Style Psychology: Ugly, But Cool
Where strategy meets style
content marketing, strategy, personal branding, style, cincinnati, fashion, photography, midwest, creative
post-template-default,single,single-post,postid-552,single-format-standard,stockholm-core-2.0.2,select-theme-ver-9.10,ajax_fade,page_not_loaded,side_area_uncovered,,qode_menu_,wpb-js-composer js-comp-ver-7.7.1,vc_responsive

Style Psychology: Ugly, But Cool


Have you ever been attracted to something (or someone) you never would have considered your type? You know, something that doesn’t fit into your usual style, something that doesn’t “look like you?”

I never bothered to take psych in college, so I’m not sure if this particular condition has a name, but I do know it’s happened to me before.  I still regret not buying some of the ugliest rings I’ve ever laid eyes on (they were on clearance, no less!) because I loved them so–and it’s been at least five years. The thing is, they were ugly but cool.

To delve a little deeper into this extremely important and world-changing psychological insight, I decided to conduct a bit of fantasy internet shopping in an attempt to create a look with items I am simultaneously repulsed by/attracted to:


1. Scarf, Urban Outfitters. Okay, I actually like this scarf, but I needed something to balance out the items I don’t like.

2. Denim jacket, Old Navy. I promised myself years ago that I would never wear regular old boxy-cut denim jackets again because I was burnt out on my (surprisingly Helmut Lang-ish) Old Navy version and SO tired of seeing everyone else in them. I guess Old Navy strikes back.

3. Sonia Rykiel dress, Milk Boutique. This is the kicker, folks. Everything about this dress is not me.  I hate plaid. It’s pastel. There’s a big bow on the chest. It’s not extra short or extra long. It looks like something a milkmaid would wear for chrissakes! And yet…something about it calls out to me.  It draws me in–unwillingly, but inexorably. What is that?

4. Bracelets, Anthropologie. I’m not usually into fairy-dust beribboned girly-girl stuff, but hey. What can you do?

And for the grotesque grand finale:


Jeffrey Campbell shoes, Free People

So much about these booties(?) is wrong: the slightly curved platform, an open toe reminiscent of pig’s feet, clown-ish front lacing . Let’s face it, they’re ugly.

But I bought them.  I bought them instead of one of the other pairs I was considering even though they don’t really meet the criteria. Why? Because, as a heavily inebriated yet surprisingly insightful friend told me this weekend, “Yes, they’re ugly. But they’re cool.”

So that, my friends, is my official scientific explanation for the “don’t like it but am strangely attracted to it” phenomenon. Am I completely off base here? Or has it happened to you, too?

  • Alicia

    April 20, 2009 at 6:05 pm

    I got Ann D. vibes from those shoes – scary, weird, but cool. I considered getting them, too.

    And yes, it happens; I find fugly stuff all the time and get it just because it’s all so intriguing. Sure, I never wear it, but still.

  • Stylish Thought

    April 20, 2009 at 8:44 pm

    I love those booties and waiting for the tan ones to come back in stock!!! I totally understand about not liking something, but being drawn to it. I think part of the appeal is the challenge it presents.

  • Fashion Fille

    April 20, 2009 at 9:33 pm

    thanks for your comment! i am having fun with all my activities!

    i tried to add you again on linkedin, but it says that because we don’t know anyone in common i can’t view your profile or add you! 🙁

  • Laura

    April 21, 2009 at 3:29 pm

    i love those shoes!!!!!!!!

  • Pingback:Style: Such a Tees |

    August 3, 2009 at 11:36 am
  • Pingback:How to: Stalk shoes online | The Style Sample

    March 24, 2010 at 8:14 am
  • Pingback:Style: Whitewashed | The Style Sample

    April 3, 2010 at 3:23 pm
  • Pingback:Backyard Island | The Style Sample

    August 22, 2011 at 8:22 am
  • Hadiza

    June 2, 2016 at 2:23 am

    Lol. This is my first time seeing this post and I’ve seen these shoes on you like a 100 times and I thought it looked just rad! I get the ugly attraction thing but I never get to buy stuff like that for fear that I might hate then eventually and never get to wear them.