A 2010 Winnipeg Fringe Fashion Moment: Should I Wear Short Short Socks?

Before leaving for the 2010 Winnipeg Fringe, I decided I would wear pants as little as possible.

Unfortunately, soon after touching down in Winnipeg, I realized flip-flops are ill-suited for long bouts of walking. How could I possibly wear shorts and good walking shoes without looking totally dorkish?

I noticed Ray sporting the short socks, shoes, and shorts look. I decided to give it a try.

Shorts, short socks, and shoes!
Shorts, short socks, and shoes!

What do you think my fashionistas? Total dorksville or boyishly cute!

14 thoughts on “A 2010 Winnipeg Fringe Fashion Moment: Should I Wear Short Short Socks?

  1. I await the replies as Jon and I frequently argue about his sock/shoe combinations. I want him to just wear a man sandal (not a flip flop, a more structured sandal that could be comfy for walking) and bare feet when in shorts. Of all my fashion prods this is the only one that he refuses me. He insists on wearing his nice Sketchers with these hideous socks all scrunched down around his ankles. It drives me mad!

    1. I don’t mind the look of socks, shorts, and shoes so much. The tan line however drives me crazy! I’m hoping the line from the lower sock is less noticeable.

  2. Agree with the Lady Rose – the sophisticated ‘mandal’ is the way to go. However, if you really need your sneakers you can buy even shorter socks – anklets really. You can barely see them peeking over the top of the shoe.

    My hubby and I disagree about short length. I think men’s shorts should hit around the knee, but he’ll wear them shorter. Scandalous, I tell you.

    1. I’ve never found a decent mandal that is also appropriate for walking. They either look OK and aren’t useful for long bouts of walking or they are good for walking but look pioneerishly dorky. I’m sure you ladies never have this problem with footwear … 🙂

      Hmm, I think I prefer a longer short as well but showing a little extra skin never hurt anyone!

  3. I don’t mind the shorter shorts at all. Based on the picture, I think this look is working for you. I like to see what’s happening up top. I can’t make a final ruling without seeing the ensemble as a whole.

    1. Sorry? Do you mean “shorter socks”? Picture a t-shirt and hoodie ensemble to finish the look…

      1. I did mean shorter socks.

        T-shirt and hoodie, eh? I’m still going to give it the thumbs up, because of your long legs. On a short person, the bulk of a hoodie combined with socks might create stumpifying effect.

        1. When next we meet, I will rock the whole ensemble, so you can judge fully and effectively…

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