Tips For Pulling Off A “Casually Tailored” Look

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A softer shoulder is much less formal than a roped shoulder.

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And patch pockets are less formal than flap or jetted pockets.

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A madder or floral print tie is less formal than traditional stripes or dots.

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And if you don't already own a denim button up, what are you waiting for?

As usual, you are rewarded by paying attention to the details

I am constantly asked by friends who have gotten inspired to start putting more time into their personal style how it is possible to wear tailored clothing without looking like they’re going to a wedding or a funeral. It’s true that donning a suit or blazer or tie can be too dressed up for certain occasions – or worse, like you’re wearing a costume.

However, and of course, it is possible to pull off. I like to call it being casually tailored. Here are a few things to pay attention to.



| WEARING | QG Custom blazer, Peter Millar shirt, Ring Jacket pants, Drake’s tie and pocket square, Frank Clegg briefcase, A. Lange & Söhne watch, Oliver Peoples sunglasses, Allen Edmonds shoes | PHOTOGRAPHY | by Rob McIver Photo

Soft-shouldered jacket. A jacket’s shoulder is one of the key details that defines its look, feel and level of formality. A roped shoulder gives a jacket more structure and, therefore, makes it appear dressier and more buttoned up. On the other hand, a softer shoulder lends itself to a more casual and easy-going look. I prefer this type of shoulder on most of my jackets for exactly this reason because of the added versatility it provides.

Patch pockets. Like the shoulder style, the type of pocket makes a big difference as well. Flap or jetted pockets are more formal and are typically found on business suits and formalwear. A patch pocket is infinitely more casual.


Denim shirt. I’m very big on the denim shirt. If you don’t already have one, now’s the time. For my money, no other button-up gives you such a range of options. I like one in a mid-blue as pairs well with just about anything you throw at it.

Printed tie. Beyond the color – I’ve talked recently about working some green into your spring transition wardrobe – a floral or madder print is more casual and fun.


Thanks for reading.

Stylishly Yours,

Brian Sacawa
He Spoke Style


Chime In

  • Paul Loudon

    Thanks Brian, as usual you have a number of good tips there. Certainly integrating different fabrics (like a denim shirt) is a good way to add some personality and versatility to an outfit without having to go wild with colours or patterns. I’ve been inspired by some of your posts to look at knitted ties to add a little extra panache to my wardrobe. Have to wait for them to arrive now…..the problem with online shopping!

  • Anonymous

    That briefcase is amazing! Do a review!

  • Anne Watson

    I mean that jacket is so well-made. You can’t buy those in shops. Love this look.