Wardrobe Staple: Comfortable Dresses

I’m more than halfway through my pregnancy now,  and I feel like my stomach has become exponentially bigger in the past month. I keep getting stuck between chairs and other furniture. While getting ready for work a few weeks ago, I realized that all my “big” dresses that I’d been saving to wear were now gaping at the buttons. While this was depressing news, I decided for my sanity and comfort that I would give myself an extra metal pregnancy allowance for my 25 item wardrobe challenge. It allowed me to quickly stock up on some new comfortable pieces.

I’ve found that I personally like looser versus tighter items for “maternity” wear, and found some great dresses that I think I’ll be using even after this period. I don’t think there’s anything that beats the right dress for comfort out there. And, just as a reference for other preggos looking for clothes, I have a 21 week bump in these pictures, and it fits with plenty of room under all of these dresses!

1. First up is this long sleeved Free People dress, which incidentally appears to qualify for Friends and Family at Bloomingdales in three colors – white, black, and fuchsia !

I bought this dress because it looked like a super easy piece that I could continue wearing after pregnancy at the beach, for an evening stroll in the summer, etc. I also loved that it comes in a bunch of great colors (though of course I ended up with black).  As a plus, this dress also comes with a full lining, which I don’t always to be the case with Free People (see my other review below).

Also, I’ll note that I could have easily taken an XS in this dress, but ended up with a Small because I wanted the extra length. I believe that this style runs very short…and maybe my bump took away some material, too!

2. Next up is Anthropologie’s Paned Cocoon Dress. This dress is uber comfortable, and fully lined as well. It’s actually quite warm, so I wear it on days where the weather is closer to 70 degrees versus higher.

This dress can be a very “beach” style on its own, but paired with heels for the summer or leggings in the fall/winter dresses it up quite a bit. It’s one of my favorites from Anthropologie this season and I would have likely purchased it, pregnant or not. I did end up choosing to go with XS Regular instead of XS Petite, just to get some added length again.

3. Next is another Free People number – one of my favorite ones to wear currently actually, a gauzy embroidered maxi dress.

For what it’s worth, this dress is the one that I’m told makes me look the “least” pregnant, which I take to mean that it hides bellies well. I fell in love when I tried it on and I realized that there was no tailoring needed on the length..even if I wore flats. I’m 5’1, so that almost never, ever happens.

For those who’ve asked, here’s a “bump” update picture for you all…see how well it hides it? Perfect for buffets!

Free People Embroidered Maxi

It’s also incredibly comfortable, and I love all the embroidery details. I do have a soft spot for “hippie” looks, and this is probably a dress that falls into that category. Also, I’d like to note that unlike the first Free People dress I recommended, this one does not come with, and requires a slip. My favorite is from Commando.

4. Last, but not least, is this relaxed fit dress, from Gap. I love the Gap, and shop there almost every season. Yes, I end up trying on lots of items with wonky fits, but the prices are great and I’ve found the quality to be quite good. This is one of their best items this season in my opinion.

This dress is perfect. It’s so simple, but the cut is flattering, the material really comfortable, and the striped pattern makes it a classic. Plus, it has pockets! At $50, I think the price is already fine, but Gap of course always has promotions. I bought this one (and a second version) for under $40 each.

Thank you all so much for your kind words about my pregnancy. I hope this post was helpful for some of you looking for some nice, loose comfortable dresses for the coming summer months!

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  • Sarah
    March 23, 2015 at 9:15 am

    All the best – you look great! Have you heard of a brand called 100%lino? (Something like that) unsurprisingly it brings out dresses in pure orgsnic linen, in lovely colours. They are not pregnancy per se, but a lot of them are a loose fit, shift style, with beading or details at the neck, like a necklace. Any way they are very nice for summer so thought I’d mention it. X

    • Katherine
      March 23, 2015 at 5:13 pm

      Hi Sarah, thank you! They have lovely items and I like the fabrics too!

  • Lisa
    March 23, 2015 at 10:59 am

    You look amazing pregnant! Wishing you all the best.

    • Katherine
      March 23, 2015 at 5:08 pm

      Thank you!

  • Tabitha
    March 23, 2015 at 11:02 am

    You look blooming lovely, I bet you can’t wait to be a mum.

    • Katherine
      March 23, 2015 at 5:07 pm

      Thanks so much!

  • tata
    March 23, 2015 at 1:20 pm

    if you can find maternity clothes that works great with nursing, you can continue wearing them afterwards too. things that button down, things with straps you can slide off, etc. those dresses will come very handy for after birth when you are still uncomfortable going back to your usual clothes.

    • Katherine
      March 23, 2015 at 5:07 pm

      That’s a great point! I’ll remember that when shopping 🙂

  • Anna
    March 23, 2015 at 1:52 pm

    You look fantastic! May I ask who makes the gold watch you’re wearing with the striped Anthropologie dress?

    • Katherine
      March 23, 2015 at 5:03 pm

      Hey Anna! It’s the Ballon Bleu from Cartier.

  • Anonymous
    March 23, 2015 at 7:01 pm

    Hi Katherine!

    Do you mind sharing what size you ended up getting for the GAP dress? Thank you!

    • Katherine
      March 24, 2015 at 9:08 am

      XS Regular

  • Alissa
    March 23, 2015 at 9:28 pm

    I love the shoes too….what are they? The espadrille wedge especially

    • Katherine
      March 24, 2015 at 10:50 am

      Thanks! They are Jimmy Choo, the other heels are Stuart Weitzman. Both are a few seasons old!

  • Wei
    March 23, 2015 at 9:28 pm

    You look wonderful! 🙂

  • Ammu
    March 23, 2015 at 11:08 pm

    You look fabulous xx

  • Olivia
    March 24, 2015 at 8:00 am

    You look fabulous!

  • Xin
    March 24, 2015 at 10:42 am

    You look great! My favorite dresses are the long blue Free People one and the Gap dress.

  • Kitty
    March 24, 2015 at 1:09 pm

    Congratulations! Everything looks great on you. When I was pregnant, I felt that the form fitting pieces that accentuated my bump looked best on me. Hiding it just made me feel fat and pregnant if that makes sense. Tight tank tops and maxi dresses with the side ruching made me feel sexier and a lot more comfortable. Old navy has a decent maternity line for basics and I loved a Isabella Oliver dress for nights outs. Rosie Pope’s line is also great. Also a really high end pair of maternity jeans was my best friend through 2 pregnancies! Best of luck in your pregnancy. Enjoy every minute of it!

    • Katherine
      March 25, 2015 at 10:13 am

      Thanks so much! And I definitely know the “fat” feeling…my coworkers all breathed a sigh of relief as they all not wanted to ask about my giant dresses and weight gain, lol.

  • Whitney Farris
    March 24, 2015 at 5:06 pm

    For dress up/ down , black leggings worked for me! Put on a nice oversized sweater, flats or heels and jewelry!
    BAM, I was ready to go. I hated maternity clothes so I usually went up a size or more with regular clothes. Maternity used to be cutesy and I don’t like cutesy.

    • Katherine
      March 25, 2015 at 10:12 am

      I dislike maternity clothes too…though some are cute that I found on ASOS, etc. In the winter I lived in leggings too!

  • Jo
    March 24, 2015 at 5:21 pm

    Congratulations Katherine! I never knew you’re pregnant. So happy for you both! I love all your dresses and the fact that you’re still wearing heels. 🙂

    xo Jo

    • Katherine
      March 25, 2015 at 10:12 am

      Thanks so much Jo!

  • MG
    March 31, 2015 at 7:07 am

    Thanks for this post. I haven’t been in a Free People store in ages but I am headed there today after your suggestions. I just picked up this cute tank from Anthro. Swingy and easy. I sized up to a small for the extra length. Will definitely be in heavy rotation for the last trimester!

    • Katherine
      March 31, 2015 at 4:11 pm

      That top is gorgeous!I think Anthro and Free People are great go to places for maternity clothes!

  • Cindy
    April 4, 2015 at 9:08 am

    Wow, what a blogger! I personally enjoyed reading your blog this morning. Very straight to the point. I am glad that I found your blog. Love all the entries, specially the ones on Hermes comparision, questions before making purchases, so on and on. Lol graphing in fashion point of view. Very well organized and interesting points of view. All the best to you and your loved ones.