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.

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."

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.

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."

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.

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?

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