Ask the Fashion Police: Jean shorts with Converse sneakers – cute or clownish?

A question from Formspring:

Q. Jean shorts with Converse sneakers – cute or clownish? What about sneakers with casual dresses?

A. We’re not fans of sneakers in general, but that’s just a personal preference, and we can’t see anything wrong with the combination of shorts and sneakers, if that’s your style. We wouldn’t describe it as “cute”, particularly – it’s a fairly basic, functional kind of style – but we wouldn’t instantly think “clown” either!

As for sneakers and casual dresses, again, not a look we’d go for ourselves (we’d rather wear almost any form of footwear than sneakers), but not crime of fashion territory either.

What does everyone else think? Denim shorts with Converse? Sneakers with dresses? Tell us!

18 Comments

  • April 22, 2010

    Amee

    Not converse, but certainly regular sneakers with actual support in them. I wore canvas shoes to my grad, and that’s about it. Depending on the style of the dress or skirt, it definitely works, but other times something dressier is called for.

    View Comment
  • April 22, 2010

    hypermuse

    Converse are amazing with most things and definately look cute with shorts. They look better once they’ve been worn in a bit though rather than brand new.

    View Comment
  • April 22, 2010

    Alex

    this can definitely be done, with shorts definitely and some dresses. I always try but think my feet just look massive! Still will wear this in the summer though. I think it’s because Converse aren’t as big and clumpy as a lot of other trainers that you can actually pull it off.
    .-= Alex´s last blog ..Gingerbread People =-.

    View Comment
  • April 22, 2010

    Lucia

    I love the shorts and converse look ^^
    I wear it myself very often too.
    If you want too look a little bit younger and more playful it is very appropriate.
    The sneakers dress look on the other hand I am not a fan of.
    I always look too… how could you say… stumpy (if thats a real word).

    View Comment
  • April 22, 2010

    Ash

    Not for me but I’ve seen certain people who can pull off the look. I feel like it has something to do with the way your hair is styled. A short bob maybe.

    View Comment
  • April 22, 2010

    Riali

    For me, sneakers come in two categories: Actual athletic shoes, with arch support and all, and shoes that look like athletic shoes, but are actually unsuited for anything more strenuous than a stroll. Both tend to try as hard as they can to look like spaceships. Real athletic shoes are necessary and appropriate, in the same way ski boots are- sure, wear them, but while doing sports, not while going to a movie. So called “street sneakers”, I have no use for. They’re unnecessary, and largely unattractive.

    All that said, I do tend except converse from the rule. They don’t look like spaceships, and at least aren’t pretending to be running shoes when they’re not. I do see the clown angle, because they tend to make many people’s feet look really long and floppy, but I can see that this is part of their unique look. I don’t wear them myself, but they are not reprehensible, even with a dress.

    View Comment
  • April 22, 2010

    Andrea

    I wear my converse with pretty much everything – shorts, dresses, & jeans – I even wore them with my wedding dress (after the ceremony, of course).

    View Comment
  • April 22, 2010

    bunbuns

    I have to defend the sneakers as regular, daily wear items. There are almost no shoes that I can wear that I find comfortable. Not even most sneakers. I have arthritis, bunions, and horribly flat feet. And, I’m only 30. I’ll probably be in some form of sneaker or some other flat that can take my $500 orthotics on my wedding day!

    I don’t always feel particularly fashionable, but it’s either that or walk with a visible limp and a grimace on my face.

    View Comment
  • April 22, 2010

    Maeve

    Dresses and sneakers is a no-no for me, I would wear ballet flats instead for a casual look that is not mismatched. But Converse and shorts are fine although Converse is not my favourite style of shoes in general.

    View Comment
  • April 23, 2010

    Alix

    I love this style! It’s one of my summertime favorites, and I love not having to worry about getting me Converse dirty. <3

    View Comment
  • April 23, 2010

    Jaynie

    I think any sort of sneakers paired with dresses belong more in the domain of the teenager, although as a rule I think it can be pulled off by anyone with enough confidence (as is true of most non-offensively-bad clothing, I think). Converse and shorts seem acceptable to me, although I always have too much trouble with sock length to go that route myself. I did go with black converse, knee-high grey socks, a plaid skirt and a red cardigan once, but I hasten to add I live in a country where children do not wear uniforms to school, so such an outfit is more sexualized than it’d probably be otherwise. Although in hindsight, the pigtails might have been pushing it. 🙂

    View Comment
  • April 23, 2010

    Katie

    I personally think Converse are the most overdone shoe ever, and I tend to avoid wearing mine except for when I’m doing something where gym shoes are required.

    Even if you do want to wear Converse, I don’t suggest pairing them with a dress. Like Jaynie said, it’s a very young look. Heck, I’m in high school and I think it looks too young for me. It strikes me more as something preteens would do when they were “forced” to wear dresses.

    View Comment
  • April 23, 2010

    Diandra

    I think it can look good with high-top Converse, but I think low-tops are alot easier to style! I think low-tops have a cute, casual look. So do any tennis shoes/sneakers. I think sneakers are fine for everyday wear, as long as they’re not clunky or bulky! It’s personal preference though I guess.
    I HATE Converse with dresses though. Yeah, sometimes it looks ok (like in the “Twilight” movie) but in general it’s a look I don’t like. It looks goofy in my opinion, like you have no idea what shoes to wear with a dress, or that you’re trying too hard to be different. Or, something. I don’t really like flats with more formal dresses either usually. It’s just too casual.

    View Comment
  • April 23, 2010

    Julez

    I think it comes off as juvenile, it reminds me of junior high students

    View Comment
  • April 23, 2010

    Sandy

    It’s a very young look. I’m 20, and I’ve tried the Converses-with-dress thing (just in front of my mirror at home, not out in public). I felt it didn’t fit me very well. I think that summer dresses and shorts are best paired with ballet flats or metallic-colored leather sandals.

    View Comment
  • April 24, 2010

    Michelle

    I love shorts and Converse. I think it’s a great look go for a walk, go to the store and go out with friends.
    I’ve worn it a lot. 🙂

    View Comment
  • April 24, 2010

    Sarah

    If it works with your style, then I say go for it. I feel that nothing is really “too young” (ok, maybe not “nothing” but not many things) if you have the right attitude. But I mean, if you don’t like the style, then that’s cool too.

    I am glad that the general consensus is that while it may not be your style, you don’t hate the look on other people. I tend to feel that fashion is relative, and while I or you may not like a particular style, that doesn’t make it automatically a bad style.

    View Comment
  • August 22, 2010

    Mary

    I personally think that jean shorts, a fun t-shirt, converse, and very long fun socks look great together. ^^” But, I’ve got a sort of dorky style.

    View Comment