How to Dress for a First Play Date

This post inspired by damselfly.

September is an incredibly busy time. It’s the capital letter at the beginning of the school/ministry year, the kick-off for just about everything, and a time for breaking in new schedules. Add to that, this year, I am doing costumes for the show and you will not begrudge me this little break in blogging routine to do something fun. I need fun!

Go crackers this winter with 10% off plus FREE delivery and returns at BodenUSA

Which of these outfits would you choose for a first play date? And why?

Oh, hey, and this will be fun, which would you choose for me? (There is one that somehow is more my idiom than the rest. Can you guess?)

18 thoughts on “How to Dress for a First Play Date”

  1. I love the skirt.

    I usually wear the middle two …the button down with jeans or the knit long sleeve with jeans. In fact, I’m leaving in an hour for a park playdate dressed like the knit long sleeve. Of course, its almost snowing here today,and I’ll need a jacket. Wish I had the one in the last picture. So cute.

  2. 1 or 2 for me. 1: because I love the yellow splash of color, and I love the leopard shoes! 2: because I wear skirts almost all the time (denim preferred for it’s versatility), and I like the cardigan (although with my body as it is, I don’t imagine it would look good on me).

    I choose 3 for you, only because of the collared shirt.

  3. I think #3 looks like you as well.

    I have to imagine a play date as we’ve never experienced one. The closest I could come was my son playing across the street, where I already knew those families and saw them every day or a stray visit to my college roommate who had a son about the same age.

    So I’m imagining being in someone’s home for the first time and perhaps there are other mothers there I’ve never met before. I’m thinking that a play date for children is an opportunity for being able to feel grownup for the parents. I would choose #6 for myself. Just because I’m not comfortable without that 3d piece. Nobody around here wears any skirts except me so while I think that picture is a good option it would be off-putting. Also what if I wanted to get down on the floor – pants seem better for that. And a cardigan with cheerful designs might be good for others but I would die a thousand deaths with that somebody else’s clothes feeling.

    I think the outer piece in #6 is supposed to be a coat but I’m imagining it as a long sweater or knit piece that I could leave on and feel snuggly in. OTOH, what if the people’s house is hot.
    Where is my third piece then?

    I can’t answer this. 😀

  4. Either 3 or 4 could have almost come out of my closet, so it would definitely be one of them. For a playdate, I’d probably go with the layered tees, since they look more comfortable in case I’m on the floor with the kids. For you, I’m guessing #4, since you wear the layered shirts a lot, and I think the overall simplicity of the outfit would appeal.

    This was fun!

  5. For Rebecca–the hoodie & green pants.

    For me–the denim skirt & cardigan which is what I wear most of the time anyway!

  6. Fun. 🙂 I would probably wear two or three. I usually wear skirts, but it depends on what we’re doing. Also, I’m always cold. Like, really, really cold. Like when I get really cold, I shiver uncontrollably. I can easily get there in a resturant–it does not have to be subzero weather. 🙂 So I think I’d better be warm….being cold on a date = NOT cute. 😉 However, I like the simplicity of # 3, and the straight trying to edge formal look. I guess the collar does that mostly. I tend to edge formal. 🙂 I’m thinking 5 for you. The hoodie, layers, and dash of fun, unique color seem like they would fit your idiom. Also the gray would repeat your hair. 🙂 However, #4 was my initial gut reaction (the one they always tell you to follow), and I can easily picture # 3.

  7. One more. So, I’m curious if this was intended to be a playdate like the “he and I are going on a play date” or a playdate like “my small child and I are going on a play date.” I suppose I possibily interpreted it all too quickly based on my season of life…

  8. #3 – The collared button-down for me. I love the jeans she has on, and I realize she’s wearing socks but it makes me think how cute a fun colored ballet flat would look with that. I also love the leopard shoes and simple turtleneck outfit of #1. For you my first thought was the button-down because of the menswear angle, but after reading other comments I can definitely see their point and I think I’m wrong now! 🙂

  9. I like the one on the top left. I might change the belt color, but I love the fun shoes. The whole outfit looks comfortable but fun and stylish. It’s very appropriate for moms of any age, too.

  10. Pingback: The Space Between My Peers » The Answer to the (Trick) Question

  11. I would definitely choose 3 or 4. I would do 3 if it were someone I wasn’t extremely comfortable feeling with. If I felt totally at ease I’d choose 4.

  12. I love #1. I see that’s the one you chose too!

    Hey, that link to Boden. I don’t see the coupon code for 10% off and free shipping. Has that deal gone by, or what does one to do take advantage of it? THANKS! :=)

  13. My understanding is that whenever you use the affiliate link (either the text link there or there is also a banner on the “online shopping” page, in the page section of the brown sidebar), it automatically gives you the deal – you don’t need a code. And I think it actually ends up being 11%, or maybe that’s just certain times of the year.

    Anyway, you don’t need a code, just use the link. Thanks for asking! 🙂

  14. I would wear the cords and grey hoodie. I live in hoodies during the Fall and Winter. I dress them up for work…cashmere ones with suits (modern edge to a traditional suit!) and with jeans and a blazer for a lunch with friends, and with a J.Crew puffy vest for kid’s skating and sports. That is my uniform!

Leave a Comment

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.