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What makes a shirt great

How to spot quality quickly when shopping for shirts, the brands making some of the best button-ups on the market, un-gatekeeping my favorite sleepers, and more!

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street night live
Nov 06, 2026
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I’m currently writing today’s newsletter while sporting the latest Poplin Dress Shirt in charcoal from Phigvel. It’s my newest addition to my overflowing shirt rotation, but when it comes to them, can you really have too many?

My shirts all serve a different purpose. They’re made out of different materials while coming together with details that make each one of them unique from the rest. A good shirt goes a long way because it’s one of the easiest clothing items that you can style in so many different ways.

But in the vast world of shirts things can feel overwhelming, because how does one decide what shirt is right for them when there are so many options?

As you may have guessed it, today’s letter is all about button ups and where to find them. We’ll touch upon what I look for in a shirt myself, what makes a good shirt great and how you can spot the difference in quality to make you a better shopper, and of course, brand recommendations for some of the best shirts you can buy right now.

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WHAT MAKES A SHIRT GREAT

I think it’s fair to say that fabric is the most important element of a shirt, but details like stitching, collar, cut, buttons, and other minor details need to all come together to make a good shirt great.

Everyone shops differently and that’s what makes our relationships with clothes so special. There is no right or wrong way to shop…to a degree, but in most cases, you’re free to make your own rules that work for you.

After all, that’s what makes acquiring clothing fun.

Stitching and buttonhole construction is one of the fastests way to find out if the shirt you’re holding is at that #elite level.

I tend to look at specific details before even checking out the fabric label when shopping for new button ups. These details might go overlooked for a novice clothing enthusiast, but to a trained eye these markers tell a larger story.

These are the details that will make it easier to spot quality quickly and help you make the right purchase:

  • Loose threads around the buttons: Although for me this isn’t the worst thing, it is a solid sign of the overall construction of the shirt. Premium shirting doesn’t have loose threads, unless they are using a specific natural yarn that tends to loosen with age… But that’s also a flag within itself because I don’t really want to buy a new shirt that has already has some sort of aging before I even wore it. I want to do that myself.

  • Hem and overall stitching consistency: They say that high-quality stitching runs at around 20 stitches per inch. To me that’s some real nerd sh*t, and if you’re into that, that’s cool, but I focus on the overall quality of the stitch and how lined up it runs across the entire garment. Crooked stitching tends to signal that the production was rushed or done with unskilled labour, which tends to mean that it costs less to produce.

  • Collar: The collar quality, how it stands and sit around your neck, and the overall shape is the heart of a good shirt. A good collar is instantly noticeable when compared to lower quality collars. It’s personally the detail I start with first. Look at the shape and how it tends to sit around the neck.

  • Buttonholes: Good quality buttonholes are made using old machines that are hard to come by. It’s a detail that plays into the final price point but it does give the shirt longevity. This detail is a bit more on the nerd side, but it is a check that’s worth doing because a good buttonhole will keep things tight and snug after pushing a button through it for the thousand time.

  • Fabric: Ok, so if you did all of the major checks, and now you look at what the fabric is. From there, you make your decision

Hopefully your new favorite shirt passes all of these tests, and most importantly, ends up fitting you well. Congratulations, you just acquired a shirt that you can be obsessed with.

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THE SHIRTS I WANT RIGHT NOW

On my recent trip to Japan I ended up buying like 4 different button-ups, and you know what? I’ll probably buy another 4 by the end of the year. A good shirt makes me happy so why deny that happiness? Plus, it’s a garment that doesn’t have seasons, giving me plenty of opportunity to wear it all year round.

Below is my list of shirts from brands that I tend to look at first when shopping:

3SIXTEEN

When I need a classic fit that I know I can rely on, 3sixteen is my first stop. Recent collections have been overflowing with a variety of shirt styles paired with great fabric development and details that make these some of my favorite shirts in my closet.

They are made well and I know that as a long time customer, so it’s a no brainer for me to return season after season.

They fit true to size, but I do like sizing up to give myself a little bit more of a looser fit, so consider that when purchasing. Some of my favorites right now are: Garment Dyed Wester Shirt, Boxweave Utility Flannel, and The Big Oxford.

You can shop all of their shirts directly on their website here.

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