We first met James Wu when he submitted to our January Giveaway with an email titled “OMG I Wanna Win Free Sh-t!”. He caught our attention, his outfit was on point, and he swiftly made it to the Top 10.

James is a medical student from Montreal with a knack for classic prep staples.

“TSBmen has really helped sharpen my look, which I would describe as collegiate prep. Classic pieces with pops of color… I’ve realized that in a classroom full of sweatpants and graphic t-shirts, throwing on something as simple as the classic combination of an oxford shirt with chinos can make you stand out, in a good way.”

Here James shows us a little about investing in smart classics.

1. Smart Casual

James sticks to the basics for a smart and clean casual look: navy quilted jacket, two-tone crewneck sweater, off-white denim, suede desert boots.

His whole wardrobe is very smart. What I mean, for example, is that every piece in this post can be mix-and-matched and he wouldn’t miss a beat.

“This is a nice transitional sweater – it’s a kind of cross between an L.L. Bean Norwegian sweater and a Saint James nautical t-shirt.”

As you can see, James is well versed in menswear classics.

“I have to admit that white denim can be a pain to keep untarnished.

Off-white denim is a great alternative. These are more of a subtle wheat color that doesn’t get dirty as easily as crisp white.”