Now in the third trimester of my second pregnancy, I’ve made enough maternity fashion mistakes to confidently give you the skinny (er, plumpie?) on how to buy dresses for comfort and cuteness as your bump grows. To illustrate each point, I’ve partnered with my favorite dress brand, Leota, which was started by my college friend Sarah, and was just named one of the 50 fastest growing women-led companies in America by Forbes Magazine!
I took the photos for this article in Dubai and Abu Dhabi during my 5-months-pregnant solo trip to the United Arab Emirates. Epic, right? Ready to get schooled in maternity dress shopping? Here come the tips!
1.) You DO need maternity dresses.
In my first pregnancy, I spent months trying to squeeze into non-maternity clothes in a desperate attempt to save money and fight the capitalist establishment. In my second trimester when I finally gave in and added real maternity frocks to my closet, I can’t tell you how much more comfortable my days became.
The extra womb room and strategically placed above-belly seam on a maternity dress make the difference between feeling like a balloon with a rubber band squishing its center, and being a glamorous gal who just happens to have a basketball belly, artfully draped in fashion.
2.) The jackpot are dresses that work for both maternity and non-maternity.
My advice is to get a few dresses that are absolutely ONLY maternity because they are so comfortable and suited to your current situation, but to save money, also aim to track down at least four dresses that can work for both prenatal and postnatal fashion.
The key is to seek a frock with a full, flowing skirt and a high waist, such as the Sweetheart and Perfect Wrap styles of Leota, or a loose style with a waist tie that can be tied in both a higher pregnancy position and a lower postnatal position, like Leota’s Nouveau Sheath. I’d bet that at least one of the non-maternity dresses you own already can work while pregnant, so give your current wardrobe a second look!
3.) Beware! The under-bust seam makes or breaks the dress.
The biggest mistake I made during maternity dress shopping was buying a bunch of low-quality (non-Leota!) garments on Amazon without realizing the “under-bust” seam was so high that it hit me in the middle of the chest and made the dress un-wearably ridiculous.
This problem may well happen to you, as a lady’s “upper torso” gains size markedly during pregnancy, and a surprising number of dresses do not account for this. To avoid wasting money on bust-smushing dresses that fit terribly, either pick a dress with NO under-bust seam, or one with a low enough seam so that there’s no bust-squashing danger. Leota styles happily fit this bill.
4.) Leggings and tank top undershirts are your best friends.
Even the best-fitting maternity dress will feel even better with smart layers underneath. Why? If you’re pregnant already, you likely know that it’s hard to get comfortable unless you’re sitting in a bizarre, ever-shifting position, such as legs up on the chair, or knees wide apart.
By slipping on opaque leggings under your dress (both maternity and non-maternity styles can be fine), you become free to sit whichever way your swollen body craves. I also recommend experimenting with loose pants under dresses, which is a style you can see in several of these U.A.E. photos, particularly because most mosques forbid leggings.
Regarding your ever-growing top region, invest in several black and nude colored tank tops or camisoles (maternity or extra long to end below your belly and avoid seams) to wear under dresses that cannot quite provide modesty in your neckline.
This is particularly important for V-neck dresses, which have the tendency to do some peek-a-boo action with your assets. Now that I’ve discovered the magical combo of cute maternity dress, leggings (with dark socks and comfy Mary Jane style shoes), plus a light tank top underneath, it’s what I wear every day of my pregnancy!

5.) Err on the side of loose dresses, though having at least one form-fitting dress is fun.
Though I love the idea of really showing off one’s bump with a form-fitting dress, the reality of pregnancy is that comfort makes a big difference. Given this, I’ve noticed that I’m more likely to pluck looser dresses out of my closet in the morning than constricting ones.
Further, though I’m usually a Medium with non-maternity dresses, I tend to feel better in size Large maternity frocks. Your mileage may vary, but my two cents would be to opt for larger choices. That said, there’s no need to look like a circus tent in order to be comfortable. The secret is a nicely-fitting above-bump tie belt for definition.
6.) Online shopping can work if you do it right, or fail miserably if you don’t.
I thought I was so smart to do all my maternity dress shopping this year online via Amazon (while lounging on my couch), but of the 10 super-discount dresses I bought, only the Leotas and two other types were keepers, and the other 6 dresses had to be returned.
My mistake? The ultra-cheap dresses ($10 range) were chintzy and bad quality, not to mention guilty of a bust-smashing too-high horizontal seam. In sum, with bad brands, online shopping stinks, but with a good brand, online shopping can be your best friend.

7.) Washability and anti-wrinkle materials save sanity.
One fun pregnancy symptom is a superhuman sense of smell. Pair this with increased sweating, and you know you’ll need to wash your maternity dresses often. Given this, plus how busy a pregnant woman’s life can get, I strongly suggest you only buy machine washable dresses. (Most Leotas are cold machine wash and air dry, which is nice and easy.)
Further, do you really have time to iron? Look for dresses that are non-wrinkling, and for even more happiness, always opt for fabrics that stretch, like Leota’s silky and stretchy jersey deliciousness.
8.) Patterns trump solids.
As I grow in pregnancy size, I unfailingly find that patterns look better on me than solid colors. Multiple colors nicely flatter my expanding girth, and also make me happy to put on!
There you have my eight maternity dress shopping tips. What advice would you add or revise from this list? Do share. Click here for a direct link to browse Leota’s fabulous dresses on their site, and click the affiliate link to see Leota maternity dresses at a discount on Amazon!
Leota provided some of the dresses shown, but all opinions and camel caresses are my own.

The author, Lillie Marshall, is a 6-foot-tall National Board Certified Teacher of English, fitness fan, and mother of two who has been a public school educator since 2003. She launched Around the World “L” Travel and Life Blog in 2009, and over 4.2 million readers have now visited this site. Lillie also runs TeachingTraveling.com and DrawingsOf.com. Subscribe to her monthly newsletter, and follow @WorldLillie on social media!
Penelope Miller
Monday 10th of September 2018
This article was so restorative. I am now 19th week pregnant and I am so thrilled about this.
Lillie Marshall
Monday 10th of September 2018
Glad to hear!
Emily
Monday 7th of December 2015
I've been interested in these dresses since you featured them last spring (or summer?) but as a nursing mom, I wasn't sure if they would work for me. Would the wrap dress (or any others) work for nursing do you think?
Thanks!
Lillie
Monday 7th of December 2015
Emily -- it is a crazy coincidence that you posted this comment today because Leota JUST opened a "Nursing" section of their site: http://shop.leota.com/collections/nursing-dresses . Basically what this section shows is that any of the Perfect Wrap or Sweetheart dresses are perfect for nursing because you can pull the bodice down easily, just set up a nursing cover or scarf over if you want privacy. I was emailing today with Sarah (Leota's founder) about how I really like this approach, because I've tried fancy "nursing dresses" with layers of flaps and openings, and frankly I think they are a waste of money, not to mention unwieldy. What actually makes a good nursing dress is the ability to pull part of the bodice to the side, and those two styles of Leota dresses do it well. Hope this answer helps answer your question!
Meg Jerrard
Friday 27th of November 2015
Fabulous post Lillie! You look fantastic in each of these, and I really do see that patterns do trump solids here. You've given me a lot of comfort in this post because I've always wondered if my ability to travel while pregnant would be restricted - hoping it'll happen soon! But I'm so glad to see that there are other women out there who are still conquering the world with baby bump in tow!! You're inspiring :)
Valen-This Way To Paradise
Wednesday 25th of November 2015
These all look super cute on you! I think that was a good decision to pick patterns over solids.
Lillie
Wednesday 25th of November 2015
Thanks! Patterns are especially key since I have a toddler at home who enjoys wiping his nose and hands on me. :)