- The fundamentals of men’s style are all about classic design, and it doesn’t get more classic than a dark brown Oxford dress shoe.
- The Allen Edmonds Park Avenue is an all-time favorite and our top pick for its timeless style, quality full-grain leather, durable Goodyear welted construction, and American-made pedigree.
Every man needs at least one good pair of properly-made dress shoes in his closet. Having a few pairs is better, but chances are good that you don’t have any. No, those shiny corrected-grain leather shoes you bought on Amazon or at a department store are not proper dress shoes – or not particularly good ones, anyway. It’s not your fault. We’ve all been there.
The modern market of cheap, imported, mass-produced consumer goods has sadly swallowed up menswear, producing an ocean of poorly-fitting fused suits and plastic-looking “dress shoes,” taking us far away from the days when men knew their local tailors and clothing was made to last for decades. Thankfully, it’s 2019, and the internet is here to help.
This digital well-spring of knowledge has made it easier than ever for style- and quality-conscious men to re-learn what every man knew 100 years ago when it came to clothing. And while we probably won’t go back to wearing suits all the time, we are clearly in the midst of a long-overdue menswear renaissance.
Men’s style is all about timeless design as opposed to trendy seasonal fashions. This encompasses not just styling, but also considerations like materials, construction, and pedigree. Dress shoes are one of the most important parts of a men’s outfit and are worthy of some thought before you run out and buy the cheapest ones you can find.
To make your work easier, we’ve already picked out five great dress shoes that cover a variety of style bases to suit any taste. All of our selections boast the material and construction considerations outlined above (full-grain leather, stitched soles, etc.), and all come from established American and European shoemakers that are well-known and highly regarded for their quality. The Insider Picks team has personally tested many of these shoes.
Here are the best men’s dress shoes of 2019:
- Best dress shoes overall: Allen Edmonds Park Avenue Oxford Shoes
- Best derby dress shoes: Charles Tyrwhitt 2 Eyelet Derby Shoes
- Best dress Chelsea boots: Jack Erwin Ellis Chelsea Boots
- Best monk strap dress shoes: Wolf & Shepherd Gambit Double Monk Strap
- Best wingtip dress shoes: Grenson Dylan Wingtip Shoes
Updated on 11/04/2019 by Amir Ismael: Updated links, prices, and formatting. Added Charles Tyrwhitt 2 Eyelet Derby Shoes and Wolf & Shepherd Gambit Double Monk Straps.
The best classic Oxford dress shoes
Allen Edmonds is a household name in the world of dress shoes, and the American-made Park Avenue Oxford shoes check all the boxes with full-grain calfskin leather, Goodyear welt, and timeless style that’s suitable for any occasion.
The dressier look of Oxford style shoes makes them the best choice for your go-to dress shoe. The classic Allen Edmonds Park Avenue is our top pick for any man looking to upgrade his style game.
Hand-crafted in the United States, the Park Avenue Oxford is a favorite of numerous U.S. Presidents and hits all of the quality considerations you want in a quality shoe. This pair is made of full-grain calfskin leather which will break-in comfortably and can properly absorb polish for a great shine.
The shoes feature a Goodyear welted leather sole with a rubber heel for added traction that can be replaced by a shoemaker if it ever wears out, and it’s built on a conservative last that’s not too boxy and not too skinny.
Whether you’re in the market for your first pair of good dress shoes or you’re just looking for a solid shoe to wear for anything from a casual evening out to a day at the office, the Allen Edmonds Park Avenue Oxford is the one for you.
These are a bit pricey at $395 retail, but they frequently go on sale, with the price often coming down to a much more reasonable $250 or so. Considering that these shoes can last for decades with proper care, that’s an investment any man should be willing to make.
Pros: Crafted in the United States, made of full-grain calfskin leather that polishes and ages well, durable Goodyear welt construction that can be resoled, and a classic style that can be worn almost anywhere
Cons: It’s a bit pricey at $395 but can often be had on sale for less, and the conservative last is not as slim as some might prefer
The best derby dress shoes
The derby remains a hugely popular dress shoe and the Charles Tyrwhitt’s two-eyelet derby is a high-quality, English-made shoe that will work with any outfit.
If you already have a good pair of Oxfords, or if you’ve just settled on the derby for its simple style, then you’ll likely want something that’s equal parts comfortable and versatile. In this case, you should still stick with brown, although if you want to keep it less formal (after all, the derby is a fairly casual dress shoe), lighter shades would also work well here.
You can take your pick from any of the top men’s shoemakers, but our pick for the derby is the 2-eyelet derby from Charles Tyrwhitt, a Jermyn Street brand most prominently known for its affordable yet quality dress shirts.
The two-eyelet derby is crafted in England using traditional shoemaking methods. Like our other favorites, it’s constructed of full-grain calfskin and features a Goodyear welted leather sole for years and years of comfortable wear with proper care.
Best of all is the shoe’s subtle styling. A plain toe and brogue-less heel give this dress shoe a sophisticated look that puts it far ahead of other Derbies, which all too often are either boring or completely overdone with stitching. The open lacing of the derby gives the wearer more wiggle room – those of you with wider feet, take note – although this does result in a slightly boxier profile that is less sleek than the Oxford.
But in America, and anywhere else where business-casual is the norm, the Charles Tyrwhitt two-eyelet derby is a great choice for a versatile leather shoe that fits in almost anywhere.
Pros: Supple full-grain calfskin with an attractive finish; durable Goodyear welted construction; hand-made in England; brogue detailing lends a subtle yet sophisticated style
Cons: Open lacing makes these notably more casual than Oxfords
The best dress boots
With traditional European craftsmanship and distinct British flair, the Ellis Chelsea boots from Jack Erwin are a modern classic.
Today, dress boots are most commonly made by shoemakers in the UK and Europe, which is not surprising given the fact that Chelsea boots were popularized in Britain in the ’60s. Jack Erwin is one of our favorite shoemakers around today, and the stylish Ellis Chelsea boot easily earns a place among our top picks owing to its craftsmanship, great aesthetics, all-day comfort, and fantastic value.
The Ellis is also made in Spain using full-grain calfskin, as are all shoes in the Erwin lineup. Instead of a Goodyear welted leather sole, the Ellis features Blake construction with an all-rubber outsole. These are built on a slim last, and this lean toe box and clean silhouette is what sets them apart from bulkier, chunkier boots that are generally not suitable as dress shoes.
The Jack Erwin Ellis Chelsea boot is definitely a modern take on the dress shoe, and although its mid-century British flair is not for everybody, this European-crafted Chelsea boot is the top choice for any man who wants a dressy shoe with a distinct and slightly less traditional look.
Pros: Quality European craftsmanship, a sleek style that is dressy yet modern, a great value at $220, and the lace-free design is easy to slip on and very comfortable for all-day wear
Cons: The distinctly mid-century British style and narrow toe box will not suit everyone
The best monk strap dress shoes
The monk strap is definitely an acquired taste, but the Wolf & Shepherd Gambits are well-made and packed with sneaker-like comfort that’s perfect for the adventurous wearer.
The strap-and-buckle closure makes monk straps more casual in contrast to Oxfords, but it’s also a fine way to spruce up an otherwise conservative ensemble. A pair built with a sleek leather upper and a slim leather sole will have you good to go whether you want to rock them with jeans and a sportcoat or a suit and tie for the office.
Our favorite pick for those looking for a great pair of monks is the Gambit from Wolf & Shepherd, a modern footwear brand founded by a former Adidas designer.
Monk strap shoes typically come in one of two styles, either single or double, so named according to the number of straps used for closure. The Wolf & Shepherd Gambit is a double monk, which is our preferred monk strap style due to the smaller (and therefore less garish) buckles and the larger strap that flows nicely with the Derby-style quartered construction.
The monk strap is a unique choice that certainly isn’t for everybody, but if you’re adventurous (or just want to spice up your conservative suits), the Gambi is the perfect alternative to the old-school Oxford and is sure to garner compliments. These shoes are super comfortable, stylish, and built to last in Italy
Styling aside, the Wolf & Shepherd Gambit is special because of the comfort technology. On the outside, Wolf & Shepherd‘s designs look like standard premium men’s dress shoes, but on the inside, you’ll find soft sheepskin linings, plush memory foam insoles, a carbon fiber shank for stability and weight reduction, an HDeva heel, and laser-cut rubber outsoles. The result is a shoe that feels as comfortable as a sneaker.
Pros: Built on a slim last for an attractive and foot-flattering shape, premium leather uppers, sneaker-like comfort, sophisticated double-strap styling, and it’s crafted from genuine full-grain calfskin
Cons: The monk strap style is highly subject to taste
The best wingtip dress shoes
Whether you want to pair them with dark denim or a dapper suit, the timeless details of the Grenson Dylan wingtips make them our top pick.
While less formal than the understated Oxford, a pair of wingtips can be easily dressed up with the right suit and can be just as easily dressed down with a pair of dark jeans.
For this style, we recommend a wingtip with closed lacing as this will make it more versatile and appropriate for most workplaces – an open-laced wingtip, especially in a lighter color, will be too casual for many business environments. Closed lacing also creates a sleeker profile which is important for avoiding a shoe that ends up looking too busy and boxy when combined with its wingtip brogueing.
Having taken all of this into consideration, our top pick for a solid pair of wingtips is the Dylan from Grenson, another historic British shoemaker with a 150-year-old pedigree that rivals (and arguably surpasses) that of Loake.
Crafted in England, the Grenson Dylan features closed lacing and an attractive light brown pebble grain, making it the perfect “summer shoe” for wear with casual outfits and lighter suits. Full-grain leather and Goodyear welted construction ensure years of comfortable wear with proper maintenance as well. The quality of Grenson’s manufacturing process is readily apparent in its fantastic attention to detail, which is simply unrivaled at this price point.
Admittedly, the wingtip is not for every man – nor is it the best choice for a first pair of dress shoes – but this classic has been around for more than a century and it’s thankfully not going away any time soon, so grab a pair and make grandpa proud.
Note that British shoe sizes are generally marked one full size down from U.S. sizes, so be sure to check Grenson’s sizing guide to find your fit.
Pros: Quality English craftsmanship with fantastic attention to detail, calfskin leather vamp with a Goodyear welted leather sole, great wingtip styling that isn’t too garish or busy, and the attractive light brown pebble grain works beautifully with casual outfights and lighter-colored summer suits
Cons: The distinct brogued wingtip styling is too casual for formal wear and is not for everyone
How to find a high-quality pair of dress shoes
Quality full-grain leather
A good dress shoe should be made of full-grain leather. Full-grain leather (in contrast to top- or corrected-grain) is comprised of the whole grain of the cowhide. This means that it will be thick and durable, will age wonderfully, and will absorb polish properly. Note that “genuine leather” is meaningless jargon – all cheap low-quality leather still counts as “genuine.” Look for “full-grain” or give it a pass.
Goodyear welt or Blake construction
Most shoes today are made by gluing the sole onto the foot box. Such soles are almost certain to eventually come apart and cannot be repaired. Instead, go for a dress shoe with Goodyear welt construction (where the sole is stitched to a leather welt which is then stitched to the upper) or Blake construction (where the sole is stitched directly to the upper). These methods create a shoe that is flexible, breathable, and can be resoled by a shoemaker. Note that the lack of a welt on Blake-stitched soles results in a lighter, slimmer shoe, but one that is somewhat less long-lasting and trickier to resole than a Goodyear welt.
There are a number of different dress shoe styles and the particulars of each will be covered below. The general rule is to keep it simple, slim, and conservative. For your first pair, stick with the classic Oxford. Dress shoes should feature a relatively narrow last (referring to the molds used to shape the shoes) and follow the lines of your foot without being too bulky, boxy, or squared.
Color is key
The standard metric regarding leather color is that darker is dressier and lighter is more casual. This may lead you to go with black, but this guide recommends against that. Black is easily the least versatile basic shoe color – dark brown is the best choice for your first pair. Brown goes with virtually any suit color (save for black), can be easily dressed up or down, and is appropriate for almost any occasion. That said, you’ll probably want one pair of black shoes in your rotation, and Oxfords are a solid choice for these due to their formal styling.
What’s the difference? Oxford, derby, Chelsea boot, monk strap, and wingtip styles explained
The venerable Oxford, also known as a “Balmoral,” sets the design standard for men’s dress shoes. Its sleek lines and subtle styling look great with almost any casual or formal outfit. It’s the most versatile dress shoe a man can own, so if you’re in the market for your first good pair, then dark brown Oxfords are exactly what you need. Take special care not to confuse these with Derby or Blucher dress shoes which are often falsely advertised as “Oxfords” (especially in America where this distinction is less often made).
The defining characteristic of an Oxford is what is referred to as “closed lacing.” With closed lacing, the lace tabs are sewn underneath the vamp (the upper part) of the shoe rather than on top of it as is the case with open lacing. Closed lacing results in a clean silhouette and a slimmer shape, making it more formal, whereas open lacing is decidedly more casual.
If the Oxford is the father of the dress shoe family, then the derby is the more laid back – although far more popular – uncle. What sets them apart is all in the lacing: Whereas the Oxford has the lace tabs sewn under the vamp (i.e. closed lacing), the derby shoe features three-piece construction with two-quarters of the shoe, including the lace tabs, sewn on top of the vamp. This results in a more casual style known as open lacing.
This can get confusing as the distinction between the Oxford and the derby is blurred by some shoemakers, especially in the United States. Many shoes with open lacing are sold as “Oxfords,” and this is likely due to the popularity of the derby style as well as more lax dress standards in America (wear a pair of brown shoes – especially Derbies – in London’s business district during working hours and you might get some disapproving looks).
Often associated with European style and the British “Mod” subculture, dress boots might seem a bit foppish to many men today. Contrary to this perception, however, is the fact that the dress boot is a very traditional choice that predates the modern dress shoe. In centuries past, boots were, in fact, the norm, slowly giving way to dress shoes worn with ankle spats, which themselves gave way to the exposed-ankle footwear we wear today.
The only fundamental difference between a boot and a shoe is that a boot has a longer shank that extends up past the ankle, and many dress boots are simply Oxfords or Derbies with a taller shank. Certain styles, on the other hand, are almost entirely unique to dress boots. The two most common of these are the Chelsea and the Jodhpur, neither of which use laces. Chelsea boots feature elastic on the sides to slip onto the foot. Jodhpur boots are based on traditional riding boots and feature a strap-and-buckle closure.
Little-known trivia: White Chelseas were also featured in “Star Wars” as the footwear of Imperial Stormtroopers.
Monk strap shoes
The modern monk strap is a relative newcomer to the men’s style scene, and admittedly, reactions have been mixed: Men either seem to love these laceless shoes or think they are a youthful fad. You’ll have to decide for yourself if monk straps are for you, but there’s no denying their growing popularity which doesn’t seem to be waning any time soon. Somewhat ironically, the monk strap – while considered a younger style relative to classics like the Oxford – actually has its roots in medieval Europe, where shoes with buckles were quite common.
The defining feature of the monk strap is right there in its name. This shoe’s design is similar to that of the Jodhpur boot in that it forgoes laces in favor of a strap-and-buckle closure, which offers a unique modern look that is simple and sophisticated. They’re definitely the most fashion-forward of the picks on our guide, but monk straps enjoy a dedicated following for a reason – this stand-out style really does look great. Those medieval monks must have had pretty good taste.
When someone says “wingtip shoe,” you might get a Great Gatsby-style vision of the Roaring ’20s complete with flappers, gangsters, and men clad in double-breasted peak lapel suits. That would be a mistake, however: Wingtips are enjoying another go in the spotlight today, undergoing a revival in popularity among men who are, largely thanks to the web, re-discovering the classic styles of days gone by.
Your grandpa likely owned a pair of wingtips and it’s time to give this style another go-around. The name “wingtip” refers not so much to the actual style of the shoe, but rather to its styling; a wingtip can be an Oxford, a monk strap, a dress boot, or another type of shoe. A wingtip is simply any shoe that features a punched pattern, known as brogueing, that forms a wing-like shape one the front of the toe box.
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