Classic Men’s Style Simplified: The 5 Step Guide to Dressing Sharp

There are two ways to approach modern male fashion and style: dress to keep up with the latest fads (e.g. flannel shirts or wacky socks), or stick to classic men’s style. I personally think the classic style approach is best, and in this post I aim to show you why. Let’s get started!

Dressing with style changes everything.

Classic men's style: Yves Saint Laurent

“Fashions fade, style is eternal” – Yves Saint Laurent

Well, maybe not everything. Still, becoming a well dressed man will change how society perceives you. Some typical consequences of looking sharp:

  • You will get more attention (and compliments), especially from women
  • You will hear smart ass comments from guys who can’t (or won’t) dress well
  • You will feel more confident and at ease (this effect may be permanent)
  • You will develop an appreciation for others who make an effort to look good

The list goes on. The effects are multiplied in North America, where the bar for men’s style is set very low.

It is actually not surprising that most men have no idea how to dress – it is a classic case of the blind leading the blind. Most guys will copy what their friends are wearing, happy to fit in and not attract any unnecessary attention. Some go one step further, emulating looks on billboards or in men’s lifestyle magazines. Others try to show off with luxury brands. A few give up entirely.

It’s not hard to dress well. It certainly requires far less money than most assume. However, it requires some patience and a willingness to try something new. Just as with any major undertaking, the first step involves a change of mindset.

Step 0. Becoming comfortable with the idea of dressing well 

You have to convince yourself that it’s good to dress well. This is very important. Become comfortable with the idea of permanently changing how you look. Give yourself the permission to reap the rewards.

Additionally, realize that there is a big difference between fashion and style. Fashion is about showing off the latest in designer trends, while men’s style rarely changes over time. The goal is not to have the clothing do the talking for you. Instead, the idea is to find and develop your own image. A way of showing the world who you are, even before you do or say anything.

Finally, you must also understand that this is a life long project. One does not become stylish overnight. It is a learning process, and it will take time to work out the details. But there are rewards at every step of the way.

Step 1. Making the most of your physique

As a general rule: the more fit you are, the better most clothing will look on you.

You have heard it all before. If you are overweight, work on slimming down. If you are underweight or skinny, work on gaining some mass and build muscle. A good ideal to aim for is the classic v-shape: at least a 10 inch “drop” between your chest and waist measurements (for example, a 42 inch chest and 32 inch waist size). This is not easy, but it can be done if you keep up a good exercise routine and make sure you are eating healthy.

Perhaps the biggest advantage of a toned body is that it simply can’t be faked. It is not something you can buy. By staying fit and healthy, you give yourself a tremendous advantage.

Classic men's style: Marlon Brando

Marlon Brando in “A Streetcar Named Desire”

While working out is a process of building up, the next stage of the style journey involves elimination.

Step 2. Eliminating the unnecessary

There are many traps on the road to dressing well. This includes clothing you are tempted to buy to keep up with fashion trends. It also includes clothing that should have become unpopular long ago, but for one reason or other has survived in popular culture. Common traps include:

  • White socks. There is almost no reason to own any, unless they are ankle socks you wear while exercising. Keep it simple: match socks to the color of the pants (or a shade darker). I highly recommend replacing old ones with Darn Tough socks – they’re tough as hell and have a lifetime guarantee.
  • Torn or patterned jeans. Completely unnecessary. Keep it simple: stick to dark (preferably unwashed) denim. If you’re in doubt, you can’t go wrong with the Levi’s 501’s  or 514’s (for a slimmer fit).
  • Graphic tees. These are back with a vengeance, and signal instantly that the wearer has no interest whatsoever in dressing well. They are distracting and juvenile.
  • Running shoes, flip flops and boat shoes. There is a time and place for all of these. Respectively: while exercising, hanging out at the beach and while on an actual boat. Outside of the environments they were designed for, all three options look downright tacky.
  • Anything with visible branding or logos. Perhaps the most common trap of all, since it is so hard to find undecorated clothing. Still, the truth is that brands, company names and logos only distract. Avoid being a walking billboard.

There are many more examples, but this is a good starting list. To dress well, you must avoid wearing tacky or distracting clothing. The best way to protect yourself from committing major style crimes is to give all unnecessary clothing away. Failing that, lock it up and use it only for the activities it was made for (e.g. boat shoes for maintaining grip while sailing).

As you do this, you will start to see what is a good piece and what isn’t. And in most cases, throwing out the unnecessary will leave you with little else to wear. Which is why the next step is so important: rebuilding your wardrobe with what works.

Step 3. Training your eye and rebuilding the wardrobe

Congratulations. If you’ve made it through to this stage, it means you’re serious about looking good.

You now have to build your new wardrobe almost from scratch:

  • Get the best looking shoes you possibly can. Unless they are sneakers, aim to spend 200$+ on a pair of decent shoes. Avoid square toes on dress shoes or loafers – look for round toes and a leather (not rubber) sole. Good American dress shoe manufacturers: Alden, Allen Edmonds. Even better: Crockett & Jones, Edward Green, Gaziano & Girling (warning: expensive stuff).
  • Stick to the most versatile men’s items – dark blue denim, button-down shirts shirts, solid trousers, v-neck tees, grey or navy sport coats, and two-button suits (charcoal if it’s your first suit). Variations of these will be more than enough for a good wardrobe.
  • If you are not sure of which colors work best on you, try sticking to earthy and subdued tones: light or dark greys, blues, browns. Try mixing it up with deep purples and burgundy. It’s easier to make outfits work with these than with blacks, whites, yellows or bright greens.
  • Avoid buying anything with visible branding or logos. Look for pieces that will look good in any outfit – don’t expect luxury names alone to do the work of putting together a solid outfit.

Above all, think of the whole outfit when buying individual pieces. A versatile wardrobe built from quality clothing will give you many combinations to work with, so you can mix it up all the time.

These are good starting points, but there is much more to style than simply following heuristics of color and patterns. Get inspiration from legendary style icons. Do some research and find images of Steve McQueen, Paul Newman, Tom Ford, Bob Dylan, Johnny Depp looking their best. Or watch an episode of Mad Men.

Classic men's style: Steve McQueen pulls off the turtleneck

Steve McQueen pulls off the turtleneck

As you look around and notice who’s doing it right, you will realize that there’s an important step missing.

Step 4. Mastering fit 

Everything must fit well. This is non-negotiable, and a cornerstone of classic men’s style.

  • Finding a good tailor should be your first order of business. Most decent dry cleaning places will also do alterations – check the prices and read reviews. Send in one shirt for alterations to begin with. If it’s a good place, stick to it.
  • Shirts should not puff out at the waist. Pants should not require a belt (or suspenders!) to be held up. Suits should fit like a glove – at the very least, alterations will be necessary for any suit bought off the rack.
  • Pants (including jeans) should not be baggy, or skin tight either. Aim for a “slim straight” fit.

There are many more considerations, especially when it comes to dress shirts, suits and pant lengths. These are details a good tailor can help you with.

At this point, you are ahead of 99% the competition (unless you live in Milan). You have experimented with what works for you, and you have started to personalize your clothing by making it fit to your body only. It is likely that you now own (and use) a tape measure. There’s really only one stage left.

Step 5. Setting your own style 

The real fun begins when you start breaking the rules.

You no longer need inspiration or help from others, although you certainly won’t refuse it.

You start introducing your own ideas and modifications, and start seeking out individual items that you know would work great in your wardrobe. Chances are, you are already somewhat of a style icon in your local community or social circles.

You say “to hell with guides, I’ll make my own.” And you start wondering how you can give back.

Classic men's style: Yves Saint Laurent

Once you have your own style, you can break the rules

I hope you enjoyed this introduction to classic men’s style. For practical ideas about which pieces to buy, check out my article on the 8 Most Versatile Pieces of Clothing a Man Can Own.


Add yours

  1. hair weaving for men

    January 30, 2013 — 6:54 pm

    I think other web site proprietors should take this site as an model, very clean and fantastic user friendly style and design, let alone the content. You’re an expert in this topic!

  2. I think the above points are quite true particularly the deference between style and fashion makes things very clear that style doesn’t come over a night.its a process and I would say inbuilt as well.
    Good tips for those who want to be stylish and want to remain in the main stream

  3. Screw you, the quality of a nice button-down Polo shirt can’t be had without the little Polo player. No other brand holds up as well. Those shirts are indestructible, are classy, come in every color of the rainbow, and fit extremely well, even untailored.

    THEN you make up these nonsense rules and your last rule is DO YOUR OWN THING AND FORGET THE RULES.

    No. That’s what an idiot does. There are some rules STILL in force – for instance, your wearing a black belt? Better have black shoes on then. A brown belt? Brown shoes. You don’t mix leather colors. PERIOD. EVER. Unless, of course, you want to look like an idiot. Do you want to look like an idiot?

    If you do – listen to the a hole who wrote this article.

    • If you have tried other brands and Polo works best for you, go for it. In my opinion, the “little Polo player” (or any variant) looks somewhat juvenile.

      As to matching leather, I am very much in agreement.. If you’re dressing up (formal), I would suggest going so far as to get the shoes and belt from the same leather.

      I can tell you make an active effort to dress well, and I respect that. I hope we can have a constructive conversation.

    • Come on man take the article for what it is. Your definately lacking in style if your trying to justify a horse on your shirt. Polo has shirts without the horse also very nice shirts with no logo so to each is own.

      • Definitely ….. it is spelled spelled definitely isn’t it?
        ……….. Phaek Bob. Looks like your hardliner attitude to dressing is not the only thing that needs working on. Calm down man..the author just wants us guys to be a bit better dressed…that is no reason to start displaying behavioral disorders.

      • Really. I didn’t know that. I didn’t know you could buy polo with no logo. I too do like the fit and look of Ralph lorern polo shirt. But. I will definitely check it out. Thanks for the info.

    • Where did the author say you can wear mismatched shoes and belts? You’re taking the author’s thoughts out of context and blowing it out of proportion.

      I think the author is implying that not every traditional rule of dress from bygone eras applies now. Sorry to tell you this but times change. Traditions evolve. Example: it’s okay to wear brown with black.

      The author is simply encouraging people not to be pedantic — that is obnoxiously adhering to silly formalities and driven by snobbery.

      There is room for creativity, individuality, and sprezzatura.

      If you rigidly make things difficult for people then they won’t even try and before you know it you have a bunch of slobs showing up to their desk jobs in hoodies and Hawaiian shirts, or not even having the courtesy to wear a tie to a formal wedding or a funeral.

  4. Dressing is very important ! Look at a person going to court for a crime. They make sure the person does not look the part. Dressing in a suit. And tie is crucial. Going for a interview, Dress for Success it could make or break you. A study was done, wearing the wrong color’s also could be held against you. Lastly why do people look down at your shoes ? What does the shoe hold about the wearer. ?

    • Is this freestyle rap?

      Shoes tie the outfit together, in a sense. We spend about a third of our life in bed, and another third wearing a pair of shoes. Don’t skimp on either!

  5. $200 for a pair of shoes? This obviously isn’t for us low income guys who wouldn’t eat for a week if we spent that much on shoes. I’ve read thru this and I do like most of it, for example I almost never wear at shirt unless it’s under a button down, and I refuse to wear polo shirts, the remind me of frat brats. Guess I’ll have to stick with my own intuition and I’ll cling to my boots for now. Was an enjoyable read, however.

    • Hi Ken, I agree $200 is a lot of money. My point was that a nice pair of shoes will end up being more affordable in the long run, if taken care of properly. I would even suggest saving on the other items so as to not compromise on the shoes! In any case, thank you for your comment.

      • Marshalls and TJ Maxx are fantastic places to get high quality shoes for half the price of regular retail, if you happen to find them there.

        • Thanks for the tip, eric! What are some of the high quality brands available at these stores ?

          • Rockport and florsheim would be decent brands to start out with. I got a pair of Steve madden at Nordstrom rack for 60 or 70 that I am happy with. I wear a 14 or 15 so it’s hard for me to find something but they are decent so far.

            I’m looking for quality over quantity and want my stuff to last.

            I would look into different construction processes like Goodyear welted and Blake stitch. Goodyear welted shoes tend to be more expensive but from what I’ve been told they last much longer and are easier to resole.

            I got a pair of Goodyear welted plain black derbys from shoe passion, a German company, for my wedding and they looked slick as hell. Expensive but I expect to pass them on to my son. Hopefully he has some big ass feet too!

            Edit: when I typed this up I didn’t realize you were the author but this is more for other people like me who need this guide lol

  6. Brilliant article, the only thing I would suggest is in relation to step 1, a 10 inch drop is quite significant and if you aren’t going to spring for a tailor-made suit, most reputable suit manufacturers deal in a 12cm (4.7 inch) standard drop in size from jacket to trousers. Having a 32inch waist but a 42inch chest can make you look out of proportion and as if you should be wearing a tank top instead of a suit. For ease of purchasing and to be kind to your tailor, aim for around a 5inch drop!

    Keep up the good work neuro!

  7. Thank you for posting this about men and our need to dress sharp. And I love the one about mastering the fit and your suit should fit you like a glove. Because that will compliment your body type greatly and hide all imperfections while amplifying your greatness. Thanks again

  8. Hi, I can only afford a good pair of pants, a nice shirt, or a 3mm wetsuit. Seeing as I can’t wear my shirt and pants surfing in winter I decided to go with a wetsuit. However I do get some funny looks at the supermarket.

  9. What a dumb article. Who is spending $200 on shoes??? Who wrote this, gweneth Paltrow?? This guy doesn’t live in the real world.

    • The real world is an illusion.

      • I’ll tell you shoes are important. 150 the most I ever paid. Sometimes it depends on ones evolving knowledge of what’s good quality. It took me some time. That’s why I read and learn. Humility is not a fad.

    • I have spent more than that on boots and shoes. One pair of my boots is 25 years old. And i wear them ever winter in Canada. You get what you pay for.

    • Many guys in the real world spend $200 on shoes. This article is about dressing well and the author is talking about a more formal style of shoe. In fact its hard to buy a well made shoe that is comfortable to wear for much less. Hes offering tips to people that want to improve the way they dress. Pay more up front and reap the benefits for many years to come.

  10. Great read!
    U had me at …”You’ll get more attention (compliments) from women! “

  11. Like the article a lot. More of the same please.

  12. Thanks for the article. The tips are really good. For the people criticising, you can take the good points from the article and leave the ones you don’t like or consider not worthy. I agree on the shoe part. Btw you get all the good brand shoe within 60$ at my place India.

    Keep up the good work author

  13. I would like to reprint this articale on my site, can you email me and let me know if you would allow me to, and of course leave you a link back

    • Hi Robert,

      Thank you for your comment.

      I would prefer that you do not simply copy my article – perhaps you could simply link to it, and write an article with your commentary and thoughts. Let me know.

  14. I just wanted your opinion. I am 32 years old. I dress well( I think your rules above were good). I don’t have an office job so I don’t need suits. So I would say my everyday style is classic casual. I think there are a time and place for leather boots or saddle shoes with dark jeans and chinos but I also want the ability to dress down but still look classic and put together. As of now my go to are navy canvas with brown gum soles (vans). I feel like you could see guys in the 40 and 50s wearing them but, am interested in what you think and/or if you have any other ideas.


    • Hey there, Trey. Thanks for reading!

      I looked up those shoes – I think they would go well with shorts (day at the beach, for example). They would also work with slim-cut khakis for casual spring/summer wear. I think the soles are a bit thick on those, but that’s just me. You have to be comfortable in whatever you’re wearing.

      With that said, I would recommend some casual boots. Clarks Desert boots are a good entry point (painful to break in, so wear thicker socks to start). I would even push you in the direction of R.M. Williams boots – it’s a classic style (and quality leather).

  15. Food for thought = Words, fashion and effectiveness = to be or not to be taken seriously = that is the question…
    A..Words: choose your words wisely,,,,,,,,,,,,, to be taken seriously.
    The use of wishy washy words such as kinda and sorta take the
    speaker and the listeners \ audience into a state of not being taken
    For examples = listen to, mostly, artsy fartsy people, over and over,
    using those two words when being interviewed on the radio and TV.
    1. I kinda wrote that song ­ sorta on the weekend, etc..
    2. I sorta had sex and kinda ­ like ­ became / got pregnant, etc..
    NOTE: The interviewer has an opportunity to give the interviewee
    constructive criticism and/or feedback if the interviewee needs / wants to be taken more seriously, in the future.
    B..Fashion: choose appropriate fashions to be taken seriously…
    Appropriate fashion for a given situation adds to a person’s
    credibility and contributes to the possibility that what they want to
    present / offer, verbally, will be taken seriously.
    NOTE: For a man to inappropriately wear shorts and/or short pants gives the impression, to others, that he was foolish enough to allow himself to be sold a half of a pair of pants and to show that the top
    half of the pants, fortunately, is what he purchased rather than only
    the bottom half of the pants, to be worn in public…
    Example: It would be inappropriate for a female or male to wear a
    bathing suit and/or PJs to a serious job interview, church, mall, etc.,
    just to show off her or his shaved legs or night cloths …
    C..Effectiveness: choosing the most appropriate fashions for a given situation …….. + using and choosing your words wisely will
    contribute to allowing others to take you more seriously…
    Examples above in A. and B….. or not to be taken seriously.
    PS: Birds of a feather flock together… what kind of birds do you
    want in your flock…
    What you demonstrate influences what you get ( sew and/or reap ) + a change of fashion, now and then, keeps one from becoming
    bored and/or boring….
    Be especially careful about the distraction of tattooing and piercing if your intention Is to be taken seriously, in developing significant
    future possibilities / options for yourself, regarding employment…

  16. The response you get from literally everyone when wearing a sharp suit is immense. I absolutely love it and strive to wear one wherever I go. Even people who usually could be classified as ‘jerks’, think doormen and aggressive cops, treat you completely differently when you dress sharp.

    While I’ll probably never have his bankroll, I believe Conor Mcgregor is emerging as a male style icon. In future years we’ll see his clothing line come out, I’m pretty sure.

  17. So what about us body builder types that still want to look good in a suit(or something other than tank tops and gym clothes)? In regard to the ten inch drop, I’m about a 48 in the chest and a 32 in the waist(I also plan on growing everything else, but my waist). The quadzillas (my legs) make buying pants an extra pain in the rear end, because I want my butt to look good, but without splitting the fabric. If any of that made sense, or if you have advice I’m a listening ear.

    • First of all, congrats on the 48-in chest. Takes hard word to get there and maintain it!

      Bottom line: you will have to get a suit custom-made (or at least MTM, Made-to-Measure). Standard off-the-rack (OTR) suits will not be flattering for your body type. I recommend talking to a tailor in your area to get some advice and measurements. Once you have finalized the kind of suit features you’d like, you could always go with an online tailoring service like Indochino.

      These guys have some tips that you will find interesting:

  18. Just came across this article from a few years ago..better late than never to comment I guess. I think your 10″ drop chest to waist rule of thumb is spot on. The other reader seemed confused between chest size and jacket size. My chest is 47 with a 36 waist. My jacket size is 44, so he’s right about a 5″ drop being accurate in regard to jacket size but your original statement was chest and waist size. Guys always get confused about the chest size/ jacket size..two different things. One tip I would add is to find out what your measurements are. You can do much better buying clothes with your own measurements in mind. Such as buying a shirt with specific neck and sleeve measurements as opposed to buying large, xlarge, etc.. Know your chest size and what you like your shirts to measure across the chest. Check online sizing guides for this when ordering. This will help prevent looking like you have a parachute following you around when your shirt is tucked in (which it almost always should be).

    As far as spending 200 dollars on a pair of shoes. I would say spend at least that. Unless you like spending 50 dollars every six months on a pair of shoes. You get what you pay for. In the long run its much cheaper to buy quality shoes. Guys who cant imagine spending that much are not interested in dressing well and thats fine. If you can spend 300 dollars for the latest game console you should be able to invest in some quality shoes if youre serious about dressing well. A 200 dollar pair can be polished and maintained without falling apart and last several years, not to mention look 10 times better. You can spot a cheap pair of shoes a mile away and so can the ladies. Nothing ruins an otherwise nice outfit than a bad pair of shoes. Details gents, details! Great article, I enjoyed reading both it and the comments.

  19. It takes some time but style is something you develop over years, great points though 🙂

  20. What is with the present fashion in men’s suits? Skin tight pants, blue suits with brown shoes, jackets that fit where they touch and how about unbuttoning your jacket before you sit down! Oh, and then letting the bottom end of the tie hang out below the suit button. I guess this is OK for kids that don’t know any better but MEN please read these articles by Neuro and become a classic stylist. Your women will love you for it!

  21. Excellent advice!!! I have been following this philosophy for several years now and have found it to work VERY well for me. In the end it is also much more economical. Once you know what you are looking for you wait till you find it on sale. By and large you are free of seasonal fashion whims. And yes expensive shoes … and learn how to care for them. My first good pair is now 7 years old and still look new. Again, once you know what makes a quality pair of shoes (Goodyear welded, full grain leather etc) you can wait and find some real deals on them. My go to Oxford cloth button down shirts are from a supermarket and 29.00. I get levis on sale for 39.00. My one suit is very expensive made to measure. This works.

  22. Sorry… welted not welded!

  23. One more comment on the shoes issue… The reason that the goodyear welted (stitched) shoes are more expensive is the labour cost. It’s far cheaper and faster to just slap glue on everything but that doesn’t make a shoe that lasts. Once you have a pair of Goodyear welted shoes with stacked leather heels and the heels start to wear down you take them to a shoe repair shop and they will put on a new set of lifts (the bottom rubber layer of the heel) which makes them good as new for far, far less than the cost of new shoes. That’s why they last. An added bonus is that the shoes are now worn in to your foot and really comfortable.

  24. I like looking through a post that can make people think.
    Also, many thanks for allowing for me to comment!

  25. good one

  26. The only thing better than the advice in this article is the way in which the article is written: blade sharp, punch, no-nonsense. Thank you – a joy to read.

  27. Great article, I have 10 superbly tailored made with 100’s or better I keep my eye out and also sport another 20 that cshould be tailored yet fit well enough, easily 50 fine tailored shirts I dod not spend a lot of money. I enjoy wearing ankle boots with stacked heels made from calfskin, they’re not expensive and wear well, my first pair of them I wore for almost three years most every day I don’t like socks and the soft leather lining always smells like leather where if I wore tennis shoes with socks after half a day they become odorus, they have a bicycle toe and are stylish and noticed I’ve bought three pairs since 2015 the first worn to six months ago and need heels the leather sole is barely worn, I bought another pair on sale for a bit more than the first the heel is of lesser quality and two weeks later the on line seller had a great additional price knockdown and with all the discounts it cost me $55.00 theyre still in the box, I’ve seen them selling for $190. (almost a Cuban heel) I’ve collected more than 200 fantastic ties there is seldom any man that is dressed as well as I. There are 6 other types of $200. shoes from patent to brouges to wing tips some have been soled and heeled, also have nice suede high top “Naked” casual shoes natural with a thin blue welt. I know there are more I just havent looked, As of late i’ve been in distanced gatherings held in public parks into the late evenings, (bring a knock down chair) it does get cold. The outcome of this is the appearance of an extra long Racoon coat out of a cold storage vault in Germany it came freshly serviced and cleaned actually I won a few bids including 2 jackets and an extra long deep purple black Mink with a detailed collar spent less than 2 pairs of shoes for all, less than the cost of cleaning, wore one of the jackets out and about including a stop at the leather findings and shoe supply, the guys there really appreciatred the detail I liked it so much wore it 18 hours, what a rush of comfort and style my grandfather was a tailor my eye is developed by the way Igot a few cat calls and other fine exclaminations, the weather turned unseasonably warm, thats all I have for now

    P.S. The cold storage fur vaults are chock full of Minks many stored and paid for through generations forgotten. There are a lot of furs up for grabs, best to find the ones that are serviced before shipping, If you bear the carriage to wear one you will understand the presence and you will know what luxury feels like, it’s not what you spend rather how you spend it

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