Hats on Men and Caps on Pipes

Steve Morrisette
My friend and colleague Brian Levine,
host of The Pipes Magazine Radio Show, recently suggested I write a column about choosing a hat type or style that works for a man’s face. Brian pointed out that he definitely had a face for radio and as I agree it seems his best choice would be a full-face balaclava that matches his sport coat or suit.

Putting collegial joshing aside, he did have a sincere and timely suggestion. Fall weather will be upon us soon and as it cools down this may well be the first time out for men thinking of experimenting with a new style of headgear.

A New Look

If you are a ball cap guy, or if beanies are your go to lid, perhaps this fall will be a good time to try a hat with a brim that goes all the way around the hat. A fedora, bowler, pork pie, Homburg or trilby. A hat hat – headgear of a gentleman. A man’s hat.

I wholeheartedly advocate and encourage the wearing of a nice brim.

It isn’t necessary to spend a lot on a hat to look well. In fact, if you are new to wearing a fully brimmed hat, I would caution you to avoid overspending.

Were you a novice fly fisherman, it wouldn’t be wise to commission a custom fly rod before you have enough experiences in streams to know what will suit you. Likewise, also with hats.

Making the Choice

Just as with choosing the right load for bird hunting, or the right shaped board for a particular wave, there are several factors to consider when choosing your hat. It’s not string theory level brain work, but it is best to give some attention to the elements involved to get you under a topper that enhances your appearance.

Stacks of Hats

Most men that are "hat guys" have quite a few hats. These collections generally fall into two roughly loose categories.

The first is a collection of several unsuccessful acquisitions and one or two "keepers". This is unfortunately fairly common.

The second is often a smaller collection of hats that all see good use depending on the outfit and the weather. This is what we are aiming for.

Some Guidelines

I doubt it is possible to avoid the occasional disappointment with a hat purchase, but I shall try to fore arm you with some well earned knowledge acquired over many years of hat wearing.

The first major consideration is the shape of your face. Since most men have never truly tried to classify the shape of their face and many are unaware that there are more than two – round and square – we have here a face shape chart with several shapes.

Few of us fall precisely into one category, but each of us will have a mug that is more like one than all the others. You will want to do your own interpretation.

So first, decide on your face shape. It’s OK to ask  your wife, girlfriend, sister or mother. Perhaps not your hunting pals – unless they are sartorially enlightened.

With that done we have these suggestions for each type. Please keep in mind that there is only one rule with hats, or anything else you decide to wear; you must look well, or good, or handsome. However you term it, the point is enhancement of how you look and feel.

Some Suggestions for Face Types (from: theartofmanliness.com)

Short, Full Face
A round face tends to look short, so you want a hat that will give you a little height.

Crown: Medium height and size

Taper: Slight

Hat Band: Narrow band of a contrasting color will add height

Brim: Moderate width.

Tilt: Back from face; tilting it over your face will make the face appear shorter.

Recommended hat: Fedora, Gambler, Panama

Long, Thin Face
Look for a hat that shortens the appearance of your face.

Crown: Shorter height. Avoid crowns that are square, full, or too high.

Taper: Moderate

Hat Band: Wide (will make you face shorter) with a contrasting color to break up your vertical lines

Brim: Moderately wide, snapped from ear to ear

Tilt: To the side with a slight back tilt

Recommended hat: Fedora, Homburg, Derby, Pork Pie

Triangular, Diamond shaped Face
This face is wider on the top half and tapers to a more narrow chin line, or may have a diamond like shape. You want a hat that will balance the top and bottom out.

Crown: Medium to short height, pinched toward the front. Avoid crowns that are full or too high.

Taper: Moderate taper

Hat Band: Medium to narrow, in a color similar to the color of the hat.

Brim: Medium width, rolled at back and sides, flat in front

Tilt: To the side, and not too far back on the head or you’ll show too much of your wide forehead

Recommended hat: Fedora, Homburg, Pork Pie

Square Face
Pick a hat that will add some curvature to your face and make it appear less boxy.

Crown: Medium height, full and round

Taper: Minimal to non-existent

Brim: Wide width, fully snapped or turned up at the rear

Tilt: A side tilt will break up your square face lines. Don’t push it too far back on your head.

Recommended Hat: Homburg, Bowler, Fedora

How Do I Look?

Now that you have your face shape and some hat suggestions, go and try on some lids.

Test these suggestions out for yourself. Compare a hat of the suggested type with one that is not recommended and note the difference in the effect.

This can help sharpen your eye and build confidence in your choice making process.

Try various crown heights, brim widths and note the effect a narrow or wide band produces.

Smart Shopping

This is my favorite method to aid my decision making for all garments: make a cell phone video or take some "selfies". Your smart phone is an invaluable tool in shopping for new wardrobe additions. Mirrors are OK, but relative stone axes compared to the digital assistant most of us carry religiously. Sometimes I will video myself in two or three choices and review them later in private- away from the shop. This is how I decide if I really wish to spend that much on a hat, shirt, sport coat, etc.

This may seem like a lot of effort, but if you really want to look your best – and you aren’t gifted with Tom Ford’s eye – then a little time well spent can go miles toward bringing home "keepers" and not amassing a collection of disappointments.


A quick word about the subtleties. Here we have the same guy, the same shirt and two different hats and two different hair styles. Note the differences in the hat/hair combinations.

I throw this in just to make a point that there are many factors that go into wearing garments that suit you.

Who’s the guy in the hat?

Hats these days are still uncommon, at least proper brimmed hats are. Therefore, they tend to attract attention. How much and what kind of attention will be determined by the choices you make.

By incorporating considerations of style, color, shape and your personality, you can do your best to attract the quality of attention you want. Your wardrobe choices make a statement. This is particularly true of a hat.

Michael Corleone in " The Godfather" wore a sober, conservative, Homburg to project a solemn, serious, and no nonsense image – that of a solid citizen.

Samuel L. Jackson’s Kangol caps present a sporty and casual air. Turn it around front to back and he becomes a bad ass.

Humphrey Bogart in a fedora comes off confident, well dressed and a serious guy, not to be toyed with.

Harrison Ford in the Indiana Jones fedora gives a sense of carefree disregard for convention and projects the sense of an adventurous guy – a risk taker.

John Steed in "the Avengers" puts a rakish tilt on his bowler and becomes a mischievous, yet elegant lady killer.

Put the same bowler on, all squared up, and it can give an air of the gravitas of an important diplomat.

Robert De Niro as Al Capone in a broad brimmed, flashy and raked fedora shows stylish sophistication as well as a confident menace.

And… Frank Sinatra, in a Milan straw pork pie: Cool, stylish and the personification of hip sexiness.

You want to be comfortable in your clothes, especially in a hat. Wear the hat, don’t allow that hat to wear you. Be Bogart, Jackson, or Sinatra, but above all, be yourself.

Pipes with Caps

Most pipe smokers at one time or another have either tried a wind cap or owned a pipe with an integral cap. Now that Fall will be here soon with the dry grass and fallen leaves, a wind cap may be just the ticket to prevent the odd forest fire or hole in your sweater. They can be useful and handy, those caps. Here are some examples.

The removable type are great for a flat topped pipe with a normal-ish bowl. You’ll not find one for your blowfish or oval bored opera pipe.

That’s Hot

Smoking with a covered bowl generally requires some extra attention to moderating your technique. Sipping a bit more and drawing lighter helps keep the tobacco from burning too hot. And speaking of hot, that cap or top will likely get right toasty so be aware when removing it right after smoking, shoving the pipe in your pocket or during a relight. Don’t ask how I know this.

A capped Tyrolean type pipe can be a fun addition to a collection and a great conversation starter. Nice examples can be had as estates for reasonable prices.

Here is my recent $5 find by way of Premal Cheda at Smokers Haven:

A little Wright’s Silver polish and it became a lovely little whimsical beauty. Smokes pretty well too.

the Gentleman Smoker’s Tip

Hats in the rain

A good beaver felt hat is quite happy in the rain. Beavers live in the water – right? I’ve worn beaver felt fedoras in very heavy downpours – once while fixing a tire- and my trusty lid suffered no ill effects at all. And this was a nice hat too, not a beater.

It kept my head dry and warm in a nasty storm. When I got home I just placed the hat upside down on a clean towel on a table and let it air dry completely. (never apply heat)

It didn’t even need to be re-blocked. The shape held up perfectly. Band also. A well made hat with a good percentage of beaver in the felt will laugh at rain and snow. I would avoid much moisture with a wool hat. Much rain at all and you often have a soggy, shapeless mess.

Cheers to all,
Steve Morrisette
the Gentleman Smoker


Steve Morrisette is an artisan pipe maker, relentlessly snappy dresser, and self-confessed Virginia gentleman. He makes artisan pipes for discerning collectors, and scours the internet and shops of all types seeking information and fine garments, hats, watches, shoes, and jewelry – anything related to the gentleman’s lifestyle. Steve also spent several decades as a working drummer and photographer/photojournalist. You can find his pipes at www.smpipes.com, and catch his style photos and latest pipes on Facebook and Instagram.


Drucquers Banner

More Pipes and Tobaccos Articles

24 Responses

  • I wear baseball caps or flat caps. Personally, I think it looks far too pretentious to wear any of the above hats if you’re under the age of 50 nowadays. I love tweed jackets, odd vests, brogue shoes, trouser braces … but I don’t think I could ever wear a full brim hat. I would be willing to try, but that’d have to be an exceptionally brave day for me to go out with one on my head.
    The pipe garners enough looks and I have never really been concerned with it, but something about these old hats says “I am trying far too hard” if anyone without some grey or white hair were to wear one nowadays.

  • I’ve worn fedoras for over 25 years now. Until my retirement two years ago I also wore suits. I’m finding that, now that I’m out of suits, an 8/4 cap sometimes fits the look better. But I never leave home without a hat of some kind.
    I don’t have any cap covered pipes but I do have a couple that have caps that are really just trim around the top. A nice complementary wood cap has a look I personally enjoy, just like wood inserts on stems or shaft.

  • Steve, wow what an impressive article you are giving us here! It comes very handy for me as I am considering more and more to purchase a gentleman”s hat in the near future. Your infos will help me make the right choice.

  • So would the guidelines be gender neutral? Being that, I have a top hat that I wore with a tux to my school formal (Kinda like the Aussie prom) and a fedora that I wear almost all the time.
    Now you’re planting the seeds of hat acquisition syndrome for me…

  • Dear Commander McBragg,
    Sir! ( coming to attention )
    Surely a commander is accustomed to wearing his regulation headgear and I am wont to believe that attaining such rank
    required the ability to, …er, command respect – yes?
    OK. I am aware that it is particularly challenging to overcome one’s self-consciousness the first few times out wearing a fedora.
    Especially if you haven’t reached an age or appearance of solid maturity that is all too often associated with the grey you mentioned.
    Certainly this is all to be chalked up to your attitude, and how you allow it to be swayed by what you perceived from others.
    It strikes me as curious that you draw the line at a fedora style hat while fully embracing a much more ( to me ) anachronistic
    style – brogues. And vests and tweeds are fine too? I say: “in of a penny, in for a pound”. ( since vests, tweeds and brogues are English historically, this old saying seems apropos )
    Let’s imagine that young men in fedoras are as common as young men sporting ink. Would you be self-conscious then?
    Tattoos are very recent to the broader public and celebrated – with TV shows , no less. ( Now THERE is a recommendation! )
    If you WISH to wear a fedora, then do so. The public be damned. Even at my age ( ancient to be sure ), I was razzed when, a few years back, well actually a decade ago, I began to wear fedoras. I worked them in with my Kangols, summer straws and the occasional discreet ball cap. Let me tell you, ten years ago I really was singular in a crowd.
    I claim absolutely NO great courage or self assuredness, I was just stubborn, loved the way men look(ed) in fedoras, and
    really hated the notion of letting other’s comments and looks cow me. I was defiant, mostly – not brave.
    I have to admit that I have always felt that while individual people are amazing, gathered into large groups they tend to become morons.
    So, and finally, more helpful I hope are these two bits:
    1). Please check out this thread on the Fedora Lounge – an interesting and valuable resource – which is directly to your point:
    2). Choosing a fedora that truly fits your face and personality makes a world of difference. If you have a very tall crown and
    very wide brim, you’ll likely look quite out of place. Like the ultra wide tie and ballon legs trousers of the thirties, such hats
    were faddish even in those days. Like the guys in shorts and suit coats today. Some stuff is just wrong for most of us.
    I would say that if you wear an appropriately proportioned fedora, in a grey or nice rich brown, tweed vest, blue oxford shirt and a simple, attractive striped neck tie, you will find folks ( esp. women ) remarking on how well you look. If this ensemble is a bit too stiff, loosen the tie, unbutton the shirt neck and roll up the sleeves and just slightly push the hat back on your head.
    These adjustments make it all very casual. Take that same outfit and add a solid color sport jacket, button up and square away all the details and you’ll have a fine look for a more formal setting.
    Also, forget Depp, Pharrell Williams and Timberlake! Check out Matt Bomer on ” White collar” and James Spader
    on ” Black List “. These two have it right.
    Best of luck – Sir!
    S. M. the Gentleman Smoker

  • Mr. Morrisette,
    I wish I was a commander, though being prior service I do know a thing or two about wearing hats, at least of the sailor variety.
    I am not opposed to the wearing any of those style of hats you listed, I just personally cannot see myself (at 29) combining them with any of my other fall/winter attire. I’m not saying that it would look bad, but it is such an uncommon sight and a hat -especially one so uncommon in the present- sticks out quite a bit. Yes, the idea of what others may think does sway me because I would most likely think the same thing, unless it was well put together.
    I may be confusing the use of these hats inappropriately because the times I recall seeing them in public they are worn with incorrect clothing choices. I don’t think I’ve ever seen anyone step out looking like the guys from Mad Men. I may just be used to seeing poor pairings.

  • I love hats. For many years I wore more ballcaps than anything, but realized they have about as much style as the 5 year old wearing one beside me. I began a real journey to find hats that fit my face and a style I was comfortable with in my late 20’s. First came straw fedoras, leather Aussie hats(still great for inclimate weather) and have progressed to ivy caps and stingy brimmed hats. Since I started this years ago, I dont get much grief from friends, but I dont care. My only gripe is “hat hair” I love my hats but still have a nice hed of hair at 43. So, I really hate removing my hat indoors(except while eating). My wife is a big fan of my hats and ladies are ussually very honest about how it looks on you. So, if they like it. all the better.

  • What?! men don’t wear hats? Is this like that nasty rumor that there aren’t any places you can smoke your pipe in public any more? I rarely see a guy without a hat in the Alabama sun (unless its a silly baseball cap). Cowboy hats, straw hats, newsboy hats, planters hats, fedoras, bowlers, etc… I don’t leave the house without a hat. I take it off when I enter any building, and tip it to the ladies.
    Jeesh, you guys should all move down here and smoke anywhere you please… with your hats. ha ha!!
    I think ya’ll are just displaced Southerners at heart.

  • How timely! Just a few days ago, in a men’s shop, I put on a fedora to have a laugh with my wife. But to my surprise, her eyes lit up, face beaming, and said, “You look awesome in a “cowboy” hat. So then she had me trying on a few. The actual cowboy hats didn’t fare well against the Stetson fedora, which finally won out. “Get it!” she said, so I did. And… so then I come here, and it looks like we made a great choice. Thanks for the validation! (You must have been in the store listening to us, weren’t you!). Thanks, Steve.

  • “Brian pointed out that he definitely had a face for radio and as I agree it seems his best choice would be a full-face balaclava that matches his sport coat or suit.”–“and as I agree…”
    Really enjoy Steve’s articles…keep up the great work!

  • I’ve always loved hats, but own very few. In fact I only own one nice hat, a fedora that was my father handed down to me. Unfortunately he has a bigger head than myself and I cannot wear it.
    Cut me… I bleed black.

  • Anthony,
    Check this site out:
    I own a few of theirs and for entry level pricing is very good. Also ever hear of “hat sizers”? Felt or cotton strips with one sticky side to stick inside the hat,on the sweatband to decrese,or tighten a hat: http://www.villagehatshop.com/product/view-all/451139-6391/-hat-sizer.html
    I’ve used these in several of my hats,I have a small head and my hat size falls between a small and a medium. These work very well.
    Gabrieli Pipes

  • Dear 12pups,
    You and your wife have given another example of what I passionately advocate: using your own eyes!
    I’m sure you do look well in your Stetson. Judging how one looks and ” feeling ” how you look is paramount and
    when it is right, it becomes obvious. It just ” looks” right – balanced, harmonious and satisfying – almost relaxing and peaceful.
    Trust your gut, over your head – about your head! And everything else. Your gut cares not for the opinion of others.
    We each have an inner plumb bob for what works for us.
    To paraphrase ” The Most Interesting Man in the World” ; ” Stay balanced , my friend”.

  • Dear jessicac,
    Absolutely the guidelines are gender neutral! Fine style is about personal expression and a harmony.
    The harmony is best when it encompasses as many aspects as possible; visual balance, personality, color, texture, comfort – both emotional and physical and financial.
    It’s all about facilitating your communication of ” yourself ” to the world. Celebrating what makes you feel really good in yet another arena. Have fun, stimulate your self expression and, by example, encourage others to do the same.
    Example: I would never get full, technicolor sleeves of ink ( tattoos). It’s not me, BUT I really admire greatly those that go for it full bore and have the most amazing art work wrapping around their bodies. I am stimulated to further express myself in MY way.
    BTW- the fedora get’s it’s name from a female character in a 19th century ( I believe ) play. The character’s name was “fedora” and she wore a hat of the style we now call a fedora. Who’s going to name their next female child ” Fedora”? LOL
    Best to all and thanks for all this great discussion!

  • ONE LAST COMMENT ( today):
    Thanks to all that offered suggestions , comments and links.
    Here are two of my link suggestions:
    http://www.thefedoralounge.com – great source for many topics of interest, not just hats. Vintage clothe sources, a great classified section, wonderful and knowledgeable discussion of hats of all types, life style interests, etc. It is active and well run.
    The is is a man that can make a truly fine bespoke hat for a decent price: Art Fawcett-
    The best fitting hat I own came from Art.
    Thanks again to all.
    My hat’s off to you.

  • Great article!
    I have been a hat lover since I was a little boy.
    For everyday dress I am usually wearing a flat cap, 8 panel, or tweed walking hat.
    The fedoras, porkpies, and such only come out for special occasions.
    Straw or linen for me in the summer.
    Wool or tweed wool in the colder months (which is most of the time here in Minnesota :-P)

  • Ok fine, I finally bought the grown up hat I’ve had my eye on. This website is hell on my credit card.

  • Thanks to the genes of my mother, I have a great head of hair for a 53 year old, so most of the time I don’t wear one.
    I have a Greek fisherman’s hat, a Bailey Stetson roper 5x beaver, (both bought new) and a Stetson Mallory that was NIB at a goodwill for $2…kinda, Indiana Joenseish, but not really…green felt with a leather band.
    I sympathize with the younger guys been there….no matter what you do, some of your peers are going to perceive you a certain way, but screw em. In the final analysis, like pipe purchases, go with what speaks to you…or if it doesn’t…pass on it.
    I have been wearing Ray-Ban Wayfarers for years because they are a sturdy frame, look good and never really go out of style…As of a few years back, my daughter’s friends thought I was pretty hip.

  • I have always worn hats. Had an extensive collection at one time. I am now down to a few ‘functional’ types. My favorite is the Saxon Royal Stetson. This holds up in all the weather Oregon likes to toss at me.

  • I usually where a flat cap, but do enjoy wearing a fedora sometimes also. I’m trying to find a nice derby hat with a wider than normal brim.

  • I’m rekindling my adolescent love of hats – I had a wool flat cap that I wore throughout high school and into my early college years, at which point I switched to a wide-brimmed “Godfather” fedora and a (military surplus) trenchcoat. Got out of the habit when I sought gainful employment after college, and until recently, had only worn ball caps.
    With my interest in Steampunk, I’ve now acquired a customized topper, a gambler-style cowboy hat, a bowler, a fez, and black leather Glengarry to complement various outfits, and I’m in the market for a John Bull and a Panama hat to round out my collection.

  • Interesting article.
    I sport a beard and have for years.
    As for hats and caps, in the summer for formal attire I wear a straw fedora. In the fall and winter, it’s a fedora but of felt or different material.
    For less formal wear it will always be a baseball cap with different logos. One I wear quite often has my nickname “Old tom” with a pipe embroidered on it. I have it costumed made at hat shops.
    My wife likes both types that I wear.