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.

    • 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
    • Burgundy suit trousers
    • Grey herringbone socks by Marcoliani
    • Black leather penny loafers by Bass Weejun

    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.


    Thanks, as always, for reading.

    Yours in style,

    Dan Trepanier


    Photography by Alex Crawford


    • Pat

      I really like that grey leather baseball jacket by Hugo Boss but can’t seem to find it anywhere online or in-store. Is it an exclusive/limited piece or am I just really unlucky?

    • Brian

      Every time I see that Mont Blanc watch I get insanely jealous

    • Mike

      Hey, dan. Love your site, great inspirations for me. So I was wondering if you would show us how you do your hair. Like the products you use and how you create that look. I really like it. Thanks…

    • Anon

      Looks 3 and 5 are my favorites. I like the mix of different textures and patterns and the way you pull them off like it’s no biggie. Also, the beard’s looking good now. It needs it’s own site!

    • TimL

      Love the looks, especially the black mixed wool and leather jacket… very cool

      My question is how come all the side bars are so expesive that probably 80% of the people could not afford that kind of expense?
      I can get great ideas and find similar looks for all this stuff at about 1/10 the price. Nothing special about some of the clothing but the combination is what stands out.
      Leather jackets for $1200…. I can find them for brand new under $100. Same with the shoes-$60, sweaters-$30 and watches-$50, glasses-$20 for the same look, Your posting really expensive brands that most people ( especially college kids) could never afford.

      Just my two cents.

      • Dan Trepanier

        Hi Tim,

        Thanks for your two cents.

        We are doing our best to suggest items that are close in quality to the ones featured in the post, or at least items we recommend as a good value online (which doesn’t always mean cheapest price).

        Also, keep in mind we are not writing exclusively for college students. Out of curiosity, where are you getting leather jackets brand new for $100?


      • Keaton

        Uhhh maybe a polyurethane jacket that looks kinda similar to the look and feel of leather, AKA pleather jackets maybe. I don’t think you could get a leather jacket for under $100 if you harvested the animal yourself. haha.

      • Hunter

        As a college student I have to pick and choose what I buy. I think it makes me value my clothes more and has definitely taught me how to be stylish on a budget. This site has also had somewhat of a impact on my career choice (as I want to be able to afford a wardrobe like Dans in the future haha).

      • TimL

        Hey guys…. here is 1 outlet store I go to.
        Burlington. Here are several nice coats for just around $100.

    • Jarrod King

      That last look is the best. Love the black jacket!

    • Chad M.

      Great job Dan, I’ve been looking in to getting a leather jacket recently.

    • Omar M.

      Hey Dan! u just like Ben Roethlisberger stylish

    • Nour

      Hi Dan,
      Big fan of you site. i’ve been following it for years. Any suggestions on vintage shops that i can get my hands on a nice leather jacket like this on look 1. Thanks A lot. keep it up.

    • Sam

      Not posting my comment because I actually had an opinion? Your site gets worse and worse as time goes on. Hope you’re capitalizing on it nicely though!

      • Alex Crawford

        Hey Sam/Dennis/Sidd,

        Every comment made on the website has to be approved. Sometimes we aren’t sitting at our computers waiting for your feedback. I’m sorry if you feel like we dont value your opinion, because we really do. You’ve been a consistent commenter, and I would be upset if you stopped.

        Thanks for reading,

      • Dan Trepanier

        Love your passion. I’m more curious as to what you don’t like about the new site?

        We’ve put countless hours into improving the user experience…

    • Dennis

      It’s funny that you think your grooming is sharp in the last look. You look like a mountain man that stumbled across some pomade!

    • Sam

      Great looks! Number four is my favorite. I don’t know how “laid back cool” a quality leather piece is, though. Some of us don’t have the money to look laid back apparently!

    • Joe

      Love the jacket in #2. Though I gotta say, you mean to tell me that you aren’t particularly fond of moto jackets because of their collar?

      Mind you, I’ve seen jackets from the likes of Belstaff/Barbour and even Schott and they seem pretty okay with collared shirts. So what kind of leather jacket do you call #2?

    • Matty J

      Greetings from Spain my man! Those APCs are looking good! Glad you inspired me to pull the trigger on mine a few years ago… love how they individually transform to each person. Regarding the beard, I vote you bring back the post no-shave-november stache. Your best look to date.

    • mathieu Lavoie

      Just out of curiosity, how much space do you need to store all your clothes? Seriously

      I’m obviously totally jalous here, what a nice collection of leather jackets. Great post! :)


      • Dan Trepanier

        Hey Matthieu,

        I have clothes stored in several different places around the city. As a collector, it’s the NYC way :)


        • mathieu Lavoie

          wow impressive, do you have a database to keep track of every item? Seasonal rotation must be quite a burden ;-)

    • Tom

      What does the comment mean, “it is a jacket, not a blazer”?

      • Dan Trepanier

        My advice is to invest in a leather jacket, not a leather blazer (ie. tailored jacket with lapels).

        Thx for reading Tom.

    • Keaton

      Dan, just noticed your Paul Smith boots are named “Columbia.” I, for one, find that a little ironic.

    • Kris

      Good post.
      Those Florsheim x Duckie Brown beaded longwings are so damn sexy. Best shoeporn to date.

      My favorite type of leather jacket is the perfecto. I recently bought a vintage one in Rome, just €100 for a really good quality jacket. I usually wear with a plain cotton crewneck in grey or black, and sometimes I change it up by wearing a chunky knit sweater. Combined with my grey Acne jeans and beat up chuck taylors/black leather derbys, it’s easily my favourite outfit right now.

      I’ve really gotten into thrifting now, and Rome got some very decent vintage shops!

      • Dan Trepanier

        Thanks Kris.

        Sounds like a great find. There is no better place to thrift menswear than Italy!

        Hope all is well with you in Rome.

    • Don Pierre

      Brilliant Final Look. Creative Yet Classic.

      • Dan Trepanier

        Thanks Don Pierre. Simple with subtle details is a good way to go.

    • Herbert Morrison

      That RLPL never gets old–it’s been in countless posts and still stays strong, steady. Woodbury eh Dan; all these years and I thought you copped it in the city. Still haven’t picked up a leather yet cuz have yet to find one half as nice. “Milestone” had a similar navy one, but I never pulled the trigger. Any suggestions besides RL, Edun, Varvatos? Thx bro.

      • Dan Trepanier

        Hey Herbert, nice to hear from you again. There are plenty of options, at all kinds of different price points. The key is finding one that fits properly and makes sense with your lifestyle.

        We share our favorite values online in our “Shop This Look” section…

        Best of luck brother.

    • dp

      good points here dan. what’s up with the beard look though, looked much better sans facial hair

      • Dan Trepanier

        Thanks. I’m loving the beard, personally.

        • MJ

          The beard is amazing. Keep rocking it.

        • Jack

          I know people develop a personal fondness for their own facial hair, but, speaking as a disinterested observer, your beard is weird. You’ve got to at least trim it.

          • Dan Trepanier

            Thanks for your opinion Jack. I find the term “disinterested observer” interesting…