A Simple Guide on Dress Shoes

There is nothing that will make you look more stylish and give you a confidence boost like a nice pair of shoes.

Every man needs a few pairs of great dress shoes for the unavoidable occasions that will call for them. If you’re a man who knows how important quality dress shoes are, then you probably don’t need to read further. But for everyone else, this may be one of the most important fashion articles you read.

What you have on your feet can make or break any look. It doesn’t matter if you have the most amazing suit in the world, if you have bad shoes, you might as well roll around in a puddle of mud.

Shoes can get expensive, but if you’re smart about your choice, you’ll be able to wear them for years. Not only that, but the confidence you get every time you put them on will be well worth the price.

Whether for business or for that hot date, nothing will make you look more successful or sexy. Get yourself a pair of high-quality shoes and tell me if you don’t get compliments.

How Much Should I Spend on Shoes?

With shoes, you really get what you pay for. The minimum you should be spending is around $200-300.

If that’s too much for you, just remember the rule of “cost per use.” The shoes will last you years, if not decades, and the amount of use you’ll get out of them will exceed the price. If you need dress shoes for work everyday or you go out on the weekends a lot, then a good pair of dress shoes is of monumental importance to your outfit.

If money is an issue when shopping but you still want to look good, check out our article on how to look good on a budget.

What to Look For

With shoes, it’s all about quality, quality, quality. It’s better to have two or three pairs of good shoes that will last a long time than to have fifteen pairs of generic-looking bargain brands.

How do you know what’s quality?

High-quality shoes are all about construction, and there are few basic things to look for:

  • Your shoes should be made of real leather and have leather soles as well. (If you buy quality leather shoes, they can be refurbished a number of times and will last forever, which is ultimately going to be less expensive than having to replace crappy, poorly made shoes every few months.)
  • The soles of well-made shoes will be stitched, not glued, to the bottom of the shoes.
  • Also, the lining in better shoes is made of high-quality calfskin or natural leather, not synthetic materials.
  • Finally, check out the stitching. It should be neat and should be barely noticeable.

Here is a great diagram and rundown of the basic construction of a quality dress shoe from our good friends at Details:

Shoe Basics

1 The Laces

It’s an inescapable fact that a lace-up still looks better with a suit than a slip-on.

2 The Color

Black will always be dressier than brown. If you’re suiting up for a board meeting or a formal event, go with the former. If necessary, however, you can pair brown lace-ups with suits – especially navy or charcoal – as long as they’re scuff-free.

3 The Material

Glossy leather is the fail-safe choice, but you should feel free to experiment with suede – starting with a pair of classic bucks and progressing to exotic materials like alligator and ostrich or the growing number of antiqued leathers.

4 The Toe

An elongated toe is unequivocally classier than a square. That doesn’t mean all your lace-ups should be pointy – lots of elegant cap toes have squared-off tips – but unless you’re aiming for mid-nineties nostalgia, no shoes you wear should have a blunt, squared-off toe. I suggest staying away from them.

5 The Welt

Well-made lace-ups should have a close welt – the seam where the upper meets the sole and creates the outer edge of the shoe. It should be visible, but it shouldn’t extend so far past the edge of the shoe that it creates a ledge.

6 The Sole

A thin sole is the hallmark of a cheap shoe – plus, it not only looks cut-rate, it wears out more quickly. Yours should be at least a quarter-of-an-inch thick and preferably leather, not rubber.

7 The Broguing

Traditionalists will tell you that the more broguing – decorative stitching and perforated and serrated edges – a shoe has, the less dressy it is. But while it’s true that heavily embellished bucks look better with sport jackets and tweed than with pinstripe suits, this rule is flexible.

Dress Shoes for Business or Dressy Occasions

Cap-toe oxford

The cap-toe is the dressiest and most popular of all the business shoe styles. It looks best when worn with the more serious suit fabrics and styles. If you get one in brown, wear with navy suit, or an earth-toned suit of olive, brown or tan. Black is fine with all of the serious dark colors of gray and navy but not at all with any of the earth tones. Cordovan is the one color that seems to go with everything except black – and is understood everywhere. If you want more information on choosing a suit to fit you, read our article on finding the perfect one for you.

Wing-Tip Oxford

Because of its texture and heft, the wing-tip can be worn successfully with the more textured and heavier fabrics like tweed and flannel. They’re too formal for khakis or jeans, so avoid the mismatch.

Plain-toe Oxford

The plain-toe is less dressy and more simple. It’s appropriate for all business settings. If you’d like to read more on dressing for work and office attire, read our article here.

Monk Strap

The Monk Strap is a European classic which has a buckle on the side. It is most commonly made of calfskin, but brown suede leather is very popular with the man who would like a touch of uniqueness in his dress footwear. The suede leather version is seen as casual and a very elegant alternative to the loafer.

Dress Shoes For Casual Wear


The loafer has moved beyond its preppy roots. Wear this basic with any casual look involving jeans or trousers.

Slip-On Dress Shoe

If you’re looking for a dress shoe that will always look good with a pair of jeans, go for a slip-on instead of one with laces.

Driving Moc

The driving moc was invented to let you feel a car’s pedals better. Now it’s an alternative to wearing slippers in public. You can find upgraded ones like this one that are more elegant. Best worn with khaki shorts in the summer with no socks. Check out our article on dressing for summer here.

Dress boots

Dress boots look fantastic with dressy and casual clothes, such as a great-fitting pair of dark colored designer jeans, a pair of dress trousers, or a casual suit.

Boat Shoes

These once strictly functional piece of footwear has become very popular to wear casually with khakis or even jeans.

Cowboy Boots

Classic version of American’s contribution to footwear. The perfect combination to the other American casual standby – the blue jean. Can be plain and simple or elaborately tooled leather or made from the exotic skins of ostrich or reptile.

Desert boots

This is a high-cut shoe usually made of calfskin or suede and always seems to remain in fashion. Has a cushy rubber sole making it a great walking shoe for uneven terrain. Goes very well with a pair of khakis or jeans.


An old standby among lace-up shoes for summer wear, the white buck comes with a red rubber sole or can be worn in shades of brown, tan or buff.

8 Fit Tips for Shoes:

1. Shop after you have been out and about a bit, since feet do swell. This way you will get the most realistic measurement.

2. Shop only at a store that uses a Brannock foot measuring device for determining your exact foot size.

3. Almost everyone has one foot larger than the other, usually it is the right foot; fit the shoes to the larger right foot. Do not rely soley on the size you have always worn. Different makes can vary significantly from each other, even though the numeric size is the same. Always try them both on, walk around in them, and buy them by how they feel on your feet – not just by the size.

4. Allow a half-inch between the tips of your toes and your shoes. If the toes of the shoes are pointed, be certain there is enough room for your toes to move comfortably. Shoes should never be tight over the instep of ball of the foot. You should be able to stick your index finger in the back for wiggle room.

5. When considering an oxford-style shoe, you should not be able to tie the laces so tightly that the two edges of the shoe meet. If you can, then a narrower size is probably better for you.

6. Buy leather shoes. Though more expensive, because it is porous, leather is the best for the health and comfort of your feet. In leather shoes the foot can breathe, discouraging the build-up of bacteria.

7. Shoes should fit from the moment you try them on. Do not accept the salesperson’s, “Once you break them in they will be fine.” The man-made materials used today do not stretch significantly, but leather adapts to your foot shape quite well.

8. When shopping, wear the same type of sock you will use with the dress or sports shoes. Too heavy or too thin socks will distort the fit.

Shoe Care Tips

  • If you want to extend the life of your shoes, a professional shoe shine is worth much more than what you pay for it.
  • If you’re after a winner’s style and you’ve invested good money in your shoes, it’s really unbecoming to be shy about a professional shine.
  • If you’re nervous about getting a professional shine for the first time, take it from me, the men shining shoes in hotels, airports, train stations or street corners are some of the friendliest people I’ve ever met. From the minute you sit down in the chair they will take care of everything with gentle, knowing taps or touches. Just be friendly and enjoy the experience.

If you’re the do-it-yourself type, here’s a great how to video that I’ve found by a mustachioed Englishman: [youtube=http://www.youtube.com/watch?v=IeScJ_Hemno]

The Value of Shoe Trees

The average man produces up to a half pint of perspiration per day and most of it is absorbed by the leather lining and uppers of the shoe. Shoe trees draw the moisture away from the leather allowing them to dry more efficiently and to retain their shape. Also, by discouraging bacterial build-up, shoe odor is kept in check.

Many experts claim that the average man would double the life of his favorite pair of shoes by simply putting a pair of shoe trees into them as soon as he took them off at the end of the day.

Shoe Shopping Tips

  • For the best fit and selection, go to specialty dress shoe stores.
  • For the best deals, visit department stores, wholesalers, and outlet malls. Don’t shy away from buying shoes on clearance, either. The only thing these shoes are usually guilty of is being a season or two “out of style.” But honestly, when you get out on the street, nobody can tell the difference between a 2005 Kenneth Cole oxford and a 2007 Kenneth Cole oxford.
  • If you are going to buy shoes online, a good trick is to try on the same pair in a store to ensure a comfortable fit, and then go online for the best deal. But if you have previous experience with a particular brand, then ther’s no need to worry about purchasing shoes online without trying the on first. IN any case, most reputable online retailers offer full refunds.
  • Visit shoe stores on Sunday mornings, or late on weeknights. Chances are you will be the only customer in the store, and the sales-person will be able to concentrate on you. The result? Knowledgeable, one-on-one service.


The next time you put on your pair of dress shoes to go out, take a good look at what you’re wearing. Are they a quality pair of shoes? Is it fit for the occasion? Is it scuffed up? Does it need repairing or shining? Is it out of style? (Boxy, square shoes look good on nobody)

Your shoes will make or break any look. Next time, give the attention to your shoes first, before anything else.

In your opinion, how important are shoes to a look? Share with us in the comments!

If you liked this article, please share it on digg or give it a thumbs up on Stumbleupon! Thanks!

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  • Alex says:

    Very cool article, once again. After having hassle trying to find new casual shoes, I wonder if there could be an article about normal shoes? That would be very helpful…

  • jon says:

    been looking for an article on dress shoes. Thanks!

  • WilliamG. says:

    Love the tip about the thickness of the soles. I’ve never thought about that but it does show in the pictures you used. I also, personally, think a sole that protrudes around the shoe and forms a shelf around it makes a shoe look cheap.

  • sunil says:

    very very informative, thanks a lot!

  • Pefifos says:

    I got a really nice piar of shoes, made of leather and the toe is really pointed, like a round V …
    and when i bought it i was walking in the street and a girl actually stopped me to compliment on the shoe :O what a confidence booster 🙂

    this week a friend of mine was mocking me, saying that i was using a woman shoe, because they are pointed … and then a girl that was togetehr with us said “i like your shoes :O”
    it was really nice to see the expression on the face of my “friend” lol! he was using a pair of dirty sneakers 🙂

    Good shoes really rock :=)!

  • Askme says:

    Great post Jae! I can’t begin to tell you how many men I see at the office with great suits but terrible shoes. You’re completely right about them being an excellent investment. I’ve spent up to $500 on blackberries that have broken down or become obsolete in a year or two. But I’ve spend less on unbelievable dress shoes that have lasted me over a decade.

  • Richard says:

    Wingtips and monk straps have to be my all-time favorite.

  • Denise says:

    This article is a godsend. I wish all men read this.

  • Reader says:

    This is a perfect complement to the suit articles (which is the reason why I found out about Kinowear) – thanks for taking the time to write this. This website is the reason why I started caring about my image again. Thanks.

  • Nick says:

    I agree with you completely about the importance of dress shoes, let alone shoes. I can’t tell you how many times I’ve caught women looking me up and down and then smiling.

  • Vince P. says:

    Wow. Great article. This article puts my scuffed up oxfords to shame. And I love the youtube video on shoe care – very helpful.

  • Red says:

    Jae I agree with you that shoes are a pain in the ass to shop for – It takes me days to decide on a pair. However this will help tremendously. Thank YOU!

  • Kush says:

    Jae – Gotta love your articles. This is why I recommend your blog to EVERYONE.


  • William says:

    Amazing guide – I especially like the part about shoe care. My dress shoes are in horrendous condition (they have creases all over) – I’m going to go shopping tomorrow and even get myself a shoe tree to start treating them correctly. Thanks for all this.

  • Clason says:

    To answer your question – I think shoes are really the most important piece in any look. I can’t explain why – but I’ve had a past girl friend who went out of her way to get me new shoes because she was bothered by mine.

  • Jon says:

    This has to rank up there as one of the best articles on dress shoes I’ve ever read.

  • James says:

    Excellent article Jae!

  • Maxx says:

    best dress shoes article EVER.

  • Joe says:


    This is an EXCELLENT article in every way (informative, thorough, structure, presentation).

    The only thing that I’d like to see added on or as a continuation would be how to match up different colored trouser/pants with shoes. For example, are grey slacks okay to match up with black shoes and brown shoes?

    Thanks again for providing a great blog about a passion of mine.

  • Chase says:

    First, thanks for writing this great article!
    I live in the Northeast area and winter is starting to creep up. I recently just bought a nice pair of dress shoes but would rather not wear it when it’s snowing/sleeting outside. I’m opting to get another pair more casual dressy like the one you have posted. What kind of shoe is the first pair you posted under “Casual Dress Boots?” They look great and rugged, like the look I was going for this season…


  • Ghola says:

    Good article Jae. Just a couple of points that come to mind… First, it’s not really a problem to wear brown shoes with a grey suit. It’s less common in the US but for this very reason it comes across as a more distinct look. One person who pulls this off well as an example is Matt Lauer from the Today show. The second thing I’d like to add is that if you are going in for a more trendy look – where you might not really want to make the investment for the long haul – it’s worth comparing the slightly less high end brands. For example I was looking at a really sweet Kenneth Cole pair and then discovered that there was an almost identical version in the Reaction line that was quite a bit less expensive. Several of the big online shoe retailers have free shipping both ways so you can buy two or three pairs, pick the ones that fit best, and then return the others. If you can handle the cash flow hit between the initial charge and when you get the refund, this is a very convenient way to shop.

  • FeedMe says:

    I like shoes, but every time I get a new shoe I get creases in them. HOw do you stop the creases and wrinkles.

  • Kev07 says:

    awesome, i’ve been looking for a pair

  • Sebastian says:

    Great article, I really enjoy this website since fashion and especially shoes have always been sort of an enigma to me.

    I am confused about one thing though after reading this article and also doing some other research: Isn’t the wing tip Oxford the only real Oxford pictured in this article since it’s the only one with enclosed lacing (except the three shoes in the picture right underneath the title)?

    I’m just throwing this question out because I’ve been trying to understand what qualifies an Oxford shoe, and got the impression that the above pictures of the cap-toe and plain-toe Oxfords are actually less formal Derby shoes with open lacing.

    Keep in mind that I don’t know much about shoes and might be completely mistaken about this, but I just feel kind of confused about it.

    Another question, when you say Cordovan goes with everything, does that mean you can wear Cordovan shoes with a black suit?

  • steve mcqueen says:


    Cowboy boots: tucked into jeans or jeans over boots?

  • Josh says:

    I don’t wear leather so am constantly up the creek with respect to high end dress shoes. I wish an elite manufacturer would consider materials other than leather.

  • jim says:

    what’s your opinion about velcro?

  • heksaurus says:

    What is a good website to order hi-quality shoes (and in canada)?
    Also, where can you get wooden shoe trees?


  • Himmler says:

    Desert Boots?? I’ve never heard of that type of shoe. The one you posted looks so awesome! Time to find some of my own 🙂

  • bLaKcEo says:

    Excellent article – great knowledge. Worthy of pinting out and adding to the arsenal.

  • aa says:

    Its somethinng most guys neglect. To paraphrase a good female friend of mine – It will make or break your outfit. As well as this, a pair of old, tatty or dirty shoes tells girls the exact same thing about your personality. You’re not exactly going to impress anyone without good shoes.

  • Amit says:

    Excellent article. You really answered all my concerns and more.
    Thanks a lot.

  • MR las vegas CASSIUS MILES says:

    That’s just what the shoe gods ordered. Someone to educate these young men on shoes, so thanks a lot and remember when you take a step in life everyone – watch your feet they’re the leads in your act of life.

  • mf says:

    another great shoe shine video. enojy

  • Aphotic says:

    Informative article Jae. Looking forward to reading more articles.

  • JD says:

    Excellent article but you missed one detail. A tell-tale sign of poor quality is when the upper is joined with a vertical seam placed at the arch of the shoe. It is cheap, unsightly, indicates mass-production and that the upper of the shoe is crafted of remnants and scraps instead of a single piece of hide.

  • m2st2 says:

    So where would these Sketcher’s Alley Cats belong? I understand they are quite cheap as compared to the $200-$300 mentioned, but in terms of style, can you elaborate on Alley Cats and Dr. Martens going with suits? Especially when a person has to be in a snowy area and wide width.

  • Desmond Jackson says:

    Great article on dress shoes.Have 60 pair wear them all and always shined after 3 times and shoes trees applied after wearing.Take notice of goodyear welted and blake construction and last have a good cobbler to extend the life of the shoe

  • Justin says:

    could I still carry black oxford captoes with a pair of black/grey jeans?

  • Jay Song says:

    @Justin Absolutely!

  • Gazman says:

    It’s perfectly ok to wear wingtips and monkstraps with jeans and chinos contrary what the article reckons.

  • Tedd says:

    If someone else already pointed this out, I’m sorry for repeating. But the photo of the “plain-toe oxford” is actually a plain-toe derby. Oxford means that the shoelace tabs are sewn underneath the vamp, and a derby (or blucher)has the shoelace tabs sewn over the top (like the bucks, desert boots, and boat shoe). The derby is less formal than the oxford, and I think that is worth noting in the article.

    I think that this article was a great intro, though, and I’m glad to see it!

  • Independent Shoe says:

    Great advice all around about Men’s shoes. Great shoes can make or ruin an outfit quickly. The only thing that gives me pause is going in to try on a shoe at a specialty, usually local store to then find a size to go online and buy. If enough people do this then the local stores will no longer be there to give you the great service and knowledge that leads to a great fitting pair of quality shoes that will last for years if properly taken care of. Support your local independent stores – shoe and non-shoe to keep unique product and knowledge in your communities.

  • Chris says:

    Great article, but one quibble: lumping all brown shoes together. Cordovan will (almost) always be dressier than other browns. A good cordovan shoe looks great with any shade grey suit or navy suit.

  • Chris says:

    A couple more points about color:

    Depending on your fashion tips source, black shoes with navy suit is either acceptable or fashion faux pas. I was raised not to pair black shoes with navy slacks. For this reason I have relied on cordovan wing tips paired with navy suits for years. This looks boardroom formal.

    Regarding “black will always be dressier than brown.” This assumes all else equal. In my experience, shoe style and a fresh shine are far more important than color. A newly conditioned and shined cordovan wing tip will look much more formal than a dull and weathered black cap toe.

    If you’re going into your closet tonight your best bet is to find your most recently conditioned & polished shoes. If you’re planning in advance, then get your black cap toe shoes to the cobbler for a condition & shine. (And while you’re out take your black or charcoal suit and best white shirt to the dry cleaners.)

  • Jordan says:

    Great article! I’ve always considered myself quite shoe-conscious but even I have learnt a little bit from this article. You have put into words things which i would have struggled to; such as explaining about the stitching on the soles.


  • Michael Vilain says:

    As soon as I saw your minimum price for shoes, I stopped reading. I am definitely _not_ the target audience for this article. I have never paid more than $90 for a pair of shoes and that was for Rockports, which I still have 10 years later.

    I also won’t shop at Norstroms or Needless Markup. Any place that judges me on a $300 pair of shoes is a place I will never go.

    People are starving on this planet. Get real.

  • Corey says:

    Article seems great, but I don’t know if I can trust someone who confuses the contraction and the possessive.
    “The loafer has moved beyond it’s preppy roots.”

  • eustace says:

    First: a nice guide!

    A couple of comments, though: that plaintoe oxford pictured is not really an oxford, but a blucher.

    I also disagree about wingtips with jeans — IMO, wingtips go fine with jeans, although I’d prefer brogued/wingtip bluchers over oxfords in that case, and definitely not black.

  • VanessaElizebeth says:

    I have been reading about this article since a week .I had read many of them but your writing taste has amazed me.I think this author has extensive knowledge on this.

    Learn How to buy

  • Ivan says:

    I’ve always liked lighter brown wingtip oxfords with dark selvedge… Any reasons not to?

  • Thanks for your comments Chris!

  • Todd Kim says:

    There’s no doubt that these shoes will last for years. Good quality for reasonable price.

  • Baba Bouie says:

    This article is not for you. If you don’t care about your feet, buy cheap shoes. Eat cheap food, sleep on a cheap mattress. There are ways to get quality at lower prices, either from discount places or previous years’ models – doesn’t sound like you’re a fashion plate… Nordstrom Rack, for example. Do your research and get yourself some high quality stuff at a decent price.

  • Jesus says:

    What if I told you, that you don’t have to spend $$$ to get quality?

    Like you’ve said, “Do your research and get yourself some high quality stuff at a decent price.”

  • Bobby says:

    Wrinkles just happen in leather. It creates a more worn look. A leather conditioner may help

  • You have an awesome choice in shoes! Love your collection!! Keep in touch!!

  • Thanks, Aveitos! 🙂

  • Average__Joseph says:

    Jeremy, I have a couple pair if crocodile shoes (black and brown), not the over the top sort but capped toe with a kilt and tassle. I love wearing them with a suit for work or even just with a sport coat/no tie when going out but I was wondering about wearing them in spring/summer with some linen pants and a casual full button front short sleeved shirt. Would you consider them to formal or too “wintery” to wear this way?

  • Kosher Leather says:

    Nice Blog

  • Kinowear Staff says:


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