Break Out the Leathers!

November 21st, 2012

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)

  • Gold Plated hand-engraved shades by Matsuda ·
  • Brown leather jacket Vintage ·
  • Olive/Brown Henley by Guess x Marciano ·
  • Slim brown leather belt Vintage ·
  • Olive cotton chinos ·
  • Suede chukka boots by Scarpe di Bianco ·
  • Brass railroad spike ring by Giles & Brother ·
  • “Stella” Watch by Brera Orologi

2. Office Sharp

There are a milllion options when it comes to buying a leather jacket. The most important thing, in my opinion, is to keep it simple and treat it long-term investment.

Avoid “statement details” like excessive zippers, flashy hardware, contrast stitching, obnoxious logos, etc. These types of notable features get tired after a while.

The neckline is also very important. Think about how you will wear the jacket and how its neckline will work with your look. For example, a motorcycle/racer collar looks great buckled on a motorbike, but looks unnatural hanging loose over a collared shirt.

A sharp black leather can replace a tailored jacket, for your commute to work or to transition from the office to a night out.

Remember, go with a leather jacket, NOT a leather blazer.

I broke my bank account in college (months of eBay hustling) for this one at the RLPL outlet at Woodbury Commons.

Eating peanut butter & jelly sandwiches for two weeks after this purchase was definitely worth it. Five years later it’s still one of my favorite pieces and it looks better than ever.


Burgundy Worsted Trouser

  • Black/Grey shades by Matsuda Eyewear ·
  • Black leather jacket by Ralph Lauren Purple Label ·
  • Grey/Burgundy windowpane shirt ·
  • Grey wool tie by Thom Browne ·
  • Silver 2″ tie bar by Tiffany & Co ·
  • Watch by Montblanc Timewalker Automatic ·
  • Nato Striped grosgrain watch strap by Corvus ·
  • Grey herringbone socks by Marcoliani ·
  • Black leather penny loafers by Bass Weejun
  • · Burgundy suit trousers

3. Designer Piece

After you have a couple classic leather jackets, I would consider investing in one that’s a bit more of a unique statement.

There’s nothing cooler than a simple outfit (black boots, black faded jeans, grey sweatshirt) combined with a killer designer leather.

After all, sometimes you just want to be simple but rock something that nobody else has.

I lucked out and found this limited edition design at a sample sale.

Off-white, distressed leather, asymmetrical collar, vented sleeves…pshhhh…had to have it.

Leather jackets are like footwear. Invest in quality because 1) you will look and feel better every time you wear them and 2) it will save you money over time.

For example, I paid $300 (on sale, retail $550) for these Paul Smith boots. They are now five or six years old and (after a quick shine) look almost brand new. I can eventually have them resoled since the handmade uppers have almost no damage. They also hold some resale value: I could probably get around $150 for these on eBay or consignment.

On the other hand, had I purchased a lower quality boot, let’s say for $150 retail, I would be replacing them every other year due to wear and tear on the cheaper leather and lower quality construction. (Not to mention they wouldn’t look nearly as fly!)

  • Grey tortoise shades by Matsuda ·
  • Distressed off-white leather jacket by Helmut Lang ·
  • Grey crewneck sweater by Levi’s ·
  • Watch by Montblanc Timewalker ·
  • Black faded “thin finn” jeans by Nudie Jeans ·
  • Black leather wingtip boots by Paul Smith

5. Mixed Media

There are some very cool jackets on the market that combine leather with other fabrics, like cotton or wool.

This one combines smooth black calfskin and wool flannel with a subtle graphic print, making it a very unique piece.

Black leather jacket + white button-down shirt + grey flannel trousers + black lace-ups = a can’t fail recipe for a “continental cool” look. Simple, masculine, refined.

To properly finish a simple look like this, keep your grooming sharp. Here I had my barber trim and edge the beard with a slight fade.

Like the jacket, these beaded longwings are “classic with a twist”. Definitely head-turners.

We shot this on the set of an upcoming video I did with Conde Nast and Cosmopolitan magazine. More on this soon.



Wool Flannel Trouser in Mid Gray

White USA Oxford Shirt

Thanks, as always, for reading.

Yours in style,

Dan Trepanier


Photography by Alex Crawford