street in this fall.

Find the best mens boots at the best price with the help of our experts who search the Web for leather boots from the hottest designers. These mens leather boots feature Gucci, Ralph Lauren, Cole Haan and others.

Best Boots For Men by Preston Konrad

The Best You Can Get

  • Gucci Boot AGJ10

    Preston says: These are some serious boots, gentlemen. These brown leather boots are made of 100% calfskin leather and slouch through the body like you’ve had them for ten years. The sole in thin and is worn in easily, and the hardware at the ankle is just too cool. Equestrian inspired buckles and grommets meet in the front of the boot with a leather patch embossed with the new Gucci crest logo – for extra snootiness. Castle and Knights of the Round Table not included.

    • Made in Italy
    • Brown calf leather
  • Ralph Lauren Fresno Boot

    Preston says: The old-school British riding boot is reinvented with a contemporary spin. This time around, the boot is chunkier and more masculine looking, featuring a hand stitched leather sole with a reinforced stacked heel. The dark brown color is rugged yet classic at the same time, and it really wears well with age. The double straps across the ankle of the boot give authentic detailing while still looking masculine and smart. This boot is worth investing in.

    • Made in Italy
    • Adjustable double ankle strap
  • Red Wing Classic Irish Setter Boots for J.Crew

    Preston says: J.Crew sure had the right idea when pairing up with legendary boot manufacturer, Red Wing to bring back the Classic Irish Irish Setter Boots. Originally introduced to Americans in 1952, this legend is back with all of the original detailing to be expected. The old-school Irish setter label and the Red Wing logo have been stamped into the leather just like the originals – this was done just for J.Crew, kind of cool huh? This is a man’s boot, guys. Crack open a beer, lace up your Red Wings, and go… chop some wood or something.

    • Antiqued brass eyelets
    • Rubber sole
  • Hunter Wellington Boots

    Preston says: Maybe you’ve heard people reference rainboots as ‘Wellies’ at one time or another. If you have, this boot is the inspiration for that catchphrase. The Hunter Wellington, or ‘Wellie’ has been the staple rainboot in the UK for decades. This Scottish boot has been around for years in the rainy moors of England but still looks modern and cool hitting the pavement in Boston or New York. The boot is rubber all over and features a quick drying, antibacterial lining which is actually very comfortable. If you are a half size, I would buy up. This is a boot you will end up having for years.

    • Quick to dry
    • Antibacterial lining
  • Cole Haan Air Lucarno Chelsea Boot

    Preston says: Paul McCartney called… he wants his boots back. These Beatles-era boots are some of the coolest most retro boots on the block. The traditional Chelsea boot is back as it was in London in the 1960s and almost every major footwear retailer is producing a pair. Why did I choose the Cole Haan pair? Hidden in the well crafted, lugged sole is Nike Air Technology, literally making you feel like you are wearing a pair of your favorite sneakers – How cool is that? These boots are hand crafted in Italy of calfskin leather and are a bargain at this price, seeing as many other retailers are selling their fall boots for upwards of $1,000.

    • Available in black or brown leather
    • Nike Air Technology
    • Made in Italy

You will be happy with any of these

  • John Varvatos Chain Motorcycle Boot

    Preston says: Inspired by a pair of vintage motorcycle boots, this pair by John Varvatos is a new classic in my eyes. The antiqued black calfskin leather is aged to perfection and the silver brushed hardware is equally as authentic. The studded strap channels the days of Steve McQueen. Wear with a fitted pair of Levi 501s for an authentic look.

    • Made in Italy
    • Antiqued leather
  • Frye Harness Boot

    Preston says: Frye is the oldest owned and operated shoe company in the United States, producing shoes since 1863. The Frye harness boot was worn by the American and confederate soldiers in the Civil War and are the epitome of cool. These boots are made of great chocolate leather that really wears well with age. The strap across the ankle is connected with the traditional brass or chrome ring and the sole is a sturdy rubber construction. Warning, these take a little bit of time to get used to, so wear them often to break them in. Speaking of breaking, these will certainly not break the bank for you guys.

    • Made in the US
    • Steeped in history
  • Salvatore Ferragamo Niccolo Boot

    Preston says: The Chelsea style boot, made famous by the Beatles has been making a comeback for the past few months; paired with skinny jeans, slim pants, etc. This boot by Ferragamo is one the best reinventions of the classic. The chocolate “caffe” brown leather is rich, slick, and classic in color. The perforation details across the foot are traditional wingtip details making this boot look suitable for more formal occasions. Pair this boot up with a skinny jeans and a camel topcoat for a pulled together look this fall.

    • Made in Italy
    • Stacked heel
    • Elasticized Shaft
  • John Lobb Tudor Boot

    Preston says: Another remake of the Chelsea boot, this option is the most refined and most classic. You guys that work a nine-to-five job or in a more conservative workplace, this is the one for you. The boot is bench made in England (not on a machine, but by hand) and is available in chestnut brown or black leather. The boot also features the elastic inserts in the side of the ankle for added comfort. It’s important to keep in mind that when buying a shoe that it bench made, you should expect to pay a bit more as each piece of the shoe is made by hand by a trained shoemaker.

    • Bench made
    • Available in brown or black
  • Ralph Lauren Brickston Boot

    Preston says: Tally Ho! This horseman inspired boot from Ralph looks like you may have picked it up from a luxury equestrian shop. The boot is meant to be pulled on and off, features no zippers or elastic (sometimes this gets tricky if it’s warm outside) and is all black with a calf brown ‘hunters' top’ at the top of the boot (this comes from the English sport of fox hunting). The sole is made of stacked polished leather and insole is padded for extra comfort.

    • Made in Italy
    • 16” widest in the calf

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We suggest the best mens boots made of supple leather in designs that are stunning with work clothes or a night with the boys. These mens leather boots are must-have for fall and winter weather. Choose from mens black boots and other boots for men from Ferragamo, Lauren, Haan and others, always at the best price.