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Our Most Comfortable Dress Shirts & How To Wear Them

Stefan Loble

Some of you may remember our capsule wardrobe guidance from previous posts. When I started Bluffworks, I had never heard of what a capsule wardrobe was. My goal has always been to produce simple wardrobe essentials that are durable (meaning, ready for years of use), never go out of style, and set you up to look great in just about any situation.

Given the moment we’re in, the way we’re dressing has changed. But regardless, it turns out a capsule wardrobe remains exactly what we need. Think of a few pieces that are both amazingly comfy work from home clothes, and also the best travel outfit at the same time. 

For me right now, our dress shirts are a key - and sometimes overlooked - item. We made them to be comfortable, easy care, and ready for multiple wear.

Right now, I am pulling these shirts out of my drawer to wear time and time again; just like I always did in my pre-pandemic life. Honestly, it makes me giggle every time a shirt that was shoved in my drawer a minute ago suddenly looks so good on a Zoom call. 

If you can wear a shirt a couple of times, what you need is to be able to wear it multiple ways. So today, we’re bringing you a roundup of different ways to pair our shirts, to show how a few different items can be mixed and matched into lots of combinations. 

Styling for Comfortable Dress Shirts

Boy, have I noticed the difference it makes when I wear a nice shirt. Not only do I think, "Stefan, you look great”, more importantly - I feel great - taking calls and working from home. It tells the people I am meeting with that the occasion matters. 

Here are a few collections that are organized around pairing our best selling dress shirts with comfortable dress pants, soft t-shirts, and - if the mood strikes - a casual blazer and other accessories.

Option 1

Given khaki pants are a staple in any men’s wardrobe - and a natural match with our blue Gramercy Blazer - an easy addition is our Meridian Shirt in Crimson Pine Plaid. The shirt provides an ideal casual look when paired with our relaxed fit pants alone, but becomes a simple, well put together outfit with the casual blazer added on top. 

Option 2

Going a darker direction, our Meridian dress shirt in Blue Black Plaid is a sleek pairing with our black 5 Pocket Ascender Pant. Layering is an old trick, not just for comfort but for a put-together look. To double up on comfort, you can wear the Meridian shirt with an open collar over our soft performance t-shirts for a combination that doesn’t sacrifice comfort for style.


Option 3

With the blazer, our Zenith Dress Shirt in Maroon Grey Tattersall reads as more formal. And adding a lighter colored t-shirt underneath gives it a pop of color. Plus, our Voyager Grey Ascender Chino is possibly our best selling pant - not only is it one of our most comfortable dress pants due to the sneaky stretch waistband hidden inside, but it looks like a formal trouser.

Option 4

It’s a special thing to find such an elegant, easy care blouse that can power a woman's go-to outfits. When paired with our Petaluma Ponte Pant or Palma Chino, the Azores adds elegance to comfortable work from home outfits. Everyone's favorite feature seems to be how the sleeve of the blouse stays rolled up.  It also turns out that our t-shirt fabric makes an amazing scarf that you can layer to add warmth and interest.

Grab one, or two, now

When I first founded Bluffworks, I started with pants, because I assumed it would be so hard to ever wear the same shirt for multiple days. We’ve since done it. Now, I literally pull the same shirt out of my drawer to wear time and time again, as they are always comfortable, and they always look great. I never could have foreseen that the moment we are now in would lend itself so well to the core values in our assortment.

You can shop all our button-down styles at the links below.

Bluff on,

Stefan Loble


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