man wearing pink v-neck sweater over a shirt and tie

16 Menswear Style Rules Broken by the Experts This might have you rethinking it all

Traditionally, menswear has been limited to a generic suit and tie, but there’s much more to men’s style than meets the eye.  The GentleManual set out to see if there were any established menswear style rules that style experts would recommend breaking or proudly sporting with panache. We asked some of the leading menswear style gurus what their rules to break are and what personal style means to them.

Table of Contents

1. Rule to Break: Don’t Mix Different Patterns

men Mixing various Prints

Derby Peach Tie

Say aloha to your new favorite tie! Refresh your style with our floral prints which will make you feel like you’re on the beach in paradise.

“When it comes to breaking the fashion rules men tend to play it safe never risking pushing the boat too far for fear of their unforgiving male counterparts, but things are changing; men are far more open minded to changes in fashion, with the industry welcoming new men’s lines weekly. However it can be hard to stay ahead of the curve and keep things fresh so if you want to breathe new life into your wardrobe then it may be time to start breaking the rules.

Pattern Clashing is a great option as it is quite uncommon on the street being mostly left to the runways and magazines, meaning if you pull it off you’ll definitely turn some heads. Plus with check prints, block stripes, floral and polka-dots all on trend, what better time to get clashing? Follow my tips to make sure you nail it.

Start Small: Start small by simply wearing one of your print blazers with a patterned pocket square or even some patterned socks with those check trousers or my personal favourite – a print shirt with a patterned tie. If you can pull these off then you’re on your way to clashing with success.

Don’t Overdo It: When you decide to introduce a little more pattern remember to always keep a neutral colour as a base. As a rule of thumb don’t mix more than two patterns. A nice patterned blazer with patterned pants and a plain base layer is perfect for this style.

One Rule at a Time: Pattern Clashing when done correctly will make a big statement so try not lose the run of yourself, yes black and navy can go together and trainers can be done with a suit but one rule at a time fellas.

Stay dapper.”

– Deano | The Voguish Vagabond | @VoguishVagabond

“I love to mix prints. It may be “too much” but if done the right way, it works. Polka dots with floral or a plaid with a stripe–if they are the right colors the pairing is excellent. I say, ‘do it.'”

– Dan Chizzoniti | Real Men Wear Ties | @DanChiz


2. Rule to Break: Match Your Belt to Your Shoes

“Alexander McQueen once said, ‘You’ve got to know the rules to break them.  That’s what I’m here for, to demolish the rules but to keep the tradition.’

We’ve always been fans of McQueen, and we love his take on rules.  It is good to know the basics, what goes with what and how an outfit should look, but it is just as important to throw that out the window from time to time.  Rules should be learned and then broken with taste, bent to the point of individual style.  There are plenty of these little fashion faux pas that have been acquired with time.  Wildly colorful socks for instance, were gawked at when they first became popular, now they are more mainstream in the dapperly dressed than solid black.

We would like to address another “rule” of men’s fashion that we think too many men are getting hung up on, when really it looks better broken: matching your belt to your shoes.  Don’t get me wrong; you shouldn’t be wearing brown shoes with a black belt, or vise versa but there is no need to find a belt that hits on the exact same tone of brown, like I have seen so many men do.  Grab a belt, grab some shoes, if they are in the same basic color-wheel and compliment each other nicely, then go for it.  I have more brown belts than I’d care to admit, and even more brown shoes.  I have never spent more than a minute pairing them up.  Put on what you like and wear it with confidence, and the next day you may just see a few guys in the office who have fallen suit.

Feel like going even further outside the norm?  Go for it!  Grab red belt, a blue belt that compliments your outfit, or a neon green one (I have a neon green Diesel belt that is one of my favorites).  Once you stop limiting yourself to one belt for one pair of shoes you’ll realize these standout belts can up your sartorial game by a long shot.  Enjoy your new look!”

– Mike Maroney | Life Tailored | @aLifeTailored

3. Rule to Break: Don’t Wear a Suit Without Socks

Men wearing Suits Without Socks

Everyday Argyle 4 Multicolor Sock Pack

If the Duke of Windsor wore Argyle, then Argyle is definitely approved by us. We’ve taken the classic pattern up a notch by adding a dash of personality and fun.

“It may seem counter intuitive, but you don’t always have to wear socks when sporting a suit.  In fact, as temperatures rise, ditching socks when you dress up is a stylish way to stay cool.  The look pairs well with more casual suits, especially ones worn to warm summer events like  outdoor weddings and parties.  Breaking this rule isn’t as simple as walking out your front door without dress socks, though.  It’s important to remember to care for your feet and your shoes, because let’s face it – your feet will get sweaty under the blazing sun.  Gold Bond powder is a sockless suit wearer’s best friend since it helps absorb moisture, preventing your shoes from effectively becoming a sweat sponge.  This will not only keep your shoes from smelling ripe after a long day under the sun, but will also help keep your feet feeling comfortable and fresh.  A pair of no show, low cut socks work great for this purpose, too.  If you do decide to take the powder route, applying a moleskin patch to sensitive areas will limit the pain you experience in the name of fashion.  We love stylish looks that are practical too, so it’s no surprise we love ditching our socks and baring our ankles in the name of cool relief and dapper attire.”

– Matthew and Steven | The Sharp Suit | @TheSharpSuit


4. Rule to Break: Don’t Wear Shorts With A Blazer

“As spring turns to summer the average temperature inevitably rises.  As a result, many men chose to trade in their pants for shorts.  A small minority of men swear off shorts altogether, which is something I don’t get.  Another set of men swear off shorts with a blazer or other odd jacket, which is more understandable and also more polarizing of a debate.

Those who are more conservatively or traditionally minded would scoff at pairing shorts with a blazer.  However, those who are either more adventurous, contemporary or perhaps even snarky wouldn’t look twice at such a combination.  I personally side strongly in the latter camp, despite often gravitating toward a more conservative mindset.

So what makes breaking this rule both attractive and acceptable?  There are the arguments for comfort; I doubt anyone would argue that pants are more comfortable than shorts in 90 degree weather.  There is also the argument for pushing the ‘rules’ of men’s style.  Not to mention pushing the limits of certain dress codes, such as ‘cocktail attire.’  But lastly, the most emotional and perhaps strongest argument for pairing shorts with a blazer is that it embodies that fun loving spirit that only summer seems to bring out in people better than most other pairings.  There is certainly none that say ‘business on top, party on bottom’ better.”

– Justin Jeffers | The Fine Young Gentlemen | @FYGblog

5. Rule to Break: Neckwear Needs to be Subtle

Collection of Loud and bright Neckwear

Chandler Navy Blue Tie

Our Chandler tie in navy blue features a black and charcoal pattern and is made of soft and durable cotton to keep you looking sharp without holding you back.


Pink Edged Linen White Pocket Square

Could your pocket use some company? Add an unexpected touch to your everyday suit with one of our edged linen pocket squares.

“There are some fashion rules that should remain untouched, wearing socks with sandals for example will forever remain a fashion faux pas, whilst others may have a little leeway. For me it’s the little details that make outfits stand out, and these can range from pocket squares to vibrant sock colours.

You always see these rules about how ties should be a certain length or tied in a certain way to give the best look, and this is where I tend to disagree. The details are meant to amplify and enhance your look rather than making you look like a generic cardboard cutout. Don’t get me wrong, if you’re going for a job interview, the Mad Men look is likely to put you in good stead but it’s always good to show a little personality.

Colour is your best friend, don’t shy away from it. A nice bright bow tie or a floral tie can really enhance your look as well as experimenting with different knot types (e.g Eldredge, Trinity). In the past if I didn’t have a skinny tie to hand, I simply put a normal tie on in reverse with the wide end tucked in neatly into the shirt and it worked a treat.

These days you should just have fun and experiment, try something new and if you’re comfortable with it why not tweak it some more? Wear a wooden bracelet, wear your watch over your shirt cuff or simply start wearing a woven belt instead of a dress belt – the combinations are endless.”

– Anton Dvorakovsky | The Style Division  | @StyleDivision


6. Rule to Break: Don’t Wear Brown Shoes with a Black Suit

“It seems like every day I see more and more style “rules” being broken for the better.  Men are taking ownership of their style selections and combinations and having fun with it.  Besides… it’s style, it should be fun and not put in a box.

You would never wear brown shoes with a black suit or slacks right???  WRONG!  That’s exactly what I thought until I decided to give it a try and actually leave the house.  Now as you know there are about 45 different shades of brown and I feel the more contrast the better.  Lighter browns like chestnut, mahogany or even tan look awesome!  The nice contrast between the black and brown adds an interesting richness and dimension to the outfit.   Since implementing this style curve-ball I have been approached by a ton of guys saying ‘I thought brown and black didn’t go together but that looks AWESOME!’.  Make sure to wear a matching (both in color and leather texture) belt to your shoes in-order to look like you did it on purpose.

Happy Styling!”

– Aaron Marino | I Am Alpha M. | @IAmAlphaM


7. Rule to Break: Boots Are Only for Casual Wear

men wearing boots with various outfits

“Breaking rules can be harder than following them. This might sound strange to some, but it’s true! Affirming your own rule, in any field, from creating art to putting an outfit together requires your understanding of the rules and of what “correct” is. In order to make a new sound or a new look, one must first strongly control how it’s done. Then, you can really do anything.

One of the style rules we like to affirm for ourselves is to wear high boots –whenever, wherever! Even though many people would not consider this necessarily “breaking the rule”, we know that according to many men, certain shoes go with different outfits and with different occasions. We like to wear old-fashioned, but modern boots in many settings and at many occasions, making them a personal style statement.

Boots can replace oxfords, brogues, wingtips and even monk strap shoes and give any outfit a note of elegance. Of course, we also like to wear other types of shoes, but picking out a pair of boots to break an outfit is a thing we enjoy doing. Our tip for those who want to wear a special item that has clear cultural and historic references is to make sure you are not wearing too many pieces that make such a reference, otherwise you risk looking like you are wearing a costume.”

– Fraquoh and Franchomme | Attire Club | @AttireClub


8. Rule to Break: All the Rules. Make Your Own!

“Men must understand the need to have style and make an effort to enhance it.  This is often difficult for you college kids that may not have a lot of money or time to worry about it, or quite frankly even care about it. As you evolve into young men, or maybe you’re already there, figure out what type of person you are and express that in your clothing.  Whether you like it or not, your clothing, hair, shoes, etc., are all going to send a message to everyone you encounter. This will not change for the rest of your life.  You might as well try to control that message for accuracy.

Your personal preferences and behaviors can help define your style.  For instance, maybe (like me) you hate tying your shoes.  I stopped buying shoes with laces about 10 years ago. Its all boots and slip-on dress shoes for me.  The only shoes I have with laces are running or basketball shoes.  Incidentally, I have the same rule with underwear.  I only wear it when I’m at the gym, or running.  I never understood how men stuff their boxers into their jeans like a diaper.  Boy that looks comfortable!”

– Max | The Rugged Male | @TheRuggedMale

9. Rule to Break: Short Sleeve Shirts are Passé

Men wearing Short Sleeve Shirts

“Designers are going CRAZY for the short sleeve shirt, why? I have no idea. You’ll see them in GQ and in AskMen’s recommendations (even though in years past they have advised against it).  It has always been the most abysmal garment for men and still is.

There is a golden rule for short sleeve shirts – If your bicep is muscular enough to fill the aperture of the arm, wear a short sleeve. This will show off the muscle and the work you have put in. If your arms do not fill the aperture, wear a long sleeve shirt with roll sleeves instead – this will add mass around the bicep making you look stronger.

Myself and renowned dating expert for men, Kezia Noble, did research on ‘what girls want men to wear’ and as part of this ebook we asked women to pick the garment that they absolutely hated the most. We had an awesome list however by far the most hated garment, decided by women? The short sleeve shirt.”

– Daniel Johnson | The Rules of Style | @TheRulesOfStyle


10. Rule to Break: Don’t Wear a Sweater Vest With a Suit

“In my opinion, breaking fashion rules doesn’t always have to be overt. Sometimes, taking an understated route can help to create a really elegant look. I’m a massive suit fan and wear them quite often. What I typically tend to do is wear a pair of patterned socks that do stand out when visible but somehow feel “put together” with the outfit as a whole. For example, on a navy blue suit, I’ll wear a pair of grey & maroon checkered socks with dark brown shoes. Here, the checkered socks are different and stand out individually but when you look at the complete outfit – they “fit”.

Another really cool idea is to pair a sweater vest with your suit. It allows you to add an extra layer to your outfit which you can use to create quite varied and interesting looks (especially when the vest is of a bold colour or pattern). Depending on the occasion, I might wear a light yellow, pink or blue sweater vest with one of my black suits – it’s different from the norm, looks great and I’m always warm as toast. 3 birds with 1 stone, life’s good!”

– Russel Menezes | Modern Man’s World | @MMWonline


11. Rule to Break: Office Shoes Must Be Basic & Neutral

“Over the years it has become increasingly more socially acceptable for guys to appreciate and care about this notion of “self-presentation.”  Guys are spending significantly more money on clothes and grooming products now then they ever have in the past. With this cultural change the unwritten archaic style laws for men’s fashion are being challenged.

It used to be that in the office or in a business casual setting you would have to match your shoes to your belt. By default your dress shoes would probably be either black or brown and they would most likely blend in with the rest of your ensemble. Now days your shoes can be the focal point of visual interest for your entire look. Dress shoes now come in spikes/studs, bright colors, mixed textiles, bold patterns, etc. Now I’ll be the first to say that I wouldn’t recommend that every guy go out and buy a pair of Christian Louboutin spiked dress shoes for work. However I would encourage guys to explore their options in footwear. For a subtle pop in your footwear, buy contrasting laces for your dress shoes. For a more noticeable pop look for shoes with a contrasting color sole. To make a bold statement, look for shoes that play with color, pattern, texture, or shine.”

– Robert Bahia | The Journey 21 | @TheJourney21


12. Rule to Break: Men Should Never Wear Pink

men Wearing Pink

Oliver Herringbone Pink Dress Shirt

Daily armour for tackling your rise n’ grind, from client meetings to date night. Finely crafted with 100% cotton, the Oliver dress shirt is unmistakably durable but also soft with impeccable detailing.

For a long time I was against the idea of men wearing pink because of it’s long standing history as a girls’ color. Recently, men have been incorporating this color very effectively into their wardrobe. A pink tie/bow balanced with a darker suit does wonders for a man’s style. A nice pink shirt balanced once again with dark pants can also be easily pulled off as long as they stay within the limit.”

– Leah Hogan | Sereine Magazine | @SereineMagazine


13. Rule to Break: Only Wear Black, Grey and Navy Suits

“Suit colors: Will only charcoal gray, navy or black do? While these colors should be the foundation for a guy’s wardrobe, adding a brighter color always adds a nice element. For interviews, depending on the industry, you can opt for a tan or wheat colored fitted suit. For casual time, seersucker is a good look even a nice breathable cotton in a pastel color (think baby blue, soft green even peach). Of course, you want to use good judgement and find a color complimentary to your complexion.”

-Leah Hogan

14. Rule to Break: Don’t Wear Suspenders Because They Are Old Fashioned

man wearing Suspenders

I would love to see more men embracing them [suspenders]! Instead of treating them as an old relic reserved for grandfathers, men can turn suspenders into something they can dress up for work with a nice suit or dress down for play and add contrast with a nice pair of sneakers or casual top. Many of them come in a variety of colors so they can have fun with different looks as well as to suit their fashion aesthetic (preppy, edgy etc).

-Roberte | Sereine Magazine | @SereineMagazine

15. Rule to Break: Don’t Out-Dress Your Boss

“Don’t out-dress the boss: Some claim that this is an unwritten no no in the business world, but why not dress to impress? Many times we want that promotion and to simply be taken seriously and the easiest way to embark on this endeavor is to look the part. In addition to working hard to be a real asset to a company, the first step is to be noticed and quality work pieces can make all the difference.”

-Leah Hogan

16. Rule to Break: No White Between Labor Day and Memorial Day

“I love it when people try to shame me for wearing white before Memorial Day or after Labor Day. It gives me an opportunity to shame them back because most of the time it’s just something they heard as a hard and fast rule, without actually understanding why it exists. The spirit of the rule is that you shouldn’t wear summery clothes or colors when it’s not warm. Lucky (?) for us, global warming is in full effect so it’s definitely warm enough before Memorial Day and well after Labor Day (in Washington, DC at least). So go forth and wear your white with pride, and then shame the shamers shamingly into shamedom.”

– Aninda Maitra | Men’s Lifestyle DC | @MensLifeDC

Now that we’ve heard from the experts, what style rules are you breaking? Which are you sticking steadfast to? Let us know in the comments!

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