This might have you rethinking
it all

by Jacob Sigala
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.
Rule to Break: Don’t Mix Different Patterns

“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 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.
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.
Rule at a Time:
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

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

“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.
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
  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

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
Rule to Break: Neckwear Needs to be Subtle

“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

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
Happy Styling!”
– Aaron Marino | I Am Alpha M.
| @IAmAlphaM

Rule to Break: Boots Are Only for Casual Wear

“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

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 |
Rule to Break: Short Sleeve Shirts are Passé

“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 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
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

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

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
– Robert Bahia | The Journey
21 | @TheJourney21

Rule to Break: Men Should Never Wear Pink

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

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
-Leah Hogan
Rule to Break: Don’t Wear Suspenders Because They Are Old Fashioned

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 |
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
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!
Kayode Ojo
Kayode Emmanuel Ojo is the Co-Founder and Managing Director at SHEFFA Limited. He is presently studying Computer Science at the National Open University, Victoria Island, Lagos.