The Only 5 Dress Shirts You’ll Ever Need

How Many Dress Shirts Do You Really Need?

If you’ve been a regular reader and viewer of the YouTube channel over the last couple years, you’ve probably noticed I wear many of the same shirts all the time. Every once in a while I might throw in a wildcard, but in general I don’t step outside those core pieces.

The reason is one of the things I believe in most when it comes to style is building a versatile wardrobe. You want pieces you can plug in easily to a variety of situations- and down below, we’re doing just that with my five essential dress shirts.

1. White Poplin Dress Shirt

Essential dress shirt number one is a simple white dress shirt in a poplin fabric. Poplin weaves, because of their construction, are an ideal choice for shirts that are thin and cool but still retain a crispness to them. This one features a 150g cotton cloth by Thomas Mason. Poplin also has a great natural luster, which makes it perfect for more formal or suited looks. But, you can also use it to lend a bit of elegance to an outfit with chinos or even jeans.

For this outfit, though, I wanted to highlight the poplin shirt in a classic, dressy, suited way. This is a dark navy suit with a subtle herringbone pattern in it. A brown patterned tie takes the formality down a little, but and the simple white pocket square and brown Oxford shoes finish the look.

Let’s talk about the collar style, too. It’s a longer collar, so you don’t see the tip under the jacket. I think the way the collar interfaces with the lapel of the jacket really polishes up the whole look.

SHOP HERE: White Poplin Dress Shirt

2. Ice Blue Oxford Cloth Dress Shirt

The second of the essential dress shirts is one of my favorites-an ice blue Oxford cloth shirt. This is also 100% cotton by Thomas Mason; a little heavier at 180g. You always hear about the OCBD, or Oxford Cloth Button Down. While it’s a certainly a staple casual shirt fabric, a classic collar like this gives you the versatility to style it in a more dressed-up way.

Which is what I’m doing here. I’ve paired it with a brown sharkskin suit, which seems to have become one of the fan favorites in the shop. A Glen Plaid tie keeps things in the sweet spot between formal and informal dressed-up styling where an Oxford shirt like this really shines. And, in the same theme, a pair of tassel loafers anchors the look.

SHOP HERE: Ice Blue Oxford Cloth Dress Shirt

3. Striped Oxford Dress Shirt

A striped shirt is a must-have.  Fabric is also an Oxford cloth by Thomas Mason. It’s 100% cotton with a weight of 150g. I particularly like the size of this stripe. It’s not too thin, it’s not too wide. It’s just different enough while still being classic; therefore, very easy to style.

I always think of a striped shirt like this as kind of fresh and lending itself to a more relaxed approach, which is why I’ve paired it here with a patch-pocketed hopsack suit. The lighter tan on the medallion tie plays into the less buttoned-up vibe. Sunglasses are old favorites from Oliver Peoples and the derby shoes are by Enzo Bonafe.

SHOP HERE: Light Blue Stripe Oxford Cloth Dress Shirt

4. Pencil Stripe Dress Shirt

This is what you might call  a ‘reversed pencil stripe.’ The 100% cotton poplin fabric is by Canclini, and it’s lightweight at 110g. This is going to be your darkhorse shirt in the collection, but’s one with serious depth and range.

This shirt feels like low-key elegance and pairs beautifully with the dark blue suit with the subtle herringbone pattern from the first look. It’s totally on purpose, though. The richness of the grey, with the addition of the stripe, while still on the formal end, gives the suit a completely different feel. For a shirt to transform a suit? Now that’s versatility.

SHOP HERE: Grey Block Stripe Dress Shirt

5. Denim Dress Shirt

Essential shirt number five is a denim shirt. Fabric is also 100% cotton from Canclini with a weight of 210g.  It’s great to have a sportier shirt in your rotation, and one of my favorite things about this it is how easily it dresses down suited or business casual looks.

And business casual is what I’m doing here. I’ve paired the denim shirt with our brown Donegal tweed sport coat, some navy cotton trousers, a classic pocket square, and the Enzo Bonafe derby shoes.

SHOP HERE: Denim Dress Shirt

Styling Details

After getting the the fabric down, there are two big details to consider: the type of collar and cuffs you’re going to have. A lot of this boils down to personal preference.

My preference is a classic collar and a one-button, rounded cuff. Now, these aren’t the most unique styling details. You might say they’re kind of boring. No initials. No hidden patterns on the inside of the cuff. But, if we’re leaning into getting the most out of these shirts, a classic collar and a one-button rounded cuff is a safe bet.

Full disclosure: I like a French cuff shirt. I like a turnback cuff too. But, those have a very specific look and feel. It’s pretty hard to put cufflinks in a casual setting. A one-button rounded cuff, however, slides more easily between dressy, business casual, and casual scenarios.

Same thing goes for button-down collars or aggressive collar spreads.  Those do have their place, but again, if you’re looking for maximum versatility in only five shirts, a classic collar is the way to go.

All of the shirts above are available in the HSS Shop. If you want a different collar or cuff than my preference, you can customize it. You’ll be going through a comprehensive measuring process to get the fit right for you.

What are your essential dress shirts?