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Loafers with shorts?

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  • Loafers with shorts?

    I know traditionally, you're not supposed to wear nice/dressy loafers with shorts. Fair enough. But it seems like I'm seeing slightly more casual loafers paired with shorts increasingly regularly.

    How do you feel about loafers with shorts? If it's acceptable in the case of certain loafers, which ones would you suggest?

    I'm trying to add some versatile warm-weather shoes. I already have 2 pairs of boat shoes and don't feel like adding a third. I've also already got a canvas pair, and really don't like espadrilles or flip-flops. If I can get away with a pair of loafers (something in suede or a lighter brown leather?), that would be ideal. Any thoughts?

  • #2
    Penny loafer style driving shoes with shorts are what you're looking for.

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    • #3
      I just picked up a pair of these for that exact purpose. Only $77 when they had that sale last week. (Not me in the photo, BTW--AE photo)

      https://www.allenedmonds.com/shoes/s...588-120-D.html


      WHY ARE THE GUYS IN SUITS HERE? HAS SOMETHING GONE WRONG?

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      • #4
        I too picked up a pair of loafers during the AE sale for this very purpose. The shoes haven't arrived yet, but I'll let you know when they do and what they're like.

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        • #5
          Originally posted by Hebrew Barrister View Post
          Penny loafer style driving shoes with shorts are what you're looking for.
          Thanks! I've thought about that as an option quite a bit! Any particular recommendations?

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          • #6
            Originally posted by mebejoseph View Post
            I just picked up a pair of these for that exact purpose. Only $77 when they had that sale last week. (Not me in the photo, BTW--AE photo)

            https://www.allenedmonds.com/shoes/s...588-120-D.html


            I noticed these as well! Sadly, they don't seem to have my size :/

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            • #7
              Originally posted by DocDave View Post
              I too picked up a pair of loafers during the AE sale for this very purpose. The shoes haven't arrived yet, but I'll let you know when they do and what they're like.
              Do you mind if I ask which ones you went for?

              The ones I've noticed most often are the McGraw, Cavanaugh, and recently the Catalina. With the first two, I thought they might be slightly too formal for shorts? In the case of the Catalina, I've just seen no information on them.

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              • #8
                Originally posted by jikaasik View Post
                Thanks! I've thought about that as an option quite a bit! Any particular recommendations?
                Originally posted by jikaasik View Post
                I noticed these as well! Sadly, they don't seem to have my size :/
                Jack Erwin has these on a rare sale for only $80:

                https://www.jackerwin.com/collection...12411182776406
                WHY ARE THE GUYS IN SUITS HERE? HAS SOMETHING GONE WRONG?

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                • #9
                  Originally posted by mebejoseph View Post
                  Jack Erwin has these on a rare sale for only $80:

                  https://www.jackerwin.com/collection...12411182776406
                  I got mine last year when they were down to $40 and they are surprisingly comfortable and hard to pass up.

                  The disadvantage to drivers is that they don’t have a real sole, so don’t expect to much service from them. Other disadvantage - depending on what you drive, these might veer into ‘trying too hard’ territory, if that’s a concern. That said, I think these are a good suggestion.

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                  • #10
                    Loafers with shorts is a Trad/Preppy staple. It goes with the idea that the style is slightly overdressed in most scenarios(and also slightly underdressed in most scenarios). Drivers are pretty easy to pull off, but as noted above, can come across as trying to hard. Easier still are suede loafers. I find CXL/pull-up leather pretty easy to style with shorts. Shell seems to be the hardest to pair with shorts in my mind.

                    I am a big fan of penny and tassel loafers with the former being my choice for shorts. I tend to keep the shape more of a traditional round moccasin toe and avoid elongated European styles.

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                    • #11
                      One thing about driving loafers or mocs to keep in mind is that the majority of them have that pebbled sole and theyr'e shiiiiiiiit to walk in for any length of time. I prefer a more traditional smooth or normally treaded sole; my most recent purchase was these https://www.amazon.com/gp/product/B07FKWBKFZ Geox driving mocs.

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                      • #12
                        Originally posted by Loafer28 View Post
                        Loafers with shorts is a Trad/Preppy staple. It goes with the idea that the style is slightly overdressed in most scenarios(and also slightly underdressed in most scenarios). Drivers are pretty easy to pull off, but as noted above, can come across as trying to hard. Easier still are suede loafers. I find CXL/pull-up leather pretty easy to style with shorts. Shell seems to be the hardest to pair with shorts in my mind.

                        I am a big fan of penny and tassel loafers with the former being my choice for shorts. I tend to keep the shape more of a traditional round moccasin toe and avoid elongated European styles.
                        I'm not sure I follow this line of thought. Penny loafer style drivers = trying too hard, but penny loafers = all good?

                        Maybe I should be more clear, but I'm a bigger fan of suede penny loafer style drivers than calf.

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                        • #13
                          For a more casual loafer, how about a suede navy like this AE? https://www.allenedmonds.com/outlet/...S_color=69130S

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                          • #14
                            Originally posted by Loafer28 View Post
                            Loafers with shorts is a Trad/Preppy staple.
                            i constantly am doing my Red Leather AE Kenwoods and my Red Shell AE Patriots with shorts of all colors. add surgincle belt and you're totally fantastic for the entire summer 8-)

                            maybe if i'm going to the beach or fishing i might even do the boat shoes.

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                            • #15
                              I am wearing a pair of Sebago penny loafers with shorts and a Reyn Spooner Hawaiian shirt as I write this. The Sebagos are waxy full grain leather in the classic Weejuns pattern. It’s either a fashion disaster or high style...
                              Mark

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