Putting Together a Comfortable and ‘Dressed Up’ Outfit

Dressing well is a form of personal expression, but it also shows that you give a d!mn about whatever it is you do – even if it’s going to get a coffee in the morning. And it doesn’t ever hurt to put in a little bit of extra effort.

Sometimes, the deterring factor is the fact that we just want to be comfortable. It’s completely normal, like who wants to wear something uncomfortable?

No one, duh. Unless you really have to.

But I find myself associating certain items in my closet with being too ‘dressy’ or uncomfortable, so I end up opting for more comfortable casuals, such as tapered sweats or stretch chinos. One of those two doesn’t look so good dressed up though, (tip: sweat pants) so choosing a good stretch chino usually does a great job at substituting most dress pants.

They’re really a fool-proof option that makes you look good, without feeling too restricted. In my experience, or based on what I have, most dress pants or jeans don’t quite hold up (in terms of comfort) for those longer days.

So I played around with a couple of pieces and came up with a dressed-up-looking outfit that really can carry you throughout the day. Hear me out:

  • I opted for a cotton polo instead of a dress shirt or button-up (those usually work really well, but it doesn’t hurt to try a polo instead). Usually polos are reserved for casual outings, but it doesn’t hurt to elevate a polo with some comfortable and sophisticated layers.
  • This Massimo Dutti cardigan is a good choice to layer because it’s a cashmere/linen blend, which means it’s super comfortable. It won’t give you that itchy feeling since it’s soft to the touch and really thin. I love the brown colour as well, since it’s neutral and versatile, meaning you can mix it up with multiple colour combinations.
  • Tweed blazers usually don’t fit the bill for ‘most comfortable wardrobe pieces’, but if you find yourself a good-fitting wool merino-wool blazer, you’re in for a treat. Merino wool adjusts to your body’s temperature so you’re never too hot or cold, but it can get a little warm if you move around in it a lot. This particular one is the Ludlow jacket from J.Crew, and surprisingly fit me well off the rack.
  • The shoe choice is optional here. I’ve broken into my pair of monk straps, and they’ve become one of my most comfortable shoes. I picked up these guys from Hudson’s Bay – they’ve got some really good shoes for great prices.
  • Finally – the pants. I left these guys for last because they’re the most important staple in this look, and can honestly do so much for you. This pair is from Dockers’ new line of chinos, the smart 360 flex, which is probably the most comfortable and stylish pant I own. Dockers has always made amazing chinos, but these ones are genuinely some of the best I’ve worn – in terms of comfort, versatility and style. Again, I chose a neutral tone here to match with the rest of the outfit, but this Olive Green colour really goes well with anything.


Photography is courtesy of Julie Yeh (@julie_yay)

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