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My Pregnancy and Postpartum Wardrobe Staples + Style Tips

My Pregnancy and Postpartum Wardrobe Staples + Style Tips

Last photo taken before I had June! Wearing this (non maternity) Amazon tank dress and ABLE Merly jacket 

Happy Friday!

We are currently en route to Napa as you’re reading this–hooray! Here on the blog today though, I’m sharing ALL my pregnancy and postpartum reccos, and answering all your style-related questions in one place. Every time I post a Q&A I get flooded with questions on this topic, so I thought it was about time I published a guide on it!

Whether you’re expecting or looking to buy some stylish staples for someone you love, I hope this blog post is a helpful place to start!

My Pregnancy and Postpartum Wardrobe Staples + Style Tips

Favorite go-to’s for maternity clothes?

My experience with curating a “maternity” wardrobe: 

I really didn’t buy very many maternity specific clothes, rather, would size up in regular clothing when possible, opted for drawstring pants, regular dresses that accommodated a bump, etc! That being said, I did have a handful of maternity specific staples I ordered closer to the end of my pregnancy–I had two favorite retailers for that purpose:

The dark horse: H&M! Seems a bit random, but I think their MAMA line is by FAR the biggest hidden gem in the pregnancy dressing category. I ended up ordering quite a few things from there! Nice because they don’t break the bank!

Also, Kindred Bravely! I had never heard of them before they approached me about a partnership in my third trimester, but I ended up LOVING them and I got so many dm’s from so many of you saying you adore the company as well! (Lots of you recommended them for nursing essentials–which I can’t comment on as we did bottle feeding from day one but you all raved about them!) They have really amazing basics, loungewear, and more.

When do you need to start buying maternity clothes? 

Many of you asked this question! The answer will vary by person! If it’s your first pregnancy, you may not need to start buying maternity items until well into your second trimester. I also think your due date will affect how long you can get away with wearing regular non-maternity clothes (you may not need maternity clothing at all!) And I think I was lucky in that regard (June was born at the end of June) because by the time I really started showing, it was getting warm outside, so I was wearing a lot of flowy dresses that transitioned perfectly into postpartum life as well and I lived in those clothes all summer.

I also think it just depends on what makes YOU comfortable. Some people LOATHE maternity jeans, for example, others LOVE them because they provide support and coverage. Some people love living in leggings–others hate them and want to wear “real” pants. There is no right or wrong way to approach curating your pregnancy and postpartum wardrobe, it’s all about what works for you.

Kindred Bravely maternity tank dress | My Pregnancy and Postpartum Wardrobe Staples + Style Tips

Wearing Kindred Bravely maternity tank dress (c/o)

My reccos for “Maternity” Clothes and Jeans: 

I will say I got two pairs of maternity jeans (both of which are no longer in stock so can’t link them) but I didn’t wear them that much because we were in deep quarantine for most of my pregnancy until it got warm outside, and then I switched to dresses. However, depending on where you live and what season you’re visibly pregnant in, you might wear jeans ALL the time–I think it depends on a lot of factors! Only you can decide what is worth it for you in terms of the investment.

A quick tip for when you’re “in between”–I.E. not big enough for maternity, but busting out of your current jeans:

rubber band your jeans or order a belly band and/or jeans extender so you can keep wearing your existing pants as long as possible! This set comes with a bunch of options and looks like a great buy.

For what it’s worth, I preferred the lower cut, under the belly side-panel style of jeans (vs the over the belly jeans) simply because they allowed me to front-tuck my shirt. (As we all know, I am an avid front-tucker.) However, I will say those got pretty tight at the end of my pregnancy (which is fine, because again, it was June, and it was hot outside, so I wouldn’t have wanted to wear them then anyway), but you may think differently depending on your situation.

If I were shopping now, I’d definitely buy these straight leg maternity jeans from H&M as they have the full over the belly for more comfort, but still allow you to front-tuck. GENIUS! (Shop all their maternity jean styles here!) Old Navy has some really cute maternity jeans, including overalls, which are so cute! Madewell also makes really cute maternity jeans, but they’re more expensive.

I think I only wore one true “maternity” dress, and that was this tank dress from Kindred Bravely (*gifted from the partnership as I mentioned above), which is just as cute after baby arrives.

(You would never look at it and think it’s a maternity dress!) It’s SO soft, but super flattering. I even wore it to my 39 week appointment the day I ended up going into labor! Otherwise, I just wore flowy dresses that were easy to wear over a bump! (Luckily by the time I had a bigger bump it was summer so that was easy!)

I also really liked wearing the Spanx faux leather maternity leggings–which I would’ve worn more of had my bump been bigger earlier on in pregnancy, but for about a month I wore them nonstop. Before I had a larger bump to fit the Spanx leggings, I just sized up in regular leggings!

Pregnancy/postpartum underwear and bras

My favorite bra/crops from Amazon

Pregnancy/postpartum underwear and bras: 

Do you *need* postpartum underwear? No, you don’t! I think your favorite underwear in a larger size if needed will totally do the trick. (Maybe you won’t even need a larger size? I definitely did though! Everyone is different.) However, pregnancy/postpartum specific undies are nice too!

To sleep in at night, I lived in (and still wear them to sleep in every night) this set of briefs from H&M and this high rise set from Kindred Bravely. (Both are great for postpartum and c-section recovery as well as they are low rise and high rise!) These are nice because you’ll want some underwear with coverage that you can fit pads in once you graduate from the mesh/disposable undies.

For everyday underwear when I was pregnant, I just ordered more of my favorite no-show thongs in the next size up.

Luckily they’re super stretchy so they were still super comfortable. Thongs are most comfy to me and I hate wearing full coverage underwear unless I’m sleeping in them or wearing a very loose dress, so I was back to wearing my regular thongs (in that larger size I bought while pregnant) a week or so postpartum (with some thong pantyliners when needed for any minor bleeding still happening! FYI–Your body will still be shedding blood/fluid for a while post baby!) I also have friends who didn’t touch thong underwear for months. It’s just about whatever makes you most comfortable!

For bras, I just ordered my favorite True & Co bras in a size up.

No sense in starting from scratch trying to find a bra you like–just size up! I also lived in these lounge bra/crops from Amazon and still wear them ALL the time.

For nursing bras specifically, like I mentioned above, I can’t comment on those but you all raved about Kindred Bravely’s (especially their pumping bras).


I don’t think you necessarily *need* maternity pajamas (you can just size up in any pajamas you like–you may deal with some belly showing for a few weeks at the end of your pregnancy, but I don’t think that’s a huge deal?) BUT I did end up living in/loving this button-up nightshirt from Kindred Bravely (again, was gifted as part of a partnership) I wore it in the hospital and wore it a ton postpartum, and I still wear it!

Another honorable mention in the nightgown category is this grandma-chic house dress/nighty from Amazon. Perfect for a bump and kept me cool at the end of pregnancy. I wore it around the house constantly!

As for a bathrobe, you don’t need a maternity specific bathrobe, but you will want one that is super soft and in a dark color to wear in the hospital. (You don’t want to be worried about getting blood on a light colored bathrobe while changing your postpartum pads). Because June was born in the summer I had one very similar to this lightweight bamboo robe and it was perfect! If you want a warm/cozy robe (perhaps delivering in the winter), I cannot–repeat–CAN NOT recommend the Barefoot Dreams one more. Worth every single penny. 

I also think it’s REALLY lovely to have some nice loungewear sets to wear postpartum. It’s so nice to feel comfy and cute at the same time! I LOVE the Terry sets from Summersalt (use code JESS10 for $10 off!)–they are to die for (so soft) and so cute.


I only purchased one “maternity” bathing suit, which was a chic black one-piece from Summersalt–the style is sold out now, but this one is very similar and has great reviews! It was super flattering and had the right amount of coverage and support while still feeling stylish! Sharing my other non maternity favorite below.

My Favorite $27 Amazon Bathing Suit | My Pregnancy and Postpartum Wardrobe Staples + Style Tips

My favorite bikini that isn’t maternity but works great for a bump. Can be rolled up or down for more coverage (so great for PP too!)

My Pregnancy and Postpartum Wardrobe Staples + Style Tips

Cute accessories like a neck scarf and a jean jacket are an easy way to dress up leggings!  Aerie offline leggings (sized up to M), ABLE’s Mae drapey tee (use code JESSKEYS15), ABLE Merly jacket (use code JESSKEYS15) ABLE ABERA backpack purse (use code JESSKEYS15 for 15% off discount!)

pregnancy outfit ideas

Accessories can make all the difference when you’re dressing a bump! Here I used a belt bag (mine is old from ABLE but they still sell it in other colors–use code JESSKEYS15 for 15% off!)  to “create” a waist as I didn’t have one and threw a jean jacket on for a really cute casual look that is a lot more interesting than if I had just worn the regular old t-shirt dress! Wearing Freda Salvador d’Orsay white leather sneakers and ABLE Merly jacket (use code JESSKEYS15).

Non-maternity items that I found to be essential in Pregnancy/Postpartum: 


In the colder months, I also lived in longer/flowy sweaters and faux leather leggings. The Amazon tunic sweater was my #1 MVP. I also wore my Dudley Stephens Cobble Hill tunic a LOT. (Vello fleece is their warmest, Terry fleece is for warmer climates) I wear a size small but I went up a size for pregnancy and it worked really nicely–and I still wear it all the time now!

Leggings and bike shorts:

My favorite leggings in pregnancy and non pregnancy have always been the Aerie offline leggings, which I sized up to a medium in and they took me all the way through my entire pregnancy. They feel JUST like Lulu Aligns but will barely make a dent in your wallet. I also LIVED in bike shorts as it got warmer. I rounded up all my favorite bike shorts in this post–I just sized up and they were ideal for postpartum in the summer as well.

Drawstring shorts and pants: 

Particularly linen drawstring shorts and pants! The ones I have are several years old, but the drawstring really helps and the fact that they are loose and flowy to begin with.J.Crew and Old Navy have some cute shorts options, and I think this pair of drawstring linen pants from J.Crew is super cute! Everyone is different of course, but I was able to wear drawstring bottoms up until my last few weeks of pregnancy. Both of these look cute with oversized flowy tops and button-downs. (I wore a lot of gauzy button downs like this one!)

Comfy tees: 

ABLE’s Mae drapey tee I wore a lot (knotted above the bump with leggings or bike shorts–no need to size up, like the name says, it’s very drapey and accommodating for pregnancy/postpartum! Use code JESSKEYS15 for 15% off your order) I also loved the oversized tee look–I’d size up two sizes and then knot it above the bump for more of an 80’s vibe.

Boyfriend button-downs:

A go-to top to wear with maternity jeans, bike shorts, and leggings! (I just wore what I already had in my closet and for the most part they were oversized enough for the bump!) This one from Summersalt (can use code JESS10 for $10 off!) would be great for that purpose and also be a great essential for work, as would this one from Madewell.


Two kinds of dresses to look for: tight stretchy dresses (that show off the bump–I loved this one from Amazon) and flowy, billowy dresses to accommodate the bump (I shopped for these mostly at Mango, Old Navy, and Amazon! Many of which are sold out but I”ll link the ones you can still shop below!) If you feel frumpy in the loose flowy dresses, look for some that are tighter around the ribcage (either with elastic or drawstring) but flow out just above the ribs. (Like this one or this one!) This will still give you a waist but accommodate a bump at the same time!

Majorly honorable mentions for comfy pregnancy/postpartum dresses:

Go to the Hillhouse Nap Dress which is so comfy and flattering and due to the smocking, you don’t have to wear a bra! Truly the best postpartum essential (I have the Ellie in multiple colors–size down, I wear an XS!) and the Dynasty George Daphne (which I wore for June’s newborn photo shoot) and Clementine dress. Of course, there’s also the famed Amazon Mumu that I own in multiple colors and lived in during pregnancy and postpartum!

Cute footwear: 

Obviously comfort is key here (and the ability to put on shoes–slip ons are ideal when it becomes hard to bend over!), but finding some really stylish shoes can be the perfect way to elevate your outfit when you’re feeling “meh.” When I was pregnant I invested in the Freda Salvador d’Orsay white leather sneakers (slip on, they were the most perfect pregnancy shoes and they are still my favorite white sneakers! Reviewed over in this blog post on my favorite white sneakers), the Loeffler Randall Emilia knot slides (the slip-on + low heel is kEY), and gold Birkenstocks. These are basically the only shoes I wore for my entire third trimester through the rest of the summer! (Let’s be honest they’re probably the only shoes I’ll wear this summer, too!)

Non-maternity swimwear for pregnancy/postpartum: 

Highly, highly recommend this Amazon bikini (reviewed here) for pregnancy and postpartum! Won’t break the bank and is really great because you can roll the bottoms up or down to be high or low waisted! Plus, it’s really affordable.

Amazon + Abercrombie Try-On

This Amazon jumpsuit is so comfy and would be perfect for pregnancy (first-second trimester) and postpartum! One and done outfits like jumpsuits and dresses are key during postpartum especially when you don’t have a lot of energy to put into getting dressed, but want to feel put together!

linen drawstring shorts

I loved wearing linen drawstring shorts (that I’ve owned for years!) they were very accommodating for the bump when worn with a flowy blouse! (Everything else is old so can’t link!)

What about workwear options?

I don’t have a traditional office job so I can’t speak personally on maternity workwear for the office, however, what I’d recommend is going with a tight/formfitting dress and layering a cute blazer, jacket, or cardigan over the top! You can also wear flowy dresses (I always recommend opting for black as it looks more formal/professional) and you can always add a cute belt (I love Sezane’s belts and also wore this one from Amazon with spring/summery dresses) to define your waist above the bump!

You could also invest in a pair of dressier maternity pants, like these or these, to wear with button-downs and sweaters! I also think the Dudley Stephens Cobble Hill tunic can be dressed up easily for the office and looks super cute with leather leggings and loafers!

Shop pregnancy/postpartum workwear options: 

Best Outerwear for a bump/postpartum

Best Outerwear for a bump/postpartum?

If you need a warm coat to accommodate a bump, can’t recommend the Amazon parka enough! It zips to expand at the sides so it’s perfect for pregnancy and also for baby wearing!

How do I make the outfits I’m already sick of more stylish and cute? 

Accessories are your best friend! 

Accessories, like fun earrings, cute shoes, a scarf (see how I tie my scarves here!), or a pop of lipstick will be KEY here! I often find that accessories can make even the most basic outfit look really cute and put together! You probably know this by now, but a neck scarf is my #1 go-to and I think it can make such a big difference in taking a boring outfit to a polished one.

Don’t forget about belts! 

Sometimes the difference between feeling chic and feeling like a big ole pregnant blob is just a belt! Wear it above the bump and it really helps define the waist! (I love Sezane’s belts and also wore this one from Amazon with spring/summery dresses)

My Pregnancy and Postpartum Wardrobe Staples + Style Tips

postpartum outfit for warmer weather

A go-to pregnancy/postpartum formula for warmer weather: A cute boxy collared top or button down (like this one from Madewell) bike shorts (these are Lulu Aligns which I wore the most postpartum and were the stretchiest to fit me best at 9 months pregnant–I went up to an 8 and I would usually wear a 4 or 6 in Lulu leggings) and sneakers.

Tips on dressing a new postpartum body?

My biggest tip is to buy some new staples you love that fit you now.

The best thing I did was buy new jeans in my new postpartum size the week after June was born. I walked into the Levi’s store and grabbed a style of jean I had been wanting to try out (but couldn’t because I was pregnant), and bought the size that fit, not the size I used to be. I then had jeans I felt super confident wearing and loved pulling on! And I thought they made me look like a million bucks, too–because I wasn’t trying to squeeze myself into a size I wore previously–and my new jeans in my new size hugged everything in all the right places–and that is SO important!

I also ordered these jean shorts from Abercrombie in my new size so I had a pair of cutoffs to wear that were comfortable and cute those first weeks postpartum. (While I love dresses and still wore them often, being able to wear REAL pants after not being able to wear them for so long felt so great!)

Luckily, I don’t wear a lot of ton of tight tops to begin with, so many tops in my wardrobe were already flowy, making them easy to pair my new bottoms. I also bought a couple cute new tops that were smocked/stretchy around the ribcage but flowed out to accommodate post-baby bump. (This one from Hill house would be great!)

Long story short:

I had no idea if and when I would ever fit into my pre-pregnancy clothes again, and I didn’t want to wait to wear stylish clothes that I loved! The minute you stop obsessing about fitting into your pre-pregnancy clothes, you will be a much happier person! (This goes for anyone in general in any phase of life–your clothes should change to fit YOU, YOU should not change to fit your clothes!)

So if you have a pair of jeans, or shorts, or whatever you’ve been wanting to try–buy them–in the size that fits you as you are. (I would recommend trying on in person OR just ordering from somewhere with free returns and buying a couple sizes to choose from!) Having something you’re *excited* to pull on vs just the same old leggings you’ve been living in your months makes a huge difference in your confidence.

If you’re on a budget, that’s okay! I highly suggest checking out poshmark or eBay, or even asking friends of similar sizes to exchange/borrow some postpartum clothes that you love that they may not be using anymore!

Dynasty George dress

My Dynasty George dress was the perfect postpartum dress (I wore it for June’s newborn photos too!)

postpartum outfit ideas

Jumpsuits are awesome for postpartum, especially those that are cinched at the waist as they give you a flattering shape but are also forgiving in the tummy area! This one I’m wearing here was gifted from ABLE and was what I reached for postpartum when I needed to feel polished. Perfect for dressing up or down!

Shop flowy dresses that would be great for both pregnancy and postpartum: 

Diaper bag + purses:

I use my Able Alem backpack (use code JESSKEYS15 for 15% off!) as my diaper bag (see full review and everything you need to know about it here!) For quicker trips where I don’t need a bunch of stuff with me, I often will use my Abera backpack purse (code JESSKEYS15 gets you 15% off) It’s a much smaller purse size, but fits everything you need for say, a couple hours out to lunch or drinks–a couple diapers, wipes, changing pad, and my essentials too! Another bag I absolutely LOVE is my Kibou fanny pack diaper bag! It’s so awesome, I love it so much I often wear it even if I don’t have June with me! (It would make the BEST gift, too!) I love that it’s a small, mom-owned company!

One more tip: Consider renting!

I have always been familiar with Rent the Runway, and will often rent dresses for occasions like weddings or bachelorette parties! And I think this makes so much sense not just for specific occasions (like weddings, whether or not you’re pregnant!) but also everyday dressing when you are trying to dress a body that is constantly changing.

I also recently discovered Nuuly as my friend works for the company! I personally think the clothing is more fun/unique than RTR. So I just signed up to scope them out–they happen to have a great maternity section! I also love that you also have the option to purchase anything you love at a discount, which is awesome! If I were pregnant now and needed more “real life/out in public” clothes, I would definitely go with this option–especially because you don’t want to spend a lot of money on something while you’re pregnant that you won’t end up wearing later on.

Hill House Nap Dress postpartum

My Hill House Nap Dresses were an absolute lifeline those first few months postpartum (and I still love them just as much now!)–no bra required and so comfy to wear around the house and out and about!

I hope this was helpful in curating your pregnancy and postpartum wardrobe!