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The Key To Wearing A Hat In The Winter And Beyond

From funky fedoras to fluffy fake fur, hats are certainly making a statement this season. Whilst we are all more than happy to pull on a beanie when the temperature plummets, for some reason, it often feels like a step too far to sport a hat as an accessory rather than a necessity.

The thing with hats is that they immediately define a look, and possibly even overtake it. So much so that a person's choice of headgear can quickly become their 'brand'. Take a look at characters from history (real or fictional) for example:

  • Charlie Chaplin - It is impossible to picture Charlie Chaplin without his black bowler hat, with even his silhouette being instantly recognizable.
  • Jackie Kennedy - The pillbox hat was the signature style of the former First Lady. In keeping with her clean lined style, these iconic hats were designed for her by Oleg Cassini.
  • Indiana Jones - Indiana Jones' wide-brimmed fedora has become as iconic as Harrison Ford's portrayal of the character.
  • Sherlock Homes - Until his most modern incarnation, Sherlock Holmes was barely recognisable without his plaid deerstalker.
  • Alex DeLarge - DeLarge and his troop of 'droogies' marked themselves out with their sharp derbies in Stanley Kubrick's A Clockwork Orange.
  • Abraham Lincoln - Only the extremely brave or incredibly thick-skinned could follow in the footsteps of Lincoln and carry off the distinctive stovepipe hat.
  • John Wayne - The infamous cowboy hat christened 'The Hat that won the West' can only be John Wayne's iconic Stetson.
  • Michael Jackson - Jackson's fedora was as sharp and natty as the smooth criminal himself, giving the hat a totally different twist to Harrison Ford's casual look.

With so many stereotypical associations to different types of hats, a lot of styles have been permanently retired to the dressing-up-box, reserved only for Halloween and novelty costumes. On the catwalk, however, hats are far from novelty pieces, as recent collections confirm.

Raising the Glamour Stakes

As fashion has now become so eclectic there is literally not a style of hat that cannot be seen worn by both sexes, apart from perhaps the stove pipe, but with the current onslaught of bearded and mustachioed hipsters, who knows?! Critics, designers and wholesale clothing manufacturers have been religiously championing the return of pure, unadulterated, high-octane glamour to both the catwalk and the high street.

Continental fashion houses have quickly been followed by wholesale clothing manufacturers and ladies-wear wholesalers, eager to build on the resurgence of glamour, with accessories, namely headwear, taking center stage in many collections.

Millinery designed traditionally for men, such as the fedora, bowler and deerstalker are increasingly becoming unisex styles, whereas headwear for women had previously been reserved for Mother of the Bride's and race-goers. Lady Gaga made a great attempt at giving women's dress hats a quirky new lease of life, although her take on the accessory is possibly a step too far for every day wear. Kate Middleton, however, has brought hats into the realm of glamour.

The Hot Hat Hit List

So, what's the best way to carry off a hat without making a statement for all the wrong reasons? Here we take a look at the season's top styles and how best to wear them:


The fedora is a cool classic that can be dressed up or down, and is easily customised to complement your look. Studs and feathers are good for adding a quirky twist, and don't be afraid to try a bit of colour. Alternatively, go for the understated look and top it off, quite literally with a simple black fedora.


This winter, hats of all styles are hitting the high street in a whole rainbow of colours. A bright pop of colour will brighten up any outfit, make an impact by matching your hat to your lipstick or go for the kill and rock the head to toe monochrome look.


A big fluffy, (fake) fur hat will add a snuggly twist to any look, especially if teamed with a chunky knit or leather jacket. Pompoms, pockets and oversized trims are big this season, especially when glammed up with a slick of deep berry coloured lipstick. Clean, crisp white fur is great for giving a 'posh' edge to an outfit, whereas a close fitting black fur hat is the perfect way to inject a bit of punk rock into your winter wardrobe.


The beanie continues to be a fashion staple, and this season the style has moved on from classic black (although, there will always be room in every wardrobe for a black beanie). This winter we are looking at deep berry hues and customization in terms of different fabrics (waffle is hot right now), pompoms, lettering and even Goth inspired quirky net veils.


A sure fire way to up the glamour stakes is to take the military route. Berets, when teamed with a belted coat and leather gloves create a very striking look. On the other end of the scale, sport an 'army-esque' cap, complete with military style pins and medals.


One way of wearing a hat without taking yourself too seriously is to go for the animal inspired look with a structured hat complete with animal ears molded into the crown. Cats and rabbits are hot right now, and they give a fun, ironic twist to an otherwise smart outfit.


Caps keep reinventing themselves on the high street, with glam adornments setting them apart from traditional sportswear. Gold bands, leather embellishments and even pom-poms take the original baseball cap to a whole new level.

How to Wear a Hat (opposed to the hat wearing you).

The key to carrying off a hat is to ensure that it is balanced within your outfit. If your hat is glam, ensure that your make-up is equally considered. Unfortunately a distinctive hat will not detract from an unmade-up face, it will only highlight it. However, if your make-up complements your hat, you can get away with making less of an effort with the rest of your outfit.

At the other end of the scale, when it comes to everyday chill out wear, the beanie is the most forgiving of all hats. As it is brimless the edge of the hat offers a clean line, which, when pulled back can make the most of the 'day off' fresh faced unmade-up look. However, if you want to go one step further for full on incognito, it can be pulled right down over the brows and, hey presto, you are invisible! And, after all, what use is a hat to anyone if you cannot use it to hide a dreaded bad hair day?

Raise Your Hat to Fashion week

If you feel brave enough to go a step further in the hat stakes, the looks rocking the London, New York and Milan Fashion weeks were seriously hitting new heights. As heel heights plummeted, hats got taller and wider. And whilst these millinery creations are undoubtedly striking in the confines of the catwalk, mere civilians may run the risk of channeling the cone-head look by taking these styles outside! However, as with all trends, they have to start somewhere, and once the high street has got hold of this look, there will no doubt be a wearable version hitting the shops soon, so prepare to see head wear get lofty!

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