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Why I Am Suddenly Dressing Like a Toddler (and What Does Brian think?)

As I was shopping for our affordable spring dress roundup (coming next Tuesday), I found that I was quite attracted to so many dresses that felt, well, the words “toddler”, “baby” or “christening” come to mind. I mean, we are all already wearing one-sies everywhere, so I suppose it makes sense that “toddler-core” is a thing. Or at least it is now. So today I have some baby-inspired looks for you, how I wear them (with a tip or two) and what Brian’s reaction is to them (not that it matters, but I love a straight man’s perspective on weird lady clothes).

Up first is a baby doll dress in a tiny floral pattern of which I DEFINITELY did not think I would like on me.

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Dress | Hat

But I do. A lot. It’s from Doen and has puffy sleeves, a good cut AND pockets. Now, the rule that I was given was no heels with super short dresses, but I just got these vintage heels at the flea market and since they have a playful vibe, I think it works. Anything higher or more serious can look, well, it can go the way of “sexy baby” to quote Tom Hanks.

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The benefits of these baby doll dresses are:

1. You can eat nine burritos for lunch and nobody would know.

2. You can hide your pregnant stomach for 3-4 months, at least (and before you ask, no I am not).

3. You only have one tiny piece of fabric to potentially pack, steam, and cover your little body (also cute for swimsuit coverups).

Brian’s reaction to this particular dress went like this:

Me: “Hey, do you like the dress that Suzanne wore to Sabine’s birthday party because I’m thinking of getting it.”

Brian: “In what world do you think that I remember a dress that your friend wore to a kid’s party five days ago?”

This makes sense coming from the guy that literally doesn’t notice when I’ve changed rugs in the living room FOR THREE DAYS. One time, he didn’t notice for SIX WEEKS that I changed the light in the dining room. SIX WEEKS!!!

So I tried it on for him and he said “oh yeah, that’s cute.” I’m pretty sure the hemline has a lot to do with it.

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Dress | Shoes | Hat (similar)

Typically, these baby-doll dresses have a higher neckline (to balance out the shorter hemline) and generally, I don’t love high necklines on me, due to my secret larger ladies. So I had to try on a lot to find a few that I felt good in. The straight-across lower neckline on this one dictates the lady area and while it is definitely a great maternity dress, (eventually your growing bump will shorten the hemline, but then just wear leggings), I really liked it.

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When I showed it to Brian he said, “Yeah. Don’t return that one.” Which means he really likes it, I guess. Again, I know that there are a lot of you who literally don’t care what men (husband, partner, boyfriend or friends) think about what women wear but I like his opinion because he generally has great taste and when we are on a date I want him to (GASP) be attracted to me. (Side note: a fun game we do is show Brian the Manrepeller “What We Wore This Week” posts…and listen to his commentary—it’s HILARIOUS).

Anyway, because that above dress is blue, striped, short and has ruffles (kinda a lot happening), we toned it down with simple nude mules because I literally only wear nude mules. I have had these ones for years and they are still my favorite.

Emily Henderson short spring dresses5

Dress | Shoes | Hat (similar)

I’m not totally convinced about this one now that I’m seeing it in photos. I mean, I think what we are all staring at is those amazing boots (they are my friends but I will borrow often). This one is a starter “baby doll” dress.It’ss definitely way less of a risk because it’s in a simple chambray and a light ruffle.

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Yes, these dresses easily blow up and open, a lá Marilyn. But feel free to wear biker shorts underneath (I know the kids do this).

Next up is our actual favorite and while I was on the fence about keeping it, these photos just convinced me.

Emily Henderson short spring dresses3

Dress | Bandana (similar) | Shoes

The dress itself is a bit, well, “baptismal.” The puff sleeves, the lace detailing, the Peter Pan collar all just scream “ready for that big church moment.”

I think if you try and dress this up (with heels) it could look very silly. But thanks to Suzanne and my styling entourage (Grace, Veronica and Ryann all weighed in), they helped make this look work. We tried it with two jackets just to see, and they really liked it with the sherpa jacket (see below).

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Denim Jacket | Sherpa Jacket

But I liked it more with the black jacket.

What did Brian think?

He said, “Cute. For a picnic, right?” I asked him if he would be bummed if I wore this on a date night he said, “Not bummed, but it’s not what I’d pick for you.”

Okay, that’s all I’ve got to show you on my body but we went ahead and rounded up some of our favorite toddler-, baby-, or general “child prairie”-inspired clothes. They are all babydoll dresses OR ones that feel like only a three-year-old could pull them off (but hopefully I’ve convinced you that “gromups” as Birdie calls us, can, too).

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1. Ghospell Southern Hemisphere Plaid Frock Mini Dress | 2. Mini Dress With Stripes | 3. Ruffle Bib Shirt Dress | 4. Long Buttoned Blouse | 5. Ganni Cotton Poplin Dress | 6. Embroidered Dress | 7. Ruffle Collar Mini Dress | 8. Relaxed Puff Sleeved Midi Dress | 9. Openwork Embroidered Dress | 10. Ruffled Striped Dress | 11. 3.1 Phillip Lim Striped Dress | 12. Short Chiffon Dress | 13. Slim Fit Button-Down Flowy Tiered Mini Dress | 14. Rose Embroidered Plaid Mini Dress | 15. Kate Prairie Dress | 16. Cecilie Bahnsen Alberte Dress | 17. Velvet Vesta Dress | 18. Palm Embroidered Scallop Dress | 19. UO La Petite Tie-Back Frock Mini Dress | 20. The Flutter Cami Dress | 21. UP Houston Linen Button-Front Drop Waist Dress | 22. UO Samantha Seersucker Long Sleeve Mini Dress | 23. UO Jules Gingham V-Neck Mini Dress | 24. Openwork Embroidery Dress

SOOOO, are you convinced? Would you try? Or should this be strictly left in the day care?

***photography by Veronica Crawford for EHD


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73 thoughts on “Why I Am Suddenly Dressing Like a Toddler (and What Does Brian think?)

  1. Love the Urban Outfitters dress with the low back. Are you able to wear a bra with it or is the back too low? Considering buying it but definitely prefer to wear a bra.

    1. Ok. so this is a thing and I’m totally with you and thus my hesitation on that dress as well. My friend had these pretty amazing pasties that hold up the ladies that I wasn’t wearing in that sho (more out of lack of time), but I wore them in another shot (you’ll see tuesday) where you’ll see the back. I’ll try to get the link but she was like ‘don’t tell everyone or they’ll sell out like you did Perfekt” so I need to buy her 10 pairs before I link them up. So long story is I was wearing a bra, but i’m so excited that I finally found some pasties that work!

      1. Need the pasties hot top PLEASE. My secret boobs need lifting in a backless bridesmaid dress soon ?

  2. By any chance do you know where you got the lace-up cap-toe boots from the last photo? They are excellent.

  3. It’s funny the one I felt looked the most borderline toddler is the chambray with the tiered ruffles, still cute though and those boots are great. I absolutely love the other ones though and how you styled the floral and white dress ?? pinned!

    1. These don’t really do it for me. I am very tall and also kinda old for this look. I might wear one over pants, but sleeveless, backless, or low cut are not my thing. I see a lot of high schoolers wearing dresses like this…I am a teacher, so for me this look is just too “try hard.” I don’t want to look like a student. On you, it’s definitely cuter, but it’s not my fave. I do not like the white dress with either jacket or the boots–that’s just imho. Remember the prairie style craze from the 80’s? Maybe you don’t, but I do. No thanks.

      1. I was thinking the same thing, Susie Q! I was in middle school home economics and I sewed my own prairie skirt … all the rage. So do I want to wear what I wore when I was 12? Nope.

        I think all these styles look silly on a grown woman … sorry Emily!

    2. I would not be able to help myself, and would be wearing some cute kitten tights, or ruffled Bobby socks with the boots. Because, why not? Make all the boys cry.

  4. To be clear: those first 2 dresses look ADORABLE on you (esp the second!!)

    But as a size 18? NOPE.

  5. Love the Urban Outfitters one on you! So feminine and youthful and it works well for your proportions!

  6. As someone who also has secret boobs I don’t like to go w/o a bra. I’m curious about what you did w/ the blue UO dress that’s backless? Do you just not wear one? Or do you have a bra that works for it you’d recommend?

  7. These look great on you. But they would look ridiculous on me. Partly it’s the ruffles.

    I confess, and this may come as a shock: I hate ruffles.

    There. I said. I feel better. 😉

  8. Online I ordered a linen dress from TJMaxx that was full and breezy with some cute detail at the neck. When I tried it on at home, I heard my (deceased) grandmother’s voice in my head saying, “it looks like a gunny sack”. Aside from never having seen a gunny sack irl and not even knowing what a gunny IS, I agreed with her and back it went.
    Thanks for this post, maybe one of these dresses won’t awaken the voice in my head…

    1. Lol! I just did the same thing with a pretty blue breezy babydoll-ish dress from H&M — I nabbed one before it sold out online. Well the dress arrived, I tried it on, and returned it a day later.

      I just googled “gunny sack” and, yep, that’s what this dress looked like on me. But I gave it shot.

      1. you guys. Gunny sacks are BACK. not saying we should be into them, but they are going to be everywhere very soon … should we do it?

      2. I think I got the same H&M dress. I decided I’m keep it tho. Flattering? Not really. But I love I and thought at a minimum I’d wear it over my swim suit…..but now I find myself wearing it all the time!

    2. Ha! I don’t know what a gunny sack is either, but your comment cracked me up.
      And for the record, I often hear my deceased grandmother in my head (usually commented on my manners or hair)

    3. Ha, there was a brand called Gunne Sax back in the day. I wore quite a few of them. In my youth, we called them granny gowns.

  9. These dresses are all so cute on you! It’s kind of all about the edgy shoe choice. I however am barely 5 foot, and these kinds of things invariably swallow me.

  10. Love the first 2 on you, both are super cute. Not a fan of the 3rd one, but I do like the last one either with the denim jacket or without. The Sherpa jacket reads like winter or fall with a summer dress. I wish I could wear this style, but, alas, I’m 50 year old and 5′ tall, so it’s a no go for me. 🙁

  11. First off, I really enjoy these Saturday fashion posts, whether I like the clothing or not. ??
    I like a well selected baby doll dress, but its the shoes that make it work or not. I think they require sandals or sneakers. Not sold on the boots with them, even though they are cute boots. The first two dresses are my favorites on you. ??

    1. Nope, not feeling it. I’m all for a good sack dress, but the short length and ruffle details on these definitely make them look more preschool play date than artsy sophisticate.

      I was just recently looking for some spring wardrobe inspo and went back to your summer picks from last year — such cute and classy stuff there! I think the blazer/shorts/wedges combo from that shoot was one of my all time favorite outfits on you

  12. I love the blue one with the square neckline, and the white one! I think the white one would be so cute with some leather sandals and a cropped jean jacket (cropped is nice because it keeps that 1/3 to 2/3 proportion.) Sadly I’m a little pear shaped so the baby doll style is not my friend. Looks great on you.

  13. Can there please please please be a recurring series of Brian commenting on Man Repeller outfits?

    1. YES. We should. Although one of my life goals is to work with Leandra on something so I don’t want to alienate her or offend her in any way…. will think on this friendship strategy and report back 🙂

      1. It’s a mixed bag to my eyes. The simple, dark-floral-print dress works because it’s simple and there are no overly “baby-ish” details. The grown up but still lighthearted and chunky heels serve to ground the look.

        The light blue with shoulder ruffles is too similar to an empire-waisted, tulip-skirted dress I made in high school that was sweet and slightly sexy when I was 15-16. The chambray, while I agree the fabric is appropriate, has too many tiers and is too short for my preferences.

        The white prairie dress is something I admire, especially styled as you have it here. There’s something about a solid white dress that can cross decades, regardless of the details. I don’t know if I could, or would want to try, and pull it off in this iteration myself. I do love a deep ruffle hem though!

        Gunne Sax was my dream designer when I was 10-12 but if I saw a vintage dress by the designer today I would pass.

  14. The third dress links to the shoes instead of the dress for me. Love them all though!!!

  15. Here’s comment #2. I like the black dress w the green shoes. I like the tiered ruffle dress, but not with the boots. I think the hats make these outfits costumey–“Look! Madeline goes to the zoo!” The boots also add to the “prairie costume” look. Flat, simple shoes or sandals would look better.

    1. You are making my day, Susie Q! Agreed with the shoe thing, but I am dying over the hat comment. I don’t like hats, and costumey is the vibe I’m getting. OK, I will stop laughing now. And Emily, more power to you for rocking this look … if you love it, you should wear it. 🙂

  16. Hi Emily,
    Hoping you will share the brand of tan espadrilles (with the sensible wedge heel!) that you are wearing in your Fashion edition/Instagram Story yesterday. The outfit includes a cute velvettes blue coat and jeans. I love that the heel isn’t crazy high!
    Please advise.

    With thanks,

  17. I’m sorry, but you are so lovely that I don’t think these dresses

    do you justice. There are so many beautiful classic clothes for young women. I recall hearing a guideline for dressing that if you wore it once you shouldn’t wear it again. So if you wore these toddler dresses as a toddler don’t try it again. With all due respect and adoration for your genius in decor!

  18. Ick! I am way to old for this trend. They all look like costumes for a 70’s play. Sorry. But you, do you. That’s what makes the world go ’round.

  19. I feel like there’s this trend lately where women with really great bodies (that would be you Emily!) wear really voluminous, unflattering clothes in the name of being quirky and stylishly off beat. I’ve seen it a lot in magazines like Vogue and Elle and I just don’t get it. If you have a rockin’ bod, it’s okay to wear clothes that actually fit and show off your cute shape! I love of all the accessories and the way you’ve styled your voluminous clothing, but the clothes themselves…. not a fan. Sorry!

  20. Emily, that white dress can take you anywhere! It’s so attractive on you. Those other, shorter, dresses don’t really fit your image, in my mind. They remind me of rompers, which on a grown woman, are not a good look.

    There are some women who, even when they are adults, always look childlike and cute and they can present like a kid and get away with it. To me, you have classic beauty. You are enhanced by a more elegant look….like the white dress. I see you as regal and feminine and graceful…not baby-like, even if it is in style. To me, you are above this look.

  21. Emily, the dresses are cute but you need to ditch the mules and show off some tan, polished toes once in awhile! Those mules and boots tend to make feet look like hooves. IMO.

  22. Sorry, I don’t care for this look at all. The first dress with those awesome vintage shoes would be a possibility, but that is it. The second one is the worst in my opinion, you are bending forward and it is still incredibly short! I can only imagine the view from behind. I think anyone over 25 should NOT be wearing this style.

  23. I’ve had this question for a year- do your nude mules actually work for you when you’re with your kids too, or are they more for office days?

  24. I like most of these, but the white one is a bit too 1800s prairie girl for me – especially with the boots. I actually think I would like it better with a pair of strappy sandals or flat, pointy toed mules in a neutral color. I also think I would like it better if it were shorter – the mid calf length leans in hard to the prairie vibe. But I wonder if it’s better in person.

    I find Brian’s reactions funny – he actually seems very respectful with his opinions, and he’s entitled to like some things on his wife better than others! I definitely have things my husband doesn’t love, and while I can wear them all I want, I think his opinion is sometimes a good reflection of whether the clothes actually flatter me, rather than just being cute in theory. He has a tendency to not like super childish outfits on me though, and I think a lot of that comes from the fact that I have a very young face and am really short, while he is a tall, bearded guy with broader shoulders – especially when we were teenagers and first dating, childish clothes on me made me look like his baby sister, not someone age appropriate for him to date (we’re only a year apart). It’s gotten a bit better as we’ve gotten into our late 20s, but that anti-toddler-chic is deeply ingrained by now.

  25. Do YOU love it? Only thing that matters in the end!

    I wouldn’t wear any of these as I’m 5’2″ and babydoll styles look badly juvenile on me (and I’m 45).

    (They also don’t look like they’re easy to sit down in without riding pretty high.)

  26. Sorry, Em. You are far too old to rock this look. The dresses are too cutesy and too short. How can you even work if it involves lifting and reaching? And shorts under mini-dresses really are for the school-age set. Why not accept the look that makes you most comfortable? I’m guessing it’s jeans and a white shirt.

  27. Love so much. I grew up watching what not to wear and I guess maybe that’s where the idea came from that somehow one should always pick the most flattering option? But maybe just question that for a minute, why?
    I just had baby no2 and am a solid 170lbs, size 10,5’7”, belly flab and maybe it’s just me but I honestly do not care if it’s flattering (? Whatever that means) or not, I just want to feel pretty. Changing dirty diapers is 100x better in a pretty dress or top, high waisted jeans and really cute shoes. And if it matched my three year olds wardrobe she would be Over the moon thrilled !

  28. The first two I thought were cute. The chambray was meh. Return the white dress. It may be fun once or twice, but you’ll never grab it to wear much.

  29. You, in that second dress is just perfection! So comfortably chic and accidentally sexy (does that make sense?)
    Anyway, I’m smiling just imagining Brian’s thoughts to man repeller. Would love a post on that. Their clothes seem so confusing in real time….but I know they are fashionable. (??)

  30. I love all these dresses! I find myself in a lot of similar styles because – comfort! Ha. You guys need to check out Gorman – it’s an Aussie store but dresses in a similar cut to some of these but the most amazing patterns.

  31. I hope you don’t take this the wrong way …. but that dress with the ruffled sleeves? I had the exact same dress in a patchwork fabric back in 1973. I was 20 years old. No way would I be able to wear one now, but you look adorable. My favorite “babydoll” dress back then was one with puffy sleeves and a smocked placket at the top. It’s the one dress I’ve kept forever, not to wear… just to help me remember when I was that young woman….

  32. Don’t think the white prairie style dress works on you. It just kind of takes your adorable looks down a notch. Don’t like the boots/booties at all but love the vintage shoes and the nude mules. (My first question was going to be, “where can I buy those shoes?” until I saw “flea market” and “years ago.”). The babydoll dresses look good with your great legs!

  33. Well, you got me to order one of the Zara ones. I’m excited to see if I can make it work. I agree that it’s all in the styling. It is so Alexis from Schitt’s Creek! I think you are rocking the look. Go with it!

  34. Oh no. No, no, no, no, no, noooo.
    I love you, you’re everything, I admire your work, and twenty other disclaimers so you know my intent is only constructive and I will throat-punch anyone who is mean to you.
    Your 20’s are way too far in the rear-view mirror. You are a middle-aged (do the how-long-do-I-think-I’m-going-to-live math, and let’s be nice and call it the first chunk of middle age); a badass, boss-lady, grown woman.
    Of course, anybody can wear any ding dang thing they want for however long they want; I’m not suggesting dowdy or Talbots or boring or matronly. Just consider leaning into a more elevated look. Dressing sexy? Sure! Like an adult? Obvs. Kittenish? No, please.
    Can you even imagine Grace Kelly in a baby doll dress? (I get that we don’t all live in Monaco.) Watch Rear Window or To Catch A Thief and tell me how you feel about the baby doll/mini prairie look.
    I love you gobs.

    1. Blair…Well said…I am way beyond middle-aged and I’m definitely not an expert in fashion so take me with a grain of salt. In my opinion, these dresses belong on your toddler. You are a class act and as the previous poster said, a badass, boss-lady, grown woman. Ditch the ruffled sun dresses, that are meant to be warn with Mary Janes and lacy bobby socks, and find something more age appropriate. God I sound like the old woman that I am. Just my two cents.

  35. My husband’s reaction to these short dresses would probably be something like: “Did you lose your pants somewhere?”
    Emily, you have an amazing figure, and I think these dresses just don’t do you justice. You look amazing with anything you wear. I would leave these short ones out.

  36. Cry laughing at the “church moment” comment ??? also I wouldn’t normally be drawn to these dresses but now you make me want to try one on… just to see! Love that Doen one

  37. I love the dark flowered number in the first photo. This is the one that I think looks best on you Emily. Clothes and interiors in something other than blue and white are always a good idea.
    But, as someone with a really broad torso and not particularly thin legs I think these designs would not be highlighting anything that needs highlighting.
    The white ‘baptismal’ gown is just too toooooo much for me. And when would you wear a summer light weight dress with a sherpa jacket?? Perhaps a dark worn denim jacket???
    I think the shoes are what makes this look. Wearing something unexpected can make the dress look modern and a bit edgy. I always like a boot, often a doc marten as this is often unexpected.
    Thanks for the roundup, I love #16. But this one and many of the others make my think of mumus.

  38. I know a lot of people commenting have not loved these looks, but I think they look ADORABLE on you and I definitely want to go shopping to add some similar dresses into my wardrobe, especially that last white dress. Maybe it’s my younger age – so I don’t have horrific memories of any previous fashion crazes? Or maybe it’s my love for all things vintage? (Love the vintage boots too ??) Either way you can 100% pull them off and should wear them if it brings you joy!

  39. Those sage shoes in the first photo are to die for. I have to find a similar pair.

  40. When I clicked on the link for the denim dress (second to last), the link to me to the boots and not the dress. Is there any way you could send me or repost the link to the dress?

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