Top Tips On Wearing Hats (For People Who Don’t!)

Joanna Zara Unique Hats

The sun has put in an appearance and Royal Ascot and Henley Regatta are on the horizon, which can only mean one thing – hat season is here again.

However, whilst the days for only wearing hats at official or celebratory occasions are over, hats are quite simply not for everyone.

Hats create excitement and transform outfits, adding visual drama and personality to a carefully curated fashion ensemble, as well as a great talking point. Who can forget the story of Princess Beatrice’s extraordinary Royal Wedding hat, that then went on to raise hundreds of thousands of dollars for charity at auction?

For me, however, hats instill an aversion borne of nothing else other than an inexplicable dislike of the way “I look” in a hat. On a more specific level I am never quite sure what to do with my hair. It’s not long enough to tie up and tucking it behind my ears feels wrong as that is not how I wear my hair normally – yet hat wearing requires some adaptation to carry it off successfully and I am always a bit jealous of those that do!

That’s not to say I don’t own a hat, I have two in fact – both panamas restricted to summer usage only, in a bid to protect my face and hair from the sun.   There is something quintessentially classic and stylish about the right one worn with a big pair of shades by the pool in the summer that can make even any “non-hat person” in the right environment feel they are rocking their inner Brigitte Bardot.

The fact is that there really is a hat for everyone but wearing a hat is a skill in styling and confidence and maybe that is what I am lacking to take my hat-wearing to a new level.

To help people like me debunk any misgivings about wearing a hat, I asked Joanna of Joanna Zara Millinery to share her insights and top tips gained from more than a decade of designing and making bespoke hats when we met in London at the Handmade In Britain Fair.  Here is what Joanna has to say.

Joanna Zara wearing one of her own creations, a panama with customised trim.

Guest Post – Joanna Zara Millinery

Why have some people fallen out of love with hats?

Hats are no longer a default element of our daily dress. Gone are the days (thank goodness) when it was deemed improper for a woman to leave the house without hat and gloves. But because of this, we no longer have access to a decent choice of hats in a wide enough range of styles, colours and sizes; indeed, many women I speak to describe their heads as “too small” or “too large” for a hat.

What they are really experiencing is that hats on the high street are usually only available in one size. Imagine visiting your favourite fashion retailer only to find out that the clothes are available in just one size – you would be discouraged to say the least. Sadly, those who seek clothing sizes outside the so-called “norms” of 8 to 14 will know this feeling all too well already.

The lack of choice on the high street means that many of us no longer have the opportunity to try on enough different hats to know what really suits us. Hat wearing becomes viewed as something confined only to special occasions. As a consequence, this can strike panic in the heart of a woman who is suddenly confronted with the need to wear one to a wedding or the races and has no idea where to look or what to try.

I haven’t always been a hat wearer myself and am not a naturally extrovert person thus I can empathise if you feel that you would be making too much of a “statement” by wearing one. However, I would encourage you to try – after all, there aren’t many fashion purchases that continue to fit whatever your current dress size, and you might be surprised by how good it makes you feel.

Hats by Joanna Zara

Getting back in to hat wearing

So, if you are considering dipping a toe in the water, here are my top tips for bringing hats in to your life:

  • If the hat fits…

Above all make sure you find a hat that is comfortable and fits well. It should become an extension of your daily outfit, not a nuisance to be avoided at the first sign of a windy day. If size is an issue, seek out specialist online hat shops. Many hat wholesalers often have retail sites too – prices are reasonable and there will often be a range of sizes.

  • Work it

Styles derived from workwear (such as the sailor cap) are a good starting point. There is something about these that make the wearer feel more “grounded” and less frivolous – perhaps because they signal a utilitarian purpose rather than one of pure adornment.

Joanna Zara Modern Beacon Sailor

  • Pick a classic

Men’s styles such as trilbies* are also a good bet. We are used to seeing them around and their shape hasn’t changed over the years, so they have the status of a classic. Wearing one might well mark you out as stylish, but never a “fashion victim”.

*the trilby was originally made popular by a woman: the actress who played Trilby O’Farrell in the stage adaptation of George du Maurier’s novel “Trilby” wore a hat of this shape. The immense popularity of the play meant that anything connected with it became enormously popular too, and this style has been called a “trilby” ever since.

  • Small beginnings

Hats with smaller “profiles” can be less intimidating for the novice hat wearer – cloches, caps, trilbies and berets all fall in this category. But do bear in mind that, above all, the hat should suit you. There are many guides online about finding the right hat to suit your face shape but here are few tips to get you started:

First, remember to view the shape of the top part of the hat (the “crown”) “as a whole” with  the part of your face that is still visible. For example, if you have a long thin face, a tall narrow crown or a really wide one will exaggerate your face shape, so look for a low crown that is about the same width as your face. A slanted brim will also draw the eye across rather than upwards so this will also help. In the same way, if you have a heart shaped face (where your forehead is definitely the widest part of your face which gradually narrows down to your chin) then a hat or cap with a wide crown will exaggerate this, so is best avoided.

Secondly the overall “geometry” of the hat should be the opposite to that of your face.  For example if you are square jawed, then seek out round shapes to complement the straight lines. Round face? As you might guess, hats with angles and straight lines look great on you.

  • Protect your skin in style

If you need to protect your skin from the sun, please wear a hat! I burn easily myself and wish I had realised earlier on how much difference it makes in terms of mitigating sun damage to the skin. I feel very strongly about this, so if you need some personalised advice on what will work and what might suit you, then do please get in touch. I won’t try to sell you a hat (unless you want me too!), but I will gladly advise you on what offers the best protection, what suits your face shape, and where to find something that will suit your budget.

  • Enjoy yourself!

Finally have fun and enjoy it!  Think about your own reaction if you were to see someone walk past you in the street wearing a hat. You wouldn’t ask yourself “Who does she think she is, swanning around in that hat?”  You are far more likely to think “She looks great, should I know who she is?”

I love this picture of the lovely Jacynth Bassett, founder of who introduced Jo and I a few years ago having fun in one of my creations over the recent hot Easter weekend.

It makes good business sense for me to wear my own creations and I have found they are a great confidence booster – it is almost as if I have to live up to the confident image I am projecting.

So if you have hesitated before, I urge you to give it a go and welcome hats in to your life.  After all a whole new world of accessories awaits you!

Editor’s Note:

Joanna is an award winning milliner and has been making hats for over ten years. She developed her skills attending courses at London College of Fashion and through master classes with internationally renowned milliners such as Bridget Bailey.

In 2015 Joanna won an international competition to design a ladies’ ready to wear hat for royal warrant holders Lock & Co.

Clients visit Joanna in her Sussex based studio. She works closely with them to create hats and headpieces that fit perfectly, flatter, and above all reflect their unique personal style. She says ” I know we’ve got it right when they smile, relax – and don’t want to take the hat off!”

So if you’re looking for a bespoke hat do get in touch with Joanna. She really put me at my ease and her hats are truly unique.

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  1. May 19, 2019 / 8:15 pm

    Some great tips here. I do not really wear hats much but I must have a look out for one this Summer 🙂 #PoCoLo

    • Jo
      May 25, 2019 / 8:03 pm

      Me neither which is why I was so pleased to meet Joanna and to benefit from her pearls of wisdom. It really is all about embracing something new sometimes and taking that first step but it can be hard to know where to start. Glad you found the post useful. x

  2. May 17, 2019 / 5:04 pm

    I love wearing hats and need no excuse for a wedding at all, sometimes I feel a little conscious just wearing a hat for the sake of it though, but will stick a base ball cap on at anytime #pocolo

    • Jo
      May 25, 2019 / 8:07 pm

      Oh Suzanne good for you I admire those that have the confidence to carry off a hat whatever the occasion or not – after all why wait for a special moment? You are no doubt one of those ladies Joanne refers to in her piece – that we all look at and think – “Who is that? Do I know her?” Hope all is well with you. X

  3. May 9, 2019 / 9:15 am

    Hi Jo, I love a hat! Not so much of a formal hat but a nice woolly winter warmer.

    My own personal challenge is, the summer ‘sun’ hat. I always wear a hat on the beach to stop my face getting even more wrinkled or red but mainly as I’ve exposed myself to sunstroke a couple of times, so definitely a prevention tactic. I’ve done the baseball cap, the straw hat (often bought abroad as they tend to be more stylish!!) but I’ve yet to find the perfect one.

    Interested to see if you or any of your readers have any suggestions (nothing too big/floppy)? Thanks for the hat therapy!

    • Jo
      May 9, 2019 / 3:54 pm

      Yes Jo I know what you mean it is the back of the neck that is the most susceptible in the sun isn’t it and also there is something about a baseball hat in midlife that just feels a bit wrong! Like you I have purchased those straw hats abroad although I did invest in one at Chelsea Flower Show a couple of years ago which is looking a bit tired now. I am treating myself to one of Joanna’s glorious panamas – I think custom made is the way forward. Contact Joanna – she is more than happy to answer any questions and offer advice. x

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