1 Piece/3 Ways: Leather Moccasins

April 12th, 2012

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Looking for something more comfortable and relaxed than a hard-bottom loafer or wingtip, but dressier than a sneaker? Try a pair of leather driving shoes.

This particular pair, by Botticelli (available here), has a sturdy but flexible rubber sole that is more stable and durable than the popular pebble soles – which are made more strictly for driving.

I don’t have a car here in the city, so for me these are walking shoes – and they are one of the most comfortable pairs I own, including my collection of sneakers.

The best part, of course, is their versatility. In a sleek leather, these driving mocs are the perfect high/low combination that can have you ready for just about anything. They can quickly dress up a casual look, or dress down a formal look.

Here are three examples.

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1. Sharp Weekend

I wore this late afternoon bar hoping with some friends. You never know what’s going to happen…if it runs late in NYC some “fancy” places look down on sneakers, so the drivers keep your options open.

The shoes here make this casual look borderline dressy.

When looking at drivers, make sure the lining (preferably leather) is smooth and the insole is firmly set in place – you’ll be wearing them without socks and you don’t want rubbing or slipping.

Use a slim rugby as a sweater and layer it over a short-sleeve button-down shirt. It’s easier and more comfortable than having 2 bunchy sleeves.


  • Brown leather drivers by Botticelli
  • White s/s button-down shirt by American Apparel
  • Slim washed denim jeans by Polo Ralph Lauren
  • Watch by Montblanc Timewalker Automatic
  • Striped rugby shirt by Michael Bastian
  • Nato Striped grosgrain watch strap by Corvus
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  • Ben

    I recently bought a pair, Allen Edmonds. They are indeed great for walking and they really filled the bill when I went to Manhattan recently and didn’t want to walk around looking like a tourist. I wore driving shoes alternated with some Rivieras

  • Carlo-Antonio

    Man I love that shirt in the Sharp Weekend look! however, I cannot, for the life of me, find that rugby shirt anywhere! Any suggestions from anyone on where that specific type of scoop neck, no idea if that’s the term, rugby can be found?

  • Street Lovely

    Those mocs make me want to run out and purchase a car today. Then put the top down and drive south until I run out of gas. At which time I’d throw on the rugby and grab a margarita at the nearest cocktail lounge.
    Street Lovely

  • Billy

    I like the Gucci bamboo drivers that you sometimes sport as well!

  • Bjorn

    Great blog/site!

    Keep up the good work.

    Greetz,

    Bjorn

  • Jim

    Loving the 3rd look! I just ordered one of Frank Clegg’s ziptop briefcase in belting leather. My gosh I can’t wait to carry that.

    Keep up the good work,

    Jim

  • thatguy

    hey SB, springs here.. can you do more posts on sandals, there probably the hardest things for me to wear without looking like a frat boy.

    thanks,

    • Jaap

      I discovered your blog wtbisee on google and check just a couple of of your early posts. Proceed to preserve up the outstanding operate. I just extra up your RSS feed to my MSN Info Reader. Seeking forward to reading much more from you in a whilst!

  • http://MensStylePro.com Mr. Sabir P.

    As you know I am a huge fan of driving mocs. I think that the oxblood (with a bit of chestnut color) are extremely versatile. Also, watching shoot the corporate commuter look was funny as hell that day. Great work.

    - Sabir

    • HarrisonK

      Where do you get your driving mocs for a reasonable price? I have RL mocs which are great and I’m looking into Tods, but I just cant justify spending upwards of $500 on a pair of driving mocs that’ll last two years tops.

  • Thom

    Good look, I’ve been thinking you needed some new shoes. Most of yours are looking a little tired. I think if you review you’ll see what I mean. Good update I was starting to worry.

    • Adyna

      I prefer to see not only brand new items but also shoes or shirts after you wear them 2,3,4, 10 times. This way you can see how specific items from specific brands look, not only when they are brand new. I consider this to be a good information..this is my personal opinionn, even if I haven`t seen Dan wearing something that looks tired.

      Best, Adina

  • James

    Are those Boticelli shoes comfortable, what are they on a scale of 1 to 10?

    I just want to know before I drop 350 on these shoes?

    Thanks for this post, I don’t own any driving loafers yet, but they seem smart.

    • DCRob

      Driving mocs are typically stiff as boards, lmfao

  • Herbert Morrison

    Dan, you say many a great thing and this statement is no different: “you don’t have to limit the pieces in your wardrobe to specific uses/occasions.” I have been preaching this also myself almost as long as you’ve had this site. At my new post as a professional clothier I tell my clients the same thing, much to their surprise/delight. My superiors, on the other hand, almost had a stroke when they learned I merely suggested the idea of breaking up a suit or pairing more casual elements with dressier ones. I know you can wear whatever you want and answer to no one, but my question for you is this: How can I reconcile or marry/blend/connect what you do (classic with a twist) with the old school (clothing/tailored wear vs sportswear) mentality/approach to men’s clothing?

  • TO

    Those shoes are prestine Dan:O Great find. Love the ‘twists’ in look #2! Those colored frames are great.

  • Khalid

    Looking sharp as usual!

    Do you have any additional special tips for folks who would like to commute by bicycle? Ever since I started dressing more nicely, I find myself reluctant to cycle, because of all the issues with sweat (putting stress on the clothing, feeling grungy, etc.) and weather. I know that light fabrics (like the cotton suit) help, and it’s preferable to have a second set of clothing at the destination, but I like to think you have more tricks up your sleeve. Perhaps a subject for a future post. :-)

    • Thom

      Khalid, remember when your riding to work it doesn’t need to be a race. Keep the sweat at bay with an eloquent stroll.

    • Daniel

      On this note, your bike is too small for you – both the seat and the handlebars are too low. I get that you stop more often on a city bike, but ideally your knees shouldn’t be anywhere near the handlebars when you pedal.
      Think of the cycling motion as a running motion. Does one squat when running? A proper-sized bike and properly-adjusted seat will make pedaling a lot easier, resulting in less sweat – and also fewer creases in your pants!

      Keep up the great work!

  • Dan O

    Might have to check these shoes out. I have ripped the front of 3 pairs of driving mocs. They are my go-to shoes, and I’ve had a cobbler literally apply a thin layer of glue to the front of the toe, just to prolong them before they rip. The only pair that I’ve found have enough sole are from Florsheim (Imperial series), and they run about $100.

    My 2 cents.

    • http://www.thestyleblogger.com SB

      Thanks for reading, and commenting Dan O.

      This proves that when it comes to footwear, buying quality saves money in the long run. $100 shoes tend to come “unglued” after a few months of hard wear, especially if they are go-tos. After 3 pairs and adding up cobbler fees (not to mention time and trips to the shoe repair shop), you’ll be spending more than if you bought one hand-sewn Italian pair in the first place (which would be more comfortable and look sharper/more luxurious every time you wear them).

      And if you can find good quality on sale, than it’s a real no-brainer when you crunch the numbers.

      My 2 cents.

      -Dan

  • Desmond K

    This is kinda unrelated to the topic of this post, but every time I see you in that Michael Bastian rugby I think to myself “man, thats a nice shirt”….

  • Ian

    Great post again. Some great looks as usual!

  • AFJ

    Looks like plastic those loafers…

  • Adyna

    I know what you`re saying..I keep in my car 1 or 2 pairs of drivers in case I want to change plus jackets (if the weather changes:). Good post!

    ps: luv the bicycle..it keeps you moving..planning to buy one soon and not get killed by crazy car-drivers