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    Ever Wonder What Your Boss Thinks of Your Clothes? We Find Out

    A few weeks ago, I received the most important phone call of my post-college life. I officially got my first "real" job. Finally! I felt beyond amazing … until that giddy excitement faded into some minor anxiety.


    Related Link: Worst Interview Disaster Stories


    Besides worrying about screwing up on the first day, I had another concern. What should I wear? I had my interview look down -- check it out here -- but now I needed a whole wardrobe that was "work appropriate." Luckily, I have a pretty cool (but brutally honest) boss, who had no problem telling me what she thought of my outfits.


    Click here to see my first two weeks of office outfits, or scroll down for the first five looks.


    Day 1: Suit Up

    Today's my first day and I'm really nervous. I want my boss to know I'm taking this job seriously, so I decide on a professional look. The second I walk through the door, my face turns bright red. From what I can see, the dress code in the office is definitely more trendy and creative than business casual. Which means I'm way too overdressed. Note to self: leave the blazer and pearls at home next time.

    Boss says: "Chelsea definitely looks professional, but since she's working at an editorial position and not an accounting gig, I'd say to tone it down a bit. Maybe lose the jacket and the pointy heels and swap the pearls with a funkier necklace. The way she's dressed makes her a little unapproachable, and it completely hides her bubbly personality."


    Day 2: Adding Color

    After yesterday's fiasco, I decide to put together something a little more high-fashion. I love wearing color because it definitely makes a statement on its own, so I don't overdo it with too many accessories or a crazy hairstyle. Instead, I do my hair in a simple ballerina bun and add a long gold necklace with some colored jewels.

    Click here to see if my boss liked my trendy look.






    Day 3: Button Down

    In my opinion, an oversized button-up shirt over black leggings is the new T-shirt and jeans. Maybe even a little more sophisticated than the jean/tee combo. It's comfortable, cute, and casual. Add my favorite pair of riding boots and my sister's funky chain necklace, and I'm ready to go. (Sorry sis, I'll put it back.)

    Boss says: "This is a fun way to keep a classic white button up looking modern and young, and the pulled-back hair and cat-eye show she put in a little effort. Even when she's wearing something tight (like the black leggings), Chelsea knows what to wear so that it works (the oversized blouse). I would play around with the accessories more and maybe try out different shoes, but overall this is a good look for the office."



    Day 4: Leather Love

    I've got a Katy Perry concert tonight, and since I'm going straight from work and don't really feel like changing, I wear my concert outfit to work -- this comfy motorcycle jacket and my favorite strappy heels. I'll be out pretty late, and I know we'll be dancing all night, so an updo is a must.

    OK, so the boss didn't love this one, see why.






    Day 5: Casual Friday?

    Last night went a little later than I thought. OK ... a lot later. It doesn't help that I pressed the snooze button three times this morning, but I'm more worried about being late than looking great today. So glad I was able to find a beanie to cover my bedhead.

    Boss says: "I think someone is taking 'casual Friday' a little too literally. Flip-flops are a no in almost any office. They're just not professional and definitely aren't a good choice if you're trying to impress the boss. The slouchy sweater and tee could work separately with other pieces, but together they say, 'I just rolled out of bed,' not 'I'm ready to work.'"

    To see the rest of my outfits (and if I did any better), click here.

    Now, I want to know: What's the dress code at your workplace?

    And for more fashion dares, like us on Facebook and follow us on Twitter.


    More on BeautyRiot.com:

    13 Must-Have Wardrobe Essentials
    You're Wearing the Wrong Bra

    10 Ways to Wear a White T-Shirt

     

    51 comments

    • KathyL  •  San Francisco, California  •  3 months ago
      The only outfit that works at our office is Day 1. The others are too casual for business dress. Day 3 would work for Casual Friday, but the other outfits show that you're not ready to work...they show that you're ready for the weekend. Day 5 is definite NO at any office, unless you work from home.
      • A Yahoo! User 3 months ago
        "Day 5 is definite NO at any office"... you've never been at my office and I'm glad I don't work at yours. I wear what I want. My skills are more important to them than what I'm wearing. They hired me for my brain, not my wardrobe.
      • Robin J. Sky 3 months ago
        You must not work where people (clients) can see you, Cruella. Like it or not, your clothes are a reflection of the company and how it does business, and I can't imagine ANY office job that would allow their employees to be seen by their customers in an outfit like that. Granted, "office" job covers a wide array of actual fields and occupations, and office cultures vary, but I still have to agree that looking like a college freshman who just rolled out of bed is not generally a good way to score points with anyone.
      • A Yahoo! User 3 months ago
        Good thing I don't give a flying$##@ about 'scoring points' with anyone. I'm not an #$%$
    • TH  •  3 months ago
      I work remotely from home. So I go to work in my PJ's mostly.
      • Martha 3 months ago
        Hehehe...Feels great, doesn't it? My favorite "work outfit" is a ratty tee shirt and an old pair of yoga pants. And fuzzy slippers. Gotta have fuzzy slippers! :D
      • D 3 months ago
        ME TOO!!!
    • vnsa  •  Pleasanton, California  •  3 months ago
      The problem with this "article" is that these are intern outfits (which you find out if you click to the original piece). No one cares about you that much if you're an intern.
    • JetSetter  •  Kingwood, Texas  •  3 months ago
      I've noticed my boss dressing like me latley. I take that as a good sign.
    • JoAnne  •  3 months ago
      i still think a pair of jeans ( no rips or frayed edges ) paired with a blouse or modest t-shirt, shoes or boots ( no running shoes ) and a blazer if fine for office wear.
      • LJmommy 3 months ago
        I totally agree, and jeans were totally allowed in my former office if worn in this manner.
        The problem is, someone would abuse it and come in in tattered jeans and a too tight top or something and then it was over for the rest of us. My favorite outfit was a silky black (not low cut) blouse under a blazer with dark indigo jeans and black heels.
      • JoAnne 3 months ago
        you are so right LJ. that style of dress states "i'm professional and approachable".
    • Mary  •  3 months ago
      my superiors personally tell me that they love my fashion sense...
      from my first day of work even up to present :)
      • A Yahoo! User 3 months ago
        sounds like ur doing everything right, good for you, hold on to that job!!!
    • Disgruntled  •  3 months ago
      I work in a public library and for once the administrators seems to have figured out that the job requires a lot of standing, walking and movement as well as dealing with a lot of dusty books so we're allowed to wear jeans and sneakers to work. Even so, I would never wear the casual Friday look from this article because it's far too sloppy and unprofessional for work. I wear nice jeans and a nice top, never a printed t-shirt or flip flops and I frankly don't understand why anyone who works indoors feels the need to wear a hat to work.
    • Stef  •  3 months ago
      I could never do #3 regardless of the environment. Leggings look like you're wearing opaque pantyhose and you forgot to finish dressing. Get some black pants, and wear an Oxford that actually fits, and then you'll have a decent outfit.
    • Jacce  •  3 months ago
      Is this writer really that stupid to wear some of this stuff to the OFFICE, no matter WHAT office? She goes from one extreme to the other. Somebody teach this woman how to dress appropriately for the situation and stop her from writing articles and advice about it, PLEASE!!!
    • ♥♫♪♥MadeInAmerica♥♫♪♥  •  3 months ago
      When I worked, I was a lady long haul trucker. I didn't work in an office, but came in contact with company customers often. In trucking, the customers are the shippers and receivers. In between arrival and departure, it didn't matter what I wore as long as safety was kept in check...closed toe work shoes, preferably boots. My cowgirl boots were my everyday wear, along with jeans, leather belt with a big, ornate silver belt buckle, western tops, and my cowgirl hat. :^D

      At any point en route I could have been pulled over by either law enforcement or D.O.T. officers, whether at a weight station or roadside, and had a vehicle inspection done. If that were to happen, appearing safety conscious never hurts. Arrival at a shipper or receiver, for me, meant making cleanliness top priority. Right before arrival, if my clothes weren't totally fresh, I'd stop somewhere along the way, shower, and put on something crisp and clean.

      Not only does it give the company you are representing a good impression, it often times allows a driver preferential treatment, getting them in and out of the docks faster than other trucks waiting to be loaded or unloaded.

      When I had students on my truck, when I occasionally trained truck driving student recruits, I dressed a tad more conservatively while out on the road until they graduated to their own truck. I trained both male and female drivers. Females didn't care what I wore (with the exception of one lesbian student), but the males I had to be careful with the way I dressed around them since they lived on my truck for weeks on end while in training.
    • Pam  •  3 months ago
      This is why I work in the mining industry, we all dress alike. And living in Alaska if you don't wear jeans you are a politician or lawyer.
    • Rent To High  •  Dallas, Texas  •  3 months ago
      I won't wear leggings but I do wear slimming pants that almost mimmick leggings but not. I have always liked to dress up, I am a girly girl. I wear classic clothes that never go out of style. I don't like tight clothes but just enough to make one look slim.
    • PAM I AM  •  3 months ago
      I dress according to my company's dress code...therefore, I really don't care what my boss or anyone else thinks about my clothing choices. You don't buy my clothes...so #$%$ if you don't like them.
    • me  •  Cleveland, Ohio  •  3 months ago
      I can't wear any of this. I have to wear a nice sweater or top, with khakis or black pants. In the summer I can wear a knee length skirt. For shoes I have to wear new sneakers, that are comfy, or I can wear rubber soled flats in the summer with the skirt. I work in a pharmacy so that means long hours on my feet. And we are required to have our white lab coats on at all times.
    • garykuta  •  Manteno, Illinois  •  3 months ago
      I am very familiar with the finer points of what is now termed office casual. In fact, that is part of the problem. When office casual was first introduced during the Clinton years, the federal government never stepped in an established any kind of guidelines as to what this new office casual was actually going to consist of. Everyone was basically in favor of it, it's just that nobody could actually define it.

      The feds left it up to the individual companies to lay down the law and determine the boundaries, which automatically set up a recipe for disaster. And so not surprisingly, it being the 90's, lawsuits proliferated. You had a bunch of baby boomers who were formerly rebellious teenagers telling their employers that nobody had the right to tell them how to dress. The attorneys had a field day. It was, and still is, a contestable case.

      Deadlocked, leave it to the British to step in and teach us bloomin' Yanks how to dress. An English gentleman by the name of Andy Gilchrist self-published a book where he broke all (men's) apparel down into five levels, from casual to formal, and once the groundwork was laid down, he revealed how certain sets of closet coordinates could either be dressed up or dressed down, depending upon the weather and/or how the situation warranted it. Vertical integration. God Bless the British.

      Now, office casual aside, if I were taking a lady out on a date I'd like her to look like the example in Day 4: Leather Love. To me, this is a classic rock'n'roll "look" that can never go wrong.
    • Jennifer  •  Augusta, Georgia  •  3 months ago
      I work remotely from home, so whatever I cook in is what I typically wear. However, when I do have an office day: Uniform, usually. For a presentation or a business after hours: Casual business. For the occasional Saturday: Jeans and a respectable blouse with boots or my slip ons. My boss is pretty awesome, so clothes aren't too big of a worry there.
    • Elm  •  Middletown, New Jersey  •  3 months ago
      I say if you're not dealing with clients or public outside of the office why not wear what you want (as long as it isn't flip flops or showing too much skin).
    • Han  •  Fargo, North Dakota  •  3 months ago
      I can't stand to wear shoes. Every summer, I wear my flip flops when I get the chance. In high school, I hated wearing shoes so much that I'd wear my winter boots to school during the winter season and change into my flip flops once I got to school. To work somewhere where flip flops were fine with the boss would be awesome.
    • CONDOR  •  Saginaw, Michigan  •  3 months ago
      Most women forget that the workplace is there for business and not a venue for sexual tactics for favors or dressing to the borderline of smut just to attract attention!! If the wrong person does make a remark on how much skin is being displayed, then these morons run to HR for intervention only when the one they were trying to impress ignores them!! ITS A WORKPLACE NOT A SINGLES BAR"!!
    • greene_teeth  •  Chattanooga, Tennessee  •  3 months ago
      It seems one of the purposes for us meeting to have lunch was reminiscing about the past glory days. My friend did not know that one of his encounters of the close kind was a woman who had introduced his encounter to me. I had nothing to do with the setting up of these encounters.

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