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Dressing Smarter Than Your Boss

Anonymous

I've got a slight dilemma and am wondering if anyone has some similar experiences:

I'm hesitant about dressing better or 'smarter' than my boss (a woman). As soon as I started working at my new job other co-workers said that they knew I'd be fun to work with based on my interview outfit (mainly my yellow shoes). I take pride in dressing smart-casual and feeling put together helps me be confident in this new job. However, my boss seems... uncomfortable at times. I know I feel uncomfortable about 'upstaging her' and I don't want to make her feel uncomfortable.

Usual outfits I will wear to work are pencil or A-line skirts (or dress pants), a sleeveless dressy top, comfy flats and a cardigan for my chilly office. I'm dressing at the same sort of level as most other co-workers, the dean, and the president. My supervisor dresses following the elements of our dress code, but it comes off (to me) as more thrown together or casual. I don't want to sound snotty... we've all been there and are always working to 'learn' how to dress in flattering ways. It's like my supervisor hasn't seemed to figure out her style yet. I recognize I was there pre-YLF too, but it's hard for me to gauge how I should dress around her. Usual outfits for her are sleeveless dresses layered over tee-shirts and cords or dress pants. (Prepare yourself for the next statement, Angie!) Yesterday we met with the president of a housing corporation that we rent from - and my supervisor wore wide-leg pants that were THREE inches above her shoes. They were not meant to be ankle pants.

What am I to do? I can't dress down any more - since I'm still getting to know her I can't try to offer 'advice' - I don't want to be rude. My husband thinks I need to be careful about how I dress, so I don't damage the new relationship - what do you all think?

Dressing

24 replies

Latest reply was from Sihaya

rute

Veteran

eh eh loved your post!

Never dress down.. you are rising the style level.. I'm sure your boss will learn with you!

That's what happend with me.. my boss is also a woman and my other co-workers always said that everythime I left the room she would stare at me (from head to toe), many years have passed but I feel that her style has increased! She even has one shirt equal to one I have!

RoseandJoan

Veteran

I think your consideration should be applauded, I have never found myself in this situation myself, however I'm inspired and respect people I meet everyday who have developed their personal style. I do not feel you should tone down your style to fit with your boss, however I would not offer style advice unless asked.

It is important to remember that not all people place the same impetus on style as the people on this forum, and for the most part these people are happy going about their lives dressed this way.

If her style is not appropriate for her role in the workplace then it would be an issue for her superiors to address.

Sarah

(website)

Veteran

I'm in a similar situation except my boss and co-workers are male. It definitely makes it easier for me to dress smarter than they do, though. I say dress in a way that you feel is appropriate regardless of how she dresses. Just be warm, respectful, and appreciative of her and you should be fine.

medusa

Veteran

I'm not sure what you think about this suggestion, but: why don't you ask her? You could say something like, "I'm new at Company X and I want to make sure I fit in to the workplace culture. Do you think that the way I dress is appropriate here?"

I suggest this because I've learned from working with students that sometimes they worry a lot about things that I'm not aware of...I wish they would just ask me. I know with your boss it's not a student/advisor relationship so it's different. But maybe it's worth a try.

Sihaya

Veteran

LE - as long as you're dressing in what's work appropriate, then I would say you want to be yourself. If you start to give away who you are, it's a slippery slope. You're not huring anyone. And your boss did hire you.

Melody

I would definitely not dress down because of anyone else. Maybe your boss will pick up your cues and be inspired.

Besides, if she is uncomfortable, it doesn't matter what you do, she will still be uncomfortable. You dressing down does not improve her. Nothing will help pants that are too short by 3 inches.

Angie

(website)

Fashion Stylist

Fab post, LE! So nice to see you back on the forum. I’ve missed you.

I have often been in your situation. My approach towards your new boss is therefore less complicated and less sensitive (I am hard with this type of thing). Do not lower your dressing standard. You’ve come in dressing a certain way which I know is appropriate – keep it like that. Inspire others.

Isn’t it interesting how your personality was judged by the look of your shoes. Food for thought.

shiny

Veteran

I agree with Medusa - why don't you broach this subject directly? Perhaps over lunch?

I had a boss who didn't give two figs about clothes and fashion. Her clothes were clean and fit into the dress code - it's just that she probably bought her work wardrobe 25 years ago and that was that. No updating. She was candid about it, even when her boss told her she needed to step it up if she was going to get ahead. She is a very rational person who is quite secure in her own self, so it did not faze or ruffle her in the least. In fact, she'd joke about it, how she didn't inherit the "fashion" gene.

I do have a point here: make sure that it's the clothes that are making her uncomfortable. Maybe you are only assuming that? Perhaps it's not the clothes per se, but that, for example, when you met with the president he reached to shake your hand first, assuming you were her boss. Or there is some other subtext going on that you are not privy to. Or when you saw her PPL, you had a fleeting microexpression (we often can't control these) and she picked up on it?

I guess what I'm saying is that if you are new, and feeling insecure about your job in general (which would be expected!), you may be misinterpreting her body language and/or making it all about you, when it's not. Or your own body language - unbeknowst to you - is sending her signals! Maybe when you saw her PPL you had a fleeting microexpression she picked up on?

To illustrate - a year after me and my ex-boss, first started working together, she confided in me that I completely intimidated her - because I knew more about marketing than she did. I was floored. Because SHE completely intimidated me - with her deep background in engineering! She is the smartest woman I have ever met in all my years. I was literally terrified of opening my mouth and saying something stupid in her presence! She'd misinterpret my quietness as my looking down on her lack of knowledge in marketing, and vice versa for me. We had such a good laugh over that.

marianna

Veteran

I always say: Dress for the job you want, not the job you have. I see no problem in dressing well and better than your boss. In my eyes it shows motivation and determination!

garmenta

This is a tough situation to be in. Women are much more attuned to appearance than men, and bosses aren't an exception. The last thing you want is for her to think that you feel superior because you're more stylish!

Work on gaining her trust with your ability, and make her look good in her role as your boss (don't even mention how she looks in her clothes!). Don't dress down to her level--you wouldn't feel comfortable!--but focus on looking crisp and professional rather than fashion forward.

If I remember right, aren't you in an academic environment? That complicates things--some academics are proud of being badly dressed because it proves how little they care for appearances--that may be playing into this as well. I wouldn't dress sloppily or badly to put other people at ease, but keep in mind that academics feel differently about fashion than people in many corporate environments, where self-presentation matters a lot.

Be good at what you do, be personable with everyone, have fun with the people who liked your yellow shoes, and make your boss look good in her role as your boss . . .A tall order!

Antje

Veteran

Very interesting post/issue! I'm with those who suggest to not change anything about your own look, given it is professional and appropriate. I disagree with the posters who suggest bringing up the issue with your boss, and here is why: You think that she is uncomfortable with how you dress, but this is really just an assumption on your part, correct? There is always the possibility that your boss is totally happy with how she dresses, in which case there is no reason whatsoever to talk about dress codes with her, and in fact it could just make you look too focused on this issue. On the other hand, if your boss is indeed unhappy with her own look, and/or is envious of your style, then she certainly wouldn't enjoy a direct conversation about this, either. My suggestion is to just try and ignore the difference in dress and to not dwell on it yourself; hopefully you will influence her indirectly by setting a great example of professional style, but otherwise just accept that you dress smarter, be relaxed about it, and focus on your professional interaction with her.

Angie

(website)

Fashion Stylist

There are opposing yet super empathetic responses on this thread. You have a lot to think about, LE!

This is going to come as a huge surprise I’m sure and I *almost* didn’t post it. But I really don’t think you should speak to your boss about this matter at all. Things will get hopelessly misconstrued. I can feel it in my bones! Dress how you normally dress, sass out the culture of the org and do your job to the best of your ability. Over thinking things *can* be dangerous.

Sorry I’ve given you more to think about :0(

shiny

Veteran

Reading Angie and Antje's post, I change my position. Don't bring it up. My initial thought was why waste a year like my ex-boss and I did, when you can clear the air now. But re-thinking it, the difference is that my boss brought the subject up first, not me.

Angie

(website)

Fashion Stylist

I didn't even see Antje's viewpoint - I think we posted at the same time, and I was very focused on not mincing my words, so I didn’t read any further comments on this thread.

Let us know what you decide to do, LE. Good luck with the new job!

Anonymous

Wow, what great input! I can see the pros and cons of everything that was proposed - thanks!

I wasn't able to look at any responses until after work, and I too had come to a decision not to talk to her about it. I will be working very closely with my supervisor, and I want the relationship to build well - so I may be reading into things more than I should to make sure I'm performing at expectation. I think that after a month or two, if I am still picking up on the 'vibes' or feeling like I am still make those assumptions, I'd rather have a conversation along the lines of "is there something wrong? I feel like we're "off" lately..." than a "is my dress code okay?" conversation.

I want to be true to myself, and I know that dressing up is important to me - like Antje said, she may be completely satisfied with who she is, and if that's true she may not be bothered at all! After all, she is adjusting to a new employee as well; my predecessor may have been very different and it may take some getting used to for her and my coworkers, who knows?!

Thanks to all for such profound thoughts!

wilson

Ooooohhh how I love the opportunity to share this poem by Nelson Mandela:

OUR DEEPEST FEAR

Our deepest fear is not that we are inadequate.
Our deepest fear is that we are powerful beyond measure.
It is our Light, not our Darkness, that most frightens us.
We ask ourselves, who am I to be briliant,
gorgeous, talented, fabulous?
Actually, who are you NOT bo be?
You are a child of God. Your playing small
does not serve the World.
There is nothing enlightened about shrinking so that
other people won't feel insecure around you.
We were born to make manifest the glory of God
that is within us.
It is not just in some of us;
it is in everyone.
As we let our own Light shine, we unconsciously
give other people permission to do the same.
As we are liberated from our own fear,
our presence automatically liberates others.

Angie

(website)

Fashion Stylist

It's UNCANNY that you chose today of ALL days to quote Madiba (Mandela’s nick name in Xhosa). Watch today’s blog post.

LE, I think you did the right thing.

Laura

(website)

Veteran

I think you did the right thing too. Be yourself and be confident and kind and it will work out for the best.

Kristen

(website)

Veteran

I absolutely think you did the right thing too, LE! You may come to find, like Shiny did, that the vibe you are feeling is due to something entirely different. Let her work it out and come to you, and don't worry about dressing down for anyone. You may find that the standards of dress start to raise up all around you, jsut because of your presence! I've found that to be true in my job; I haven't done anything but keep on dressing nicely, and a lot of the other women have raised their game too. It's been nice to see!

Michelle

(website)

Veteran

This has been a fascinating thread to read, and I absolutely concur with the consensus here; you've done the right thing by not mentioning it. I also support continuing to be yourself by dressing well; doing anything else would feel unnatural and ultimately wind up being counter-productive. I know maintaining the status quo probably doesn't feel like much of a resolution, but I believe it's the best approach. Hopefully the rest will fal into place soon! Keep us posted.

Laura

I wholeheartedly agree with Angie and others who recommend you dress your best!

I'm curious, do you work in the tech industry?

Anonymous

wilson, the poem you posted has always resonated with me. Thanks for the reminder.

LauraN, I work in university housing.

An interesting thing happened today - during lunch, my supervisor and another coworker and I went to J. Crew! It was very fun - I felt like we loosened up and could chat away about things that we liked or thought would look flattering on one another. I hadn't picked up my last paycheck from J. Crew either, so that was a bonus.

Angie

(website)

Fashion Stylist

That's brilliant. All sorted :0)

Sihaya

Veteran

A clarfication - that quote, which is one of my favorites, is often mis-attributed to Mandela but is actually by Marianne Williamson. LE - great that this got resolved so well.