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The ‘Work’ Outfit

We have a rule in design that you can’t have ‘fast, cheap and good’. You can have fast and cheap (but it probably won’t be great quality), cheap and good (but that takes a long time to find) and fast and good (but it ain’t gonna be cheap). So two out of the three is what we strive for.

When dressing ourselves we all want comfortable, flattering and stylish, right? And unless you are an Olsen twin and can look sexy in a sack, it’s really really hard to look/feel all of those things at the same time. So I generally go for ‘comfortable and stylish’ during the day and then ‘flattering and stylish’ at night (especially if I’m on a date with Brian). When pregnant I definitely throw in the towel on being all three, so I focus on being REALLY comfortable, kinda stylish and if I also can look cute and on the less troll-ish side, then WONDERFUL.

This outfit is great for work and meetings with clients, and it’s a go-to for me for a few different reasons.


I’m carrying this pregnancy a lot lower and wider, which I find rather rude, but Miss ‘low and wide’ in there wants to roll that way and there ain’t nothing I can do about it. Of course horizontal stripes around my hips are probably not helping the situation. But lets stop talking about my hips and talk about my outfit instead, kay?

Here’s why I like this outfit:

The dress is knit and SUPER stretchy. It’s not a maternity dress but it’s giving me a lot of movement. I was 25 weeks here (I’m 30 now) and while the leather on the bottom keeps my hips/thighs reigned in, the stretch in the fabric allows the belly to properly bulge out.


The crop top is short enough that it shows off the belly, so that I look obviously pregnant and not just kinda like I’ve had a burrito…or four. I’ve been buying and wearing a lot of structured/fitted crop tops, layering them over longer shirts and dresses, which is proving to be a good move (I think).

This outfit is very comfortable (for not being pajamas or a muu muu) and is totally my style (a bit of color, a bit of pattern, kinda fun and professional enough that I can wear to meetings). As far as the flattering scale goes, it does the job just fine – I feel cute enough in this, whilst knowing that yes, I have other outfits that show off more curves (those outfits just tend not to be as comfortable or forgiving).

Of course that hat (for which I should be a paid spokesperson because I wear it EVERY SINGLE DAY) tweaks it up a notch in a good way and the necklace breaks up all the red (and pulls your eye away from other regions).


1. Hat 2. Top 3. Dress 4. Shoes 5. Necklace

Again, none of those pieces are maternity and the red Suno top was a total splurge that I LOVE and I have actually bought it now in a pattern as well (on sale, thank goodness) – I wear them both with collared shirts underneath that is always a big hit. If anyone knows a good affordable version of that bad boy, leave in the comments. That dress is really forgiving and so easy to layer over because the jersey is so thin (and stripes go with everything).

Lastly camel or nude leather shoes make your legs look longer even though there is an ankle strap. I think I knew all of that (and you probably did, too) but when analyzing why I feel good in this outfit and why I always wear it I realized a few things about it that are consistent with how I dress in general and thought to point them out (hopefully y’all are interested).

That’s me … well, pregnant me, prioritizing ‘comfortable’, ‘stylish’ and then ‘flattering’ in that order – at least for work.

Now its your turn – how do you prioritize those three things? Or do you? Or, AM I CERTIFIABLY CRAZY???

*All photos by the lovely Stephanie Todaro.

Wanna see more maternity fashion posts? Check out my Muu Muu style, my ‘play outfit’ and ‘the one where I hold a piano‘. Also last time I was pregnant I wrote this ‘Maternity Must-Haves‘ post which I need to update, but its still pretty relevant. Lastly if you want to watch the birth of Charlie (yes, you read that correctly) go HERE.

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6 years ago

Great outfit! – I love Suno, even if it is a bit spendy. Not sure your size, but the price is right on this one :

6 years ago

Love this outfit! You look beautiful, and that lip color on you is super fab!

6 years ago

I love that dress! And I love these posts–keep ’em coming. I’m 18 weeks pregnant with my first and need all the help I can get in the maternity-wear department. I’m wondering, did you buy the dress to wear for maternity, or did you already have it? And if you already had it, are you worried about stretching it out so you can’t wear it post-baby? I’m trying to utilize as much of my current wardrobe as possible with this pregnancy but have wondered about the stretching out factor.

6 years ago
Reply to  Joy

Regarding dresses, before becoming pregnant with my first I happened to buy a stretchy striped column dress from Bailey 44 with which I became obsessed (like, wear it to anything at which it could conceivably be appropriate obsessed). I wore it to a looong, hot daytime wedding when five months pregnant, and it survived unscathed, so I wore it a few more times… and it was still fine post-pregnancy. Second time around and it’s going strong at seven months pregnant. And it feels like a nightgown and is so flattering. Not a paid spokesperson (I wish!), just seriously, seriously in love with it.

6 years ago

Very cute outfit! I’m following these posts closely because they’re so helpful, and I’m curious about whether you avoid maternity jeans entirely or if there’s a pair that works for you. I went shopping for my first pair last week and it was quite a discouraging/hilarious experience!

I’m definitely a little envious of the fact that the Olsen’s literally look good in everything, OR maybe it’s just the fact that THEY know they look good in everything so it makes it seem like that to the rest of us? I’m a firm believer in if you think you look good in something, then you’re bound to look good in it.

Josh | The Kentucky Gent

6 years ago

I hope you continue this series forever. You are bringing the em Hendo magic to the look of rooms and people.

6 years ago

I bought the madewell necklace, these sandals from your first time, and the muu muu….
But what I REALLY NEED and would promise to buy it all and thank you a thousand times…
Can you do a “running errands all day, I’m not looking super cute, but I don’t want to have to hide when I see someone I know” look!!?!???
Because that is my life (but I’m sure everybody has some days)….and if I could have some of your advise on that, I’d be LIFE CHANGING!!!
Thanks for all you do!

Kate Hand
6 years ago
Reply to  Emily

yes! this! for maternity wear.

6 years ago
Reply to  Emily

id like non-matetnity, but even tho i’m not pregnant any more, i’d probably be willing to rock the look!

6 years ago

I love those two colors paired together! That is genuis layering right there!


6 years ago

My eyes can’t get past that tooled leather bag. Who? How? Is it still? OMG.

Karen Stacey
6 years ago

I’m not sure this has been said often enough, if at all…but you’re a really, really good writer, in addition to being funny. A rare gift, my friend. A rare gift.

6 years ago

The two of of three rule works for many things in life. To keep items in my home they have to have at least 2 out of 3: sentimental value, function, design. For my husband to accept a job in his business: 2 out of 3: quality of people/clients, level/interest of work being done, pay. Great outfit!

6 years ago

This outfit represents a great style, red and navy blue go wonderful together:

6 years ago

Nice look! Love it

6 years ago

You look absolutely darling.

6 years ago

That first photo stopped me in my tracks. You are stunning, mama. And I was soooo wishing you were standing in a kitchen. Wouldn’t those be stunning kitchen cabinets?!?!

6 years ago

What are the shoes you are wearing in the photos?? Love them!

6 years ago

You look great! And so does that wood floor. Care to share the details/finish?

6 years ago

I love the dress design specially some others posts on your blog. I am fan of hats. Hat is really cool.

Thanks for sharing

~Dr. Diana

6 years ago

Our babe just turned 1 month old, so thinking back now I think I prioritized flattering and comfort only because I learned REAL fast that I felt terribly frumpy and about 10x bigger in anything too flowy, or even kind of flowy. By the end of my pregnancy I was basically living in stretchy striped (non-maternity) shirts. I looooove this idea of layering up a crop top over it for a little more on the stylish side.

6 years ago

Gosh, you are just beautiful! And I love this outfit. Its sophisticated yet playful. Pregnancy looks so good on you.

6 years ago

Adorable as ever!

Jilly D
6 years ago

I’ve always loved your blog but now that I’m pregnant with my first baby (a boy!) I find that I’m obsessed with it:) Loving all the great tips. Trying to be comfortable and cute is no easy feat. I was ready to buy this top and dress when I saw the pic but top is sold out and the dress is only available in large (what size did you get?). Bummer! You look amazing. If you ever want a pro bono design job gimme a call 😉 Oh and lastly, I laughed at your reaction when you found out you were having a boy the first time around because mine was the same…but seeing your pics and posts about Charlie gets me excited! Thanks!

6 years ago

Your fashion posts make me so happy. I bought the boxy collarless chambray shirt from Madewell after you featured it in another post, and every time I wear it I think to myself, “I’m basically as adorable as Emily Henderson right now.”

6 years ago

You look fantastic Emily! In that last picture where you’re facing forward, you don’t even look pregnant. Love your outfit.

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