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Published by Real Men Real Style

P.O. Box 415
Wittenberg, Wisconsin 54499
United States

This e-book is copyright. Except for the purposes of fair reviewing, no part of this publication may be
reproduced or transmitted in any form or by any means, electronic or mechanical, including
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© Real Men Real Style 2016

The author asserts his moral rights in the work.

First published 2016

Written by Antonio Centeno

A Man’s Guide to Wearing Hats – 1st Edition 2016 – Copyright Real Men Real Style
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Contents
Chapter 1: Why Should A Man Wear A Hat........................................................................................................................ 4
Why a Hat? ....................................................................................................................................................................... 4
Defining a “Classic” Hat ................................................................................................................................................... 5
Chapter 2: Choosing a Hat .................................................................................................................................................. 7
Material............................................................................................................................................................................ 7
Shape................................................................................................................................................................................ 8
Size ................................................................................................................................................................................... 9
Budget ............................................................................................................................................................................ 10
Chapter 3: Classic Hat Styles ............................................................................................................................................ 11
Fedora ............................................................................................................................................................................ 11
Trilby.............................................................................................................................................................................. 12
Homburg ........................................................................................................................................................................ 13
Porkpie........................................................................................................................................................................... 13
Bowler/Derby ............................................................................................................................................................... 14
Western Hats ................................................................................................................................................................. 14
Panama Hats .................................................................................................................................................................. 15
Boater ............................................................................................................................................................................ 16
Top Hats......................................................................................................................................................................... 16
Chapter 4: What to Wear with a Classic Hat .................................................................................................................... 17
Caring for a Hat ............................................................................................................................................................. 18

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Chapter 1: Why Should A Man Wear A Hat

Ignore, for a moment, the changing winds of
fashion.

Classic hats — the kinds of hats our grandfathers

used to wear — have had their ups and downs in
popular culture.

Sometimes they’re in, sometimes they’re out;

sometimes they’re co-opted by a particular
entertainer or subculture.

None of that matters much.

If you want to wear a hat, wear a hat.

They’re comfortable, practical, and a good way to

add a touch of personal style to your outfit.

A high-quality hat is a fantastic addition to any

man’s wardrobe.

That said — if you’re going to wear a hat, wear one

well.

Why a Hat?
Hats aren’t a mandatory piece of men’s clothing. They never have been, really. People may speak fondly of
“the days when men wore hats,” usually meaning the 1940s through the 1960s or so, but it wasn’t
required.

The reason you see so many men in old photographs wearing hats is that it was comfortable and
convenient for them. Clothes weren’t waterproof, buildings weren’t climate-controlled, and sunscreen
didn’t exist.

A sturdy piece of wool that could stand up to the battering of the elements was a nice thing for a man to
have on his head.

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These days, we have a much more comfortable lifestyle, and if we need weather protection we can invest
in serious sporting wear. That leaves classically styled hats in the realm of accent pieces: optional
clothing to express your personal style.

Hats are mostly worn outdoors. That means the accent is going to be dressing up your outerwear more
than your other clothes — nice if you’ve got a fairly bland looking jacket or coat and you want a little
more pop to your look.

Of course, they can be worn in the summer too, at which point they’ll be dressing up your lightweight
jackets, shirts, and slacks.

Defining a “Classic” Hat

Remember, for most of the history of men’s style, hats were functional articles of clothing. They needed to
look good, but they also needed to keep off sun, rain, and wind.

From those practical necessities, we get the classic style of men’s hat. Don’t get too hung up on details
here, but broadly speaking a “classic” men’s hat refers to the stiff-sided, structured styles popular in the
middle 20th century.

Most share the same basic elements, in different angles and proportions:

• felt material (typically wool)

• a stiff crown
• a circular brim
• a band or ribbon around the base of the crown

Different styles of hats are usually nothing more than variations in the sizes and shapes of the brim and
crown. There are a few outliers (soft flat caps, for example), but most classic hat styles fall into the stiff-
sided felt family.

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Chapter 2: Choosing a Hat

There are a few factors that go into finding the perfect hat. Everyone’s needs are different, and you’ll
want to choose the hat that’s right for your look and your budget.

Material
Most classic hats are made from felt, a condensed
mat of tough fibers.

Wool is the most common material, and by most

standards the best.

It is tough, warm, and breathable, and it keeps its

shape well.

The quality of the wool used affects the texture

and durability of felt hats.

An ideal hat should feel soft against the hand, with

a bit of a fuzzy knap, and it should keep its shape
but bend easily under pressure.

A slick, hardened surface or a brittle stiffness is a

sign of cheap construction.

A few classic styles of hat use non-felt materials:

Panama hats are woven from straw, and there are several other styles of straw hats as well, and flat caps
are usually made from a woven wool cloth like tweed.

Another alternative to wool is fur felt, which can be made from nearly any kind of hair.

The hair of beavers and other small, aquatic mammals are still used for luxury hat felts, and cow and
horse hair are used in tougher, more rugged styles, especially Western hats.

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Shape
You want the shape of your hat to balance your
face.

In this context, “balance” means the hat should

help bring out the facial features that need
strengthening and de-emphasize the ones that
are already strong.

So, for example, a very round-faced man is going

to look better in a hat that tapers to a peak at the
crown, like a sharply-angled fedora or trilby.

A man who thinks of himself as very angular in

feature, on the other hand, benefits from
something that will round him out, like a
porkpie or a bowler.

Most men don’t fall neatly into obvious extremes

like that, of course. Expect it to take you a while
in front of a mirror with lots of options to try on
before you figure out what’s perfect for your
face.

But if you’re starting with something that adds some curves or angles that you don’t already possess,
you’re probably on the right track.

Keep in mind that brims are malleable, to some degree.

A fedora with the brim tilted down all the way around gives your face a different shape than one flipped
rakishly up on one side.

So you’ve got options here — but the shape of the hat should definitely be one of your main
considerations when you’re buying.

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Size
Hat size is easy to measure, if you’ve got a soft,
flexible measuring tape.

You can buy one at any craft or fabric store, and

of course most hat shops and tailors will have
them on hand.

You can also use a piece of string, and then

measure the string against a ruler.

Measure the circumference of your head where

you want your hat’s inside rim to sit.

Generally speaking, that should be just above the

tips of your ears.

A little higher will give you a tight fit; a little

lower will be loose enough to potentially rest on
your ears.

Most manufacturers will have their own sizing

charts to convert inches to hat sizes. As a loose
rule of thumb, though, you can use the following
benchmarks:

Measurement 21- 22″ 22- 23- 24″ 24-

1/4″ 3/4″ 1/2″ 3/4″
Hat Size 6-3/4 6-7/8 7-1/8 7-3/8 7-5/8 7-7/8

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Budget
Be realistic about buying a quality hat. It’s like a
suit or a dress overcoat — you’re not going to pick
one up at Target for twenty bucks.

Plan on dropping upwards of $50 at the very

minimum for a basic wool felt hat.

For high-quality wool or fancy construction, it’ll be

up into the three digits.

That’s not a bad investment. Well-made hats will

last several lifetimes.

In terms of dollars-per-wear, a real wool felt hat

from a reliable manufacturer might be one of the
highest-value items you ever purchase.

Look for deals where you can get them, absolutely.

Sales or coupons are your friends here. But look for quality hats from brands that specialize in headwear,
and don’t make the price point your determining factor.

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Chapter 3: Classic Hat Styles

Down into the nitty gritty! Do you know your homburgs from your porkpies? If not, don’t sweat it. We’ve
got all the specifics here.

Fedora
This is what most people think about when they
think of classic men’s hats.

It’s such an iconic style that low-grade

manufacturers will call just about anything with
a brim and a fixed crown a “fedora,” regardless of
accuracy.

For the purist, though, a fedora is a felt hat with

pinched sides and a lengthwise crease down the
crown.

That gives the front a roughly wedge-like shape,

though it can be molded to the wearer’s taste.

One of the big advantages of a fedora — and one

of the reasons for the style’s widespread
popularity — is the wide, flexible brim.

Fedora brims are flat, with no constructed edge or curl, and can be bent up or down as the wearer
pleases.

The flexible brim gives the fedora a little more versatility than a stiffer style.

It can be tilted down over the eyes for a hidden, mysterious look, or angled slightly upward for a more
open profile.

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Trilby
A trilby is little more than a shortened, angular
fedora (and is sometimes called a “crumpled
fedora,” although the term is old-fashioned these
days).

It has the same crown shape as a fedora, but the

back is shorter than the front, creating an angle.

Trilbys are typically worn with the brim snapped

downward in front and upward in back, adding to
the impression of a narrowing angle at the back of
the hat.

The brim is smaller than on a fedora, usually only

an inch or so wide.

The style dates back to the turn of the 20th

century, but in the 21st century it saw a revival as a youth style, particularly in music culture.

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Homburg
The fedora’s dressier cousin, the homburg is your
best bet for a formal business look.

It has the same creased crown, but without the

pinches at the sides, and the brim is stiffer and has
a slightly upturned lip all the way around.

This is still the go-to dress hat of businessmen,

politicians, and other well-to-do gentlemen in the
western world.

Porkpie
A shorter style (and therefore a good one for men
who are already tall), a porkpie has a flattened top
without a crease down the center.

It is pinched at the sides like a fedora, creating a

slightly triangular or wedge-shaped front. The
brim is usually small, and turned up around the
edge.

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Bowler/Derby
The two names mean the same thing: a stiff,
rounded dome of a crown with no creasing or
pinching, and a short brim curled up at the sides.

Pop culture has made the bowler hat into a stuffy

British icon, but its origins are working-class, and
it is considered less formal than styles like the
homburg and the fedora.

Western Hats
Broadly speaking, Western hats are high-
crowned, wide-brimmed hats.

The most common style have a “double crown,”

where the felt is stiffened with a crease down the
center and a dimple on either side of the crown,
but other shapes are possible as well.

The origins of the style are practical, but these

days fine felt cowboy hats (with the Stetson
brand leading the way) are just as much a
fashion piece as anything else.

They are somewhat more “macho” and less

formal than other styles.

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Panama Hats
Confusingly, Panama hats come from Ecuador
(they were shipped to Panama to be sold to sailors
and workers on the Panama Canal in the early
20th century, and the name stuck).

The weaving is an art form, and true Panama hats

cost hundreds or even thousands of dollars — and
they’re well worth the price for men in hot, humid
climates.

Most Panama hats are shaped like fedoras or

triblys, but they are made from woven palm leaves
or straw instead of felt.

The flexible weave can be crumpled or rolled up

and still retain its shape, and unlike most straw
hats it can endure many soakings and dryings
without distorting in shape.

Panama hats are slightly more relaxed than their felt counterparts, but that makes them ideally suited to
the lightweight styles and loosened formality of tropical climates.

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Boater
Flat-topped straw hats with a wide brim, boaters
are mostly novelty items these days, but are still
considered appropriate (and desirable) attire for
rowing and regatta events. Many barbershop
quartets wear them, as well.

While you won’t usually see them outside those

settings, they are technically still a perfectly
acceptable summer alternative to a fedora or a
homburg. If you want to wear one with a summer
suit, more power to you.

Top Hats
The only modern use for a top hat (outside of
costuming) is as the accompaniment to morning
dress or white tie. Morning dress, the daytime
formal standard, calls for a light-colored hat
(usually dove gray), while white tie, worn at
night, calls for a black hat.

Unless you happen to attend a lot of formal

events, or you need a top hat professionally (as
with some coach drivers), it’s probably not worth
investing in one.

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Chapter 4: What to Wear with a Classic Hat

It’s worth noting that not all outfits are suited to fine
felt hats.

If you happen across the phrase “fedora guy” or

“fedora wearer” on modern social media, it’s not a
compliment.

The implication is a sketchy guy who wears the

same ratty fedora with every outfit because he
thinks it makes him look classy.

Don’t be that guy.

Dress hats should be worn with dress outfits.

Suits are always safe. Blazers and nice slacks are

probably fine too.

Sports jackets can work, but keep them on the nicer

and less “thrift store” looking side of things. Wool
overcoats are fine.

Once you get into the realm of blue jeans, however,

even nice ones, or of practical working clothes like
barn coats and plaid hunting jackets, you need to
step your headgear down a notch as well. T-shirts
are right out.

Save the fine felt fedoras, homburgs, and porkpies

for when you’re dressed well.

Western hats, straw hats, and derbies have a little more flexibility, and can be worn with less dressy
outfits.

Trendy pieces like the brightly-colored triblys that were in fashion a few years back are more flexible,
and can be worn without classic menswear accompanying them, but of course the converse is also true:
you shouldn’t wear them with your good suits or overcoats.

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Caring for a Hat

Felt hats are sturdy, but the material requires
specific care and treatment.

You should always handle hats by the brim, not the

crown.

Use your hands to shape the crown when you first

buy the hat, if you have to (or better still, have the
manufacturer shape it to your specifications), but
after that keep your hands away from the crown,
especially where it creases.

Dirt and oil from your hands can weaken the fabric,
and the creases are the points that will wear
through first.

When a felt hat gets wet, set it down flat on a towel

and let it air-dry naturally.

Heating a wet hat with a hair dryer, radiator, or

other heat source can warp its shape.

Your hat should have a sweatband on the inner

edge, and the name tells you what it’s for: when it
soaks through with sweat, take the hat off and turn
the sweatband inside out, so that it can air dry
without soaking into the felt.

Every few wears, give your hat a light brushing with a suit brush. That will get rid of loose dirt and other
gritty particles that can eat their way into the felt and wear it away.

If you get a dirty smudge or other stain, wipe very lightly with a damp cloth, or pat the stain with a gum
eraser to pull it up without damaging the felt.

For storage, a dry box with a frame for the hat to rest on is best.

If you’re not quite willing to shell out for an individual box for each of your hats, use a large wall hook, but
cut a slit in a tennis ball and slip it over the hook so that your hat isn’t hanging on a single point. Felt has

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“memory,” and if you leave it too long on anything

that applies pressure (like a small hook), it will bend
into that shape.

The best way to keep a hat in its proper shape is

simply to wear it!

If your hats are seeing a good, regular rotation of use,

they should do just fine.

If they ever need to lie idle for a while, switch

between hooks, boxes, or storage on flat shelves, so
that they’re never resting on the same part of the hat
for too long.

With proper care, a felt hat is an investment that

won’t just last for your lifetime — it’ll last for
someone else’s lifetime after you’re dead and gone.

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