How to Wear a Hat with Confidence

How to wear a hat without feeling a bit foolish? If you’re considering the purchase of some smart headgear, but your sole prior hat experience has been confined to truckers and beanies, then contemplating a move up to a panama or fedora may leave one feeling slightly intimidated. Do you have what it takes to pull off an elegant hat without looking – and feeling – a tiny bit ridiculous?

Fear not! In this guide, we’ll consider how to wear a hat with confidence, identify the most common associated insecurities, and suggest a few simple ways by which they might be overcome.

How to Wear a Hat Without Feeling Self-Conscious?

Many people who are unsure of how to wear a hat with comfort share the same handful of doubts. That being the case, let’s examine a few of the most common hat-related insecurities and see what can be done.

Does a Hat Suit My Style?

Just because you didn’t wear an elegant felt or straw hat a year ago doesn’t mean that you
shouldn’t wear one today. One’s tastes in all things mature over time. Generally speaking, the more experience we have of something (such as making sartorial selections for ourselves), the better we get at it. It’s perfectly normal that you may venture into unfamiliar territory and experience uncertainty as to whether a particular look is really “you.” Just bear in mind that “you” in this context is a moving target and will very likely continue to change over the course of your lifetime. Growing as a person – with ever-evolving tastes in all things – is simply a part of the human experience.

Think of it this way: if you’ve arrived at the point where you’re asking how to wear a hat
with comfort, then you’re obviously interested in wearing a hat and, if you’ve reached this point but are still unsure whether a hat will fit with your personal style, then perhaps the issue isn’t the hat, but your style. That is, all of the other items with which you plan to accompany it. In short, don’t rule out the possibility that you might need to alter some of
your other dressing habits to suit. It’s a completely normal concern. For example, if you’ve spent most of your life in sportswear and sneakers, but have recently become fixated with the idea of owning a stylish panama hat, this might be a sign that you’re also ready to change some other areas of your look.

The art of dressing well is about making everything you wear your own. If some of the items which you wear every day no longer reflect the appearance you desire to project, then change them. If you feel as though smart headgear and casual sneakers make for an odd combination, then rather than perhaps it’s time to ditch the sneakers (or at consign them to another outfit for another day).

Of course, there’s no reason why a panama hat shouldn’t be worn with sneakers – it all
depends on which sneakers and what other items you’ll be wearing to complete the look. So, please don’t feel as though you need to radically alter your entire look overnight. The key to wearing a hat with confidence is feeling good in it – and that means wearing it with
whichever other items leave you feeling most comfortable.

Is This the Right Hat for My Face and Body Type?

Choosing a hat that will make you look and feel great isn’t only about personal style, it’s also about your physical attributes. You may love the look of a particular hat – and it may mesh precisely with your style of dress – but if it’s not the right shape for your face and body, it’s probably never going to look good on you. Remember: if it doesn’t look good, it
won’t feel good, either.

So, how does one choose a hat that’s right for one’s face? Nowadays, the simplest method is to google “pick the right hat for my face” or some other similar phrase. You’ll find countless guides claiming to provide the definitive answer to this most perplexing of questions. Just how useful any of them really are, though, will depend on how precisely your features coincide with the half a dozen or so physical “types” typically identified by such guides.

Do you have a round, heart-shaped, oval, long, or diamond-shaped face? Having identified your basic facial structure, you should, theoretically, be able to quickly establish which hat styles will best suit you and which to avoid. For example, someone with a long, thin face will generally be advised to wear a wide-brimmed model similar to our 3” Santa Fe panama hat. Tall crowns, however, will be an absolute no-no. Similarly, for a more flattering look, someone with a receding chin may be encouraged to go for a medium-brimmed hat such as the Havana Retro.

Santa Fe
Santa Fe

Havana Retro
Havana Retro

On the surface, this advice may seem quite reasonable. The problem, however, is that we
don’t all neatly fit into these simplified categories. What if one has a long face and a receding chin?

To be clear, such guidelines may be helpful as a starting point in learning how to wear a hat
which suits you, but they shouldn’t be taken as ironclad rules. Someone may have a long, thin face and yet look much better in a short-brimmed hat such as the Riff; it just depends on what kind of long, thin face we’re talking about.  The point is that making the call is an entirely subjective exercise and one best conducted to suit oneself.


What’s not in doubt, though, is that you will feel much more confident wearing a hat
knowing that it’s the right style for your face and body. So, yes, do plan to use these face-shape guides as a rough indicator of the most likely hat styles to try first, but understand that the only true predictor of whether a particular hat will suit you is the mirror.

Won’t I Appear to be Overdressed?

If you’re not accustomed to wearing a smart hat, the first few times that you venture out in your panama, fedora, or other stylish headgear you might feel as though you’re overdressed. This sensation is only likely to render you even more uncomfortable in your choice of hat. As we’ve already noted, the key to being confident in a hat is to feel utterly natural wearing it – almost as if it were a part of you.

Aside from simply getting accustomed to having the hat on your head (possibly by wearing
it around the house for a day or two before stepping out in public), one of the most
important things you can do to avoid the sensation of being overdressed is simply to make
certain that you’re wearing the right headgear for the occasion. Indeed, being overdressed
is an entirely relative concept and it all depends on the type of hat and the context.

For example, although our elegant felt fedoras and fine toquilla palm panama hats are
guaranteed to make a smart impression in virtually any social situation, there are certain
events where they would actually be considered as insufficiently elegant. That is, you would be underdressed if you were to show up so attired. This is only really true for white and black tie events; for all other formal and informal situations you’d be well-covered with the majority of our hat models.

Felt/Wool Hats - Brooklyn
Felt/Wool Hats – Brooklyn

Straw Hats - Portofino
Straw Hats – Portofino


However, the rules vary significantly for different styles of hat, so be sure to brush up on your hat etiquette rules prior to heading out. Obviously, if you were to show up to a
wedding or other formal event in a Yankees snapback or a floral bucket hat, you’d be
anything but overdressed (for more info about this topic, check out our guide to
choosing the right hat for the occasion). In practice, though, the kind of situations in
which you are most likely to appear (or at least feel) overdressed will be less-formal ones.
Here, it’s a question of judging whether your choice of headgear might risk being seen as a little over the top.

Even if it is though, the great thing about elegant hats like panamas is that they can
easily be dressed down by applying a couple of simple changes to the rest of your outfit –
without the need to ditch the hat. For example, it only takes a second to loosen a tie or
remove it altogether. Likewise, if you feel as though you’ve overdone it with a suit, the jacket can easily be removed and the shirtsleeves rolled up. For a really informal outfit, you
could just wear jeans, t-shirt, and leather boots. All will look great with a panama, as it’s
just a question of what you feel comfortable wearing in a particular context.

Will People Think that I’m a Poser?

In a similar vein, if you don’t often wear a hat or have only recently branched out into
wearing one, you might feel as though you’re being a touch pretentious when you don a classy bit of headgear like the Hollywood fedora. After all, aren’t fedoras and panamas solely for old-school actors such as Steve McQueen or Cary Grant – or for modern-day musicians and celebrities such as Pharrell Williams, Donald Glover, or Justin Timberlake?

How to Wear a Hat and Not Look Like a Poser?

Aside from simply taking care not to overdress for the occasion, avoiding looking like a
poser in large part comes down to carefully judging the situation. So, before heading out
in your new hat, consider where you’re going. What kind of event is it? Where does it
take place? Who will be there? Looking like a poser isn’t just about what you wear, though, but is equally about how you wear it, i.e. how you carry yourself. Someone who behaves in a highly self-conscious (or, worse still, self-important) manner, would probably look like a poser even if wearing nothing more glamorous than an old potato sack.

The fact is that the more comfortable you feel, the more relaxed you’ll be and, therefore, the less likely to carry yourself in an uptight or defensive manner – both of which attitudes are guaranteed to make you appear as arrogant or pretentious without regard to your intention. Feel good in your hat – and stay humble – and you’ll look good in it, too.

Final Thoughts

If anything is likely to make you look awkward in a hat, it’s feeling awkward in a hat. How
to wear a hat without looking – and feeling – like a self-important idiot? Well, if you’ve worked your way through the whole of this article, you now have a much better idea of how to wear a hat with complete confidence. In large part, it’s as simple as selecting a hat which fits your face, personality, and style. Remember, though, that it’s also about choosing the right hat for a given occasion.

Here at Ultrafino we offer a 30-day return period, so even if you’re still not 100% sure which is the right hat for you, there’s nothing to stop you from experimenting.



  1. Having never worn a hat, let alone a Panama ( I’ve always liked the look of one ), I instinctively wore it around the house for a few minutes a day for 2 or 3 days ( classic fedora in wheat with a cocoa colored band) just to get the feel and look of it. Then I put it on and ventured out to a casual, outdoor birthday dinner (mine) at a local restaurant with my wife and son. I wore it as though I had worn it for years and kept it on during dinner as there were two other hatted men and a woman present, and it was an early sunny evening. I received compliments from two men and a woman as well as our waiter. The men wanted to know where I had purchased it. Two referrals to Ultrafino !!

  2. I have many hats and several Ulrafinos. I love each and everyone especially my Ultrafino Panamas. Most every time I wear them I am complemented on the style and the look. I am asked where to get them constantly. Of course I refer them to the website.
    I sell Constructon equipment in the San Francisco Bay Area. We have cool winters that I use felt, fur felt hats, and great spring and summers for Panama hats. Hats have become my trademark. Hats need to make a comeback. Think about it start a new trend with Ultrafino. You won’t be sorry!

  3. Do you deliberate how to wear underwear? Probably not. So don’t do it with a hat either, but put the bloody thing on, and wear it! The more philosophy you put into the way you impress others, the more uncertain you will feel and the more foolish you will look. So be natural, be yourself, create YOUR OWN style, and remember: if you don’t like yourself, nobody else will.
    Dr. D.
    PS. I wear hats of all sorts at all times and do not split my hair over what to put on top of my head. I simply put the ruddy hat on and it covers the split hair rather well. Or so others tell me.

  4. I wear a Panama Hat every day of the week as long as the sun is strong in our area . These hats can go any where from weddings to farming and never fails me. It protect my face from the sun , that’s first and they are classy hats and I love them.

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