Reader Feedback: Navy Loafer Question

I love reader questions.  It’s really interesting to me to hear what’s on RCS readers’ minds.  Please keep sending them…as you know, I do my best to answer as quickly as I can…whether it’s about the quality of a brand, a good tailor, or the proper jacket length, I’m more than happy to help.

I got an interesting question via from a long time reader regarding navy blue loafers:

Italian Navy Pennies from Sids or Navy Pennies from Oak Street?”

I thought I’d open it up to the readers…what do you think?

My answer: it depends on what you plan on wearing them with…the Sids are a little more formal, and could be worn with wool pants and suits, but probably not with shorts.  The Oak Street option is a little more casual, and will look great with jeans, khakis, and shorts.  Short answer: BOTH.



  1. 08/17/2014 / 12:28 PM

    I think I’d have to go with the Oak Street Navy Pennies, the Sids are nice but seem to be different shade of blue, not quite navy. Both look awesome and look better than the sea of browns and tans but I’m leaning toward Oak Street.

  2. 08/17/2014 / 12:44 PM

    The Oak Street’s would be my choice in my jean and chino wardrobe, but as you noted – it’s really about what your style is. The Sid’s have a more polished look to them and are clearly exceptional. I do think in spite of their formality, you can dress up a nice pair of dark denim with these style and it would look a little more crisp. All in all, I like the versatility of the Oak Street.

  3. ron payne
    08/17/2014 / 12:48 PM

    Both would be best, of course. But I like the truer navy of the Oak Street pair.

  4. Greg
    08/17/2014 / 12:53 PM

    Great feedback guys

    Last question. Are Oak Streets true to size or should you really go down 1/2 a size when going sock less?


  5. Robin
    08/17/2014 / 1:42 PM

    I’d go down a full size if you want to wear the Oak Streets sockless, a half size for socks.

  6. 08/18/2014 / 8:44 PM

    I wear a 10 in most shoes. I purchased a pair of 9.5. They are too big – a 9 would be perfect. It’s not the initial wear. Initially they were good but the leather is rugged but supple to the point that they do mold, stretch in some spots, etc. I feel their recommendation of 1 size less is dead on for sockless wear.

  7. BMO'C
    08/19/2014 / 3:56 PM

    Definitely Oak Street.

  8. JJ
    08/21/2014 / 6:18 PM

    First off these shoes are in totally different ballgames, the only things that are the same the “color “and style name.

    Oak Street is a standard LOW vamp penny loafer, like your Bass Weejun or Alden loafer; riding the edge of frat Topsider. Clean leather bottom, like most shoes made in New England; sturdy but collegiate leather bottom still.

    The Sid Mashburn loafer has a HIGH vamp, better for trousers and jeans than shorts and Chubbies. And the comfort level is much higher, these all have a studded rubber bottom; like a softer Dainite if you will.

    The Oak Street looks good, but Rancourt, Quoddy and Sperry make a shoe like this. Sid Mashburn’s penny loafer if a full Italian grade and styled take on the American loafer, which is sober and actually kinda boring. You can polish and burnish all you want to the Mashburn loafer to create some fun dressier finishes, like an Edward Green or Saint Crispins shoe; the Oak Street; is still at the end of the day just a plain penny loafer in navy

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