All summer I look forward to breaking out the leather jackets from my closet (or storage unit).

Nothing says “laid back cool” better than a quality leather piece.

Here are five favorites from my personal collection.

1. Vintage Character

Looking to invest in your first leather jacket? Make it a vintage brown piece with beat-up character like this one, or a sharp black number like in look 2.

Quality is very important, as a leather jacket should be an investment that lasts a couple decades, not a couple years. Run the leather through your hands and give it a good feel. It should be soft, sturdy and organic feeling, not rubbery, coated or plastic-like.

It should fit snugly through the shoulders, slim through the body (just enough room to zip over a sweater) and hit a few inches below the waist. Make sure you try it on, and don’t factor in alterations. It’s really not worth the hassle or price, even if you find a tailor willing to work on leather.

I picked up this guy from a vintage shop in Montreal last year.

The advantage of buying second-hand, other than saving at the cash register, is the leather has had time to break-in. This particular jacket, for example, is cut from a super-stiff leather that, when new, probably could have stood up on its own. After years and years of wear and tear, it’s now soft, comfortable and has the perfect shade of worn-in brown.

This piece also has some amazing vintage details that make it one-of-a-kind, like the reverse-stitch princess seams, asymmetrical pocket flaps, rear side adjusters, baseball stitch across the shoulder seams, etc. (We probably should have taken more pictures)