Rules of the Modern Gentleman

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


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


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


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)


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.


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)


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.


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)


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.



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)


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)


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)


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)


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.


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)


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.


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.



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.


4444

C A S U A L


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.


www.tr istanoconnor.com

www.tr istanoconnor.com

Documents

Rules of the Modern Gentleman