7 Essential Fall Boots

I told ya! Once we started talking about sweaters and cardigans, the heavier footwear wasn’t far behind. And now here we are! It’s finally time to look at our Bond, McQueen and Craig inspired 7 Essential Fall Boots!


The Wing Tip Boot

James Bond Skyfall Crockett & Jones Islay Wing Tip Boots

We know ’em, we love ’em. For Skyfall’s big finale in Scotland, Daniel Craig’s James Bond wore the Crockett & Jones Islay in Brown Scotch Grain, which you can still get for £495.00.

Why are they essential fall boots? Because they’re a timeless style that can work with almost anything except a proper suit and a tuxedo. Pair them with jeans, tweed, corduroy, flannel, you name it and you’re good to go. And despite the design originating as a country boot, people have come to see wing tip brogues as being more “formal” footwear. So they’ll add a touch of class to almost any casual outfit.


Hawes & Curtis Tan Leather Wing Tip Boot: £149.00/$229.00

James Bond Skyfall Crockett & Jones Islay Wing Tip Boots alternatives

These are more recent discovery, mentioned in our “Best Budget Style Finds” for September. Hawes & Curtis makes the boots in Portugal from a pebble grain leather with a full leather lining. And they’ve used a studded Dainite type sole. There’s no mention about the construction, so I’m going to assume it’s Blake stitch. They’re out of UK sizes 9 and 10.5, but everything else is in stock.


Meermin 101504 Wing Tip Boot in Dark Brown Country Calf: $245.00

James Bond Skyfall Crockett & Jones Islay Wing Tip Boots alternatives

Grained French calf leather, a double rubber Dainite-like sole and Goodyear welt construction. What’s not to like? Well, I’ve heard from Meermin owners that breaking in their footwear can take a bit of work (and a touch of suffering). But Meermin has a lot of fans out there in the #menswear community that really appreciate the value for the money the company offers. Sizes are getting spotty on their website, but there’s still a decent selection left in stock. Just remember that they use UK sizes and order accordingly.


The Moc Toe Work Boot

Steve McQueen Red Wing 877 Moc Toe Boots

So many of the pieces that create the foundation of classic men’s style achieved their status in part because of their association with Steve McQueen. The Baracuta G9, the suede Playboy chukkas, the Persol 714s, Barbour and Belstaff waxed motorcycle jackets and the shawl collar cardigan are just a few of the items that owe much of their popularity today to the example he set fifty years ago.

The Red Wing 877s are no exception. First launched in 1952, to this day they continue to be a popular choice with workers and hunters. However, McQueen’s use of the boots for motorbike racing introduced this practical and rugged style of footwear to a whole new audience.

Maybe the soles of your moc toes will never touch a construction site or dirt track. But when you wear them, people know you understand what “boots” are supposed to be. And that you mean business. You can still get the original, made in the U.S.A. 877 at Amazon for $249.99 to $391.67. If you’re in the UK, you can get them directly from Red Wing for £299.00.


Thorogood American Heritage 8″ Moc Toe in Tobacco Oil-Tanned Leather: $199.95 to $214.95

Steve McQueen Red Wings affordable alternatives

Like Red Wing, Thorogood proudly makes their footwear in the U.S.A. (that tag should be a clue). And like the 877s, their version of the moc toe work boot uses a Goodyear welt construction, this time with a Vibram Christy blown rubber wedge sole. Aside from the branding on the heel, there are some other minor differences between the Thorogoods and the Red Wings. The big one is the use of the speed lace hooks. Some folks will love them, some not so much. The positive is they make getting the boot on and off easier and quicker. However, speed hooks also have a nasty habit of tearing up the inside of pant legs, especially if you’re walking around in trousers with a tighter fit or narrower leg opening. So it’s a trade off. Amazon has some of the best prices for the Thorogoods, and they’re stocking sizes 7 to 14 in narrow, medium and wide widths.


Red Wing Heritiage 875 6″ Boots in Oro Legacy Leather: $279.99/£269.00

Steve McQueen Red Wings affordable alternatives

For many people (myself included), the 8″ boot is just overkill. So if you want the moc-toe workboot look, but in a height that’s more practical for day-to-day use, the 6″ 875 model is the way to go. Made in the U.S.A. with the same full grain leather uppers and Goodyear welt construction as the 877, they’ll easily handle what most of us are going to throw at them. Zappos has sizes 7 to 14 in stock. Those of you in the UK can order them directly from Red Wing.


The Suede Chukka

James Bond Church's Ryder III chukkas

One of the very first posts I published on Iconic Alternatives way back in 2015 was on alternatives for Bond’s now iconic Quantum of Solace footwear. And the Church’s Ryder IIIs continue to be popular eleven years after Bond wore them for riding a dirt bike through Port-au-Prince and blowing up eco-hotels in Bolivia. You can still get the originals at Herring Shoes for £410.00. But sizing options are running a little low.

Suede boots may not be the ideal choice for those rainy fall days (although they can handle getting wet much better than folks think). But if it’s relatively dry outside, there are few styles that look as good with jeans or chinos. Basically, a good pair of chukkas should be a staple in every guy’s wardrobe.


Herring Canterbury Chukka in Brown Suede: £155.00/$164.00

affordable alternatives James Bond Church's Ryder III chukkas

A LOT of boot for the money! Not only do they have the look we want. They’re also leather lined and blaked stitched with a Dainite-like rubber studded sole. The Canterburys are made in Portugal, not England. But the reviews are very good and Herring has sizes 6 to 13 in stock. Shipping in the UK is free. However, they charge £20.00 (about $25) to get them to you in the States. I can’t deny liking Herring Shoes. As I’ve frequently said, the owners and staff there know footwear and make customer service a priority. That’s something I think we can all appreciate.


Velasca Artista in Dark Brown Suede: $195.00/£178.00

affordable alternatives James Bond Church's Ryder III chukkas

Put aside the three eyelets, and these are a very solid alternative for Ryder IIIs. Velasca makes the chukkas in Montegranaro, Italy from “overturned” full grain leather and finishes the interior with a Vacchetta leather lining. The Vibram Eton studded rubber sole is attached using a Blake stitch construction. So the boots can be resoled and tend to have a softer flex than Goodyear welted footwear, which some may like since it minimizes break-in time. Two other points in Velasca’s favor. First, the Artistas have 4.4 stars after 331 reviews. And shipping and returns are free for customers just about everywhere.


The Leather Chelsea Boot

Daniel Craig Layer Cake Chelsea boots

We recently took a deep dive into Daniel Craig’s Layer Cake Chelseas in this post. And as we mentioned, they were most likely the now discontinued R.M. Williams Henleys. Although R.M. Williams is most famous for their sleeker Craftsman model, the style that comes closest to the Henley from their current collection is probably the Comfort Turnout ($495.00 U.S.).

I understand that Chelsea boots may not be for everyone. But I’m a huge fan personally. What I like most is their versatility. It’s a style that balances “sleek” and “rugged” like few other boots can. Let them get a little beaten up and they’ll look great with jeans and a leather jacket. Give ’em a brush and polish and they’ll fit in with most “business casual” looks.


Baxter Goulburn in Brown: $191.53/£158.18

Daniel Craig Layer Cake Chelsea boots alternatives

Like R.M. Williams, Baxter also makes their Chelseas using one piece leather uppers. And it is very much an Australian heritage brand in its own right. Started in 1850 by Henry Baxter in the town of Goulburn, most of their footwear is now made in Asia. However, at least up until a few years ago, their signature Goulburn model was still crafted in Australia. And that’s where they’ll be shipped from. Which will set you back another $25 to $50 depending on how fast you want them. But even with the extra cost, these are a heck of deal as long as you can get your size dialed in on the first try. Note that they use Australian sizing on their website!


Meermin 101050 Chelsea Boot in Dark Brown Calf: $230.00

Daniel Craig Layer Cake Chelsea boots alternatives

Another model from Meermin. And I was very happy to see that they’ve updated their version of the Chelsea. The biggest improvement? They’ve started using a whole-cut leather construction, with a single seam up the back of the boot. Just like R.M. Williams. But … and this is the really awesome news … they’re about half the price! Meermin uses a French boxcalf leather upper built around their popular Hiro last, a Dainite like studded rubber sole and a Goodyear welted construction. So a LOT of boot for the money. Just a warning that sizing options are getting low on their website.


The Black Dress Boot

James Bond Skyfall Crockett & Jones Tetbury

When the weather gets a little cool and damp, switching from a dress shoe to an ankle boot can be a smart move. And when we’re looking for a great dress boot, Bond’s Tetburys from Skyfall are among the best we’ll find. You can still get the originals at Crockett & Jones for £430.00. Made with a full grain leather upper and Goodyear welted Dainite rubber outsole, the boot’s most distinctive characteristic is the chisel toe of their 348 last. Definitely an investment. But they’re built to last years.


Carlos by Carlos Santana Corazon Chukka Boot in Black: on sale for $138.95

Skyfall Crockett Jones Tetbury affordable alternatives

Not only is Carlos Santana (not to be confused with Carlos Santos) a legendary guitar player. But he also designs a hell of a good boot? Honestly, I was ready to write these off as more “celebrity promoted garbage”. And then I read the specs and customer reviews on Zappas. First, we’re getting a full grain leather upper and full leather lining. The design is three eyelet, but the stitching along the quarters is close to the edge to give the boots a clean, streamlined look. Plus the toe box has that chiseled shape we want. The reviews are very positive, with a highlight being the fact the boots come with cloth storage bags. But they do note that the fit on these is a little small and recommend ordering a half size up.


Herring Shoes Cannock Chukka in Black Calf: £165.00/$174.00

Skyfall Crockett Jones Tetbury affordable alternatives

The toe shape is a little more rounded than the Tetburys and the cut of the quarters isn’t the closest match. We’re also getting a Blake stitched boot rather than Goodyear welted. However, that particular construction method is still a solid way to make footwear. It’s lighter and tends to be more flexible, it’s almost as strong as a Goodyear welt construction, and it still allows the footwear to be re-soled. Blake stitching also creates a more streamlined look since the less of the sole is exposed directly below the upper. Which nice design feature for a dress boot we may want to wear with suits or pressed trousers. Herring currently has UK sizes 6 to 13 in stock.


The Suede Boondocker

J Crew Kentons boot James Bond SPECTRE

Bond’s whole SPECTRE Morocco look quickly became a fan favorite as soon as the promotional photos appeared. From the Brunello Cucinelli sport coat and chinos to the Tom Ford tie and sunglasses, it probably runs a very close second to the Skyfall Scotland outfit in terms of “inspirational Bond style”. This was something you could imagine Bogart wearing in the desert, a throwback to a more romantic era of the gentleman traveler. And the J.Crew Kenton suede boots added that utilitarian touch that gave the whole look a more adventurous feel.

The Kenton is now long gone from J.Crew’s shelves. But it’s definitely worth tracking down an alternative in a similar style. Not only will they look good with some taupe chinos and a linen blazer, they’ll also work with almost any work wear or military inspired outfit.


Golden Fox Footwear 6″ Boondocker Boots in Khaki: $74.95

J Crew Kentons boot James Bond SPECTRE budget alternative

A long time favorite around these parts. Honestly, the fact that Golden Fox Footwear is able to offer a Goodyear welted, double stitched suede service boot at this price still amazes me a little. I wrote a review of the Boondockers more than two years ago (you can read that here). Over the last 24 months, I’ve put the boots through their paces. And I have to say they’ve held up incredibly well. There’s still almost no wear on the soles. The uppers haven’t gone soft or floppy and have really kept their structure. And they’ve definitely broken in so they’re super comfortable to wear. Overall, I’m very happy and have no hesitation continuing to recommend them. Amazon currently has that ridiculously low price. But they’re missing some sizes. If they don’t have what you need, check out the Golden Fox website. The price there goes up to $129.99, which is still very reasonable considering the quality.


The Hiking Boot

SPECTRE Danner Mountain Light 2 Boots

Bond was really prepared for that quick walk from his plane to the front door of the Hoffler Klinik in SPECTRE. The classic Vuarnet PX5000 glacier glasses, the watch cap, the Tom Ford jacket and heavy wool trousers, the N.Peal mock-neck sweater. And, of course, the black leather Danner Mountain Light 2 boots. I understand that a secret agent should be ready for anything. But I honestly think the biggest risk he faced was overheating in Madeleine Swann’s office!

About those boots. The Mountain Light 2s are a pretty traditional style. But despite their “heritage” design, they’re actually relatively light-weight and shouldn’t be too hard to break-in. Made in the U.S.A, they feature full-grain one-piece leather uppers with a waterproof Gore-Tex liner, a stitchdown construction (so they can be re-soled), a fiberglass shank, and a Vibram® Kletterlift outsole.

There are still plenty of places to buy the Mountain Light 2s. I’ve linked to Backcountry, where they’re selling for $379.99. But they’re the same price almost everywhere. Why buy them? Because they’ll be a great boot for day hikes off the beaten path to check out the fall colors. And when the cold and slushy weather hits, they’re going to help keep your feet warm and dry.


Merrell Wilderness: on sale for $259.99

affordable alternatives SPECTRE Danner Mountain Light 2 Boots

This is an excellent price for these boots. Merrell has been making their classic Wilderness model for decades and hikers recognize them as serious boots. They feature full-grain leather uppers with a wicking liner, Norwegian welted construction, a crampon compatible Vibram Roccia Block sole, and Italian metal hardware. And Merrell makes them in Michigan. In short, they’re a slightly more heavy-duty version of the Mountain Light 2s. Regularly four hundred bucks, 6pm.com has them on sale and is stocking sizes 9.5 to 13. Just don’t expect an easy break-in period. These puppies are stiff at the start!


Have some suggestions for our 7 essential fall boots? Tell us about them in the comments! You can also visit our Facebook pageInstagram account, Twitter account and Pinterest Boards for more James Bond style advice and inspiration! And don’t forget to check out our Amazon Store. That’s where we’ve organized the alternatives we’ve found on the massive online retailer.

Iconic Alternatives

The search for classic and affordable menswear, inspired by the style icons of today and yesterday.

8 thoughts on “7 Essential Fall Boots

  • November 3, 2019 at 7:51 pm

    John, a quick note. While finding the J. Crew Kenton Sahara boots, is a daunting task, I did find a pair of them with the moc toe on eBay. Shockingly, they were in my size 12 and I managed to snag them this evening for a ridiculously low price.
    The original J. Crew Kenton Sahara boots do occasionally show up on eBay as well, if anyone has the patience to keep searching. I was never able to locate them in my size however, so the moc toe Pacers will have to do for me.
    Again, continued thanks, for your tireless efforts on behalf of Bond fans.

  • November 2, 2019 at 2:49 pm

    Considering the popularity of the J. Crew Kenton Sahara boots, you would think that some enterprising boot manufacturer would produce a pair of similar boots and really clean up. But, that’s just wishful thinking on my part and I would imagine a number of other guys too.
    I am searching, and using some pretty esoteric keywords to search with, thus far without success though. If I ever do come up with an iconic alternative, you, John, are the first person I’ll contact.
    Thanks again, John, for all you do with this website. This is the one place where so many of us fans can pool our resources and work together to locate the clothing styles we all seem to enjoy. Also, kudos to you for dishing out credit for those out there that go the extra mile in that search.

    • November 2, 2019 at 2:58 pm

      Thanks! And it’s my pleasure. Honestly, the Golden Fox Boondockers are still far and away the best value for money alternatives I’ve found for the Kentons. I’ve had mine for almost 3 years now and they’re still going strong. And that price for Goodyear welted boots is pretty hard to beat. They don’t have the brick red sole. But other than that, I think they’d work for 90% of us that want the Kenton style. Cheers!

      • November 7, 2019 at 3:19 pm

        Well John, the Kenton Pacer Saharas arrived today and they’re quite nice. It would appear that the person who owned them rarely, if ever, wore them. I really like red soles since they are very soft and don’t make a lot of noise when you walk. Love ’em!

      • November 7, 2019 at 3:21 pm

        Congrats! It always feels good when you score a deal!

    • September 29, 2019 at 10:27 am

      Those look great and I’m going to try and include them in an upcoming post! Thanks for sharing!

  • September 25, 2019 at 12:58 pm

    Look CLARK’S / FRAU shoes


Leave a Reply

Your email address will not be published. Required fields are marked *