That’s It: Episode 5, Mistakes

Style mistakes are sometimes inevitable but usually avoidable. How though?

This week’s show is all about mistakes. Style mistakes, to be exact. We’ve all made them and they can be embarrassing and regretful, to say the least. Especially if there are photos…

In this episode of That’s It, I describe and discuss one of my worst and least favorite outfits on HSS and reveal the reasons we are sometimes driven to make poor style decisions.

Plus, advice on how to stop yourself before you do. Because what good would identifying a problem be without proposing a solution?

Assignment: Share your worst style moment with everyone in the comments.

Hey, I broke the ice. Describe it in great detail, upload a picture if you have one. And think – really think – about what led you to make this mistake and then share that insight with everyone. There’s no shame. This a community/safe zone and we can all learn from each other.

Thanks for listening.

Stylishly Yours,

Brian Sacawa
He Spoke Style

That’s It is edited by Mack McLaughlin.


Chime In

  • Matthew Pike

    I may have a photo of this outfit somewhere, and I remember it very well. Circa ’05 I took a trip to Dublin while at college. The outfit goes like this; white grounder lo PF Flyers, skintight bright red jeans, a turquoise and navy vintage track jacket I picked up in Amsterdam, a off white v-neck t shirt with a mutlicoloured bird print on the front. And finished off white a vintage tweed triby, and tartan scarf. Ah, to be young.

    Buckets & Spades

  • Seth Nelson

    For most of my life, I really did not care about fashion, and did not give it much (if any) consideration. So my mistakes are pretty juvenile. During my undergraduate days, I had forgotten that I was supposed to accompany a singer, in front of all the other student singers. I was very casual that day, dressed in workout shorts. Embarrassing.

    A few years ago, working as a piano accompanist at a local university, I used to dress what I would call casual. Not workout clothes, but sometimes shorts and a T-shirt, rarely even what we would call sharp casual. Once a voice student said to me after a rehearsal, “You know, Seth, I admire how you always dress so casually here. I mean, most professors have to dress in a suit and tie. But you are always dressed down, and you make it work.” That comment struck me. It finally occurred to me that I was in a professional environment, and I should dress to match. It wasn’t an overnight change, but thus began my journey to better quality dress. Nowadays, I am almost exclusively dressing formal, business, or at least sharp casual.

    Not exactly the style mistakes you had in mind, I think, because it’s not like I was trying to be stylish and just messed up. Just regrets about years past. I still feel young when it comes to the world of dressing well. I’m playing catch up now.

  • DeJuan McGuire

    This story took place in 2006. I was interested in dressing well, but not obsessed with style like I am now. I didn’t have the resources to help me. On my first day on the job at an engineering firm, I wore a lime green oxford button down and olive green chinos. Shoes were probably square toed. I thought it was a good monochromatic look, but now I can see in hindsight that it looked awful! The next day, I wore something else that was just as bad. Finally, my girlfriend (now wife) did an intervention to keep me from looking foolish at my new job. So I toned it down and kept it basic. About seven years later, I started to discover style websites, YouTube channels, books, etc. Now I am much more comfortable putting together stylish outfits.