Reader dilemma: Sneakers. Need help.

Here’s a great question from a reader/former client who’s looking to stay both cute and comfy:

What sneakers are “in” (aka Converse, etc)? I saw some semi-cute ones at Marshall’s that had the Converse look to them, I think they were Coach. But I have no idea how to wear them…. like with skinnies, etc? I always feel short and chunky in them when i try them on. Meh.

Sneakers can tend to be meh in general, and a double meh if you’re trying to figure out how to wear them in a non-gym kind of way.

As far as what is in, Converse will really never go out of style. I have a several pairs, and will probably continue to wear them as the years go by. That said, there are other options out there that are a bit more flattering. Because while I adore my Chuck Taylors, my partner calls me Long Foot every time I wear them (see above). They tend to make my feet look gigantic, especially when paired with skinny jeans.

So here are some other options:


Jack Purcell Converse. 

As I mentioned before, Converse sneaks are considered one of the footwear classics that won’t ever really go out of style. But instead of a Chuck Taylor version, you can try something like the above Jack Purcells, which look slightly softer and more feminine.


This Italian brand has also been around quite a while. I like them because the shape is less, well, Bozo the Clown. Plus, they come in a variety of fresh colors.


Sperry is best known for that super preppy Topsider style. But they also make sneaker styles that are perfect for attractive casual dressing. The designer, Milly, collaborated with Sperry on a few spring-ready styles, like the coral one above.

So now that we’ve established some attractive, non-Long Foot options, how exactly does one wear them? Well you can definitely rock these with skinny or straight leg jeans. (Reserve the wide-legs for shoes with heels.) You can also wear the sneaks with casual dresses in the spring and summer. That’s completely acceptable! Whites, blues, and greys are never wrong, while colors and patterns can also be fun, albeit more trendy.

Have a style dilemma of your own? Hit me up on Twitter or the TRS Facebook page… I’m always hanging out there.

[tweetmeme] 2 Responses to Reader dilemma: Sneakers. Need help.
  1. Erin
    February 28, 2012 | 10:24 pm

    Don’t forget bensimon slipons!

    • bryntaylor
      February 29, 2012 | 5:16 pm

      i just can’t get onboard with that one. :)

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