Reader Mail: What to Wear to a Very Casual Office
How do you look polished in a casual office — particularly if people are dressing VERY casually? We had an interesting discussion on what to wear to work in Silicon Valley in 2017, but haven't talked about professionalism in a laid-back office in years, so let's discuss. Today's reader Q is from reader M, who wonders what to wear to a VERY casual office as a Spanish teacher:
Hi! I am a Spanish teacher at an independent day school, grades 6-PG (post-graduate). There really isn't much of a dress code. Adults haven't begun to wear ripped jeans (yet), but they do wear flip flops and Bermuda shorts (men), and leggings (women). I am not kidding. Usually, one can gauge appropriate attire by what the management is wearing. Not where I teach.
So … my question is: How does one maintain a modicum of professionalism in attire where it minimally exists? Thank you!
Great question, M! Of course we'd recommend reading our best tips on how to do business casual without looking overdressed, how to look great for work every day, what to wear to a big meeting at a casual office,as well as how to look professional in a business casual office. But for specific tips for your situation, read on…
What to Wear to a Very Casual Office
For my $.02, I feel like schools are different from many workplaces because you want to be approachable and fun, as well as professional — the “fun” aspect may not necessarily apply to other offices.
So if I may default to the perspective of a parent: As a parent I've never thought less of teachers in leggings, or pants with crazy prints, or graphic t-shirts — but I've always appreciated their professionalism in terms of speaking knowledgeably about my child.
(In other words: Speaking as a parent, your clothes don't matter, but your words do.)
For teachers or other authorities who look Very Young, slightly different rules may apply and you may want to, say, avoid French braids, really colorful hair (purple, blue), ripped jeans, spaghetti-strap tanks, crop tops, and more, just because you may be making things harder for yourself. After all, if a parent's first thought is “I have dresses older than her,” you're waging an upward battle where the default thought may be that you DON'T know anything and are still in a very early stage of your career.
(You may want to review our older discussions on how to avoid acting young, as well as how to be taken seriously when you look young.)
From a workwear perspective, though, on days where you want to look extra polished, I think this goes back to the idea of a third piece and structure — adding a blazer, cardigan, moto jacket or even denim jacket wherever possible — even an open, untucked blouse can work. Sometimes a stand-out accessory can also count as a third piece, like a belt used in an unusual way or a scarf (like the woman in the stock photo).
And while no one needs to have “perfect hair” all the time, if you're very young and tempted to do some very young hairstyle such as with pigtails or French braids, now might be the time to look at our roundup of easy office updos. (The inverted Gibson in particular is SUPER easy.)
Accessories can go a long way towards adding polish, too — a watch is always a great way to denote “I'm responsible!” As we noted in our post on “classy, understated” jewelry, strive to avoid jewelry that makes noise, like stacked bracelets.
Readers, what are your thoughts? What would you wear to a very casual office? How do you maintain some modicum of professionalism in a Very Casual Office?
Great Third Pieces for Teachers to Wear
Blazers as Separates
Some of the best blazers for women in 2024 — great for wearing as separates! — include options from Cinq à Sept, J.Crew (collarless and collared), Everlane, and Madewell. Hunting for a deal? Check out J.Crew Factory and Amazon (Cicy Bell, The Drop).
Sweater Jackets
Some of our favorite sweater jackets for the office as of 2024 include M.M.LaFleur (the OG, the jardigan!), L'Agence, Summersalt, J.Crew, and Jenni Kayne. For budget options check J.Crew Factory and Quince.
Classic Cardigans for Work
Some of our favorite classic cardigans for the office as of 2024 include those below — definitely check Talbots and J.Crew Factory if you're looking for plus sizes, and Quince is always a nice affordable option. Veronica Beard and Brooks Brothers both keep a bunch of options in stock.
Relaxed Cardigans for Work
Stock photo via Deposit Photos / Wavebreakmedia.
I moved to a very casual office this spring and I’ve embraced the casualness. At first it was hard because I was used to wearing the more formal end of business casual, but honestly it’s so nice to just throw on jeans and a hoodie. And I fit in with my coworkers a lot more.
Ugh, commiseration? A work superior got really upset with me last week while I was out of town on vacation (I heard via my assistant), and I’ve been stewing about it ever since. This afternoon he dropped by to say he wants to talk later. I know the air needs to be cleared, but I am still dreading the conversation. I feel defensive–I think he’s overreacted and has been somewhat unreasonable about things (look, you can’t hand me a project and then insist on controlling all the details), but at the same time, I have to acknowledge I could have handled the work deadline in question better than I did, and blaming other factors doesn’t excuse me from managing them better. Send me good vibes to handle this with grace.
Ugh! Good vibes coming your way!!
Good vibes! It’s always the worst to have those convos but hopefully you’ll both be able to move forward well.
Yuck. I used to have this issue when I first started with the manageing partner. He was a micro manager and wanted to make sure I did things exactly his way, which was a learning experience for me. But over the years, I learned what he wanted me to do and now I do it — he says even better then he is capable of doing himself! So I don’t even have to discuss difficult issues w/him any more b/c I know what he would do, and I just do it! He says we are just like two pees in a pod, and he is probably right, though he is almost completeley bald and I still have long & beautiful blond hair! YAY!!!
Good vibes! Let us know how it goes!
I’ll check in later after we finally talk. Thanks for the good vibes. He’s been in meetings all day, and hasn’t had time to talk–which was part of the original problem. I got him something to review 1 day before I left town, and he was busy all that day, so he wound up being rushed getting it out–while I was out of the office. If I had known he wouldn’t have had time to look at it that day, I’d have done the final proof myself and avoided the problem, or would have given it to him a day earlier instead of having a subordinate do a first round of proofing that day. But I didn’t ask, and that’s on me.
But yeah, a lot of the problem working with this person is that he’s very, very busy, and it can be hard to communicate.
I’m a big fan of a knit dress – I tend to favor tank styles because I like sleeveless, but short sleeve t-shirt dresses are favored by others. I find them the most comfortable (I’m in the South; it’s hot & humid and I don’t want a waist band!) To me, they’re super casual, but my in-laws (who live in Florida in shorts & sandals…) think they’re dressy. Some people see a skirt and it just reads as more dressed up. I typically add a scarf and/or a cardigan and that’s what I wear most of the time. Some people in my office do wear jeans (I might every so often on a Friday when I don’t have meetings) or shorts (I would NEVER). But some people wear jackets and ties too (academia, roles are ALL over the place).
Maybe you need to find the least casual version of “you” that you can? Whatever your preferred outfit/style, you could probably adapt to be more casual in some ways, couldn’t you? Wear a tee with dressier pants, add “nice” sneakers or casual sandals, etc?
Simple can look professional and casual. I wear a lot of: dark jeans and a crew neck or scoop neck tee with a short cardigan, Old Navy style dresses (with or without a topper), Pixie Chinos or similar (not necessarily the regular pixies) with a basic top, a sweater and jeans, etc. I very rarely wear even ponte blazers. Even the ponte does not mean they are then casual, despite what people who work in business formal may think. I do mostly cardigans and cardigan-like-jackets. I also have some longer cardigans that I’ll use to dress down ankle pants.
I like Putting Me Together for professional casual a lot.
Shoes are key too- heels make anything look dressier. Anything.
I wear ballet flats, street sneakers/allbirds, Toms, strappy sandals, ankle boots and knee high boots.
Sorey, other things as I look at my work Pinterest board:
Fabric and pattern matters immensely. A sheath dress in grey suiting material and a sheath dress in
heathered grey ponte aren’t the same thing. A black on black patterned pant and a black and white polka dot pant might be worn with the same thing but aren’t the same in terms of formality. A basic cotton foldover a line skirt and an a line skirt from Amanda and Chelsea from the rack are not interchangeable.
A midi skirt or dress is going to look less formal but still professional than a knee length or above dress. Pencil skirts will always seem above the level of casual.
Colors will always read more casual but can still be very professional.
Jewelry- a fun necklace without a lot of weight can make an outfit work that would be a bit too much otherwise.
A jean jacket makes many outfits work.
I wear wide leg cropped pants from Uniqlo a LOT in the summer.
A basic crew neck long sleeve sweater or shirt and pants can work great without a single other item.
I visited your blog on Saturday, and searched, “teacher”. Little did I know that the results would show a posting on the question I posed. I was pleasantly surprised. Thank you, Corporette, for answering it. I am grateful for your advice. And, I appreciate the comments and the suggestions they offer.
Inspired by Hermoine said something which resonated with me, and that I have been contemplating since I read it: “Maybe you need to find the least casual version of ‘you’ that you can?”