Dressing Professionally But Comfortably: What to Wear for a Long Flight

Vince Camuto Ponte Knit Ankle PantsWhat should you wear on a long flight with colleagues if you want to be comfortable but still look professional? Reader N wonders…

Could you do a post on comfortable, but professional attire for international or long flights? I have an upcoming business trip where my boss and two colleagues will be on a long flight with me. I want to look presentable but still be comfortable for the long flight. Thanks!

I’m curious to hear what people say here; this reminds me a bit about our discussion about what to wear when you’re out of town and working late all the time. (Here’s a fun question, readers — do the answers change if you’re sitting with your boss/colleagues on the long flight? Every time I’ve traveled with colleagues we were sitting apart, and I was so thankful to freely relax/sleep/read brain candy on the flight.) Some thoughts, in no particular order:

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A Feminine Approach to Business Casual

Dressing Femininely at Work | CorporetteBusiness casual can be tricky — particularly when you’re transitioning from a conservative office.  But what if the culture at your company isn’t just business casual, but ultra-feminine business casual — and you’re still most comfortable in a gray suit?  When you’re in a new job and feeling pressure to dress a certain way to fit in — even getting critical comments from coworkers — what should you do? Reader E wonders…

I recently relocated and am in the middle of a career change, and I’m really stumped about how to dress for work. I work in a business casual environment in a small, Southern city. Women tend to dress hyper femininely here: today my boss is wearing a pink ruffled tunic over flowy trousers with embellished flats. The job is entry level, but it’s an important step career-wise. I’m all for dressing to fit with office culture. But, really, yikes.

Right now my pencil skirts, sheath dresses, flats, and cardigans are getting a lot of “why are you so dressed up?” and (from the office mean girl) “do you always wear such depressing colors?” I guess these are my questions: how far do I really need to go to fit in with office wardrobe culture? and how can I femme-up my wardrobe without looking like 5’10” wedding cake?

Hmmn.  Well.  It seems like a few things are going on here, some of which we’ve talked about before, such as transitioning a corporate wardrobe to a casual office, looking stylish and professional in a business casual office, as well as surrendering a bit to office culture (but as the song goes, don’t give yourself away). I may also detect a smidgen of . . .  judgment? superiority? in your email, which we’ve also talked about before when you take a job that’s beneath you.  I know all about finding your groove with one set of work clothes, having a rough time transitioning to a new office with a very different culture, and then feeling a bit like you’ve lost yourself in the process.  So I definitely have some thoughts, but I can’t wait to hear what the readers say.

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Going-Out Clothes and Young Professionals

Going Out Clothes for Adults | CorporetteOnce you get to grad school, can you stick with your “going out” style from college, or is it time to make some changes? Reader C wonders how to dress for a night out on the town when she’s out with new friends from grad school…

I have a strange request/question. I’ve begun learning all about clothing for work, interviews, etc., and now know the difference between business casual and chic casual. My problem is that during my undergrad, “going out” almost certainly meant tight shirts, tight pants or leggings, and high heels, as well as blow-out hair and smokey eye makeup. Jackets were a never, and cleavage was a must.

I was recently invited to go out with from friends from my new school, and pretty much realized that I don’t know how to dress like a grown woman when I’m doing something super casual with friends, like going out for a few beers or even out dancing. I still want to look the part in some ways (these are, after all, my future colleagues — I don’t want to be remembered as “cleavage girl”), but still dress to have fun.

Please teach me to be a respectable adult, even while I’m supposed to be out having fun.

Great question, and I’m torn between a few thoughts. First: you’re in school; if you’re going out with friends it shouldn’t matter too much. On the flip side, I think it can make an impact on how people remember you, and the bigger the dichotomy between your work or student persona and your “weekend persona,” the more people will remember it.

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Are Skirts and Dresses Unprofessional?

Are Skirts and Dresses Unprofessional? | CorporetteAre skirts and dresses unprofessional? What if you have a boss who has a firm opinion, one way or the other? What if you have a boss who forbids YOU from wearing dresses and skirts, when other women in the office can and do? Reader A wonders…

I recently started a new job in a creative industry, and our offices are officially business casual but usually just regular casual. My boss hates that I wear dresses and skirts. She told me that looking feminine in the workplace is bad for careers and she only wants me to wear jeans or khakis if she’s in the office and I can only wear skirts when she travels. I’ve abided by it for a couple months since she was really persistent about it, even though other women in the office wear skirts. I’m confident that my skirts are not inappropriate length wise, they’re standard work skirts from Macy’s and Lane Bryant. Nothing ruffly or lacy either.

Anyway, my manager is leaving the company, but now I feel insecure about my clothing. Is it a bad move to wear skirts and dresses several times per week?

Wow. Honestly, your former manager sounds super annoying — particularly given that other women in the office wear skirts! I can only assume it’s a personal problem with you (something about your style irks her) or she is being sizeist, whether consciously or unconsciously. (The other possibility I thought of after Googling Reader A’s email address: The manager felt threatened professionally by Reader A, who already has an established, successful career — and wanted Reader A to look less managerial.)

Whatever the issue: I’m sorry you had to deal with it, and I’m glad the manager is on her way out. We’ve talked before about when feminine clothes are unprofessional, as well as how to look professional in a business casual environment where the guys are in jeans and hoodies, but not all at once. So let’s discuss.

  • Know your office. You say other women in the office wear skirts — how are yours different, if at all? Are you wearing them with much higher heels that you wear with pants? Are the women who wear them in different roles than you are (for example, much more senior or much more junior/administrative)? Reading office culture — and fitting in — is an important part of your job. You don’t have to give up your entire personal style, but you do have to learn when to play it safe — years ago we had a successful goth lawyer guest post on this very topic; we also recently discussed how clothes are only “empowering” if they actually help you get power. Without seeing your office it’s hard for me to make suggestions, but when I hear “creative business casual” I think of a shirtdress with flat boots, for example, or a sheath dress with a jean jacket and a scarf instead of a cardigan. We’ve talked about how to transition a conservative wardrobe to a casual office before.
  • A feminine style is one thing; being in costume is another. This doesn’t sound like it’s an issue with Reader A, but I’ll mention it briefly. If you tend toward a more girly style — A-line skirts, high heels, full makeup — you may be crossing the line from “dressed up” to “in costume.”  Particularly be wary of more vintage styles for the office.
  • Start slowly. Since you’ve been abiding by your manager’s weird “rules,” the office may perceive this as a style change — so start slowly. Wear one dress a week, not all dresses. See how people react, what comments you get. On the days that you aren’t wearing skirts or dresses, dress up your pants outfits as well — wear a blazer with jeans, or a feminine cardigan with khakis. (Some of our advice on dressing for a promotion may help bridge the gap between your jeans wardrobe and your dress/skirt wardrobe.) If you have a favorite pair of shoes you wear with your skirts or dresses, wear them with your pants and see how it goes.
  • Get an honest second opinion. If after a few times of wearing a dress you still feel uncomfortable, talk to your HR department or a more senior colleague you trust to give you an honest opinion. They know your former manager, your office, and you, so they may be able to give you better insight here.

What are your thoughts, readers? How would you handle this (now, as well as with that manager) if you were in Reader A’s shoes? Do you think dresses and skirts can be unprofessional?  

(Pictured: Hollywood 819, originally uploaded to Flickr by Jessica Hartman Jaeger.)


N.B. These substantive posts are intended to be a source of community comment on a particular topic, which readers can browse through without having to sift out a lot of unrelated comments. And so, although of course we highly value all comments by our readers, we’re going to ask you to please keep your comments on topic; threadjacks will be deleted at our sole discretion and convenience. Thank you for your understanding!

Law School, Orientation Outfits, and Dressing For You

Law School, Orientation Outfits, and Dressing For You | CorporetteHow should you dress for law school orientation? When you’re planning which outfits to wear, how much should you worry about looking professional, or put-together, or about making a good first impression? Reader N wonders…

I am extremely excited to be starting law school in the fall but I am puzzled by the idea of picking orientation outfits. Any suggestions?

Congratulations, Reader N! I still have such fond memories of law school, and we’ve covered a lot of things about it here, such as what to wear for mock trial competitions, which bag is best for law school casebooks, hornbooks, and of course your laptop. We’ve even talked about how — if you’re shopping for clothes before law school — your money may be best spent on interview and work attire. 2Ls, 3Ls, and recent grads: Anyone care to write a guest post on what bag is best these days, as well as any other tips or tricks for marrying the digital world with the study of law? For example: Did anyone like reading cases on Kindle or taking notes on an iPad (or, gah, an iPhone)?

ANYHOO: I’m sure I worried about which outfit to wear to orientation, but I couldn’t tell you what the heck I wore if my life depended on it. I was only two years out of college when I went to Georgetown, and honestly I don’t even think anything had occurred to me as not being “work-appropriate” (beyond a super short corduroy miniskirt that one of my older editor friends had pulled me aside and told me was not appropriate). Some of the older students had already formed conservative work wardrobes (particularly those who were coming from years on the Hill); others maybe just had a preppier style.

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Wearing a Dress and Blazer — Instead of a Suit

Dresses and blazersIs an outfit composed of a blazer and a dress an acceptable substitute for a suit? Reader B wonders how to mix dresses with blazers for a fairly conservative space (the DA’s office):

I start work at a DA’s Office next month, and I’m trying to round out my work wardrobe. My difficulty is this: I despise pant and skirt suits. (Yes, I recognize they’re a necessary evil and yes, I own several.) I vastly prefer to wear work-appropriate dresses (always with sleeves) with blazers that I can throw on when I need to go to court.

How do I go about matching blazers with dresses? Must they come as a set? Be the same fabric? What about colors and necklines? Basically, I have a closet full of gorgeous work dresses, but I need more blazers if I want them to work at the new job.

Hmmmn. Reader B, you’re definitely going to have to learn the ropes at your office before you buy any more dresses, because in some very conservative offices — with some judges — a dress with a blazer on top is likely not going to cut it in terms of formality. Hopefully this won’t be the case where you are, but I really caution you to play it conservatively for the first month or so and wear the separate pant and skirt suits you own, and the few matching sets (dress + blazer) that you own.

As for how to mix a dress and blazer otherwise for work:

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