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What Do I Wear There? Answering Your Questions!

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What to wear

This week’s article is a combination of two questions readers have asked me that are time sensitive, so I wanted to answer them both right away!

This article will give you some ideas for what to wear when working at a school (or anywhere where you need to dress professionally but still need to be comfortable and casual), as well as what to wear to a play (or any fancy theatrical or musical event).

What Do I Wear There? Working with Children

First off we have a question from Amanda, who wrote in:

“I just started working at a preschool, and am kind of stuck on clothing ideas. We are expected to dress ‘professional.’  T-shirts are okay, but jeans are not (except for Fridays). I’m looking for clothes that are comfortable and can take some abuse, but still make me look put together and clean. Obviously, working at a preschool is pretty messy. I’m on the floor a lot, talking to the kids, and they have a tendency to pull on my clothing when they are playing or trying to get my attention. What would you recommend for this sort of environment?”

First of all, congratulations Amanda on your new job! While many CF readers may not be working full time as teachers yet, I’m sure many of us are often in similar situations dealing with children—whether it be babysitting, volunteering, or student teaching—and still wanting to look put-together.

Teaching Outfit 1

What to wear when working with children

Product Information: Crew-Neck Tee: Old Navy, Gray Skirt: Shopruche.com, Flower Earrings: Forever 21, Black Patent Tote: Emphaticnyc.com, Cardigan: Uniqlo, Bow Tie Flats: Charlotte Russe

My best piece of advice for dressing nicely when dealing with children is to buy cute pieces from cheaper stores! Check out retailers like Forever 21, Charlotte Russe, H&M, etc. to find fashion-forward pieces that are easy on your wallet. You don’t want to wear anything you can’t afford to replace.

Here, I found a gray, high-waisted skirt (belt included!) and a simple black cardigan for relatively low prices. These are great basics to pick up, as the darker colors are professional (and will hopefully hide some stains) but also seem very comfortable. Keep it classic with a pair of plain flats that will allow you to run after the kids and a big tote that will allow you to stuff in as many supplies as you need.

Since you are working with younger children, you do want to have an element of fun to your wardrobe! Invest in a couple bright, cheap crew neck tops to wear with plainer skirts and pants—they’re not at all revealing, nice enough to wear into meetings, and so easily replaced if they fall victim to stains or tears!

I finished the look with a pair of flower-shaped studs, which are perfect because they are pretty accessories that kids will not be able to tug or pull at!

Teaching Outfit 2

What to wear when working as a teacher

Product Information: Floral Top, Wide Leg Slacks, Gold Belt: Forever 21, Black Canvas Bag: Old Navy, Matte Black Flats: Charlotte Russe, MARC by Marc Jacobs Gold Apple Studs: Nordstrom

Just like with the first outfit, I found budget-priced pieces you can stock up on. For example, these wide leg slacks and a skinny belt (get it in a variety of colors to keep your looks fresh) are the perfect mix of professional and comfortable. The black matte flats are a great investment not only for work but for going out in general—these are a classic, matches-with-everything pair that you can grab for a ridiculously low price!

I tried to add the “fun” element in again with a floral blouse that gives your look a bit of color and individuality. Since the shirt is a bit “louder” in this look, stick with a plain canvas bag for your supplies (I love the faux leather handles on the one above – you can tell it’s really durable). For the final touch, add a pair of adorable studs in the shape of an apple and you’re sure to be the envy of all the other teachers in your school!

What Do I Wear There? Going to a Play

Our next question comes from Jess, who found herself faced with the following situation:

“I am going to a play this week, “Who is afraid of Virginia Wolf?” and I have no idea what to wear. I know you need to be dressy-ish but I can’t seem to find a good outfit…”

For this question, I have devised two pretty different outfits. The first is for a play that is more of a college or local production— nice but not too fancy. The second look is for a more upscale theater production. Hopefully one of these (or a combination of the two) will be right for your play!

Play Look 1

What to wear to a play

Product Information: Ruffle Top, Light Weight Slacks, Marble Knot Tote: Forever 21, Layered Teardrop Earrings: Arden B, Mary Jane Flats: Wet Seal

For this look, I wanted something that was definitely sophisticated but was also pretty versatile (you could easily change into a pair of jeans after the play, maybe slip on some heels, and be ready for a night out)! The ruffle detailing at the neck is classic and romantic, a theme I tried to follow with the teardrop-shaped, dangling earrings and mary jane flats.

To dress the look up a bit, I chose a pair of slim-fitting black slacks that will highlight the black contrast lining on the shirt’s ruffles. The marbled, dark hobo bag matches perfectly with the tones of the outfit and adds a new, modern shape to the otherwise traditional look.

Play Look 2

What to wear to the theater

Product Information: Bow Neck Dress: Modcloth.com, Ribbed Tights, Pearl Ring: TopShop, Black Pumps: Heels.com, Quilted Black Clutch: Aldo

My inspiration for this look was a kind of old-fashioned glamour, as many of the more upscale theaters still have that traditional feel. This vintage-inspired black dress is perfectly tailored and the demure bow at the neck is a fabulous touch. Opt for a pair of neutral-colored ribbed tights under the dress and a quilted clutch to give the outfit a bit more texture in contrast to the smooth lines of the dress.

I picked these low-heeled pumps for their wonderful shape as well as what I hope would be an added element of comfort (the heel is short and sturdy so a standing ovation won’t have you wincing).

Last but certainly not least is the necessary accessory for any classic look—pearls! Or rather in this case, a pearl ring that is just big enough to make a statement without disturbing the rest of the look.

Now all that’s left to do is enjoy your play!

What Do You Think?

From your experience, what are the best clothing choices for when you have kids around? Any tips for dealing with the possible fashion-faux pas that come along with the combination of kids, art supplies, and clothes? Also, do you have any tips on perfect play attire for Jess? What has worked for you at various shows you have seen? Share thoughts in the comments below!

And if you have any more “what do I wear there” questions, let me know! I may feature yours in next week!

Posted on on October 2, 2009 / Filed Under: Fashion Tips / Tags: , , , , , , , ,

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31 Responses to “What Do I Wear There? Answering Your Questions!”

  1. 1
    October 2nd, 2009 at 3:34 pm

    Thanks for this article. I have to go to a ballet in March and I was not sure of what to wear. I didn’t realise for sure that I had to dress as smart as outfit 2 on the play series. Can start looking for more formal outfits!

  2. 2
    October 2nd, 2009 at 4:11 pm

    Hey Colleen,

    I go to art school, and am constantly faced with the dilemma of wearing clothes I don’t mind getting paint on (That are normally not that cute, old, etc etc) or wearing clothes I feel good in and ruining them…

    One of the perfect solutions:
    an Apron!

    My school sells ones with great big front pockets with their logo on it, but there are tons of vintage-looking teacher alternatives. Throw one on when you know you’re going to be messy and presto change-o…you can still go out after class and be totally presentable.

    Good luck!

  3. 3
    October 2nd, 2009 at 4:30 pm

    What an excellent post! I particularly love the second play look. LBD + heels + pearls = killer combination!

  4. 4
    October 2nd, 2009 at 4:34 pm

    Colleen-
    Great article! I’m impressed that you tackled uncommon topics, such as ‘how to dress for children/plays’! This is the kind of stuff you should focus on for your article. To be honest, when I first saw your proposal for a ‘what do I wear here…’ ongoing piece, I was a little like ‘eh’. There are so many articles like that out there, and they all are stuff like ‘what do I wear to a wedding, job, meeting the parents, ect.’ But if you continue to focus on contemporary stuff like this, I’m sure you’ll be on your way to a really successful series.

    Good luck!

  5. 5
    October 2nd, 2009 at 4:36 pm

    I love the first play outfit- I wore something similar to that when I went to a play in London. This is a really unique and original post- I will actually USE these ideas, like Kelly said.

    Awesome!

  6. 6
    October 2nd, 2009 at 5:07 pm

    yeah, i agree with Kell. These ideas are very useful!!!! Thanks(:

  7. 7
    October 2nd, 2009 at 5:13 pm

    What perfect timing! I am actually going to a play tonight, and I’ve been thinking about what to wear all day. Both of those outfits are classy…I think I’m going to try a combination of them.

  8. 8
    October 2nd, 2009 at 6:06 pm

    Wow! I love the second outfit. I have a shirt really similar to that one and I never knew how to wear it properly. Thanks so much!

  9. 9
    October 2nd, 2009 at 8:17 pm

    Thank you for posting this! I’m going to start substitute teaching soon, and I would totally wear both of the outfits you posted for school. Thanks for the inspiration (again)!

  10. 10
    October 2nd, 2009 at 10:06 pm

    Thanks a lot! I am a teacher myself and one of my daily sources of anxiety is what I’m going to wear the next day….this article will save me a lot of time for sure…
    Kisses and hugs form Chile!

  11. 11
    October 2nd, 2009 at 11:10 pm

    Cute outfits! Two tips for dressing for working with kids (I volunteer with 0-3 year olds):
    1. No low cut or super stretchy tops. Kids can pull on your top when you hold them…. exposing your bra. Yes, I know this by experience.
    2. No skirts or dresses. Young kids WILL pull them up due to their insatiable curiosity/boredom. Also from experience.

  12. 12
    October 3rd, 2009 at 4:32 am

    Really cute outfits!
    Reading your page has been my religious in the past year. And I am really happy to see that you are updating it so often these days. Thanks a lot!
    I have just came to Sweden as an exchange program and I will be here for the 1 year. The problem is that it’s damn cold here, and I am really out of ideas on what to wear to keep both warm and cute/girlish!
    The problem is that even for indoor I have to wear warm long sleeve shirts or something with cardigan. Therefore, my outfit is getting pretty boring and repetitive!
    Would you be so kind as to give some suggestion for us girls living in very cold places?

  13. 13
    October 3rd, 2009 at 9:19 am

    The second play outfit has to be my very favorite! I love going to plays and my biggest pet peeves is when people show up a hotmess.

  14. 14
    October 3rd, 2009 at 10:43 am

    The ones to wear with kids are awesome, especially since I’m in school to become a teacher. :] Thank you!

  15. 15
    October 3rd, 2009 at 10:46 am

    I hope you continue this as a series! I was doubtful when I read the title but this is well thought-out. I love all the outfits! So classy and beautiful.

    I’m so glad that you brought out cheaper options that actually look nice. An expensive item is a dangerous thing in a reaching’child’s hand. ;)

  16. 16
    October 3rd, 2009 at 1:12 pm

    I’m terribly disappointed with this article. I work at an elementary school and also at a pumpkin farm, so I know exactly which clothes are great to work with kids in, and what won’t do. Skirts are definitely a no-no. Even if they’re long, you’re constantly bending over to pick things up, and it’s best to wear pants. My best advice is to always wear pants, except if the weather is hot, then wear bremuda shorts or capris. Always make sure to carry a sweater, as kids are always running around and they generate a lot of body heat, which usually causes the teacher to turn down the A/C and since you haven’t been running around, you will have a lower body temp and thus be cold. Also, lace up shoes (converse, vans, running shoes, oxfords, etc) are best. Chances are, you’ll be chasing some kid around and wearing shoes that are restrictive is a bad idea.

  17. 17
    October 3rd, 2009 at 3:38 pm

    Colleen
    Thank you so much for answering my question. *HUG*
    I Love Love LOVE that second play outfit, since the play that I am going to is more of a professional level. Its so classy and yet my style. I am so into rings right now, so the ring is perfect.
    The first outfit is perfect for school plays. I do plan to go to all the school plays.
    I have a black dress that looks a lot like outfit two all I need is the accessories.

    Again thank you for your great ideas and for taking the time to answer my question.
    Jess

  18. 18
    October 3rd, 2009 at 6:51 pm

    I cannot believe that you posted outfits for working with children! This was great! There are not that many websites out there that have ideas on how to dress to be a teacher. I really liked both outfits–they seem comfortable yet very professional looking.
    I noticed some of the other comments were a little negative towards your outfits, but I think they work. They are supposed to be a basis and everyone has their own personal style and age area they are working with, so these outfits are not supposed to be black and white. The teachers/future teachers on here should take these outfits as a guide and then adapt them to their personality and classroom.
    I think you did a good job, personally! I have been wondering what to wear as I will be starting my pre-practicuum in 2nd grade on Wednesday! Now I have some ideas. :)

    Thanks again!

  19. 19
    October 4th, 2009 at 8:10 pm

    Hey guys!

    Holiday and OMG– What a great suggestions! I’m sure all the teachers who responded really appreciate the extra advice you were able to give in relation to the questions. And OMG, it sounds like you’ve had some interesting times getting the teacher-style down, thanks for sharing your experiences!

    Jessica–I’m sorry that you found the outfits disappointing! While I personally do not work in a teaching environment, I made sure to check my outfits with some people who do and they said that they thought they would work. However, I completely understand that it depends on each person and the environment you are in. One of the teachers said she enjoyed wearing longer skirts to work rather than pants because it gave her more mobility and was a bit breezier! But of course, I completely understand that people have different preferences and I appreciate your input, as I’m sure everyone else does! If you have any more suggestions feel free to add on, it’s always good to hear from someone with experience in the field.

    And for an overall note, I appreciate all of the positive feedback on the subject of this article. I’m writing these posts for you all, so I want it to be things that apply directly to your lives! I definitely don’t want you guys to see these “What Do I Wear” posts as generic, so keep your questions coming!

  20. 20
    October 4th, 2009 at 10:24 pm

    This was perfect timing, as I just started student teaching.

    I liked both of the outfits, but like most of the other posters I agree about the skirt. It’s not practical for working with young kids. Maybe if you teach middle school or high school but not for the youngins.

    I’m constantly running around the building and classroom, and getting on the ground in a skirt is not practical.

    I loved the shoes though, and both tops were very cool. It’s a good basis for me on what to add to the professional wardrobe…thanks :)

  21. 21
    October 5th, 2009 at 12:57 am

    What great suggestions! These will help a lot. :)

  22. 22
    October 5th, 2009 at 4:45 am

    Cut out the earrings, and anything other small or glittery (sorry – my English is not really fluent :() – I often work with small children and they grap everything, especially when its sparkly. I nearly lost my earlobe once – also, they can choke on small rings, buttons and the like.
    If your hair is long, put it up or in a firm braid – and use elastic bands, not pins…
    I second the trousers suggestion as well. Find something washable with a small pattern or a earthy colour – easier to keep neat looking.
    If wearing a skirt, Id suggest wearing a leggins underneath.
    Definitely try and find shoes you can run in for hours. You will have to chase after the children…
    Beady necklaces (or any necklaces) will be ripped apart. Use leather or strong fabric bands with a big pendant (easy to locate, hard to swallow) as a necklace if you must.
    Always wash clothes before wearing them, as some chemicals used by the clothing industry may trigger allergies. Use a unscented washing agent.
    Try also to cut back on scented cosmetic as well – children are far more sensitive.
    Just my experience :)

  23. 23
    October 5th, 2009 at 4:48 am

    btw I really enjoy your blog, my comment was not meant to be negative – more like additional tips

  24. 24
    October 6th, 2009 at 11:36 pm

    These are so cute! I have a great what do I wear there question. This is a real challenge by the way. I work at an herb nursery. This means I get messy dirty and parts of me get some water throughout the day. i still want to look cute but what would I wear. Also it can’t be clothes that cost a lot because they get worn torn and washed a lot. It would be great if my question was featured!

  25. 25
    October 12th, 2009 at 5:20 am

    hey,
    i had a question my birthday is coming up n i hv bought a converse from levi’s the model is horse dots low.i want to know what can go with it ?what dress?what hair style and accesories??????it is black in colour my shoes n has white polka dots on it

  26. 26
    October 12th, 2009 at 5:21 am

    pllzz help its my sixteenth birthday
    …i really want to look hot n lovely

  27. 27
    October 13th, 2009 at 12:24 am

    Hey Lynn,

    Since your question is pretty specific, I am going to answer it here rather than dedicate an entire post to it–hope this is ok!

    If the shoes are black and white, you’re pretty lucky–you can wear almost any color dress with it! I would go with a dress with a more flared, “poufy” skirt to give you some girly volume with sneakers and to ensure that you get birthday girl-worthy attention! Sequins, lace, and other attention-grabbing accents on the dress would definitely be a plus–just be careful that you do not chose a pattern that clashes with the shoes!

    Urban outfitters, Forever 21, and Free People would all be great places to look for a party dress. As for accessories, I would go with some funky bigger bangles in interesting geometric shapes to pick up on the shoe’s pattern.

    As for hair, I would either go more classic with a chignon (maybe even add a tiara for fun–it is your sweet 16!) or down and really loose and wavy.

    Hope this helps! If not, comment again and I will get back in touch.

    Happy birthday!
    Colleen

  28. 28
    October 14th, 2009 at 12:41 am

    I LOVE U !!!!!!!!!!!!THNKS A LOT U JST SAVED ME N MA BIRTHDAY

  29. 29
    October 14th, 2009 at 7:09 pm

    hey okay can you do a line of outfits based on Mona lisa smile and the whole 1940/1950 look??

  30. 30
    October 15th, 2009 at 5:17 am

    What a great idea and well constructed article! :)
    I was wondering if you could do an article on dressing for 21st birthday parties. In Australia they range from formal to casual dresses and some inspiration would be great!

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