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A WIP piece I had to design and write for my document project
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THE RULES OF THE
MODERN GENTLEMAN
Tristan O’Connor
CONTENTS
section 1 - general life rulesFirst ImpressionsLoyalty & ChivalryMeeting New PeopleRelationships
section 2 - style essentialsThe TrenchThe Grey SuitThe Crew NeckOxford ShirtsChinosBroguesThe HoldallThe ChronographPlaited BeltsPocket SquaresSunglasses
section 3 - style inspirationSmartCasual
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4244
GENERALLIFERULES
GENERALLIFERULES
Whether you need to completely rethink your approach to certain situations, or quite simply want to polish up on what you already know; this section will provide you with the key bits of information to help you reach your peak as a gentleman.
1. If you can’t grow facial hair properly, don’t.
I’m a big fan of beards, and wish I could grow
one myself, but know I can’t, so I don’t. Nothing
casts a worse first impression than a patchy beard
attempt, so to combat this, there’s a very simple
solution: shave every couple of days or so.This
means that you’ll always be looking your best.
Being a gentleman isn’t without it’s complications. The way one acts
second to second is scrutinised, whether you’re aware of said scrutiny
or not. A lot of it you may be completely oblivious to, but you’re
always under the watchful eye of someone. And yes, I know what
you’re thinking, “how can I possibly please people I don’t even know
are looking at me?”; and the harsh truth is: you can’t, but the following
five tips will hopefully make sure you please the majority, or the ones
that are worth pleasing anyway.
F I R S T I M P R E S S I O N S
T H E R U L E S O F T H E M O D E R N G E N T L E M A N 8/9
2. Keep your hair maintained. Nothing is more
annoying than the “Oh someone’s had a haircut”
comment, so my solution is to not give them
the chance. Choose a style, then go to the
hairdressers once a month. This way you build
up a raport with the hairdresser, meaning you
get both a better haircut, and far less awkward
conversations in the chair.
3. Have a daily skin routine. A bad skin day is
almost impossible to cover up (unless you’re a
burglar). Minimise this by having a skin routine you
stick to day in day out.
4. “Manners don’t cost a thing”. A well known
phrase and one of the most truthful, the majority
of the time it only takes a few seconds to be
polite. Whether it be holding a door open, letting
somebody past, or your simple P’s and Q’s, they
all say a lot about you as a person.
5. Don’t dress like a slob in public.This is very
important. Sweatpants and ‘trackies’ do not
radiate the active impression they used to, and in
fact do the opposite. Take a little time to pick out
an outfit that is stylish, comfortable and suited to
the weather, flip flops all year round doesnt make
you look as manly as it does impoverished.
Chivalry is a very misunderstood concept, with most thinking that it
only involves courtesy towards women; but that isn’t entirely correct.
Chivalry is defined as having the qualities and morals of a medieval
knight, thus meaning, in my opinion anyway, that it should apply to
your male friends as well. Without close male friends you’ll end up in
a similar boat to Peter Klaven from ‘I Love You, Man’. The following five
points aim to make sure you hit both nails on the head.
1. If someone holds a door open, accept the gesture.
I know what you’re thinking, and yes it is incredibly
simple, but you’d be very surprised at the amount
of people that think a ping pong like argument is
necessary in this sort of situation. The simple fix;
walk through the held open door and say thank
you. The thank you is very important, without that
you come across terribly.
L O YA LT Y & C H I VA L R Y
T H E R U L E S O F T H E M O D E R N G E N T L E M A N 10/11
2. Honesty is the best policy. Saying something
because someone wants to hear it is the worst
thing you can ever do. This especially applies to
women. Not only will it kill her when she finds
out you don’t think it (and she will), it also means
you’ll have constant attention from someone
you’re not interested in. Sugar coating the truth
on the other hand; perfectly fine.
3. Don’t be a dickhead. A dickhead is defined as a
dick who doesn’t know he’s a dick. This person is
always a bit too loud, and always assumes you’re
interested in what they happen to be doing or
saying (the opposite is normally true). If you’re this
guy, stop.
4. Compliments work better if they’re unexpected.
A phrase that is always misinterpreted, and no,
it doesn’t mean you can get away with being an
arsehole the majority of the time if you throw
a compliment in occassionally. Use compliments
when the moment is right, don’t flood her with
them, but don’t starve her of them either. I’m
afraid it’s up to you to find the balance.
5. Make sure everyone’s voice is heard. Some
people function better in a group, others better
one to one. Figuring out what type of person
someone is is a hugely important quality.
Meeting new people is a very difficult thing to be completely confident with, especially if you’re doing it without the help of a friend,
to a complete stranger. There’s a lot that can go wrong, granted, but
there’s also a very simple formula to making sure that you get it right
more times than not. The following five tips will set you on your way,
and make your meetings in the future that little bit more comfortable.
1. Extend a hand. You’d be surprised at how much
easier this makes everything. Obviously different
handshakes apply to different situations; for
example you wouldn’t use the same handshake
for a male and female. For a ‘man meet’ be
confident in your shake, and for a female be non
threatening. Oh and don’t be a bonecrusher, it
casts a terrible first impression.
M E E T I N G N E W P E O P L E
T H E R U L E S O F T H E M O D E R N G E N T L E M A N 12/13
2. “Hi. how are you?” This, in my opinion is the
easiest and most reliable opening line in the book.
It isn’t too forward, but it shows that you have
confidence both in conversations, and in yourself.
A simple lead on from here is to exchange names,
and then ask said person where they’re from. One
simple script and the ball is rolling.
3. Try your best not to swear. I for one know that
it’s not always easy, but when meeting new people
you can never be sure how they feel about
expletives. Some people are completely fine with
them, but other people will feel intimidated, and
worst of all will switch off from the conversation
completely.
4. Look happy when you enter a building. Nobody
wants to talk to the grumpy guy, it’s like walking
into a minefield. If you’re on your own however,
don’t walk into a place beaming like a cheshire cat,
or otherwise people may think that you’re mad.
Instead go in looking approachable, no vogue-
esque squinting into the distance.
5. Listen. You may think that this is obvious, but
the amount of people who come across as very
rude because they’re thinking of what to say next
is unbelievable. Instead, engage with the person
and find topics in what they’re saying.
All relationships are hard work, some more so than others, and
without this hard work they don’t work ever so well. The unsuccessful
long term relationships stem from a lot of things, but the main
proprietors are a lack of trust, a lack of communication, or a lack of
intimacy. Some relationships simply aren’t meant to be, but with the
following five tips you’ll be the best boyfriend she’s ever had for the
time you’re with her.
1. Keep her in the loop. Nothing will ruin a
relationship quicker than doing things behind her
back. I’m not saying you should tell her exactly
what you’re doing all of the time, but for example
if you’re meeting up with another girl, whether it
be an ex or just a friend, tell her. It’s much better
she finds out from you than one of her gossip
happy friends who may blow it out of proportion.
R E L A T I O N S H I P S
T H E R U L E S O F T H E M O D E R N G E N T L E M A N 14/15
2. Don’t cheat, ever. Cheating is never alright, even
if you have the best excuse in the world
(“it was Rihanna I had to”). ‘Once a cheat, always
a cheat’ is the well known phrase; and even if you
don’t cheat again, your reputation will be forever
tarnished by your mistake. Oh, and if you’re so
naïve to think she won’t find out, she will.
3. If she wants you to go shopping with her, go.
I know it can be the most boring, repetitive,
monotanous thing in the world, but it’s something
you have to do. I choose to see it as a flattering
gesture, as it means that she values your opinion
and is trying to impress you with what she’s
wearing. It also means no nasty surprises or lies
when she comes home wearing something you
don’t like.
4. Sometimes she might just want to be held. Not
everything has to lead to sex, sometimes a girl just
wants to feel safe in her mans arms, and its up to
you to supply that. If she leans over to kiss you, it
doesn’t necessarily mean she’s in the mood, she
might just be realising how lucky she is.
5. Pretend to like her friends and family even if
you don’t. This is going to be hugely beneficial in
the long run, and by doing this you’ll avoid an
awful lot of unnecessary drama.
STYLEESSEN
-TIALS
STYLEESSEN
-TIALSYou could quite easily be the most gentlemanly man on the planet and not get a chance to prove it to anyone because of your look. A lot of a gentlemans charm comes from his clothes, and in this section you’ll find out which items you must have.
18
T H E T R E N C H
The trench coat (made famous by Burberry
and Aquascutum, but you knew that) has been
draped over the shoulders of gentleman all
over the world for hundreds of years, so it’s
no wonder that this coat has become such
an iconic British staple piece. As versatile as it
is timeless, effective paired with a pair of dark
jeans, chinos, or for your every day haul to
work. this is a style of coat that no gentleman
should be without.
“There hasn’t been a slightly colder day gone by
where I haven’t fallen back into my trench coat,
it’s so effortless. Plus it look’s incredibly stylish
whatever the occasion.”
DREW SHERIDAN (ACTOR)
H I G H E N D
Gant Rugger - £250
Another incredibly well made coat, what it lacks in
heritage it certainly makes up for in quality.
(Available at gantuk.com)
D E S I G N E R
Burberry Brit - £550
Packing a fairly hefty price tag, but it’ll last, they’ve
been making them for 111 years you know.
(Available at mywardrobe.com)
H I G H S T R E E T
River Island - £70
Not likely to give you the year in year out wear that
the other two will, but it’s an absolute bargain.
(Available at riverisland.com)
T H E R U L E S O F T H E M O D E R N G E N T L E M A N 19
20
T H E G R E Y S U I T
A grey suit is quintessential to the
wardrobe of the modern day gentleman, not
only is it timeless and hugely versatile; it is also
one of the rare key pieces that will look good
on everyone. No one looks terrible in grey, or
a suit that fits, so its a match made in heaven.
Whether it is dressed down with your top
button undone, or accompanied by a pocket
square and knitted tie; whatever the season, a
grey suit is a must have garment.
“Year in, year out, season after season, every
designer will have at least one grey suit in their
collection. It’s such a versatile garment that
leaving it out is almost suicidal.”
AIMÉE NAZROO (MODEL)
H I G H E N D
Reiss - £395
Not a brand stooped in tradition, but their suits are
extremely good value and quality considering the price.
(Available at reissonline.com)
D E S I G N E R
Richard James- £945
If price isn’t an obstacle then as far as off-the-peg suits
go, no one does it quite like Richard James.
(Available at mrporter.com)
H I G H S T R E E T
Next - £99
A suit aimed at the masses, and perfect for jetsetters,
as not only is it a bargain, it’s machine washable too.
(Available at next.co.uk)
T H E R U L E S O F T H E M O D E R N G E N T L E M A N 21
22
T H E C R E W N E C K
The crew neck jumper is a sure fire way
to stay dressed to impress on your days off.
Not only will it add an extra texture to your
outfit, it’ll keep you a lot warmer than a lot of
other styles of jumper. With the shape lending
itself so well to so many different silhouettes,
materials and styles, it’s a gentleman’s must
have. Worn along with a pair dark jeans, an
oxford shirt and brown brogues, there’s not
much that can go wrong.
“I love this style of jumper, I mean, what’s not to
like? I can wear it with a shirt, with a t-shirt, with
shorts, with trousers, under a coat, without a coat.
It’s just so easy.”
BEN ARNOLD (ATHLETE)
H I G H E N D
Lyle & Scott - £100
Made in Scotland, Lyle and Scott jumpers are about as
traditional as it gets.
(Available at lyleandscott.com)
D E S I G N E R
Gant Rugger - £130
The Rugger range blends American heritage and British
country, typified in this alpaca and cotton blend jumper.
(Available at mrporter.com)
H I G H S T R E E T
Mango - £59.95
A well made, incredibly comfortable jumper. Absolutely
perfect for the weekend.
(Available at houseoffraser.co.uk)
T H E R U L E S O F T H E M O D E R N G E N T L E M A N 23
24
O X F O R D S H I R T S
Contrary to popular belief, an Oxford
shirt isn’t defined as a shirt that has a button
down collar, but more so by the Oxford
weave cotton it’s made from. As timeless as
it gets, the Oxford shirt has been one of the
most consistent performers for the every day
gentleman; more a casual staple piece but just
as effective for the man after a more collegiate
approach to his work attire.
“On the days I haven’t got a shoot, a simple
pastel oxford shirt casts exactly the impression
I’m after, casual with just the right level of
sartorial elegance. I don’t think you can beat it”
ALEX DUNSTAN (MODEL)
H I G H E N D
Ralph Lauren - £85
As far as Oxford Shirts go it’s fairly hard to fault Ralph
Lauren, this shirt will last through years of wear.
(Available at ralphlauren.co.uk)
D E S I G N E R
Kitsuné- £180
Offering a japanese fit to cater for the more slender
gent, this shirt fits as beautifully as its made.
(Available at mrporter.com)
H I G H S T R E E T
Topman - £26
A good shirt considering the price, and not one you’ll
be worried about getting your hands dirty in.
(Available at topman.com)
T H E R U L E S O F T H E M O D E R N G E N T L E M A N 25
26
C H I N O S
Throughout time, jeans have dominated the
casual scene, leaving chinos to be banished
into relative nothing-ness across the globe;
only in the past five years have they had
somewhat of a revival. Chinos are defined by
being made from chino cloth, and are more
hard wearing than the standard trouser. As far
as versatility goes, these trousers can be worn
all year round, rolled up to the ankle worn
with espadrilles, or tucked into boot socks.
“With menswear, it’s not a case of being boring.
It’s about getting the right amount of boundary
pushing with the right amount of commerciality.
The same should apply to your everyday outfit.”
JAMES LONG (DESIGNER)
H I G H E N D
Suit - £60
Bright chinos are a must have summer piece, and this
pair by Suit is about as bright as it gets.
(Available at urbanoutfitters.com)
D E S I G N E R
Carhartt - £80
With it’s main focus in the States on work clothes, you
can trust these chinos will last you a life time.
(Available at urbanoutfitters.com)
H I G H S T R E E T
Topman - £28
These chinos have become a Topman staple piece.
Hard wearing and good value: the perfect combination.
(Available at topman.com)
T H E R U L E S O F T H E M O D E R N G E N T L E M A N 27
28
B R O G U E S
When it comes to relations, be it business
or pleasure, good shoes can be a deal breaker;
so slipping your feet into brown leather is
always a safe option, especially when they’re in
the form of brogues. It doesn’t get much more
traditional British gent than this, whatever the
weather, brogues will never be questioned;
unless they’re unpolished, a scuffed leather
shoe is like wearing a bolognese stained shirt,
you just don’t do it.
“Shoes maketh the man. A man who doesn’t
think people will look at his shoes is sadly
mistaken, and will fare far worse than a man
who has thought through his outfit head to toe.”
JESSE CLARK (FASHION PROMOTER)
H I G H E N D
Kurt Geiger - £120
When it comes to brogues I feel the chunkier the
better, and it seems Kurt Geiger do too.
(Available at kurtgeiger.com)
D E S I G N E R
Grenson - £190
138 years of tradition and the first manufacturer to
feature Goodyear welt construction. Need I say more?
(Available at grenson.co.uk)
H I G H S T R E E T
Asos - £50
A very nice shoe for the price, full leather (including
sole) and hard wearing. A tempting combination.
(Available at asos.com)
T H E R U L E S O F T H E M O D E R N G E N T L E M A N 29
30
T H E H O L D A L L
Your bag says a lot about you as a person,
and it saddens me to see so many gentleman
ruining their hard work by making bad luggage
decisions. As a bag, the holdall is about as
complete as the name suggests, and suits
every situation that you present it with. Also,
living where we do, you never know when
you might have to stow away or get out your
coat, why not make sure you have somewhere
to put it? After all, carrying it becomes a pain.
“I can’t deny that I’ve made some bad decisions
with regards to bags in the past, choosing the
budget option more often than not; but once you
invest in a good holdall, you’ll reap the rewards.”
TOM BIRD (DESIGNER)
H I G H E N D
Fossil - £188
A fairly hefty price tag for a supposed mid range bag,
but this will last you for years, and it’s spacious too.
(Available at fossil.co.uk)
D E S I G N E R
Ralph Lauren - £665
As much of a statement as you can possibly make
luggage wise, no one does it like Ralph. Period.
(Available at ralphlauren.co.uk)
H I G H S T R E E T
Asos - £35
Not the most reliable of bags granted, but for the time
it is in one piece, you’ll look the business.
(Available at asos.com)
T H E R U L E S O F T H E M O D E R N G E N T L E M A N 31
32
T H E C H R O N O G R A P H
A lot of gentleman make the mistake of not
wearing a watch for a variety of reasons, the
most popular choices being: “I’ve never worn
one, it’d be weird”, and “Why do I need a watch,
my phone tells the time”. These two statements
however, couldn’t be worse excuses; the
watch is now as much about style as it is
about functionality. Not only is it the perfect
finishing touch to any outfit, it also makes
telling the time far less of a fumbly mess.
“The beauty of the watch is it’s one of the rare
things you can wear day in day out without
people looking at you in a funny way. No brown
straps for black ties though, bracelets or black.”
SIMON BURTON (EDITOR)
T H E R U L E S O F T H E M O D E R N G E N T L E M A N 33
H I G H E N D
Longines - £650
The Grand Classique is the cheapest model, but this
doesn’t mean it lacks quality, it is Swiss you know.
(Available at watches-of-switzerland.co.uk)
D E S I G N E R
J&T Windmills - £1495
A life time guarantee without the unsightly black
rubber. Need I say more? I mean, just look at it.
(Available at watchshop.co.uk)
H I G H S T R E E T
Rotary - £179
An automatic watch for under £200 used to be rare,
but Rotary seem to have made it commonplace.
(Available at rotarywatches.com)
34
P L A I T E D B E L T S
Sometimes all an outfit is missing is the right
belt. Much like a nice watch, a good belt will
add an extra dimension to your outfit, and can
really help you out in creating helpful illusions.
For example if you’re not blessed in stature,
a belt can make your legs look longer, it also
divides your outfit, and most of all, keeps
your trousers up. Don’t wear a belt with a
suit though, braces are a much better. Think
Boardwalk Empire.
“Your belt should either be the same colour as
your shoes, or a contrasting shade of the colour.
It always kills me a little when I see black shoes
with a brown belt, or vice versa.”
RICK EDWARDS (PRESENTER)
H I G H E N D
Barbour - £30
As traditional and stylish as it is rugged and durable.
Plus it doesn’t look too shabby either, don’t you think?
(Available at barbourbymail.co.uk)
D E S I G N E R
Fred Perry - £50
The interweaved tricoloured leather really sets this belt
apart from its counterparts. It adds individuality too.
(Available at fredperry.com)
H I G H S T R E E T
Next - £13
A shop that’s a bit of a hidden gem for this sort of
stuff, made to high quality, for high street prices.
(Available at next.co.uk)
T H E R U L E S O F T H E M O D E R N G E N T L E M A N 35
36
P O C K E T S Q U A R E S
Have you ever looked at yourself in the
mirror and wondered why your grey suit
makes you look like an office worker rather
than a tailored deity? Well a pocket square
may well be your answer. This is a detail that
a lot of gentleman dismiss, due to how much
thought goes into picking the right shirt and
tie. Forgetting this ever so slight addition
however could be the difference between
looking like David Brent and David Gandy.
“Your pocket square shouldn’t match anything
else that you’re wearing pattern-wise, but the
contrast needs to be a happy one. You can never
go wrong with white, that goes with everything”
PAUL SMITH (DESIGNER)
H I G H E N D
Hugo Boss - £27
Quite the statement, but surprisingly versatile with
regards to what you can wear it with.
(Available at houseoffraser.co.uk)
D E S I G N E R
Drakes - £50
When it comes to ties and pocket squares, Drakes are
the paramount. The price tag isn’t kind mind you.
(Available at mrporter.com)
H I G H S T R E E T
John Lewis - £15
Offering a wide range of 100% silk handkerchiefs, this
paisley number is the pick of the bunch.
(Available at johnlewis.com)
T H E R U L E S O F T H E M O D E R N G E N T L E M A N 37
38
S U N G L A S S E S
One of the trickiest decisions a gentleman
will ever have to make is choosing the right
pair of sunglasses, primarily down to every
man having an inner rockstar wanting to pick
the biggest pair imaginable and wear them all
the time, rain or shine. Instead you need to
find a shape that looks as good on the beach
as it does in the town, and classic shapes such
as the Wayfarer and Keyhole are the safest
option in this respect.
“ Make sure you’re glasses are a colour that
doesn’t contrast too much with your skin. Then it’s
a matter of finding the shape and size that suit
you. Oh, and if it isn’t sunny, take them off.”
TOM FORD (DESIGNER)
H I G H E N D
Ray-Ban - £120
The choice of the masses, and for good reason.
Stooped in tradition, and style in abundance.
(Available at sunglasshut.com)
D E S I G N E R
Persol - £210
Steve McQueen used to wear them, and Clooney
wears them now. You shouldn’t need any more reasons.
(Available at mrporter.com)
H I G H S T R E E T
Topman - £14
As umialik as it comes, and for the price, they make
you look a lot more affluent than you actually are.
(Available at topman.com)
T H E R U L E S O F T H E M O D E R N G E N T L E M A N 39
ATIONINSPIRSTYLE
ATIONINSPIRSTYLE
Without the right guidance and aspirations, your style can quite easily take a turn for the worse, so it’s worth finding somebody who has a style that you like, and mimicking it. This section will provide you with all the style insipiration you may need.
42
S M A R T
ED WESTWICK (left to right)
Originally sighted for his style as Chuck Bass
on Gossip Girl, Ed has taken the same sharp,
sartorial approach to his every day outfits; a
good choice I think.
STEVE MCQUEEN
Quite possibly the coolest man to have ever
lived. He has his own line of
sunglasses and self inspired Barbour
jackets for a reason you know.
GEORGE LAMB
Co-founder of A.Sauvage, George Lamb
has quite a lot going for him, and his eye for
classic British tailoring is another notch on his
belt, along with being maybe the youngest
grey haired man in the world.
NUCKY THOMPSON
More commonly known as Steve Buscemi,
Nucky is the main character from Boardwalk
Empire. 1920’s tailoring is enjoying a revival,
and its primarily down to Nucky, this look is
always a crowd pleaser.
T H E R U L E S O F T H E M O D E R N G E N T L E M A N 43
4444
C A S U A L
T H E R U L E S O F T H E M O D E R N G E N T L E M A N 45
PAUL NEWMAN (left to right)
The other contender for the accolade of
“Coolest Man to Ever Live”. Newman had
effortless style, and based his wardrobe round
staple piece essentials such as
v-neck jumpers and simple solid shirts.
TINIE TEMPAH
Combining street style with high end fashion,
Tinie Tempah certainly has a keen eye for
clothes. I’m starting to believe he is keeping
clothes at his Aunt’s house.
LAPO ELKANN
Manager of brand promotion at Fiat, he puts
as much effortless style into his advertising as
he does his outfits. Also his own model and
keen Juvé fan.
LABRINTH
A keen purveyor of up and coming brands
such as House of Billiam, Labrinth is about as
style conscious as they come. Pairing tailoring
with bold prints is a good look, and Labrinth
has it down to a tee.
T H E R U L E S O F T H E M O D E R N G E N T L E M A N 45
www.tr istanoconnor.com
www.tr istanoconnor.com
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