9 Stylish Cap Toe Oxfords that Add a Flourish to Your Feet

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Here at Irreverent Gent we like to say that shoes are the secret weapon of style, and there’s arguably no more stylish or dapper dress shoe than a good cap toe Oxford. 

With a handsome toe cap that sits atop the front of the shoe, cap toes add a touch of class and sophistication to your shoe game. 

They help elevate the (already timeless and unimpeachable) shape of a classic Oxford, making them a great formal shoe for special occasions like weddings and other black tie events. 

But what I like about cap toes is that they’re not limited to formal occasions. 

They can also help you stand out from the crowd at less formal events, like job interviews or business meetings, where you’re more likely to find derby shoes or a regular pair of Oxfords. 

To help you find the best combination of style and value, in this post we’ve rounded up the best men’s cap toe Oxfords that will help you (lame pun alert) step up your shoe game (you were warned).

At a Glance↓

We’ll take a (much) closer look at each shoe below, but here’s a quick summary of our top picks:

Best Value Cap Toes:
Becket Simonon Deans
Best Craftsmanship:
Church’s Prince
Best for Wide Feet:
Allen Edmonds Park Avenue
Best Sub-$200 Option:
Thursday Boots Chairman
Best Brogued Cap Toe Oxfords:
Becket Simonon Durants
Best Suede Cap Toe Oxfords:
Crockett & Jones Westfield
Best Cap Toe Oxford/Sneaker Hybrid:
Allen Edmonds Park Avenue Sneaker
Best Cheapies:
Bruno Marc “Formal Dress Shoes”

Who Wrote This Article

Irreverent Gent Founder and Editor-in-Chief Dave Bowden has been a service journalist for more than a decade.

His style advice and menswear recommendations have been featured in The Wall Street Journal, New York Magazine, and Men’s Health, among many other outlets.

How We Determined Which Boots are Best

Style &


Materials & Craftsmanship


& Value


To us, the best cap toe Oxfords offer a strong combination of sharp style, strong quality, and good value.

The two main criteria we used to assess each pair were their style and visual appeal, and the quality of their materials and construction. 

On the style front, we prefer a classic almond toe that’s not too round, but not too pointy.

In terms of quality we look for high-grade materials and prefer a shoe that’s blake stitched or goodyear welted. But we’re also conscious that this drives the price up, so we’ve included a few of the better cemented options to present a wider range of price points. 

Finally, we compared each shoe’s style and quality to both its own price tag and those of comparable shoes to get a sense of whether they offer good value for money.

To learn more about how we rate and review products, check out our product review and roundup policy here.

The Best Cap Toe Oxford Dress Shoes for Modern-Classic Style

“If you ain’t got a cap toe, then you ain’t crap, bro.”
– Marcus Aurelius*
*No need to fact-check that, I’m like 90% sure it’s right

Best Value Cap Toe Oxfords ↓

Becket Simonon Deans

Becket Simonon Dean Cap Toe Oxfords
  • Price: $219
  • Material of Upper: Full Grain Leather 
  • Construction: Blake stitched
  • Colors Available: 5
  • Other Notes: Also available in suede
Why They’re the Best Value:

I’ve been wearing the Deans for five years now with no complaints, so I can say firsthand that these are high-quality, classic cap toe Oxfords that punch way above their weight in terms of price point and value. 

Beckett Simonon uses a made-to-order business model, which means they don’t have to pay for expensive inventory costs, and can funnel that money into shoe quality and craftsmanship. 

All their men’s dress shoes come with a full-grain calfskin leather upper, which is sourced from a tannery in Northern Italy that was certified “gold” by the Leather Working Group (a non-profit that inspects the leather industry), and handcrafted in their workshop in Bogota.  

The leather soles are Blake-stitched to the upper, which offers a great balance between solid construction and flexibility, and the Vachetta leather interior lining is about as comfortable as I’ve felt from a formal pair of dress shoes. 

They’re comparable in quality and style to some of the most respected Italian brands, like Velasca or Ace Marks shoes, but come in a much more affordable price range, making them a great deal.  

Why They’re Not for Everyone: 

The biggest knock against Beckett Simonon is that, because the shoes are made-to-order, they take a long time to arrive. 

While a lot of other brands can deliver within 2-3 business days, Beckett’s shoes take weeks to ship, since they don’t even start making them until you click buy. 

For a lot of guys that’s not a problem, since these are the types of shoes you invest in for the long term. 

But if you need a pair quickly for an imminent wedding or special event, you’ll need to look elsewhere. 

Check Price ➤

Best for Wide Feet ↓

Allen Edmonds Park Avenue

Allen Edmonds Park Avenue
  • Price: $425
  • Material of Upper: Calfskin leather
  • Construction: Bench welt construction 
  • Colors Available: 8
Why They’re the Best for Wide Feet:

Allen Edmonds makes some of the best dress shoes on the market, and have a strong reputation for quality, craftsmanship, transparency and a reasonable (if not the most affordable) price point. 

The Park Avenue cap toe shoes are arguably their flagship model, and have a lot to recommend them, including a perfectly shaped toe box, premium calfskin leather upper, Goodyear welt construction and a solid range of color options.

But while they’re a pretty great option for guys of any shoe size, they’re the best option if your feet happen to have a wider width. 

Most dress shoes, including both of the (otherwise excellent) Beckett Simonon options on this list, only come in a standard D width. 

But the Park Avenues come in a range of sizes, including three different wide options: E, EE, and EEE. 

It’s annoyingly hard to find good shoes that come in extra wide sizes, so when you find a pair that are this stylish and well-made, it’s hard to pass up.

Why They’re Not for Everyone: 

At more than 400 bucks these certainly aren’t cheap shoes. 

If you have wide feet and have struggled to find high-quality dress shoes than it’s probably a price that’s well worth paying, but if you can fit into a regular D width, then you could save a lot of money by opting for the Beckett Deans above, without sacrificing much in terms of quality or craftsmanship. 

Check Price ➤

Allen Edmonds Park Avenue vs Fifth Avenue 

Comparison of Allen Edmonds Park Avenue and Fifth Avenue Shoes

It’s worth noting that Allen Edmonds makes another handsome cap toe in extra wide sizes, the Fifth Avenue

It offers similar leather quality and an equally classic design, but adds a little bit of broguing around the toe area. 

Other than the broguing, the main difference between the Park Avenue and the Fifth Avenue is that the Fifth is is bench welted, whereas the Park Avenue is Goodyear welted.

Park Avenue

Allen Edmonds Park Avenue
The Park Avenue is Goodyear Welted and has a clean cap toe

Fifth Avenue

Allen Edmonds Fifth Avenue
The Fifth Avenue is bench welted, and adds some broguing around the toe cap

Both methods offer a lot of durability, so it’s not a huge difference, but some guys are Goodyear purists who simply won’t settle for any other method. 

Personally I’m more concerned with the style difference. The broguing casualizes the shoe a little, which looks great if you opt for the Fifth avenue in brown and pair it with blue jeans or other more casual looks. 

But if you’re looking for black shoes to wear on formal occasions, I would go for the Park Avenue, which has a more streamlined – and in my opinion, more sophisticated – look.

Most Comfortable Cap Toes ↓

Amberjack Cap Toes

Amberjack Cap Toe Oxfords
  • Price: $195
  • Material of Upper: Full-Grain Leather
  • Construction: Cement
  • Colors Available: 4
Why They’re the Best for Comfort: 

Co-founded by the former CEO of Cole Haan and a senior manager at Adidas, Amberjack is part of a new wave of shoe manufacturers that combine the type of comfort features usually reserved for sneakers with the style and quality of classic dress shoes.   

The cap toe is their newest shoe, but it uses the same A-grade full-grain leather, heat-activated arch support and dual-density outsole as their Chelsea boots, which have held up incredibly well for me after many hours of wear. 

What I really like about Amberjack is how they manage to merge comfort and style. 

A lot of comfortable dress shoes from brands like Cole Haan and Wolf & Shepherd have a thick rubber sole that makes them look like sneakers, which might be fine in casual settings, but doesn’t really satisfy the dress code at formal events. 

By contrast, Amberjack’s soles are comparatively quite sleek, giving them a classic look that disguises how damn comfortable they really are. 

Why They’re Not for Everyone: 

Amberjack’s shoes are laser perforated, which allows for airflow and adds to the comfort, but might not be everyone’s cup of tea aesthetically.

Check Price ➤

Best Sub-$200 Option ↓

Thursday Boots Chairman

Thursday Boots Chairman
  • Price: $180
  • Material of Upper: Full-Grain Leather 
  • Construction: Blake stitched  
  • Colors Available: 3 
Why They’re the Best for Less than 200 Bucks:

It’s obviously not hard to find good looking pairs of shoes for less than 200 bucks, even when you narrow your search specifically to cap toe Oxfords. 

But finding good looking cap toe Oxfords in the sub-200 price range that are also high quality? That takes some doing. 

In that context, Thursday Boot Company’s Chairmans are pretty impressive. In addition to being handcrafted, they’ve got a full-grain leather upper, Blake stitch construction, a full-glove leather interior lining and shock-absorbing insoles. 

I haven’t tried the Chairmans in person, but Thursday is another company whose boots I love. If their cap toe shoes are anything like their cap toe boots, I suspect this is a great buy. 

Why They’re Not for Everyone: 

The $200 price point occupies kind of a funny place on this list. 

For an extra $20 bucks you can get the Beckett Simonon Deans, which come in a wider range of colors, offer a sleeker silhouette and have rubber heel caps that provide traction, without sacrificing anything in the style department. 

(All of which helped contribute to my picking them as the overall best value option, even though they cost a bit more than the Chairman.) 

But for some, even $200 might be too much for a single pair of shoes, in which case I’d recommend sacrificing some quality and opting for the cheap-but-stylish Stacy Adams pair below. 

That leaves the Chairman somewhere in the middle. They’re a great option, and a great price, but neither the best option nor the best price on this list. 

Check Price ➤

Best Craftsmanship ↓

Church’s Prince

Church's Prince cap toe oxfords
  • Price: $1,490
  • Material of Upper: Calf leather 
  • Construction: Goodyear in-channel construction 
  • Colors Available: 3 
  • Other Notes: UK Sizing
Why They’re the Best Crafted:

In many ways, when newer brands like Beckett Simonon set up shop with a heavy emphasis on construction, they’re following in the (perfectly crafted) footsteps of long-established luxury brands like Church’s. 

Founded in 1873 by Thomas Church (and now owned by Prada), Church & Co Limited has been one of the premier British shoemakers for more than a century now, and their shoes have been worn by British icons both real and fictional, including Prime Minister Tony Blair and  Pierce Brosnan’s James Bond. 

The Prada takeover was controversial in some circles, and some have accused the company of attempting to turn Church’s into more of a fashion brand than a heritage shoe company. 

But while some of the shoes they choose to make nowadays may be questionable, it’s hard to deny the quality of their cap-toe Oxford shoes. 

In addition to being made from calfskin leather, they’re built on a 165 shoe last, are Goodyear welted, and have leather piping on both the eyestay and toe cap. 

Why They’re Not for Everyone: 

Well, first and foremost, at nearly 1,500 bucks before shipping and taxes, these are pretty damn expensive. 

In addition to the prohibitive price, the other potential hurdle here is that they come in UK sizing. You can use the size chart on their website to translate UK sizing to North American. 

But in my experience it can be tricky to figure out which UK measurement translates to your proper size, so there’s an increased risk of being a half size wrong in either direction.

Check Price ➤

Best Brogued Cap Toe Oxfords ↓

Beckett Simonon Durants

Beckett Simonon Durant cap toe oxfords
  • Price: $219
  • Material of Upper: Full-Grain Leather
  • Construction: Blake stitched 
  • Colors Available: 5
Why They’re the Best Brogues:

This one’s pretty easy because the Durants are more or less the same shoe as the Deans (the first pair of Beckett Simonon shoes listed above), but with a bit of broguing around the cap toe. 

They have all the same advantages in terms of material, quality, craftsmanship and great value for money, but the brogue detail gives them a different look that’s slightly more casual, though still quite distinguished.  

As mentioned above, Allen Edmonds’ Fifth Avenues are also a solid option if you’re looking for a brogued cap toe, but these offer comparable quality at a much better price.

Why They’re Not for Everyone: 

It bears mentioning again: Beckett Simonon’s shoes are made-to-order, and take weeks to arrive. 

Which is a shame, because when you find shoes that are this well-made and this well-priced, you want to get them in hand (or on foot, as it were) right away. 

My personal experience is that Beckett Simonon’s shoes are worth waiting for, but if you’re pressed for time and have the budget, you could get AE Fifth Avenues on Amazon, which could theoretically be available today if you have Prime

Check Price ➤

Best Suede Cap Toe Oxfords ↓

Crockett & Jones Westfield

Crockett & Jones Westfield
  • Price: $790
  • Material of Upper: Calf Suede 
  • Construction: Goodyear welted  
  • Colors Available: 1 
  • Other Notes: Also available in 2 leather colors  
Why They’re the Best Suede Option:

Like Church’s, Crockett & Jones is another British brand with a rich heritage of well-made shoes that dates back to the 1800s. 

But whereas Church’s can lay claim to the shoes of Pierce Brosnan’s Bond, Crockett & Jones provided kicks for Daniel Craig’s 007

Oh, right—I’m supposed to be talking about suede. Well, to paraphrase Vesper Lynd, there are suede shoes and there are suede shoes. These are the latter. 

The Westfield is a semi-brogued cap toe that comes in two different leather colors, but the dark brown suede version is particularly impressive. 

The shoe is built from a 341 last and Goodyear welted in C&J’s Northampton workshop, and the calf suede comes in a rich brown color they call tobacco, which is dark enough to work well with a blue suit, but also warm enough to pair with casual trousers like khakis, or even jeans. 

Why They’re Not for Everyone: 

The first thing that might keep you from pulling the trigger is the price tag: 

At nearly $800, these are insanely expensive shoes.

And while I personally love the color, I can see how it might not be for everyone, especially considering the price tag. 

Whereas suede black Oxfords can be worn with formalwear in place of black patent leather, suede brown Oxfords look best with fabrics that are a little more rugged than refined, like tweed, herringbone and even denim.

And if you’re going to drop nearly a thousand bucks on a pair of shoes, you might want something more formal. 

Check Price ➤

Best Cap Toe Oxford/Sneaker Hybrid ↓

Allen Edmonds Park Avenue Sneaker

Allen Edmonds Park Avenue Sneaker
  • Price: $300
  • Material of Upper: Calfskin leather 
  • Construction: Corner stitched  
  • Colors Available: 3
Why They’re the Best Hybrids:

Nowadays it’s not hard to find hybrids that combine the closed lacing system of an Oxford with the sole of a sneaker, but you don’t often see them with a cap toe—and you almost never see them this well made. 

Brands like Cole Haan, Johnston & Murphy and Wolf & Shepherd all offer decent Oxford/sneaker crossovers, but leave it to Allen Edmonds to turn their flagship dress shoe into one hell of a hybrid. 

We ranked the “dress sneaker” version of the Park Avenue high on our list of dress shoes with white soles because it somehow manages to maintain the leather quality, toe shape and cap toe of the original with both the insoles and outsoles of a sneaker, while also offering a slightly more relaxed fit.  

Why They’re Not for Everyone: 

Hybrids are a pretty polarizing shoe style

As a middle-aged dad who doesn’t want to sacrifice style even though I increasingly find myself gravitating toward more comfortable clothes, I love ‘em. 

But for prissy little dandies sartorial purists, they’re an affront to shoemaking tradition and have no place in a gentleman’s wardrobe. 

If you’re in the latter camp you’re obviously going to hate these. 

But for those of us who prefer to merge traditional style with contemporary technology, they’re a damn-near perfect combination of classic style and modern comfort. 

Check Price ➤

Best Cheap Cap Toe Oxfords ↓

Bruno Marc “Formal Dress Shoes”

Bruno Marc cap toe oxfords
  • Price: $38
  • Material of Upper: Vegan Leather
  • Construction: Cemented 
  • Colors Available: 3
  • Other Notes: Also available as a wingtip 
Why They’re the Best Cheap Option: 

It’s pretty easy to find cheap footwear that looks great, but craftsmanship is inherently costly. 

So when you’re looking for dress shoes in the sub-50 price range, you really have to adjust your expectations and understand that you’re not really looking for the best Oxfords, you’re looking for the best you can do at this price point. 

When viewed through that lens, these cap toes from Bruno Marc are a pretty decent option. 

They’ve got a great toe shape, a stacked heel and a rubber outsole that should provide better traction than most cheaply made (and cheaply soled) dress shoes. 

I actually own a few pairs of Bruno Marcs, and while they’re obviously not in the same ballpark as the brands above, they’re actually pretty good for the price point. 

Why They’re Not for Everyone: 

While they certainly look great, cheaply priced shoes are cheaply made shoes, and these ones are no different. 

They’re made in China, use faux leather, and have a latex insole instead of memory foam. 

If you absolutely can’t spend more than 50 bucks on shoes, then don’t let any of that deter you – these are almost certainly your best bet at that price range. 

But if you can swing a higher price point, or don’t mind waiting until you’ve saved $180, the Thursday Chairmans are a much, much better shoe. 

Check Price ➤


What is a cap toe shoe?

Cap toe shoes have distinct horizontal stitching across the toe box, distinguishing it from the vamp and the rest of the upper. A cap toe is one of the rare styles that’s as common in casual shoes as it is in formal footwear, adding a touch of visual interest.

Which brand makes the best Oxford shoes?

It depends on what you mean by best. For my money, the best value Oxfords are from Beckett Simonon because they provide high quality at a great price. But brands like Crockett & Jones, Meermin, Allen Edmonds and Ace Marks all make excellent options at various price points.

What is the most versatile Oxford?

I would argue that the most versatile option is a black cap toe Oxford. You can easily wear them with casual clothes like khakis and jeans to dress up your everyday wear, but they also have enough formality to work with dress pants, suits and even a tux.

Are Derby shoes more comfortable than Oxfords?

To use a technical term: no way José. While there are some slight construction differences, main distinciton between Oxfords and Derbies has to do with the laces and eyelets, which play a much smaller role in comfort than things like the insole, midsole, and interior lining.

More Resources ↓
More Advice on Stylish Men’s Shoes:
Banner Image Credits:
Photo: Thursday Boot Co.
Illustration: Irreverent Gent

About Dave Bowden

Dave Bowden

Founder, Irreverent Gent
Author, Man in Command and Stop Doubting, Start Dating
Writer, Really Wordy Author Bios

Dave Bowden is a style blogger, menswear expert and best-selling author (in Canada—but still!) whose advice on how to look good and live well has been featured in New York Magazine, The Wall Street Journal, Men's Health and more.

When not obsessing over style and self-improvement, he can usually be found spending time with his wonderful wife and two amazing sons, indulging in a hoppy craft beer, or sobbing over the woeful state of Toronto's sports teams.

Check out Dave's Style Story to find out how a chance encounter with his friend's step-dad taught him the value of looking good and living well (don't worry—it's less creepy than it sounds!), or email him at [email protected] if you want to get in touch.