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Most men in history going all the way back to Roman times have worn a boot of some description.

Military inspired boots or combat boots were first seen on the feet of Roman soldiers, who wore hobnail boots.


In the 1800s, Hessian Boots (knee-high riding boots) were worn up until WW1. 

The 1917 'Trench Boot' was made of tanned cowhide with a half middle sole covered by a full sole and studded with five rows of hobnails. Several of the boots in this list is inspired by this particular footwear. 

The other is the combat boot. Boots with buckles were a standard issue until 1957 when the US Army switched to black combat boots, which were first employed late into the Vietnam War and called ‘Jungle Boots’.


In 2002, with the introduction of the updated US Army Combat Uniform, improved tan rough-out combat boots called Army Combat Boots were deployed. 


Aside from being fashionable, military boots have grown in popularity because they are durable, comfortable and specifically designed to be worn for extended periods, in a variety of conditions, without significant long-term wear.


The vintage military style boots in this list pay homage to the boots of the past but thankfully, they are a lot more comfortable.  

1. Red Wing No. 8084 Iron Ranger


Red Wing was the primary company manufacturing footwear for American soldiers fighting in World War I and the Company also produced footwear for American soldiers during World War II.

The 8084 is a tough, triple-stitched 6-inch boot crafted from premium Black Harness leather and featuring chrome hardware, speed hooks, Goodyear welt construction, plus a durable Vibram 430 Mini-lug sole for grip while maintaining the classic Iron Ranger construction and silhouette.

2. J Crew Kenton Leather Cap-Toe Boot


These charming cap-toe boots are made with premium leather uppers, a supple lining and heavy-duty lugged sole.


The J Crew Cap-toe Boots has been recently upgraded to Goodyear welts (the strip of leather, rubber, or plastic that runs along the perimeter of a shoe) meaning these shoes will last for many years and according to customers who bought them, they look better with age.

3. Bruno Marc Philly-3 Military Combat Boot


At Rockin' Camo we always try and feature reasonably priced options. The Philly 3 from Bruno Marc gets the nod for being a stylish and good reviewed vintage boot at a very reasonable price point. The Philly 3 is made from fauz leather, but all accounts are that they are reasonably hard wearing.

Two import things to note. As with most boots in the budget range, they do need some break-in time and will feel better after a week or so of wear. For heavy use, an inexpensive cushioned inner sole is probably a good idea to improve comfort and shock absorption. 

4. Thursday Boot Company Captain Men's 6" Lace-up Boot


All Thursday Boot Company boots are handmade with premium materials usually reserved for a boot in the $300-$600 range. The Captain is a high-end boot at a mid-range price. With a sophisticated sillouette, this minimalist cap-toe features a full leather upper that gets better with age.


The Captain features carefully designed stitching over the toe, full glove leather interior lining, Poron Antimicrobial Shock Absorbing Insole, Cork-Bed Midsole, DuraEVA Comfort Strip and studded rubber outsole for extra grip. Goodyear Welt construction ensures durability, water resistance and the ability to resole for years of wear. Two different styles are featured.

5. Vincent (Grenson Veldt) Derby Boot

Founded way back in 1866, Grenson manufactured boots for soldiers in both WW1 and WW2. The Vincent Grenson Veldt Derby Boot, however, takes its inspiration from a different war, the Boer War and the boots worn by Afrikaner Soldiers called Veldtschoens or 'Bush Shoes'.

The Vincent is crafted with black Russian Reindeer Leather with a hardwearing commando sole for durability. Made using a unique technique, the upper is stitched onto the welt, removing the gap between the upper and the sole, thus making them waterproof.

6. 206 Collective Men's Denny Lace-up Motorcycle Boot


206 Collective is an Amazon brand, which means these vintage Denny Motorcycle Boots are at the affordable end of the spectrum. While buying from wholesalers can be a gamble, in the case of the Denny it seems to be one that paid off for the majority of buyers.

The outsole is thick and of one piece, which matters when you wear them everywhere. They are also welted and feature a quadruple lapped seam on the upper to the lowers. The high padded collar is a nice touch, as it might help keep the elements out and your feet dry.

They also have a reinforced toe, which is not always the case with dress boots. The only criticism of these boots has been that the leather is a tad thin, but they still seem to represent a decent deal for the price.

7. John Lofgren Combat Boot


A California native and long time resident of Japan, John Lofgren is the creative force behind the brand and the driving force behind a design ethos of supreme quality and comfort. All of the work is done in Japan from start to finish on John's own custom last, using elite materials like Horween leather and Vibram soles.

Lofgren's most recent entry in the boot market, the Combat Boot is an updated take on the classic cap-toe military boot. The leather is Black Chromexcel from Horween, and the Vibram 705 sole and 700 heel combination is the highest quality available in the industry today. Not the cheapest boot on this list, but it may just be the best.

8. Oak Street Natural Dainite Trench Boot.


Another high quality boot this time from Chicago’s famous Oak Street Bootmakers. Oak Street shoes and boots are handcrafted from renowned Horween Chromexcel leather. Chromexcel undergoes a whopping 89 separate processes and takes 28 days to complete.  

The Natural Dainite features true Goodyear Welt construction for durability and water resistance, extremely hard wearing Dainite soles for comfort and grip, stacked leather heels with Dainite toplift and calfskin vamp lining. Built on the bootmaker's Elston last – a unique last inspired by the trench boot – these boots have been developed to embody the character of Chicago.

9 .Franco Fortini Chukka Boot Shoes


Franco Fortini was actually a poet, not a boot designer. But does it really matter when you are wearing stylish vintage boots that look this good for such a reasonable price?

Manufactured in India, these genuine leather boots from a wholesale supplier feature a leather upper, textile lining, and rubber outsole.

Like most boots at the value end of the spectrum, they will take a little longer to wear in. Once they do, however, all reports are that these are a great pair of boots for the money.

10. Nisolo Andres All-Weather Boot

All Nisolo boots are handmade in a family-run factory in León, Mexico. The Andres features a water-resistant, natural oil based & vegetable tanned leather upper, 1.25" heel, and a Vibram 430 Mini Lug Sole that will grip just about any terrain and last you for years to come. 


Nisolo went the extra mile to include a gusseted tongue that helps keep out the elements and your toes nice and dry. At time of press, over 45 people have reviewed the Andres All Weather Boot and all had given them 5 stars. A solid mid range option that has you covered regardless of the conditions.

11. Golden Fox 6" Boondocker Service Boot Pro 


During World War II, the US Marine corps stationed in the Philippines adopted the word 'boondok', which meant 'mountain, jungle, or somewhere remote'. Soldiers stationed there needed a boot that was both exceptionally durable and comfortable. They wore a type of trench boot, which they gave the nickname "boondockers." Golden Fox has taken this iconic boot and given it a modern twist.

The Boondocker features a pigskin collar, a comfortable arch supporting insole and a steel shank for extra support through the middle of the boot. The outside of the boot features a crepe outsole that is oil and slip-resistant and genuine Goodyear Welt construction ensures this boot will have a long life. 

12. Frye Addison Combat Boot


Made in the US from genuine leather with Goodyear Welt Construction, the Lace Up is a nod to founder of the Company, John Addison Frye. In 2019, the Lace-Up has been revamped in smooth pull-up Horween leather and finished with hand-antiquing.

Featuring a durable rubber sole and low stacked heel, the Lace Up has beautiful high and low tones and a rich color. These are boots for the man who is looking for premium quality.

13. Original Chippewa Aldrich Tan


A genuine heritage brand, Chippewa Boots has been supplying Americans with top-quality rugged boots since 1901. The Aldrich is a 6-inch tall men's lace-up boot featuring a rugged golden brown leather exterior and thick brown waxed cotton laces for durability.

The Aldrich is crafted for comfort with the Texon Poron cushioned maple leather covered insoles that offer lasting support, while a steel shank provides stability. A Vibram Heritage rubber outsole combines traction and slip-resistance with a flexible fit so you're guaranteed a great range of movement.

14. Thorogood American Heritage 6" Black Walnut Plain Toe


Since 1892, Weinbrenner Shoe Company has been a leading manufacturer in the American footwear industry. Despite the genuine heritage and long history of the brand, they have perhaps the most contemporary styled boot in this list. Crafted from Black Walnut, full-grain leather and with Goodyear storm welt construction, they are also designed to last.

Thorogood American Heritage boots have some unique features that distinguish them from others. A stylish work boot, the heels are capable of withstanding an application of 18,000 volts, while a Poron comfort cushion insole provides superior shock absorption and comfort.



Founded in Grand Rapids, Michigan in 1883, Wolverine is another genuine American heritage brand that worked with the US Navy in WW2, developing pigskin suede in the process. Handcrafted in the USA, the Evans 1000 Mile Boot is inspired by the Original 1000 Mile boot, which was introduced in 1914.

An impeccably designed premium quality boot, The Evans has a full-grain leather upper from the Horween Leather Company in Chicago and is paired with a stacked leather outsole equipped with a Vibram lug forepart and heel for enhanced grip.


The whole package is bound together with Goodyear Welt Construction meaning durability, flexibility, water resistance and the boot can be resoled for years of wear. No detail is spared in the impeccable design of this stylish and premium quality boot.