Would you (could you) wear a cowboy boot?

Wednesday, February 16th 2022
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A friend once told me that he gets a kick out of finding an unusual piece of menswear, and working out a way to wear it. Like a challenge: how can he make this esoteric bit of clothing wearable. 

I’ve never really taken that approach to clothes. However, I have always been interested in genres I don’t typically wear. I’m interested in the tradition, the conventions, what it’s normally worn with and why. Perhaps most interestingly: could it be worked into another genre, and if not why not? 

Cowboy boots are one of these for me. Traditional, artisanal clothing in one part of the world, and a craft I’ve loved covering in the abstract in the past, for example when visiting bootmaker Lee Miller in Austin

But would I wear them, formally or casually? What are the ways to do so without looking like either a Texan senator or cowboy cosplay? 

I’ve been having fun figuring that out over the past six months, with the help of Zephan Parker, a bootmaker from Houston, Texas. 

Zephan is Parker Boot Company. He was introduced to me by a friend last year, and we had a few calls talking about styles of western boots, as well as how they’re worn in Texas and abroad. I was also able, gratifyingly, to give him some advice in return on trunk shows, social media and other things.

The style of boot that most interested me in our discussions was the roper boot, because it sounded like something I might actually wear. 

Originally used for roping cattle as much as riding them - hence the name - a roper boot is a subtler version of a normal western boot. It usually has a lower heel, a less pronounced toe and a lower shaft on the leg. 

It’s not only toned down, it’s also more practical - easier to walk in, because (unlike a normal western boot) that was what it was designed for. 

That’s a typical roper boot above. The other shots in this article are of me wearing a fitting boot (not the finished product) from Zephan in a style I chose. 

I went back and forth on that style for a while. On the one hand, I wanted something that was subtle enough that I would wear it; but on the other, I didn’t want to remove everything that made it an interesting style in the first place. 

In the end I decided to try a roper boot with a brown suede lower half, and a brown alligator upper. It’s pretty standard to have the top and bottom halves in different materials, with the top usually the brighter and more decorated, in part because it’s usually hidden.  

The fitting boot that Zephan made was suede top and bottom, because it wasn’t really worth using alligator just on the trial. However, having received and worn the fitting boot, I think I might go with a brown leather on the upper: it’s nice to have some contrast, but alligator might be too showy for me.

Zephan also worked on an inlay design for the top half. Unprompted by me, he took elements of my tattoo design and made it into something smaller and rounder, better fitted to the space. 

That he did in alligator, because there was so little of it. On the final boot, I might switch to a stitched pattern: this design is a little intricate for inlay and some of the detail gets lost.    

Wearing these boots in London over the past few months, I think it’s interesting that most people don’t give them a second glance. They look - unless you do give them take a second glance - just like big brown boots. 

The only thing that makes them look western, until you put your feet up and show the top half, is something subtle in the shape of the foot. The last is quite wide and rounded in the joints (where the foot bends) and a little elongated in the toe. 

You definitely wouldn’t see those kinds of proportions at a European bootmaker. But they are so subtle - like the difference between a pointed toe and an almond shape - that most people are also unlikely to notice them. 

It’s worth pointing out that a normal cowboy boot also has a slim, pegged waist, rather than the full welt you can see running to the heel here. 

That along with the pointed toe, pitched heel and decoration are things that make that boot more smart, dressy. It’s why a boot in that style is what someone in Texas might wear with a suit. They wouldn’t wear a roper. 

“A roper for us is a working boot, something you might wear at the weekend to do chores,” says Zephan. “Most people wouldn’t wear either with tailoring, I guess, but here we certainly wouldn’t wear that style. 

He’s right: I don’t know anybody in London that’s going to wear a western boot with tailored trousers. But I do think that those who wear them (or are considering wearing them) with jeans could do worse than look at a roper boot instead. 

This is an interesting time for menswear. I think the erosion of tailoring as businesswear has left quite a few guys feeling stranded, not knowing quite what to wear apart from their old, lacklustre weekend clothing, or the streetwear that is pushed by fashion magazines, but which can seem both lazy and perhaps immature. 

In a way, it’s exciting because you can wear almost anything. There will probably be more mixing of genres now than there have ever been. 

But it can also feel chaotic, and most men don’t want to experiment every day. They want good-looking combinations that make them feel well-dressed and, just as importantly, give that impression to others. 

There is still a smart casual middle-ground, of quality well-fitted clothing. It’s what we cover on PS, and it seems to help having it spelt out and clearly demonstrated. But I also think it’s nice to find ways to sneak in some of those unexpected, genre-bending pieces. To take advantage of the chaos.

A pair of suede cowboy boots with a bespoke overcoat is - for me, always for me - a fun way to do that.  

These boots are not finished - they are a fitting boot, the creation of which is Zephan’s standard practice for a new customer. Mine were finished to a slightly higher standard, so I could get an idea of the style. But this is not the finished quality level. The final boots will have a full review in a follow-up article. 

Zephan’s boots start at $2500 and are all made custom, to order. Like many custom bootmakers he is in high demand, with a current delivery time of 16 months. 

Other clothes shown: Ciardi bespoke overcoat; Dalmo hand-knitted roll neck; Drake’s ecru jeans; Frank Clegg tote bag. 


By the way, a reader recently commented that he would like to see more on North American crafts. I have covered a fair few over the years. Here are some, with links:

Optimo hats, Chicago
New York tailors
Lee Miller boots, Austin
Horween leather tannery, Chicago
Stephen Temkin hats, Toronto
Red Rabbit jewellery, New Mexico
Chris Despos tailoring, Dallas
Len Logsdail tailoring, New York
- Sr Francesco, Toronto
Paolo Martorano tailoring, New York
Good Art jewellery, Los Angeles
- Navajo weaving, New Mexico
Wellema hats, California
Do shout if I've forgotten anyone!

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I like the boots.I’d probably choose to have them in suede rather than a mixture of leathers but that is rather a personal preference.


Glad you’re planning to add leather to the final boot. The all-suede make up has a touch of the Ugg boot about it.


if I may say: I used to wear cowboy boots and tooled belts as a boy in the 80s, like many in Italy at the time, only to abandon that style, unsuitable for the profession. Now, 25+ years later I’m starting to wear them again. Very sporadically, just to go to the live music club. Maybe we all subconsciously follow the same path?


I agree with you Simon, it took 25 years to me to go back to the same spot. And to be honest, I can also see a bit of nostalgia in me doing this.

Dr Peter

An interesting piece, Simon. Here, in these United States, all manner of folks deck themselves out in cowboy boots, even those who have not ventured beyond the canyons and wilds of Manhattan! I’m told it is even proper form in Texas to wear them with black tie. Whether you feel that it is easy for you to wear a pair without feeling self-conscious — now that’s a personal question. My own take on this is one of comfort. Pointed toes are distinctly uncomfortable for me, so I do not own cowboy boots.

Peter Hall

If you consider it, chukkas are riding boots,so the riding heritage is certainly there.
I’ve always thought the last of the western boot was stylish. It appears that the suede is already moulding to your foot. Do you find them comfortable enough for a lengthy walk in town?

Clifton D

I too, chose the roper style of boot, particularly because of the flat heel, for me I didn’t want the stacked heel type. So a pair in black for wearing with a suit, and another in a distressed calf skin, so I can mix with denim or lighter chinos…..


I think in all suede the fitting boots look fabulous! A really nice color.
I finally bought brown boomer leather Red Wing Pecos 1178 during the lockdown last year and by now these are my go to boots if I am wearing the right kind of trousers: Thus, denim with an opening that is wide enough. But I also like to wear them with a wide wale corduroy chino, a shirt and knitwear. It adds a little contrast and just works perfectly.
Regarding outerwear, I agree, it looks best with a nice long coat like in your pictures. Something too short makes the whole look rather rural?


Hi Simon,
It is a no from me.
I understand the attempt to try, but Cowboy boots are too specific a genre and that genre is about utility first, second, third and probably about ninth is some form of style. That is stylised/ fashion as opposed to tailoring.
I find this attempt to be a bit Heston Blumenthal, Snail Ice Cream. It may be interesting, if and only if you can make it taste pleasant, but it shows a desire to be clever rather than an overall pleasing effect.
It is more likely to fail and in the unlikely event it succeeds, I think it is trying too hard for very little aesthetic benefit.
May be I am getting old!



I think it was snail porridge!?! It may also not be the best analogy as the porridge was delicious. I agree with the specific genre point though. It feels a bit like wearing a Fez hat or Thawb. When worn out of context and in a different cultural enviorment from that where it came it can feel very unnatural. I am actually all for cultural appropriation, i believe it to be a force for good when done in a manner that doesnt seek to exploit but this is not one for me.
Can i ask when the Stetson arrives?


Western boots, like those of us who live in Texas, are not so concerned with snobbery. Looks good, feels better, has utility and embraces a proud tradition. It’s a big tent and everyone is welcome. Growing up in the most elitist environment possible on the east coast, there’s good reason we settled in Central Texas. Simon, you’re welcome any time, and if you visit Austin, hit me up for some bbq and breakfast tacos. It’ll change your life.


Very inspirational Simon! I can’t put my finger on why exactly I like this particular mix of styles and genres so much but maybe it’s because it puts the shoe so much out of it’s original context. The prime example of high/low dressing. Reminds me of the great Fran Lebowitz wearing custom made cowboy boots with vintage Levi’s and Anderson & Sheppard jackets.


Interesting article, i have to say i think you chickened out though Simon. For me these lack allot of the appealing/ intimadating aspects of a steriotypical cowboy boot. As a stand alone boot i can see the appeal but i dont think they go far enough if you are really going to explore how to fit a true ‘cowboy boot’ into you way of dressing. I would like to see a more pronouced heel, which in my opion can be very elegant. Perhaps not as extreme as what Husbands are doing but certainly more than these have would be nice. I dont like the inlay leather on the design. The grain of the leather distracts from the design itself. I would also say that the all leather version pictured are much nicer. I feel that the suede dums down the effect further. Fortune favours the brave Simon!!!


If the motivation for buying these is to provide content for the site then i would argue it wouldnt matter if the first pair didnt work out. There could still be a justafiable reason for ordering the second perhaps more concervative option. Indeed this has been the case with some of the bespoke commisions featured on this site.
If the motiviation for buying is to furnise your own wordobe then i would argue that two pairs however different would be excessive given the ammount of shoes and clothes you must own.
With this in mind i stand by my point that i would like to have seen a more adventurous choice. It would have made for a more interesting article on many levels.


These look a bit like Chelsea boots in profile, when under the trousers/denim. Curious why they appeal where Chelsea’s have not to you (too slick/sleek etc)


Nice. Would you consider wearing a bolo tie, Mr. Crompton? Leonard Cohen used to wear one and he was a well dressed man.


I´m not sure I would call Leonard Cohen a pop star, but OK. I guess the answer is no.


Always interesting articles, Simon. As a native-born American who currently lives in the South I must admit that the boot has been adopted here in almost every setting, from formal to casual. Still, it’s not really my “thing” but when executed correctly it can be a very intriguing look.
As an aside, have you considered looking into Francis Waplinger? He makes a genuinely fantastic product and has amassed a growing following on his IG page. I’m very proud to say that he is one of only a couple American bespoke cordwainers making true bespoke shoes whose primary product is not western-styled boots.


I think for most PS readers, if a boot like this was to find it’s way into their collection at all, it would be for very occasional use. Otherwise you risk becoming the “Cowboy Boot Guy”.

And $2,500, which might be justifiable for something that will get a lot of use, is quite a bit for an occasional item. Are you able to recommend RTW makers?

Relatedly, I know that you’ve previously cautioned against using bespoke makers unless you’re prepared to go through several iteration of a shoe/last. Is the same true here? That is, is it worth going with a maker like Zephan if you’re only ever going to having a single pair made?


I think most readers will be better suited with a chelsea boot. More and more, I find that if I have to ask “Can I wear this?”, the answer is “No.” The exception will be readers who grew up wearing cowboy boots or who live abs work in environments where they are common, but they already wear them.

That being said, cowboy boots do look great. But I can appreciate them without incorporating them into my wardrobe. I think they look much better in leather.


I have a black half wellington or side zip boots from carmina. I wear them as an edgier alternative to chelsea boots and love them. These look great too!


It’s a good looking boot but I wouldn’t have called it a cowboy boot had I seen it without the accompanying copy (not doubting your statement that it is). As such it’s fairly safe as you say and not convinced that it proves the point

I was surprised that you said the upper is often the more showy material because it’s hidden. Given their practical background I’d have imagined it was more to do with areas being less prone to damage


Justin is a brand of off the shelf cowboy and roper boots, and many folks wear them with smart casual and business attire. I’ve even seen whole bridal parties coordinated this way. Not my taste, but it doesn’t have to be.
That said, several US boot makers also make lace up ropers, that are very similar to a pair of balmoral boots, and I really liked the pair I had (years ago).

Peter K

I grew up in a ranching/farming environment and wore cowboy boots regularly. If you are riding a horse with a western saddle they are useful as the heel keeps your foot secure in the stirrup. They were also the usual footwear for many people around town.
I kept wearing them until I reached my 30’s. As a relatively short man I always appreciated the extra height they gave me as well!
I haven’t worn cowboy boots for a long time now as I live in the city and I find them verging on costume in urban environments. Your ropers seem to avoid that Simon but for me cowboy boots are to strongly associated with horses and ranching to wear outside of that context.

Caleb C

Could you, would you on a train? In a car? On a plane?
Forgive me, someone had to address the Dr. Seuss reference.
I do think the mix of genres is interesting, fun, and, can be, treacherous. While a certain look may work fantastic, fit the persons personality, and be on the appropriate formality level, having no set standards may mean you cross a faux pas only held by a certain group of people. ( In a finance office on any given Friday, dark Jeans paired with blazer isn’t acceptable but a golf shirt and khaki pants are, eg.) Only observing, not getting into a political discussion, but the overall global push back against any perception of elitism may more readily explain the societal move down the sartorial scale away from suits and toward a more casual wardrobe. Being a chameleon and breaking traditional norms and prescribed dress codes is freeing and expressive but can be difficult when the collective rules do not keep pace or a when a wardrobe is disjointed from occupation.
For my personal style, for some reason, I am drawn to a hypothetical image of a vineyard owner or an upscale ranch owner (probably based on the ranch owner from the kid’s movie Ferdinand). Both images are individuals who do not wear suits often because of the manual labor demands of their work, but they also wouldn’t wear a t-shirt and jeans due to their clientele.
I would be interested to hear if anyone else has a ideal image, or groups of images they think of when dressing. (Obviously we all have an ideal image that we have to filter through our appropriate environments but I wonder other’s are quite as literal, and, if so, what they are)

Caleb C

I think this is where Permanent Style is so helpful. Following set uniforms and established rules are easy. Blending and mixing is much more difficult and Permanent Style provides explanations with examples so you can learn why a certain look or piece of clothing comes across they way that it does. With that knowledge, you can accomplish the ever elusive goal of intentionally presenting yourself to the world exactly how you want to.


Hi Simon, can you comment on the Drake’s jeans? Are those the ones currently sold on their website? How is the fit?


I was born and raised in Texas, and I’ve owned several pairs of bespoke boots over the years. I think you made some really good choices in overall style and materials to get a boot that is more versatile (and frankly more comfortable) than typical. I think it’s important that your boots fit your personality. Similar to tailoring, the man should wear the boots and not the other way around. In this regard, Simon, I think you chose a pair that fits your overall style. Would that more men would do likewise. Over the decades, flashy or exotic cowboy boots have become almost a visual cliché in Texas—usually worn by men who are either recent and overly enthusiastic arrivals to the state or by men who have never ridden a horse in their lives (often both). While these sorts of boots are not offensive in themselves, they do say a good bit about the man wearing them.
I would disagree slightly with the readers who state that cowboy boots are first and foremost utilitarian items. While this is true insofar as they originated in the footwear needs of men who spent almost all of their waking hours on horseback, a trip to any of the large ranches in Texas where one still sees working cowboys would prove the point that style and decoration are now and have always been an integral part of wearing cowboy boots. Most working cowboys still wear traditional high topped boots with their jeans tucked into the shaft (for protection from thorns and other hazards). Their boots are invariably high-heeled and sturdy. However, one will also see a wide array of colorful leather choices on the shaft, and intricate stitching patterns or tooled leatherwork.
All this to say, I think that one of the great things about cowboy boots is the range of personal expression they allow. Whether you wear ropers or riders, the key is to wear a style that is authentic to yourself.


Speaking as a native Texan (who still lives here), formality in boots can be a little inscrutable to outsiders: toe-shape, heel height and style, and cultural context in particular make a big difference in how formally a pair of boots is perceived. I’ll second Zephan’s sentiment. I love your ropers, but I probably wouldn’t wear them with tailoring in Texas. I would wear them with much less formal clothing, but that’s just my cultural context.

Something you touched on a little, and I think is worth unpacking, is leather choice. Two aspects of formality I often find myself considering in a pair of cowboy boots are material expense and color/texture. Ostentatious leather choices are sometimes perceived as less formal here, even if they are more expensive or luxurious than a comparable alternative. For instance I got married in a bespoke suit, and wore black, smooth belly ostrich boots with an almond-shaped toe and a traditional high heel. I don’t know what this says about Texas, but it was an entirely appropriate, unremarkable choice; some of my groomsmen were also wearing boots. If I had worn alligator or ostrich with more prominent quill-marks, those boots would have appeared less formal than smooth calfskin, despite the obvious difference in material price.

All that being said, people wear all kinds of combinations of boots and suits here, and it seems to work out fine in general. I’m personally really happy more people are more wearing cowboy boots outside of Texas and the South. Cowboy boots are comfortable, and—to my eye—quite elegant. Wear them however you want to, and confidently!


Any kind of higher boot always look strange to me. I think it’s the fact that the last is usually a bit rough by design (being a boot) and the interesting part, the top part, goes under most trousers. I have a pair of higher shafted shearling lines dress boot that almost never gets used for this reason. Maybe I’m alone in this…


If I’m honest, those boots – to me – look a bit on the “clumpy” side. That could be because they’re “fitting” boots, not the final pair, or it could just be the particular style. Not really something I’d enjoy wearing, although I can imagine they’re actually rather comfortable. Having said which, I’m a big fan of jodhpur boots – the type with the wraparound ankle strap, for the avoidance of doubt, as I know that there can be other types of boot referred to by that term. They also have an equestrian connection, but for some reason feel smarter and less utilitarian than your roper boots. I have my eye on a pair of Edward Green “Lambourne” jodhpur boots in suede, if I ever get up to London again for fitting purposes… Yet both western and jodhpur boots are distinctly out of the ordinary, at least in the UK – do you have any views on the relative merits of the two types?

Philip Gilbert

Hi Simon,
Firstly, i think it’s great that you feature and discuss such diverse items.
Whilst the boots you feature aren’t quite my worst nightmare come true, I wouldn’t / couldn’t wear them. When I think of cowboy boots all I can think off is people line dancing………aggghhh!
Having said that my wife bough a pair in the early 80’s and wore them with second-hand 501s. At the time the jeans weren’t imported into the UK, so it was down to Camden Market.
The boots came from a shop in the Kings Rd called “R Soles”. Make of that what you will!


Great article as always, Simon. Only comment on N. American craftspeople you’ve covered before – should Frank Clegg’s Fall River factory be on the list?


Off topic, I don’t know how I missed the article about the tattoo. I’ve seen the tattoo on your Instagram but it never crossed my mind you also wrote about it. It’s a subject so dear to me and it took me 20 years of thought and a pandemic forcing me to change work and the environment to actually do it. Mo is a great artist and the one you got suits you well.


Interesting and much appreciated list of North American makers. One maker that’s not on this list is Oxxford Clothes which surprises me. Please consider covering this fine American company in the future. My guess is that you’ll be pleasantly surprised by the quality of the workmanship.


Thank you sir! It’s certainly true that Oxxford Clothes aren’t sold in many places. Then again, that’s true of many, maybe most, of the makers that you write about.


Point taken. Yes, Oxxford is basically US only. At one time they had an outpost in Japan I believe, but I don’t know if that’s still the case.

Ringo Kid

I often wear Western boots with a Savile Row suit. Mine are Boulet, a long established Canadian maker. Black soft grain. The key to pulling this off without looking silly is the heal. Mine have what are called “dress shoe heels” which are just that — heels that one would find on a pair of fine dress shoes. I find women find the look quite rakish — the toe and subtle decoration just peaking out, but no obvious heal affecting how I stand or walk.


Cowboy boots was there in the end of the 70’s and 80’s hummmm, been there done that, not sure i would wear them again. For younger man who wasn’t around back then, i can understand. If your one of them, well wear them in good health.



Robert Woerner PhD

Native Texan here. I liked your article and found it both interesting and also amusing. I don’t understand the hesitation in wearing “cowboy” boots however. Although Dallas, my hometown, likes to envision itself as cosmopolitan, it is a big state and I can drive into the country here in about 15 minutes. I see people wearing boots here frequently and I do as well. My favorites are Lucchese brand and I recently bought a pair of goat skin ropers from them (my fourth pair from that company). Go ahead, get yourself some boots and change up your routine a bit!

Robert Woerner PhD

Simon, Not sure what others think should concern anyone. Do your thing and maybe it will open others’ eyes to some possibilities they never considered! Style, to me, is an individual choice. Avoid the herd mentality. Just my thoughts.


If you have a more muscular upperbody than general person, which one of the savile row tailors should you look at?


Not my style

Nick G

1) Great choice with the ropers, Simon. They look awesome and I’m sure they are comfortable.

2) I grew up in the Western US and have lived in the American Southwest (Texas, Arizona) for the majority of my adult life. Boots, especially in Texas, are both accepted and encouraged. For those looking to make them work co-splaying a Texan senator (to Simon’s point), I suggest the following combination:
-Cowboy boots. For those looking for a good entry point, check out Luchese. Wildly comfortable, high quality, and will last forever.
-Boot cut jeans or any jeans that don’t dovetail too much around the ankle. Nothing looks more ridiculous than tight jeans around a boot.
-Oxford cloth button down, in white or light blue.
-Casual mid-gray or navy blazer.
This is my Friday “business casual” at the office.

Tony Parrack

When I visited my daughter at the Uni of Texas where she was studying just pre-Pandemic, I went to a couple of the top Austin shops for a pair of cowboy boots and I was looking at the roper boots. Just not for me really, I felt it was a bit like bringing that a few bottles of that wine that tasted so good in France back… But it’s the casualness that the locals wore them with just anything: suits, jeans, chinos – even shorts – that I admired. A really great classic if you can carry it off.


Absolutely love them. I want a pair now. Waiting +16months is too much :-).

Dominic Aiello

El Paso, Texas is the epicenter of boot making. I have a wonderful pair Sanchez Champion boots based on their El Pistolero style ( a working man’s boot ) they made over the top dress boots as well. Jose Sanchez has passed away but his grandson has carried on. https://caboots.com/
the pic is a sample what Jose was making


As a boot loving Texan (originally from Houston, but now in South Texas) I’m very eager to follow this story and see how the final boots come out. I think switching to calf, perhaps with some subtle exotic inlay, for the shaft is a smart call. But of course, what one puts on their boots is a personal decision.
Being from here, boots and tailoring is not an odd pairing, in that it is seen often enough to not be thought of as unusual. I have a pair of boots (and another pair being made) that I reserve for wear with tailoring. They have what is known as a French Toe, made popular by the Lucchese Boot Co., which is what you might call a chiseled toe on a dress shoe, but with softer angles. They’re a very dark brown and do not have the toe bug (the stitched design on the toe where a boot creases), so come off similarly to a wholecut shoe. The 1.5″ slanted heel is where it deviates from a chelsea or other dress boots. The shaft is plain in keeping with the conservative approach. I find that the toe shape, slim waist and unembroidered toe make it a nice match with tailoring. The ones I am having made will be similar, but in black, though my initials will be inlaid on the pull ups on these.

Markus Schifferl

Interesting. Your next challenge could be to incorporate a part of the “Steireranzug”, a traditional men’s garment still widely worn in Austria on festive occassions but also day-to-day (expecially in the province of Styria) into your style.


The only people I have seen wear cowboy boots in the USA are in movies or some small town in Texas. I just cannot see the utility of wearing cowboys boots outside of those situations or if you are a real cowboy still rustling cattle somewhere in Texas. Regardless, your boots could pass for ordinary boots. Just my opinion.


Agree Dan. RM Williams a much more sensible option.

Ben Frankel

The TV series Yellowstone, shot in Montana, is well styled-Kevin Costner knows how to wear western clothing, as do all the guys in this series, must have had an excellent stylist on board. Sometimes over the top-


The answer to the question posed in the title is: “Yes, yes I would”.

Don In Exile

Born in the Bronx, moved to Chicago when I was a boy. I had a pair of cowboy boots when I was in high school – and when the midwest still was predominantly agrarian. Yes, it was many years ago……but when I turned 60, I finally bought a new pair of boots. Stacked cowboy heel, pointed toe, fancy stitch work. Liked the look and find them quite comfortable. Bought a second pair while driving through Oklahoma (long story) and currently shopping for a third pair. Now that I am retired, I wear what I please and these please me very much. Fear not and wear them proudly.

Andie Nicolas

I’ve got 4 pairs of cowboy boots from pointed toes/ high heels to the roper . I find them better to wear than shoes to be frank. The only difference is that I cannot walk as fast in the high heeled pairs than in shoes. I wear mine (at times) to work, with a suit or with smart pair of slacks.
I have been horse riding in the US in them despite the crocodile skin/tooled leather pair from Stallion (El Paso) costing a few thousand USD. That is what they were made for!
The Roper pair are my cheapest pair which are my work boots and use them even for m/cycle riding.Do not forget, that the pointed toe had a use in getting the feet into the stirrups quick and the high tapered heel would be used by the cowboy to dig the heels into the soft sand whilst eg roping steers or lassooing horses. Yippee!
The high heels lost their real use when bitumen and other hard road surfaces came along. Just try walking in high heeled boots in sandy surfaces when the heel sinks in – it feels great!

Anthony Hodges

I do not like green eggs and ham.


Really struck by how much these don’t look like cowboy boots, but do look much more like jodhpur boots. Just a bit higher, so without elastic sides. So easier to pull off in a non-Western US setting, but the other side of that is that you’re far less far into a cowboy aesthetic.


That’s a fabulous taupe overcoat that you’re wearing. May I ask which tailor made that for you?

Malcolm LaneBrown

R.M.Williams elastic sided riding boots(Australian) are for gentlemen cowboys.


Good evening everybody
dear Simon, my opinion on this
I live in Athens, Greece, never been in the USA. But i use cowboy boots. They are a part of my “sartorial” life, the foundation stone of it.
Raised with south rock and rockabilly music at the late 70s – early 80s, started to fall in love with western boots. Cheaper, made in Greece in the beggining, but all leather, well constructed, hand made.
The last 15 years i buy the Lucchese brand, model “Gavin” from the ex “Classics” series. Goodyear welted, metal shanked and lemonwood peged, No 6 toe (medium round, not that much rounded as your ropers), No 4 (1,5 inch.) heel. Made of smooth, shiny goat leather.
I wear them with double breasted suits, ventless jackets, forward pleated and cuffed trousers, since all my suits are cut this way.
Looking at the miror, i find myself surprisingly well dressed. Silk 7fold ties, collar pins, etc..
I noticed some slightly ironic comments about your new try, which by the way, is a way of dress and expression for some others.
Lets say that, for me, Gucci horsebit and driving mocs are clownish. But is unpropper to say it to someone who wears this kind of shoes.
After all (always within the frame of dignity), its all about how we feel, isnt it ?? Keep in mind that boots were invented in Europe.

Congratulations on your new purchase, walk proud, stand tall !!

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Pamela Stewart

Interesting choice in TX most ropers I see are worn by laborers. The suede choice for a labor boot rather than a heavy tough leather is unique. Personally I wouldn’t associate yours as a TX style boot especially because they look so brand new scuff those up and put some wear on them and I may feel different. Also the pant leg should stack on top. Definitely not a traditional look but you do you!

Matthias Breuer

Hi Simon,

as someone who subscribes to this site more for general thoughts on style than discussion of tailoring, I love you doing these kinds of experiments.

I have worn western-style ankle-length boots for almost two decades now, starting when I was a student, graduating (no pun intended, but I’m going with it) from cheap low-quality (glued!) fashion boots to subtle, understated, solid brown or black goodyear-welted boots. They have the classic pointed-too slanted-heel riding boot shape, but they fit a lot closer than full cowboy boots do and therefore are more comfortable to walk in than one might think (they’re not sneakers, but I have done 50-60k steps/day in a pair once or twice, and I regularly do 20-30k – both in urban environments).

I wear them with jeans and generally well-fitting but drab, casual and utilitarian clothes – the boots are one way I inject a bit of unorthodox style (another being that I generally wear a military-style beret).

Looking forward to more explorations like these!


Matthias, Tokyo

Goorge Nasser

o7 Simon!
I had a friend who used to collect boots. He had a friend who used to own a shop in new yok back in 90’s! Somehow i am a collector of 30+ verities of boots! may be i got this hobby from him! lol


I’m a native Texan that has worn ropers for decades. When wearing western boots your jeans must be longer than you would wear with other shoes.

David J. Pope

Bryan Ferry has worn western boots for years and has looked very smart while doing so.


To answer your question (title of this article), not only would I wear boots, but I do wear them. The pics you included in your article look very Chelsea boot and/or roper like to me.

I began wearing boots in high school, even though they weren’t popular nor do I live in an area where they are popular either. I stopped wearing them for awhile, only wearing them occasionally. That all changed when Tecovas started up. Now I must have 12 to 15 different brands, some with only one of that brand and others, 8 to 10 pairs of a particular brand. I think it’s interesting that styles in the past I didn’t like, I now like and skins/leather I never thought I would own, I now do. Same goes for toe styles.

I really believe those who criticize others for wearing boots, most likely have never tried on a pair. I also think it’s easier to criticize someone for wearing boots than to possibly admit the guy wearing boots has more confidence and guts than the one doing the criticizing.

Unless I’m working out or wearing shorts, the majority of time I’m wearing boots. Glad I went back to wearing boots again. As the old saying goes…. “Don’t knock it until you try it!”


Thank you for this guide, it’s super helpful! I got my favorite cowboy boots from vicson.com (they are the “Juana” model). I’m going to try these styling tips for sure!


If you want the best cowboy boots, I’d contact D.W. Frommer at https://www.bootmaker.com/


How’s the full review follow-up article going?


I’m looking at some suede boots (‘City Loafers’) by Aurelien, in the shade of your boots here, it seems to me white/cream trousers are 100% the best pairing, but what else can you wear easily with brown suede boots? Flannels wouldn’t be cut to the right length, it seems. Black, maybe, bit boring though. Jeans?
This helps me justify spending £340 on them, incidentally.


Don’t mind at all. I’d love to explore that: aren’t a lot of clothes/shoes eventually a copy of something? What makes the copy more ‘direct’ than less? If a certain look or style/feature is popular, then the original brand can’t exactly patent that look or stop competitors trying to pool the same market, surely?
Just curious about why you personally think such things are unsupportable.