Should you wear shorts to work?

Casual Clothes · Casual Friday · Office Appropriate Outfits - Summer

We had a few days of 90+ degree temperatures in Chicago recently. You know, those days when taking the train and walking to work leaves you sweaty and gross by the time you get to your desk? Yeah. Normally on those days I try to wear dresses and sandals but lately I’ve been thinking: could I wear shorts to work?

Our dress code at work is literally “wear what’s comfortable but not too revealing.” Every summer we get an email about not wearing “Daisy Dukes” (aka super short shorts) to the office. But there’s no mention of longer shorts. And the guys wear shorts when it gets hot. So, why not me?

So, I did it.

IMG_2320Top – Le Tote (same) | Shorts – Express (similar) | Shoes – DSW (similar) | Purse – Stitch Fix (similar)

It helps that I saw my VP in shorts the day before. And while I truly believe that you should dress nicely no matter what your boss wears, I decided that wearing nice shorts with a nice top, jewelry and heeled sandals counted as dressing up my shorts.

I felt a bit self-concious at first but really, no one noticed or said anything. And, to be honest, I was still dressed more professionally than some people in our office.


I also ended wearing this outfit to a party at the triathlon store in my neighborhood after they put on a DIY Triathlon on Saturday morning. They set up the bike racks and had someone watching our “transition” area so we could swim, bike, run whatever distances we wanted. I needed a confidence boosting swim and I got one! I swam the full half mile distance with no stops, no backstroke, and no treading water.  I was definitely ready to celebrate after that!

7 replies on “Should you wear shorts to work?

  1. Bri Marie

    Super cute outfit! I’ve felt jealous about guys in shorts before, but I don’t have any good shorts to dress up that are long enough. One of the few times I wish bermuda shorts were flattering or in fashion!

    1. Erin @ Loop Looks Post author

      I know! I think there was a short period of time when “walking shorts” were popular. They were kind of like Bermuda length but more tailored. I had a pair that I wore a few times and would totally wear again except they are currently too big.

  2. Bethany @ Accidental Intentions

    Woohoo! Shorts to work forever! I’m wearing shorts at work right now, in fact (though mine are more of bermudas rather than shorts). I almost wore shorts the length of yours to work last week, though, and I think as long as there aren’t any rules against it, you should go for it. You did a great job of making them look nice and classy, anyway, and I LOVE how your purse matches your top!

    Also, I believe I saw you all swimming last Saturday? Ohio Street? There were lots of people swimming at Ohio Street, at least, and I figured you may be one of them. Hard to tell with all of you wetsuited up, though! Everyone looks the same!

    1. Erin @ Loop Looks Post author

      Yep, I was definitely swimming last Saturday! Live Grit was hosting a DIY triathlon and I FINALLY managed to swim the entire half mile without stopping or resorting to the backstroke!

  3. Katherine - Engineering In Style

    Ahh, I’m jealous!! We have a strick no jeans and no shorts policy, but during the summer we can wear jeans on Fridays (because half of the office is gone on summer hours). I never end up wearing jeans though – it’s just too hot! Shorts on Fridays would be SOO much better. And really, shorts like these are way more professional looking than the leggings that people get away with wearing.

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