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How to Wear a Hat Right - Everytime

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Section: Building Your Wardrobe - Blog

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There usually comes a time in every man’s life when he takes a look in the mirror and wonders why he doesn’t wear a hat with his suit. If old Frank and his buddies could do it, then why the hell can’t you?

Know what? We couldn’t agree more. Call us old fashioned – we’ve been called worse – but if a dress hat is worn right, then it’s a real mark of the man. But it’s a pretty big ‘if’. So before you charge off to your nearest hat maker, there are a few things you should know about wearing your hats correctly.

Get to know hats inside out

Ever wondered why those stars of the 50s always manage to look so damn dapper in their Fedoras and Trilbys? Well, that’s because they know their brim from their crown and their band from their taper. They also understand that each of these four components of the modern day dress hat plays a crucial role in making that headpiece look like it was designed for the wearer alone.get_to_know_hats_inside_out

You wear the hat; it doesn’t wear you

As a finishing touch to a custom tailored suit, the dress hat should complement the look rather than take it over. You don’t want the hat to become the sole focus of attention in your outfit and become the talk of the party. The idea is to have people mention how well you look, and not how well your hat looks.


Invest in quality

You know how we feel about quality here at Montagioso when it comes to adding elements to your look, we always advise checking the quality first and the price later. Hats bought from a street vendor that time you took a trip to Bali just won’t cut the fashion mustard. This hat, like a suit, is an investment that should last a lifetime.


Know what style suits you

Thankfully, we live in a world where no two men or women are the same – we’re not counting twins – so it stands to reason that certain hats as with certain suit styles will suit a particular shape of face better. Now you could spend the day down at the local hat emporium trying on style after style until you hit on a winner or you could check our suggestions below for each face shape.


Long and thin – A short crown, medium taper, wide band, moderately wide brim, tilted to the side

Try - Fedora, Derby, Homburg

Wide on top – slightly pointed crown, moderate taper, band of similar colour to hat, medium width brim, tilted to the side

Try - Homburg, Fedora

Short and full – Narrow band of contrasting colour, medium width brim, medium crown, slight taper, tilted to the back

Try - Fedora, Panama, Gambler

Square – Rounded hat, no taper, wide brim, any size band, tilted to the side

Try – Homburg, Bowler

Strong Jaw – Medium or low height hat, slight taper, medium width brim, any colour band, tilted to side or worn level

Try – Fedora

Long nose – No pinch in crown, no taper, colourful band, wide brim, tilted to the side

Try – Fedora

Protruding ears – Wide brim, full crown, slight taper, worn tilted back

Try – Gambler, Fedora, Panama

Small chin – Low height hat, significant taper, narrow band, medium brim, worn level or tilted to the side

Try – Porkpie, Fedora, Trilby

Another idea might be to wear one of your tailored suits when hat shopping as you’ll get a real feel for what each piece of headgear brings to the table regarding the overall look. And do us a favour, when you get hold of that perfect dress hat, be sure to pop in and give us a look at it.


We tailor make mens suits, jackets and shirts for all occasions. Each garment is custom designed, precisely made-to-measure and is guaranteed to fit you perfectly. Unlike others, we offer you end-to-end service and a personalised styling session where we take the time to understand your needs to ensure you get the colour, style and fit you want.

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Named in GQ Magazine's "Best Tailors" list, and the highest reviewed tailor on Google, Montagio has paved the way for discerning men to get suited up with style. We offer a truly personalised experience, specialising in custom designed, perfectly fitted suits, shirts, coats, and shoes for for business, weddings, formal and casual events. Our showrooms are visually packed with designs that inspire plus thousands of fabric options, making it easy for you to get the look you want. Our expert stylists will advise and professionally fit you and frankly won’t let you walk out until we’ve tailored your perfect garment. Since 2010, we have custom tailored looks for thousands of happy customers. To experience the same red-carpet service, book your personal appointment today.

Steve Fambo

Hats off to the team at Montagio Custom Tailoring Sydney. I was immediately impressed once I stepped into their boutique showroom... more »

Scott Lasak

The suit and shirts I received were terrific and much better quality than ones I've found in stores off the rack. I would absolutely recommend them... more »

Yun Zhi Lin

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