Guys come in two speeds with men’s dress shoes. You either get a kick out of them (so to speak) or you hate the bloody things. And fair enough. If you’re unfamiliar with the whole formal shoe thing, it can be kind of intimidating. All those Oxfords and vamps and ‘brogueing’ etc. Men’s dress shoes belong to the world of gentlemen’s clubs and cigars and plush leather wingbacks, right? Well, maybe not. Every modern guy needs at least one pair of men’s dress shoes in the wardrobe—if only for weddings and funerals. The trick is picking the right style for your outfit, and looking after them correctly. Here we’re going to break down the most common dress shoe styles, how to wear them, and how to keep them looking like you just walked out of a Rolex commercial. Men’s dress shoe types There are dozens of men’s dress shoe categories and sub-categories sub-sub-categories and cross-over categories. But we’re not going to dive into the entire glossary here. The style below are the most common you’ll find, and should be suitable for anyone who isn’t an actual prince or something. Oxfords Oxfords are the most common type of men’s dress shoe. They can come in ‘Plain Toe’, ‘Wing Tip’, ‘Cap Toe’ and ‘Whole Cut’. The style actually goes back to English college students in the 19^th century, especially at Oxford—students wanted something more low-cut and ‘trendy’ than the traditional half-boot Oxbridge shoe. You can recognise Oxfords by their ‘closed lacing’, which means the two sides of the shoe’s facing come together beneath the vamp. This is what gives Oxfords their formal vibe and slim silhouette. They really hug your foot. How to wear Oxfords For business attire, look for safe colours like dark brown, tan, black or English tan leather. For black tie tuxedo-wear, always stick to shiny black patent leather. Remember, suede or nubuck Oxfords are going to look more casual. Bonus points for colourful socks under your Oxfords, they’re a great way to add a pop of personality. derbies Derby shoes look almost identical to Oxfords, which is why so many people mix them up. The big difference with Derby shoes is that the lacing is ‘open’, attached above the vamp, giving them a more smart-casual vibe. These shoes are also known as Gibsons or Bluchers, and they evolved from sport-hunting boots in the 1850s. Because of their open style, Derbys tend to suit wider feet. Some people also find them a bit more comfy than classic Oxfords. How to wear Derbys The same rules apply for Derbys as Oxfords, but keep in mind Derbys tend to look less dressy. You wouldn’t wear these guys with black tie, and even formal suits can look a bit odd. Derbys work best under dress chinos or slim-fit rolled jeans, and you’re encouraged to go wild with the socks. Derby shoes are all about texture, style and personality. Loafers Loafers come in a bunch of shapes and sizes, but what they all have in common is laces. Or rather, a lack of laces. Loafers are slip-on men’s dress shoes, originally made as a casual slipper for King George VI of England. In the 1960’s, loafers became the go-to shoe for American businessmen, and the style kind of stuck around. Loafers are easy to spot (the lack of laces is a dead giveaway) and they tend to have an elevated seam that runs along the toe. You can get ‘Penny Loafers’, ‘Tassel Loafers’ and ‘Bit Loafers’, but your choice should be mostly down to taste—all loafers hit roughly the same mark on the Formality Scale. How to wear Loafers Loafers come in a variety of materials and colours, and this usually dictates your outfit. Blue suede loafers, for example, are less dressy that black leather loafers, and they tend to match better with chinos than suit pants. Remember: the sleeker the design, and the darker the colour, the more formal the shoe. As a general rule, you should feel comfy wearing Penny or Tassel Loafers with any business suit. Ankle Boots We’re calling these Ankle Boots, but you can think of them as Dress Boots (formal Chukkas and Desert Boots also fall into this broad category). Ankle Boots are short lace-up boots. They’re usually constructed in a similar way to Oxfords or Derbys, but obviously with a longer shaft that runs up the ankle. These styles can vary wildly, and not all of them can be worn with suit pants. Something like the OLDMAN, for example, with its side zip, would work better with chinos. On the other hand, dark leather boots like the UTAH or ADAMS could work with the right suit. How to wear Ankle Boots Here’s a good rule of thumb: the more rounded the toe, the less formal the boot. Likewise for textured materials like suede and nubuck (a formal suede boot is kind of a contradiction in terms). If you’d like to where boots with your suit, that’s totally fine, but stick to clean lines, dark leather, and more traditional styling. You’re basically looking for an Oxford in boot-shape. Chelsea Boots Lastly, we have the ever-reliable Chelsea boot. Originating from Victorian England, these guys are slightly different to Ankle or Dress boots. Unlike Oxfords or Derbys, Chelsea boots are usually made from a single piece of leather, with elastic gussets on either side of the ankle. They’re also laceless, with a plain toe (although you can find brogue and wing-tip styles occasionally). The beauty of the Chelsea is its sleek, minimal shape, which is what you generally want with dress shoes. Dark leather Chelsea boots are totally acceptable under business suits or formal suits (but not black tie). They make a great alternative to classic Oxfords. How to wear Chelsea Boots Suede Chelsea boots should only be worn with chinos or jeans, but brown and black leather Chelsea boots look sharp under suit pants. Socks don’t matter so much (nobody’s going to see them), just make sure to hem your suit pants appropriately—you’re looking for that nice, ‘natural’ break. No sags or billowing fabric. What is ‘brogueing’? A lot of people think ‘Brogues’ are a type of shoe, but that’s not really accurate. Any shoe can have brogueing. It just refers to the pattern of decorative perforations in the leather. The original purpose of brogueing was to allow water to run out of shoes in wet weather (FYI: we recommend not wearing your brogues in swamps, marshes or under the sea). You usually see brogueing on Oxfords and Derbys, but some ankle boots and dress boots have it too. ‘Full Brogues’ are also known as ‘Wing Tips’ (note the distinctive swooping wing shapes on the toe). All you need to know about brogueing is that it’s down to personal taste. Men’s dress shoes don’t need brogueing, but some guys do prefer it. The only real exception is black tie—stick to simple black patent leather shoes here, no flashy details. Caring for dress shoes Men’s dress shoes are obviously on the pricy side when it comes to footwear, so you really want to protect that investment. We’ve written a general guide to shoe care, but there are a few extra things to keep in mind with dress shoes. First, buy a pair of cedar-wood shoe trees. They’ll help your shoes keep their shape year after year. Next, don’t wear your dress shoes back-to-back, day after day. The leather really needs time to rest and relax. You should also clean and treat your dress shoes after every wear (protective leather spray is a good place to start). Lastly, store your dress shoes in their original shoe bag, if possible, and out of direct sunlight. Look after your shoes and they’ll look after you, that’s our motto. in:Featured, Shoes, Style • August 23, 2016 • Last updated: June 9, 2021 Editor’s note: This is a guest article from Joe Weber. From the most plain and simple shoes cut from a single piece of smooth leather, to intricately detailed shoes featuring fancy stitching, perforations, and edging, a man’s got a lot of options when it comes to dress shoes. The variety can really be a bit overwhelming, especially when it comes to knowing which is which and what shoes to wear with what get-ups. So let’s break it down as simply as possible. Below is a hierarchy of the common dress shoe styles, ranked from most dressy to least, what defines them as such, and a few outfit options with which they look best and pair most appropriately.

Wholecut or Cap-Toe Oxford

Characteristics: Oxfords that are either completely void of extra stitching, perforations, and other design elements, or darn near close. And what’s an oxford? Well first, contrary to popular belief, not all dress shoes are oxfords. On an oxford, the eyelet flaps do not sit unrestrained on top of the shoe. Instead, they’re stitched over where they meet the vamp (the leather that runs from the toe to the lacing flaps) and meet up with the vamp on the same plane. A wholecut is a shoe with an upper that is cut and fashioned from one single piece of leather. Think of wholecuts as being sheets, and other pieced-together shoes as quilts. Meanwhile, a simple cap oxford is a shoe with closed lacing, that has a line or two of stitching that accentuates the front of the shoe, giving the toe a bit of a capped look. Bottom line: These are the most simple, sleek dress shoes. Less is more. More… dressy. What to wear it with: Tuxedos/evening wear; suits; blazer/sports coat with wool trousers; pressed, well-fitting cotton dress pants with a dress shirt and tie and/or sports coat/blazer.

Semi-Brogue Oxford

Characteristics: Originally used by those walking through marshy fields, these are the shoes with lots of holes and decorations (the holes used to help the muck and water drain out). Now they’re considered one of the dressiest shoes out there. Funny how times change. Semi-brogue oxfords sport a cap-toe with perforations, pinked/serrated edges, layered leathers, and usually a medallion of perforations adorning the toe. They also come with closed lacing, and are thus still plenty sleek. Yet all that busyness with the design makes them less sober and more flashy. What to wear it with: Suits; wool trousers with a blazer/sport coat; possibly dark wash jeans, depending on the color of the shoe (say, a walnut version of the Allen Edmonds Strand).

Wingtip Oxford

Characteristics: Like the semi-brogue oxford, only with the classic, unmistakeable “M” wing sweep at the toe (as seen from above by the wearer), which drops down and terminates about halfway back to the heel. Oxford-style lacing makes them much easier to dress up than their open-laced cousins. What to wear it with: Suits, although some would argue against that (take a look at the Allen Edmonds McCallister though, and try and tell me those wouldn’t look great with a suit); wool trousers; pressed cotton pants; dark wash denim and sports coat.

Plain or Cap-Toe Derby

Characteristics: Now we’re getting away from oxfords, and into their open-laced brothers: derbies. Whenever you picture a dress shoe, chances are you picture a relatively simple derby. Derby shoes, unlike oxfords, have the eyelet/lacing flaps sewn directly to the upper of the shoe, and are unrestrained by any sort of line of stitching across the tops of them. This is called open lacing, and this interruption in the silhouette makes them a little less sleek, and therefore, less dressy. Note that plenty of shoe makers actually refer to their derby shoes as oxfords. I refuse to criticize this. Why? Because of the many things I personally do not know how to do, making a shoe from scratch is at the top of the list. Some men’s style purists actually believe one should never wear derby shoes with a suit. I say horsefeathers. Most men wear derby shoes with suits, and 99% of the population either doesn’t notice, or doesn’t care. An oxford, with its closed lacing, may look a little better with a suit. But wearing a pair of well-polished, slim-soled dress derby shoes with a suit won’t cause the universe to collapse. What to wear it with: Suits (yes really), especially those made of more casual fabrics like tweed, linen, or cotton; wool trousers; cotton trousers; jeans

Single Monk Straps

Characteristics: Instead of laces providing that cinch-down tension, this type of shoe is secured to the foot of the wearer by a single buckle and strap system. A little more fashion forward for sure, but what seemed like a trend certainly now appears to have cemented itself into accepted menswear for years to come. And yes, many purists would have these shoes a bit lower on this hierarchy, but monk straps can be super sleek. Especially the single monk variety, with the buckle and strap being positioned higher up the shoe, closer to the ankle. What to wear it with: For some…suits, especially when wearing a suit without a tie; wool trousers; well-pressed cotton trousers; rumply chinos, sometimes, depending on the color/texture of the shoe uppers (say, if they’re suede); dark wash jeans.

Double Monk Straps

Characteristics: Like a single monk, with an extra buckle closer to the toe. Yes, these are basically a fashion forward, dress shoe version of velcro sneakers. And some of us absolutely still love them. What to wear it with: Suits, for some, but that extra bit of flash is pushing it in some more conservative/sober environments; wool trousers; pressed cotton dress pants; dark denim.

Semi-Brogue Derby

Characteristics: Like a semi-brogue oxford, only with the derby specific “open” style of lacing/eyelet flaps. Along with those flaps, all the extra perforations and serrated edges make for a pretty busy shoe. There’s actually not many of these around. What to wear it with: Wool trousers; cotton trousers; jeans; wearing them with a suit is a little iffy since there’s a lot of visual attention that ends up at your feet.

Longwing Derby

Characteristics: An open-laced shoe with a wingtip that doesn’t terminate midway down the side of the shoe, but instead wraps all the way to the back of the heel. They’re highly versatile, and that longer wing has an almost sporty, racing-stripe feel to it. What to wear it with: Smart, casual wear of all kinds, especially if the shoes are suede; these also look great with summer fabric suits like seersucker or linen, if you happen to have them.

Suede Bucks

Characteristics: A plain toe derby-style shoe void of extra decoration/stitching/perforations that’s made from suede or nubuck (hence “bucks”). What to wear it with: Summer suits and summery pants; if the color of suede is darker (and not the traditional white or off-white), then these can absolutely pull extra duty with cords, chinos, and jeans when it cools down; grey suede, believe it or not, is hugely versatile here, since you don’t have to worry about matching a belt color to it. __________________ Joe Weber is the Director and Editor of www.Dappered.com where affordable style is the one and only focus. He believes that living right, living well, and looking good doesn’t mean you should go broke in the process. Illustrations by Ted Slampyak Previous Next

Types of Men’s Dress Shoes

Before selecting your perfect pair, it’s useful to understand the different men’s dress shoe styles available. Once you can narrow down the men’s formal shoe types that work for you, choosing some will be much easier. Here’s a run through the top men’s dress shoe names and descriptions: Oxford: Perhaps the classic men’s dress shoe, the Oxford dates back to the 1800s when it was popular with university students in the city. It is a smart men’s shoe recognisable by its closed lacing. This is a term that means the seam that runs below the laces is sewn to the front part of the shoe. This gives a very neat and tidy look, ideal for looking smart. Derby: The Derby is thought to be a later development of the classic Oxford. The main difference is the open lacing, which means the seam below the lacing is not stitched to the front of the shoe. This allows the foot to move more and particularly suits those with a high instep. Brogue: You’ll recognise the men’s brogue by the decorative perforations on the shoe. Loafer: Men’s loafers are slip-on shoes that can be used to create a casual or a formal look. If you opt for loafers as dress shoes, try to pick a leather option with a dark, slimline sole. Chunky, light coloured soles and uppers in materials like suede can make loafers appear quite casual and wouldn’t wash in a business or formal setting! Now you know the different kinds of men’s dress shoes available, you can choose which style is right for you.

Dress Shoes Toe Styles

Here are the main types of toe style for men’s formal shoes: Plain Toes: As simple as it sounds, some men’s dress shoes have a toe with no detailing. This gives a clean and elegant look. Cap Toes: Shoes with a cap toe have an extra layer of leather across the toe. The cap goes straight across the toe and may be simple or embellished. Wingtips: Just like a cap toe shoe but the cap has an ‘M’ shape that looks a bit like wings. Hopefully our classic men’s dress shoes guide now has you clued up on the different types of shoe available.

How to Wear Men’s Formal Shoes

When you need to look smart, it’s important to consider how to wear men’s dress shoes as part of your overall outfit. There are a few style rules you should follow to get it right. Men’s Dress Shoes for Suits: if you’re in formal attire you need the shoes to match. The good news is, any of the formal shoes we’ve already discussed are suitable to wear with a suit. Your main consideration should be which colour of shoes to pair with your suit. Here are some general guidelines: Black Suit: Black Dress Shoes Navy Suit: Brown Dress Shoes Grey Suit: Black Dress Shoes Light Grey Suit: Black or Brown Dress Shoes Men’s Dress Shoes with Jeans: when you’re trying to create a smart/casual look you might be wondering how to wear men’s dress shoes with jeans. There are a few simple rules to make sure you get it right:

• Start with a smart pair of jeans that fit well and have a regular or slim cut. Choose a plain dark navy or black pair.
• Select dress shoes that are slightly more casual, for example a loafer or a Derby rather than an Oxford.
• Team with a shirt to balance the look.

Read our guide on what men’s shoes to pair with jeans Aside from the outfit itself, you should also think about the season when choosing your formal shoes. The same rules apply all year round; however, you might prefer to make a few adjustments when wearing dress shoes in certain weather. Oxfords and Derby shoes work well as men’s dress shoes for the winter, but if the weather gets cold you might choose to opt for men’s Chelsea boots instead. When it comes to men’s dress shoes for the summer, loafers are the best choice for helping your feet stay slightly cooler.

Should Men’s Dress Shoes Have Laces?

Many of the traditional formal men’s shoes like Oxfords and Derbies have laces. Lace-up shoes do tend to look better with a suit than slip-ons, but dress shoes don’t categorically have to be laced. You could opt for a smart loafer or monk strap shoe if you prefer. If you do choose a dress shoe with laces, then next thing to consider is what lace length is needed. This is particularly useful if you need to replace shoelaces. There’s no simple answer to the question ‘how long are men’s dress shoe laces?’ You’ll need to look at the type of formal shoe in question and consider the number of eyelets it has. Here’s a rough guide on what to go for:

Number of Eyelet Pairs	Length of Shoelace
1	21 Inches
2	24 Inches
3	27 Inches
4	30 Inches
5	40 Inches
6	45 Inches
7	54 Inches

For the ultimate smart appearance, you’ll also want to consider how to lace men’s dress shoes. Oxfords traditionally have straight lacing which is also known as bar lacing. It’s best to stick to this lacing style to keep your look on point.

How Are Men’s Dress Shoes Supposed to Fit?

Now we’ve covered the men’s dress shoes essentials, you’re ready to choose your shoes. But you’re probably wondering how men’s dress shoes should fit. The simple answer is comfortably! Here are our top tips for getting the right fit:

1. Start by trying on your usual size of shoe but remember the style of the shoe can adjust the fit. Don’t be afraid to go up or down a size if things don’t feel right first time.
2. Everyone’s feet are slightly different sizes. Pick the size that fits the larger foot rather than the smaller one.
3. When buying laced men’s dress shoes, look at the shape created between the eyelets of the shoes. A wide V shape will indicate the shoes are too narrow. If the two sides are touching, then the shoes are too wide. A slight V shape is just right.
4. Try on with the type of socks you plan to wear them with as this will affect the fit too.
5. Feet swell later in the day, so try on in the afternoon if possible.
6. Look out for any areas of pressure on your feet or any bunching of the leather. This indicates a fit that isn’t right for you.
7. When you find a pair that feels just right, snap them up! A comfortable dress shoe is a great investment.

Here are some top FAQs on fitting men’s dress shoes explained: Q: Do men’s dress shoes run big? Not as such. The fit really depends on the brand, so try on and be honest with yourself about the comfort factor. Q: Can you stretch men’s dress shoes? If you opt for leather dress shoes they can be stretched and softened to a certain extent. However, we wouldn’t advise relying on this to make your formal shoes fit comfortably. If a little extra give is required, start by wearing the shoes in little by little to help them adjust to the shape of your feet. If you need a quicker fix, wear some thick socks, put the shoes on and hold a hairdryer to the tightest areas whilst wiggling your feet. The heat will help to stretch the leather. Q: How tight should men’s dress shoes be? They key to this is getting gents’ formal shoes that are snug but not tight. Your feet should feel supported without any discomfort. Equally, your feet shouldn’t move around too much inside the shoe.

How to Make Men’s Dress Shoes More Comfortable

If you have found the ideal fit, making your dress shoes more comfortable shouldn’t be a concern. However, there are a few top tips for making dress shoes more comfortable if you haven’t managed to find the ultimate pair for you yet. My dress shoes are too tight: Try wearing in or stretching the leather to encourage a bit of give in your formal shoes. You could also try wearing with a thinner sock to give your feet a bit of wiggle room. My dress shoes are too loose: Insoles and heel grips are the best way to make small adjustments if your dress shoes are too loose. If the heels are rubbing due to extra room, a heel grip will make things much more comfortable. Insoles can push the foot into a better position in the shoe, adding comfort to the fit.

Caring for Men’s Dress Shoes

Our ultimate men’s dress shoe guide wouldn’t be complete without including a few tips on looking after your shoes. Proper care for your dress shoes will help them to last longer and look sharper. There’s nothing worse than unloved formal shoes; they can quickly look past their best if they aren’t properly looked after. Here are our tips on how to care for men’s dress shoes:

How to Clean Men’s Dress Shoes

Before polishing or shining your shoes, it’s best to give them a clean to remove any dust or dirt. Simply use a brush or a damp rag and make sure any debris is cleaned from your dress shoes. Now leave to dry.

How to Polish Men’s Formal Shoes

Polishing your dress shoes is the key to making them look like new. It’s important to learn how to shine men’s dress shoes properly to get the best results. Use a shoe polish brush to apply a generous amount of shoe polish in the right colour. Let the polish dry for 15 minutes, then brush off vigorously to shine. Next, add some polish to a damp cotton wool pad and rub in to the toe and heel of the shoe. Continue in this way until your shoes are as shiny as you desire!

How Long do Men’s Dress Shoes Last?

Now you know about caring for men’s dress shoes you should be able to keep them looking great. But how long should they last? It’s actually a very difficult question to answer because there are so many factors that influence the lifespan of your formal shoes. For example:

• What are they made from?
• How often do you wear them?
• How long do you wear them for?
• How often do you clean and polish them?
• Do you wear them indoors or outdoors?

Each of these, and many more factors, can influence how long your dress shoes will last. Ultimately, if you find a pair you love and practice good shoe care, you will prolong their life. Choose good quality materials and go to a cobbler for repairs to make the most of your best formal shoes. By now, we hope you’re feeling confident about looking sharp for that formal occasion, whatever it may be. Don’t forget to take your time when choosing the right pair of formal shoes and check back to our men’s dress shoes guide if you ever need a helping hand.

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