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What I wore . . . May Edition

Every day I look in the mirror before I leave for work and I say to myself in a creepy-culty-self-helpy-way dress for the job you want, not the job you have.

And then one of my two babies throws up on my tunic.

Sometimes being neither proud nor embarrassed of how you leave is good enough. So here is what I wore this month.

Emily Henderson What I Wore May1

Blouse | Flare Jeans similar

That shirt is already in heavy rotation in my closet. I know that everyone’s bodies are different but this shirt is flattering and comfortable. Plus that pattern/style pops on camera (even if that photo isn’t selling it). Those jeans are also my new favorite and are sooo comfortable for being high waisted because they have a lot of stretch.

Emily Henderson What I Wore May2

Lace-up Shift DressShoes

I love this dress. It’s shapeless and yet so cute and easy to wear. I must have been playing Peek-A-Boo with Sara (who was taking the photos).

Emily Henderson What I Wore May12

Denim Shirt DressMules

Huh. Apparently I did that again. This dress is another easy one that is basically like pajamas, but if you add pretty mules, a necklace, and maybe a hat, it gets turned into an “outfit”. Although now that I see it here, I’m WAY less convinced.

Emily Henderson What I Wore May10

Striped Shirt similar | Utility Pants similarMules

Glorified pajamas that I love. Not necessarily “meeting-worthy” but for a day writing in the office, I’m cool with it. I apparently took a break from “peek-a-boo” to instead cover my face with that brass skull. Cool.

Emily Henderson What I Wore May5

Felt Hat similar Chambray Shirt | Black Skinny Jeans similar | Black Heels similar

It hurts me more than it does you. Trust me. Drop your hands EMILY.

Emily Henderson What I Wore May6

Straw Hat | Shirt Dress | Sandal Heels similar

Oh good. I just bought this dress and hat, and this is feeling like a solid daytime outfit. It’s simple/comfy and yet feels pulled together enough to go to a meeting. 

Emily Henderson What I Wore May7

Stone Pendant Necklace | White Linen Blazer similar Plaid Top | Flare Jeans similar

That photo is not doing those jeans justice. They are so comfortable and flattering. The cute plaid shirt is fun (look! I’m not wearing just blue!).

Happy Friday. I’m off to San Diego with Brian’s parents and brother for his mom’s 70th birthday. We have a house on the beach and we are going to cook, watch movies, play in the sand, go on walks and just hang out. I miss those kids, despite this being a more mellow week. I had a Drs appointment for Elliot yesterday that ran over an hour and a half behind, and sadly those 2 hours were longer than I have spent with JUST her in weeks which made me feel terrible. It was actually really nice to talk, coo, play, and bond (also because no cell phones are allowed in the doctors office). This weekend I’m going to try to spend more time with just her. Charlie is insanely entertaining right now. And he’s also really needy – he asks me to cuddle and read to him all day long which is amazing. I oblige (so happily), but poor Elliot gets second hand attention. I read to her, too, but I’m definitely more focused on making Charlie laugh during those sessions. She is still nursing so we get cuddle time, but rarely is it ever just her and I.

Anyway, I’m sure many of you have been through this and I know that there is no answer, but man, the first kid gets/got so much more attention/obsession than the subsequent ones, right? I love that baby girl so much and am dying to squeeze them both this weekend, a lot. Lets hear it for easy, low maintenance family vacations. xx

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Chaya jain
8 years ago

This website is good and always shares new thought….

8 years ago

Your vacation sounds perfect and relaxing, hope you have fun and get to enjoy those sweet kiddos of yours!

8 years ago

I have 7 week old twins and I feel bad that neither of them gets a ton of attention because I’m just trying to stay afloat half the time! When a friend comes over and we each take a baby, it’s so sweet to have cuddle time with just one. It’s time that I’m ENJOYING them instead of just working like a mad woman to keep them fed, diapered and (somewhat) happy. I feel your pain!

PS. Now that I’m a mom I’m all about high waisted jeans. I have a pair of high waisted jeggings from Gap that smush in my “twin skin”, and they are the best thing going in my closet right now. Those flare jeans are awesome!

8 years ago

That is why firstborns are so firstbornish! And it’s OK, BC second borns have such awesome personality traits all their own. And it’s okay if they can’t do rocket science at age 2.5, it really is.

The light dress is adorable on you.

8 years ago

You will get more one on one time with Elliot it just may not be in infancy. I have two kids just under 3 years apart and since my older has gone off to school, I have cherished my one on one time with my second. In fact just yesterday took him for a donut after swimming lessons. Don’t beat yourself up about it. Have a blast this weekend!

8 years ago

Love your “pajama” outfit!

8 years ago
8 years ago

You have such great style Emily! Happy Friday!

8 years ago

I suddenly realized when my youngest of two sons was a freshman in high school that when his brother went off to college, we would have him alone for the first time in his life for two years! It was great fun to have that time with him and we really did get to know him in a whole new light with his brother away. As for your current situation, it’s true Ellie will never get the undivided attention Charlie got from his parents…but she also gets Charlie and all the fun he brings to the family.

8 years ago

cute clothes this month!! how tall are you? i love the look of flare jeans and think they are very flattering on you, but i feel like i’d be too short to pull them off. hoping we are similar heights so i can be proved wrong 🙂

8 years ago
Reply to  Abby

I’m not sure how tall Emily is, but I just wanted to tell you that short people can definitely rock flare jeans. I’m only 5’1 but I have some amazing flares similar to Emily’s and they are extremely flattering on me. The trick is to have some tall platforms to pair with them and get them hemmed so that they almost skim the floor.

8 years ago
Reply to  Pam

yeah, another short person here, 5’2”, and I def rock these kinds of jeans and find them very flattering. Skinny jeans just make me look shorter somehow, and unbalanced. Plus wearing high-waisted pants makes your legs look longer.

8 years ago
Reply to  Abby

thanks for the comments–maybe i’ll go try some on this weekend!

Anna Sweeeney
8 years ago

Your comments on those outfits and your hand/prop placement are absolutely hysterical. Completely made my morning!

8 years ago

My older daughter is 3 on Sunday (what the?!) and my younger daughter is 6 mos and I TOTALLY FEEL YOU on the attention thing. Older one needs so much, younger one smiles and plays with her feet. We’re not irreparably damaging the younger ones right? We’re making them laid-back? I tell myself that …

8 years ago

nice nice nice

8 years ago

Love tunics!

emily jane
8 years ago

Did anyone else hear “There she is!” as they scrolled over the first face-showing pic after the four in a row with face covered..? : )
As always Emily, loving your blog -heck, loving everything of yours that I have the technological know-how to experience!- as well as your book which is still my #1 go-to present to give (in part so my friends & family will understand me better since whenever I mention you, it’s as though we are actual, in-real-life friends & it confuses people : ). Thanks for all your hard work & continued inspiration -in fact, thanks to all who keep the whole lovely she-bang in motion… Go EH team! Go Henderson family!

8 years ago

I have a whole bunch of kids, and what I’ve learned is that the baby is okay. Your feeding time is going to cover most of what she needs right now and as she gets bigger and requires more you’ll naturally give it to her. Don’t worry, it’s all good.

8 years ago

Love them all! Super cute! The boxy dress looks great on you because you have nice legs. Thanks for sharing! (and I even like the hat! ha!)

8 years ago


I have girls of 15 and 13.

I feel that however hard it is right now you are blessed in retaining a sense of humour and a dose of reality ( which I SO did not). Congratulations. You are doing amazingly. ?? and you write brilliantly and you look great. Any one of those is enough ! ?? have a great weekend.

Sarah, West Sussex, UK

8 years ago

Hi Emily,

I love your fashion posts! They’ve become my favourite. We have very much the same body type so it’s super helpful to see you in certain styles. And I have an extremely modest clothing budget which makes good research important. Would you mind sharing sizes, especially for the two Madewell dresses?

Thank you!

8 years ago

Love the outfits and was cracking up at you covering your face in the pictures and then your comments on it. I love a good funny fashion Friday post.

8 years ago

My very very favorite of your posts these days. I feel like I personally can get styled by em Hendo

8 years ago

LOOOOOVE ! Your self-expression is always inspiring. Very cool. Those tan mules are made for you. I love them.

8 years ago

Just read this post in the bathtub while my husband is on a walk with our baby to get us bagels and I am cracking up over your comments on your hand placement. Almost dropped my phone in the tub, ha! You are hilarious and I LOVE these fashion posts. So nice to see what real, stylish people wear for inspiration. Also, whenever I feel bad about letting my baby play alone, I think about how the next one won’t have nearly as much (if any!) undivided attention and feel less guilty 🙂

8 years ago

Emily, I am loving these outfit posts, Wry and witty as always, but I hope you know you look wonderful in each and every one of these, and need not apologize! We are starting to think about kid #2 and so I look forward to hearing about how you are managing it as it sounds like my worries are your reality. It sounds like you are doing a wonderful job.

8 years ago

Love the blue dress!

8 years ago

Emily, you look fantastic as always. I’m a Rachel Comey girl also and was thinking about getting the Dekalb clogs as well. Did you go up a size in those? Ive heard they run small but just want to confirm from a trusted source before I pull the trigger. 🙂

Thanks in advance