I’m having more and more fun wearing things that you might not typically wear together.
Females have been doing it for a while, but guys have less opportunities to pull the look off since our wardrobe is typically a bit more simplistic (read: we are a bit more limited).
The easiest way to start doing this is mixing a pair of pants that could be dressed up or down, with a more casual shirt, and an even more casual outer layer.
Here’s a straightforward example of what I’m talking about.
To start, I’m using the Club Monaco Omar Trouser as the pant option that could be dressed up or down.
I’m wearing a 32 in this photo, but after it was shot I picked up a 31, which fit fantastic. A word of caution – you won’t want to wear these pants when it’s hot out because you’ll start to quickly feel a bit toasty.
And don’t hate on the Chucks seen in these photos – they are what I had on at the time the shots were taken.
Next, I’ve added the Club Monaco Matty Classic Oxford to the mix. It’s a casual dress shirt that will quickly become a staple in your wardrobe. So, we went kind of dressy, to casual up top.
And we’ll finish up by adding the Club Monaco Kennedy Sports Jacket. When I saw this hanging on the rack I thought it was a varsity jacket of sorts due to the white stripe on the collar.
The jacket has a great fit, but fits in the casual category for me due to the detailing and material it’s made out of – almost heavy sweatshirt feeling.
So, there you have it. A pretty simple way to mix business with pleasure in order to create outfits you never knew you had.

