#Menswear: Work Your Way Up - Casual Shirts

Working my way up from last time, I will be touching on shirts that are on the casual side - basics and essentials that you should have at your disposal at all times, as well as what is currently trending around the menswear world today, and how they can be implemented into your style and wardrobe without diving into the deep end. I have included links to some recommended stores in various price ranges if you are interested in making a purchase.


It doesn’t matter if your shirt cost your $30 or $300, a well fitted shirt will help you in using it for multiple purposes and to me it makes more sense to invest more of your money into something that you will wear often. Personally I am more than happy to save up and put a bit more of my money into a garment that is made out of better materials, would easily work with some items I already have, is crafted by a respected brand and I knowingly would wear it at least a few days a week in separation.


Some of the best go to shirts in your wardrobe should be simple, easy to wear and plain - I say this because it is easier to dress up a plain shirt than something printed or in a deep colour, for example red. Most importantly they must fit you well both untucked and tucked, you never know when you may be called to something that needs you to dress up just a little bit more, say an interview for something or a dinner, and you do not want to be the guy that is there in a shirt which has a motif print of pineapples or palm trees all over it.


Here are some of the must haves in a man’s wardrobe while keeping it simple and versatile:


The Classics:

 The White Oxford Button Down:

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Pictured: Uniqlo - White Oxford Shirt


Yeah you need this shirt. I never knew how great one shirt could be until I got my hands on one. Hell, if there is only one shirt you ever need it is this, buy three – no, buy seven – it will make your life so much easier. You can wear this in summer, in winter, you can wear a t-shirt underneath it, you can wear a tie with it, you can roll the sleeves, you can untuck it - basically you can wear it in around 100 ways and it will still look good. You can have both spectrums here, the most casual when it is untucked, rolled up, buttons undone with a t-shirt underneath or alternatively you can tuck it in, put a knit tie on, a blazer and you are ready for that wedding, interview or more formal night out.


Oxford cotton has an interesting basket weave texture and wears really well, normally after a few washes the cotton breaks down nicely and creates an amazing soft feel and touch to it (also depends on how stiff the shirt is initially).


Recommended Products:
On A Budget: The Slim Fit Oxford in White - $70 from Everlane
Middle Ground: Gitman Brothers Vintage Classic Oxford in White - $200 from Need Supply Co.
Baller Status: Thom Browne Button-Down White Shirt - $525 from Mr. Porter


 The Blue Oxford Button Down:

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Pictured: Uniqlo - Blue Oxford Shirt, Gubb and Mackie - Buff Britten, P Johnson Tailors - Pocket Square


So, basically the same principles as the white applies, it is simple and it is classic. Blue can be easier to wear much more casually though, and will not give you the contrast that white does. Say if you wear a pair of deep navy trousers, the blue would be a better option for toning, alternatively the blue can be good to add contrast as well if you wanted to wear trousers in the lighter shades of beige. If you don’t want to look like you belong to a cult then you can break it up with the blue to add that subtle touch of colour without delving into the deep end of a royal blue or navy.


Again, you can easily dress this up and down in more ways than one. As shown above, I have styled it quite smart casual with a soft unlined jacket from Gubb and Mackie, the outfit is more inclined towards a summer outing, an outdoors date or if you still need that extra layer without having to reach for a jersey or sweatshirt. As well as this I back my point about contrasting - swapping the blue for a white would just wash you out.


Recommended Products:
On A Budget: The Slim Fit Oxford in Blue - $70 from Everlane
Middle Ground: Gitman Brothers Vintage Classic Oxford in Blue - $200 from Need Supply Co.
Baller Status: Band of Outsiders Slim-Fit Oxford Shirt in Blue - $370 from Mr. Porter


The Workwear Shirt:

menswear shirt 3

Pictured: Gubb and Mackie - Penney Nimes Shirt


A workwear shirt is a great all rounder, perfect if you are in a creative field, spending a long time around the city or even if you are kicking about on a farm – this shirt covers all your possibilities. The two pockets on either side of the shirt can be useful for shoving in your pens or pencils or if you just really need to put your phone somewhere. If the need arises, you can tuck it in and create a different silhouette with the shirt to break it up from being a very casual shirt.


Look for something in denim like this Gubb and Mackie one pictured, as it wears a bit harder plus once it has been washed a couple of times can create some great fading and add that extra bit of character to the shirt.


Recommended Products:
On A Budget: ASOS Chambray Two Pocket Shirt - $50 from ASOS
Middle Ground: Soulland Dark Grey Tom Shirt - $250 from Thousand Piece Puzzle
Baller Status: Warehouse Heller's Cafe Work Shirt in Black Chambray - $335 from Bureau Belfast


In #Menswear:

The Long Button Down Collar:

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Pictured: Gubb and Mackie - Vauxhall Jacket, Spelman Shirt, Firth Tie, P Johnson Tailors - Pocket Square


Okay, so you are probably thinking “It’s exactly the same as the normal button down but with a longer collar? What’s the point?”And yeah you are exactly right. Don’t get me wrong, there is nothing with the normal collar that most – if not all – classic oxford button downs have, but the longer collar sits a lot better with a tie on and has that extra roll on it that creates a much better silhouette which all leans toward making the shirt more formal. If you really want to #menswear it up as well as have a great staple shirt then this is your go-to, it serves a much larger and more rounded purpose and has very viable reasons as to why it is different. And as always, when you have a tie on - undo the collar buttons.


The look above was curated to show the longer collar with a tie and blazer but ultimately you can picture what any oxford button down will look like with those pieces in order to dress it up for a formal gathering. The collar style can be hard to come across off the rack as well unless something is being made for you, but the two choices below will be your best bet.


Recommended Products:
Option One: Pale Blue Stripe Button Down Shirt - $250 from P Johnson Tailors
Option Two: Spelman Shirt in Maize- $275 from Gubb and Mackie


The Soft Cutaway Collar:

menswear shirt 5

Pictured: Gubb and Mackie - Vauxhall Jacket, Crane Brothers - Thomas Mason Washed Chambray Shirt, Vintage - Tie, P Johnson Tailors - Pocket Square


The cutaway collar shirt is probably one of the most #menswear pieces out there at the moment, you see the dudes at Pitti rock these with their four-in-hand knotted ties to emphasise their swag and let me tell you, it’s not an easy collar style to pull off, you really need the whole outfit to make it work. For a more casually styled look you should opt for something in a washed chambray or lighter weighted oxford to soften the shirt as well as to se
parate it from the more formally stiff cutaway shirts.


In order to wear it casually you can also rock the shirt itself with the top button undone or with a sweater over the top, and on the more smart casual spectrum you can add a colourful tie with a plain blazer, as pictured above. I would suggest having a look at online made-to-measure service programmes such as Proper Cloth or even the menswear giant SuitSupply as these are very difficult to come across off the rack besides Crane Brothers.


Recommended Products:
Option One: Blue Washed Shirt- $100 from SuitSupply
Option Two: Denim Shirt - $250 from P Johnson Tailors


In the realm of menswear not a lot changes over time, fabrics and styling always stay similar, especially in shirting (the oxford button down has been around for a century or so). If anything, it is always the details that trend and if anything it should always be up to you (the wearer) what collar you would like, if you have a two button or one button cuff, if you have a little embroidery on the sleeve to show some personal touches - there are so many variations of shirting but I wanted to keep it simple and basic, all the details and finessing come down to the man.


Imagery by: Zayyar Win Thein


  1. alex 25 March, 2019 at 09:17 Reply

    Zayyar Win Thein.. if you hate Wellington so much… when you had the chance to leave ( for example uni) why did you not move on up to bigger and bigger…. As a New Zealander you should love the who of New Zealand

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