What to Wear to Kindergarten

August 28, 2006



School start September 6th. Today I will go through my kids fall/winter clothes and make an evaluation — what have they outgrown, what looks too worn — before I start shopping for school clothes. If my memory serves, their wardrobes are in pretty good shape and I won’t need to add many items, mostly just fill in a few gaps and get some new sneakers. But even though their existing clothes are workable, I like to have a brand new outfit for them to wear the first day of school. It just makes the day feel more special.

So this post is “What to Wear to the First Day of School : Kingergarten Edition.” Pictured, is the outfit I’ve picked out for Olive’s first day. Just imagine this outfit with little, beribboned pigtails and her clear blue eyes. She will be absolutely irresistible to any Kindergarten teacher. And in my experience, if the teacher loves my kid, I will love the teacher — which makes for a happy school year.

Note: I’m stealing the What-to-Wear idea from the wonderful EmilyStyle.

Dress by Old Navy. (I picked this out earlier.)
Socks by Old Navy.
Shoes by Garvalin Kids.
Sweater (if it’s chilly) from Boden.
Ribbon (to tie around pigtails) from the Ribbon Factory.

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{ 14 comments… read them below or add one }

1 Kara August 28, 2006 at 12:27 pm

So cute! How do you get your daughter to dress this way? For the most part, my four-year-old will only wear bright pink… and if it has strawberry shortcake on it, that’s even better.

By the way, I love your blog. I’m Jordan’s sister-in-law in Sacramento.

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2 Lizzy August 28, 2006 at 1:29 pm

sad i’m not there to catch the clothing windfall! love those shoes!

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3 Mom August 28, 2006 at 4:10 pm

I wish I could see cute Olive on her first day. xoxox to all of you.

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4 Mom August 28, 2006 at 4:10 pm

I wish I could see cute Olive on her first day. xoxox to all of you.

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5 liz s August 28, 2006 at 6:19 pm

for a split second there i actually wished i was a kindergarten teacher. it only lasted a second though. how will you make sure she chooses this outfit and not one of her dress ups princess outfits for her first day?

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6 Erin August 28, 2006 at 7:30 pm

Oh, it’s great. How do you work around the “it is fall because school is starting, but it’s still really hot outside, but I don’t want to buy new shorts, but all their summer clothes are thrashed and the kids are almost in the next size, so they can either wear slightly tight or slightly loose clothes on the first day” problem?

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7 Girl con Queso August 28, 2006 at 9:00 pm

I love it! You’re the coolest mom ever.

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8 Mo August 29, 2006 at 8:34 am

Gabby, I am not sure Ralph is really going to dig that outfit for his first day of school.

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9 Design Mom August 29, 2006 at 12:40 pm

Kara, thanks for reading. I know what you mean about the four-year-old style issues. My best bet: whenever possible, I do the shopping without my kids. Then whatever I bring home is new and exciting and they don’t even know Strawberry Shortcake/Barbie/My Little Pony was an option.

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10 Design Mom August 29, 2006 at 12:44 pm

Erin, I felt this dress navigated the summer/fall warmth issue pretty well. Personally, I just can’t stand to buy more shorts when they’ll only work for the first three weeks of school. The kids can make do with their worn-out summer clothes or just wear jeans and s/s tees until it’s colder.

Mo, but brown is his best color.

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11 MissEm August 29, 2006 at 7:14 pm

Super cute outfit! I want a kindergartener to dress up!

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12 laurie September 24, 2006 at 9:21 am

such a precious ensemble! do you have pictures of the first day of school?

my 4-yr-old twins won’t wear anything that i appear to like, so we’ve got to work around that. even if i only supply them with clothes that i “approve” of, they’ll still put together combos that are bizarre. choose your battles, right?

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13 Nichole November 28, 2007 at 12:50 am

Aw, that’s precious.
Do you save all their first day of school clothes in a special place?
I think I might start that tradition when I have kids one day.
I heart your blog!

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14 Rose from FineCraftGuild dotcom March 16, 2009 at 12:08 am

Well, I have to agree with Kara. My daughter will NOT wear anything BUT pink. ‘End of (her) story.’

However, I adore outfits like the ones you’ve put together. Pretty good to find all these to match, in the right size, color and season…

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