Easy, comfortable outfits for going back to the office

Fall 2021 might be a rude awakening for many of us, if enough people get vaccinated and we are suddenly summoned back from work from home to our offices. I already have a timeline for this–August 2021–and while I will miss some parts of my home office, I am a little excited to put on office outfits again. At the same time, my tolerance for structured pants (and bras with underwire!) is incredibly low at the moment, so I thought I would put together some easy, comfortable work outfits to ease the transition back to in-person work!

Midi dress + blazer

My basic philosophy for going back to the office is to definitely ease into it. First, I’m going to try my work clothes on slowly to see what fits, what’s comfy, and what I want to totally ditch (completely inspired by this post by Abra). Going from matching sweatsuits to suit-suits is just not gonna happen! But a midi dress with an elastic waist? I can tolerate a suit jacket over that. Espadrilles make it feel summery and are a reminder of how much I’ve missed my shoe collection.

Stretchy jeans + untucked shirt

This outfit definitely depends on your office dress code but I’m relying on my assumption that everyone else has forgotten general decorum as much as I have in the past year and I’m saying it: untucked dress shirts!!! No one has time for fussy tucked in skirts when we are busy grappling with the uncleaned-out office fridge from 2020 and trying to reconnect all the technology we took home! Pointed flats and my most structured blazer make everything ok, right? Also, these jeans are thankfully stretchy for sitting at my desk all day.

Blazer + sneakers

As discussed, I am over uncomfy shoes and I am reaching for sneakers daily. I love leather sneakers with a few more tailored elements, like a structured bag and a plaid blazer. Oh, and this midi dress (similar–same company!), which is sooo lovely on the skin. There’s a lot going on in this outfit. Prairie dress. Street style sneakers. Statement blazer. Clearly I’ve missed my work clothes and am willing to mix them up!

Monochrome + relaxed skirts

When I’m out of ideas, I pick one color and go with it. And my tolerance for pencil skirts with their ability to get entirely turned around while I walk is…none. Enter a-line skirts! This is a secondhand pleated skirt and it’s my complete favorite, flowy but not too voluminous. I’m also excited to break out the office sweaters again, like this linen blend one (restocking in May, get $25 off your first order with code REBECCA25), which is perfect when it’s 100 out but 65 in my building.

Casual Friday

Could my outfits get any more casual?? Hahaha. This has been a favorite recently for running errands so I’ll be happy to put it to work on more casual work days. Finding a pair of light wash but not distressed denim was a bit of a treasure hunt for me. Also, these sneakers are waterproof, so perfect for fall (and they have a little wedge and I’m excited to try them out with dress pants too just for some funky combos). Finally, this is my pitch for a more luxe t shirt, which just makes me feel so put together, and is great for layering.

Do you have a timeline for a return to in-person work? What have you missed wearing? What have you NOT missed wearing?

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4 thoughts on “Easy, comfortable outfits for going back to the office”

  1. This post makes me a bit jealous because I live in Canada where the vaccine roll out is basically non-existent … That being said, I am a teacher and so I have been going to work every day 😅


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