We’re at that point in the year where deciding what to wear can be a challenge, since the weather is changing so much. You wake up thinking it will be cold, but suddenly it’s warm a few hours later and you’re shedding a few layers to stay cool.

But sometimes it’s equally as difficult trying to dress well during the cold, since you just want to be comfortable and warm. I’ve found that this is the case sometimes, however in an effort to dress better, I’ve tried incorporating some colour and comfortable – but stylish pieces – more often. It helps simplify the process, while still allowing you to not look like you don’t care at all.

Today’s look pays homage to the classic, so-called ‘dad’ outfit. It’s simple and straight to the point, but the warm tones elevate the look and make it a little more than it is.

I started with a checked red shirt from Frank and Oak. It’s a comfortable shirt that goes well with other pieces, and it has a good weight to it – it’s not too heavy like an oxford, but looks like it. And the tone of red really caught my eye. To stay warm, I’ve started incorporating undershirts (that aren’t shown), which also help wick away sweat when it gets too warm.

The Dockers chinos I wore are also another essential that I stand by, since they look great and feel great. They’ve updated their tapers to have a more flattering shape, without sacrificing the range of movement in the pant. I paired that with a light brown leather belt from Andersons. Sometimes I get some flack for not matching my belt with my shoes, but it’s still doable if it’s not too intrusive.

To finish off the look, I threw on a J.Crew quilted jacket, that’s super light, yet warm. It’s a good piece that can carry you through all seasons surprisingly, with the exception of really warm summers. The boots are from Skechers’ new line in collaboration with Mark Nason – they’re super comfortable, and look great. Navy blue is also a fun colour to add on to any combo. Finally, the toque (Frank and Oak) and scarf (gift from London) are add ons for those chillier days, but I chose to rock the hat since I’m working on growing my hair (and it’s a little awkward right now)

All photos are courtesy of Julie Yeh (@julie_yay)