Best winter hats for women over 50. Nail your style.

Hats are popular right now so why not add this inexpensive and fun item to your wardrobe.

I’m going to look at how to style these hats when you are older and give you my best picks from UK and US retailers:

• Beanies
• Slouchy beanies and knitted hats
• Bucket hats
• Baker boy or newsboy caps
• Berets
• Cloche hats
• Fedoras

All hats take confidence to wear – as we are not living at a time when everyone wears a hat.  Today a hat means you dare to be a bit different – so you need self-assurance to wear one and feel good.

But choosing the right one is often difficult.  Here are my tips.

Decide if you want a casual or a stylish hat

Casual hats are easiest to wear and can usually be stored without needing special protection or a box.  They can usually be kept in your pocket or bag until needed.

Stylish hats are often more structured and need a box for summer storage.  They have to be styled in the mirror before you leave home so you can’t easily pull them on and off throughout the day.

Next, decide if you like a classic look or a more unique look

Classic hats include the usual basic colors such as navy and black and often look best when toning with a coat or jacket.

Unique styles draw attention to your hat.  They include vintage, artsy and chic looks.  Or any hat in a bright color that contrasts with your outfit will look unique.

How to wear a beanie

The beanie is the number one casual hat today.  It used to be just for young guys, then older balding men joined the trend and today women of all ages love wearing a beanie.

A beanie is a close-fitting simple knitted hat with or without a cuff, with or without a pom-pom. It is a warm winter hat.

It can be worn with a coat or jacket but also looks good without either, just so long as you’re in a casual outfit.

Avoid acrylic knits as your hair will fly out at odd angles when you take the hat off as static will have built up.  And the more often you put it on and pull it off, the more static your hair will become.

Go for 100% wool.  Or if you want to add a dash of luxury decide on cashmere.

My daughter gave me a cashmere beanie with a pom-pom a couple or so years back and I love wearing it because it brings with it memories of her.  However – trust me on this – a pom-pom is not an easy look to carry off when you’re older. 

First you’ll need to decide whether to wear the pom-pom right on the top of your head – which is fun.  However, you can look a bit like a cake with a cherry on top. So you might want to pull the pom-pom a bit towards the back, or the side-back, which is more slouchy and ‘safer’.

With the cuff you’ll need to practise where to position it.  I tend to wear the cuff just above my eyes as this emphasises them – a bit like darkening your eyebrows.  But that can be a bit itchy and it certainly flattens my fringe at the front.

Mess about with the beanie in the mirror once you’re in your outfit.  The position of the cuff makes a difference to your face and neck area and can lengthen a round face if placed on the hair-line  or shorten a long face if placed on the brow line.  If you are showing your neck you can wear the beanie a bit lower on your forehead but if you are wearing a scarf then you might look better with the hat pushed a bit higher up.

How to wear a slouchy beanie or other unstructured knitted hat

This is a super-casual winter hat.  It’s stretchy and usually reasonably fine knit so you can pull it around on your head until you get a look you like.  I find the slouchy beanie easier to style than the standard beanie. 

You can turn it back into a cuff over your forehead so it looks like a typical beanie but I like to use the extra length to pull some of the fullness to the back or the side to give some movement to the hat.  Exactly how it looks best will depend on your face shape and what else you are wearing.

A roll neck and jeans will call for an unstructured hat such as the slouchy beanie.

But a coat with a structured collar and lapels will demand a more classic look –a hat that can be casual or stylish:

How to wear a bucket hat

It’s quite a fun style – after all it’s a bucket.  But it’s more structured than a beanie and probably won’t mess up your hairstyle quite as much.

I like the bucket hat for country outfits.  It is ideal in the rain as the brim all the way round keeps your hair and face dry. 

For me the bucket hat suggests long damp walks in the countryside.  It teams well with other country outerwear such as a Barbour waxed jacket or coat.  So I especially like tartan or tweed bucket hats.  Worn this way the bucket hat is casual.

But if you’re more dressy than casual you could wear a bucket hat in leather which is very on-trend right now. 

Alternatively you can give the bucket hat a more stylish edge by choosing one in a similar material or shade to your coat.  Then it becomes more of a city look with a slight retro influence.  A straight cut, narrow raincoat with the collar turned right up will look perfect with your bucket. 

How to wear a baker boy or newsboy cap

This is a vintage hat so it’s for you if you like a unique look. It recalls the swinging sixties for me although it harks back to a traditional cap of the early twentieth century.

The baker boy hat is halfway between a basket ball cap and a traditional flat cap. It has a peak but is not close-fitting on the crown. It has a raised or even puffed crown. 

I think it’s difficult to look good in a basketball cap over the age of 50 but if you like that look why not up your style with this newsboy hat.

This cap looks really good with pants and jeans.  It marries up with high roll neck sweaters which elongate the neck.  This is needed because the hat itself gives a rounder and larger look to the head. You could get the same effect by knotting a silk scarf around your neck so it looks like a tall collar.

Wear the baker boy cap in a texture or pattern that goes with your pants or jeans and you’ll look smartly stylish yet young and bold.

Wear the baker boy in a contrasting fabric or a bright color and you’ll look more casual and full of personality and fun.

You don’t need to be tall to carry off the baker boy or newsboy cap but you will look better if you are reasonably slim or wear a fitted top as the hat needs to be the puffiest element of your look. It’s the contrast between a slender body and an oversized hat that makes the look.

How to wear a classic beret for a French Chic look

The beret is having a massive come-back at the moment.  It is the perfect hat to roll up and pop in your shopper just in case. 

A beret can be made of wool – usually a boiled or felted wool because these fabrics help the beret to keep its iconic shape.  But today you can get leather berets, loose-knit berets and plaids which all look good.

The beret is the quickest way to give your outfit a French chic vibe.

French Chic is a classic look with a nod to the stylish-unique.  Think old  black-and-white spy thrillers or window-shopping on a stylish Parisian boulevard.

You’ll need to keep the beret relatively flat and angle it just so.  The flatter and the more tilted to one side you wear a beret, the more stylish it looks.

If you don’t want to look too much of a femme fatale, just place the beret snugly on your head, pull one side down a bit and tweak the other side to stand up a bit. Simple but effective and still tres chic.

You might want to pin the beret into place especially if you have straight shiny hair. 

Go all out for this classic French look if you want to turn heads.  You’ll want good accessories to complete your French chic outfit such as a silk scarf and a smart bag.

How to wear a beret for a boho artsy look

But the beret can be more artsy.  Pulled down to just above your eyes, especially if it’s in a bright color, this hat works well with big sweaters, patterned skirts or pants and flat shoes to give a Boho Chic style.  It’s fun and charming at the same time. 

If that’s your style personality a beret, or a selection of different color berets, could be a great addition to your wardrobe.

By the way, if you’re not sure which style personality you are, simply take the Style Quiz – see the top right of the side bar on this page.  The Quiz gives you an insight into looks that will work well with  your lifestyle and gives tips on how to build your wardrobe.  Knowing your style personality is key to buying the right clothes and wearing them in the right way.

How to wear a cloche hat and look feminine

The cloche is a sweet and feminine hat that keeps you warm in vintage style.  Wear it with a wool coat or a pretty dress.  Choose a cloche that picks out a color in your outfit or tones with it.  The decoration on the side of the hat will provide enough interest without adding the distraction of a bright color as well.

As the cloche hat hugs your head you’ll need to think about your hairstyle.  You can push all or most of your hair under the hat and make the most of its cloche (bell) shape to frame your face beautifully.  This will give you a pretty yet dressy look.

Or you can allow strands and curls of hair to escape and give a more casual look.  Most face shapes look good with a cloche but a round face is ideal.

How to wear a fedora and look stunning

If you’ve got poise and bags of confidence then the stylish fedora might be perfect for you.  This is a large felt hat that sits straight on the head. The brim casts a deep shadow over your face, especially your eyes and adds a touch of mystery.  So it’s ideal for longer faces.

Short square types like me should avoid the fedora like the plague.

Wear the fedora over a structured jacket or coat.  As the style is simple you can have fun choosing an interesting color or play it classic with a brown or toning hat.  Either way you want to make the most of your neck so forget about scarves and make the smart neckline of your top a focus.

There’s a sub-genre of fedora-wearing that teams it with a masculine jacket or suit.  This is superbly classy and if you have the oomph required you will have the guys transfixed.

Remember hats are one of those accessories that pop in and out of fashion over time.  So don’t spend too much money on a hat unless it’s for a special occasion.  But you’ll be able to wear a hat bought this year for a decade, off and on,  so cost per wear can be very small compared with the style value it adds to an outfit.

Most of the hats in this article are reduced in price at the time of writing in mid February 2021.

If you like posts like this one then why not read this one next: The Best Winter Coats for Women over 50 in 2020-2021