Men's Fashion Hats Guide

SS10 is full of hat-worthy trends which is why I am going to turn you all into a hat-wearing cult bigger than the old-birds at Ascot! Hats, to the lesser fashion-literate, are an excuse not to be effed’ to do your hair. Booooo to you sir!

“A man should look as if he bought his clothes with intelligence, put them on with care, then forgot about them.” - Hardy Amies

Now that I have shamed you into my hat-wearing society it is time to cover the basics of ‘el arte de uso de sombrero’. – Just because I used a crappy translator which somehow conjured up the word sombrero, if I find any of you wearing one of those Mexican fancies you will be punishable by my hat-wearing court!

Literally translated it means ‘the art of hat wearing’. As with layering, texturing, styling and coordinating; it is what it is and what it is is an art… wait how many is's was that?

You cannot just throw on a trilby and expect the emanate Pete Doherty, nor can you slouch a beanie to style steal Beckham. In fact, you are more likely to ooze Del Boy’s flat cap unless you put the effort into your hat ensemble!

In this article I am going to be covering the basic premise of 3 key hats, style shrink you into wearing them right and welcome you into the exclusive club of modern metrosexuality with a newly (mild and healthy) fetish for hat's – and wearing them right!

The Flat Cap/ Baker Boy

It is in general agreement that most of lines in modern menswear are designed to enhance the height of the wearer. There is no other certain obvious aid to this than a hat. The flat cap or baker boy style draws from the lean lines of a high fastening jacket or high-collared shirt that leads upwards to the head.

To understand this, you need to understand how your styling affects your lines. Well fitting trousers or skinny jeans (i.e. lean lines) accompanied by a high-collared or fully buttoned shirt will cause upward lines. This means people will follow your look from the shoes up. In the case of looser clothes; ill fitting suits, bootcut jeans or a low-buttoned shirt, people will trail from the head down.

Luckily the flat cap favours both. The low-bearing hat is not intrusive into the casual occasion but the peak is the epitome of gentlemanly headwear. To dress for the hat you have to dress for your lines. Learn this well.

Check Flat cap Red and Black Check Detatchable Hood Gilet Dr Martens Vintage 1490 Boot

The Trilby pt 1.

Favoured highly amongst the indie scene, versatility is its middle name (if you name your hats, which I don't and even if I do… what of it?).

The variations of this design speaks volumes through their, shall we say, style appropriateness. No boss will endure your attempt at wearing a straw trilby in the boardroom, so don't. Nor will my hat-land (which I am yet to suitably name) excuse you ignoring the basic commons of season.

Ultimately, the more formal & winter months are an advent for the classic felt or wool sort. Eclectic and aristocratic in its appearance; simplicity is favoured. In these settings it is a must that the hat is worn correctly. Firstly, size: a hat too big won't just make you look like the cat in a hat, it will make you look like a tw*t in a hat. Positioning: Stylistically the pinch (the narrowest point of the hat) should be symmetrical to the centre of your face. No offsetting allowed! Also the crown (the topmost indentation) should be ever so slightly slanted forwards to favour the narrow, clean silhouette of your aesthetic.

Despite these rules being COMPLETLEY NON-NEGOTIABLE you can have fun with a felt trilby. The basic design of the hat is flawless which means it will remain the same in terms of style no matter what colour you fashion it in. A great look is to contrast your trilby with your Mac or trench. For example: a dark monotone trilby with a sand-tone Mac, accompanied by other suitable tailorings.

Here is my quick style shrink for a felt trilby:

ASOS Feather Trilby FAIRMOUNT SHORT TRENCH COAT DARK BEIGE Marc Jacobs Leather Chelsea Boot

The Trilby pt 2.

Screaming the Italian Vespa-couture cliché is the fun sibling of the felt trilby. The straw substitute for the decorous felt sort has become a staple mark for the festival youth. SS10 is going to see an even wider range of these hitting the high street and online shelves. More than ever, now is the best time to show some dedication and shop for one of these as you would a pair of jeans, with concept and inspiration.

I have had many questions asked about the wear-ability of these hats. There seems to be a common misconception that only those who fashion a mid to long length hair style can wear them. This is not true. Unlike the felt and wool trilbies, the straw slouches back, disregarding any silhouette and therefore leaving the majority of your hair on show. As long as your face shape allows the hat to sit comfortably on your head without falling off or slouching over the ears you will be welcomed into Luke’s hat land with open arms! (No that name isn't right I'll keep trying!)

Straw styling:

ASOS Straw Trilby <img src=”http://www.allsaints.com/downloads/Image/product/medium-large/MBA500-202-1.jpg” alt=”Triple Bag” height=”270″ /> Brown Leather Boat Shoes

The Bowler/ Stingy

I think bowler (or its wool equivalent – stingy) hats are somewhat the unsung heroes of the hat world. Favouring the more defined face they are considered a British iconography. Rivalling the current American Graffiti trend is the Acid Youth look drawing from the mild undertones of the rebellious 80's British fashion. This style is perfect for anyone backing the Brits in the cross-Atlantic style crusade. These hats (just to confuse you some more) follow their own principle when it comes to styling how they sit. Frank Sinatra not only set the sartorial bench mark for bringing headwear into a trend, but he even wrote his own rules on correct execution. Which makes him so cool that I could actually pee myself; here are Frank's rules:

  • Wear your hat pushed back to seem more open and accessible
  • Tilt your hat over your eyes to seem mysterious and intimidating
  • Tilt your hat up 1 inch from completely straight to project an all-business attitude

While you muse over those here are my styling tips for the Bowler and Stingy Hats:

New York Hat Company Wool Stingy Hat Whishaw L/s Shirt Chronicles of Never Double Scarf

The Beanie/ Peruvian

These have avoided an earlier mention because as of late (apparently it got cold on there was some snow or something like that) everyone has been stocking up on their winters warmest. The cold but desperately trying to stay on trend embrace the beanie and those far few who are certain they can avoid looking like a Swedish call girl yodel for the Peruvian.

When you dress with a hat, you are no longer dressing with the hat; you are dressing for the hat! If your faithful Mac wants to join you on your outing then your beanie cannot. Think of it as two relatives who, when drunk, always end up having words; they just don’t go.

However here is what does:

Tie Dye Beanie Light Blue Faded Denim Shirt KG Big Sounds Grey Boots Ankle

The Cap

After we have ravaged the English isles for headwear inspiration we head on our £3.99 Easyjet flight across the Atlantic to our colonial cousins. The cap is almost nonexistent amongst the fashion ranks and ramps. Stylistically disregarded to its connotations in the sporting world (and alas we fail to mention the ruined trademark of Burberry); have we missed a trick?

A correctly cut hat, positioned to perfection, checker cloth: reminiscing nostalgic English countryside?

Any peaked sort should sit somewhat forward within the silhouette. The same applies here. Centred symmetry is key to turn this into a trend worthy accessory. The aim when styling this piece is to draw it away from the sportswear theme and into a complimenting piece.

Polo Jeans Ralph Lauren Billy Cap Resistance Jacket Navy/Purple Dunlop Retro Bag

In Conclusion

Those are just few of the many styles of headwear, often overlooked and shelved. I hope I’ve given you the confidence to go and find your own style and make it work with your wardrobe. If I haven’t, not only have I failed but I’ve just given you another excuse to go shopping…your welcome!

Oh wait, before I go. I forgot to give a small speech. A guiding hand if you will, as I do, to help you on your way:
“The etiquette that comes with wearing a hat is by no means archaic. By wearing a hat you accept a responsibility to treat it as your signature piece. Following the standard premise of hat-propriety will be a step up for the modern style-go’er and will scream volumes in opposition to the modern ‘Get ‘em out!’ Neanderthal.”

I hope I can mould true (hat wearing) gentlemen with these basic tenets:

  • Promptly remove your hat upon entering an elevator, restaurant, or someone’s home. Never wear your hat during a meal.
  • Touch the brim of your hat lightly when greeting a friend.
  • Raise the hat by the crown when meeting a female friend in public.
  • Remove your hat during the national anthem and place it over your heart.


Luke Todd
President of a currently unnamed hat-land…