In the realm of men’s outerwear, denim jackets have a somewhat spotty track record. They never quite go out of style, although some years – like this one – they enjoy more popularity than others. While it’s pretty easy to look like a biker or a buckaroo in a denim jacket, incorporating one into a classy outfit with nice custom shirts takes some know-how.

If you’re hoping to look proper in a denim jacket, the first thing you should do is refrain from wearing any other piece of clothing made with denim fabric, specifically denim jeans. It doesn’t really matter if the jacket is dark-washed and the jeans are stone-washed, wear them as part of separate outfits or risk being lambasted for your “Canadian tuxedo”. On the flip side, avoid trousers that are obviously too “dressy”, for example, black pinstriped slacks or too-supple suit pants. Try a pair of dark grey or green chinos instead for a more sophisticated look.

Once you’ve got your trouser selection under control, next consider your shirt. For a lot of guys who love denim, a simple undershirt seems like the obvious choice for their top – unfortunately this would be a mistake. Throwing on a plain T with a jacket – especially one made with as a fabric as denim – can give the impression that you either just got out of bed or put no thought at all into your outfit. Denim outerwear really works best when combined with brightly colored dress shirt. Shades of pink, red and orange go particularly well with denim blues to create a high-contrast, but sensible, outfit. As temps get colder, don’t be afraid to try out a layered look by adding a sweater (again, the brighter the better) to your ensemble.

Finally, a great way to dress up a denim jacket is with accessorizing. The best accessories to pair with a denim jacket are usually textured – think chunky cabled scarves, or rough tweed hats. Just like the color of your dress shirt can create contrast with the color of your jacket, the perceived feeling of wool can create its own kind of contrast when worn in conjunction with denim. Either way, a brightly colored knit scarf or newsboy cap will look a lot classier than a baseball hat.