15 Easy Summer Dresses

15 Summer Dresses Under $150

There’s nothing better than having a few lovely summer dresses in your closet — they’re cool (versus sweaty), effortless (getting dressed takes one minute), pretty (and feminine) and can take you from day to night. It always feels like a relief when it’s finally dress season. For picnics, adventures and weekend getaways, here are 15 dresses, many for less than $50.

Click or tap on the images, if you’d like!

Which would you wear? Which would fit your personality best?

P.S. The chicest summer sandals, and floppy sun hats.

(Top photo by The Sartorialist. Top dress: Similar here and here. Layout design by Miss Moss for Cup of Jo)

  1. You hit the nail on the head!! All awesome choices!

    Shelby Cate

  2. Love the boho maxi dress and polka dot maxi dress!!!
    great post by the way!

    Rachel x

  3. Prudence Yeo says...

    I love summer dresses as they are so easy to put on yet look so pretty! Adore your selections especially the denim pieces, they are so chic and in trend this season!


  4. So fresh looking ! And easy to wear.

  5. Hi,
    I love your summer dresses. I don’t know if you have ever heard of Ruby Ribbon before but we are unique in the fashion/shapewear social media realm. I would love to share more with you if you are interested. Check out my website and email me. Happy Saturday!

  6. Thank you so much for bringing Everlane to my attention!

  7. I like the Peasant dress and the Cutout Stripe dress :)

  8. Gorgeous dresses! I love any dress from the Gap, such an easy transition from busy workdays to lazy summer weekends!


  9. Catherine says...

    Jo- Love these dresses, but I would love to see more sustainable companies/fabrics on your website. The cotton industry makes a huge negative impact on the environment, so buying organic cotton is important. Buying from sustainable companies also makes a big impact on the lives of the people who make the clothes. 41 people were just charged with murder for the 2013 Bangladeshi factory collapse that killed 1,100 people. The Bangladesh factories supply retailers like the Gap.

    It would be awesome to see you using your influence to encourage others to think about how their clothes impact the world!

  10. I love these dresses! Dresses are so much easier for summer than anything else – something about just having to throw on one article of clothing and instantly looking put together!

  11. I purchased the Gap cinched scoop dress in dark navy and though the length was a little long, I actually really liked the look and vibe of the dress overall! It was just so different than anything I usually wear, and I kept picturing it with a long statement necklace- but a cool/unique one with large colourful clay beads or something! I could just picture myself sashaying along Queen St (our “cool” street here in Toronto) on a Saturday. Alas, my wallet thought different and I decided to return it. Really love the ASOS denim dress too!

  12. I’ve bought a dress yesterday that resembles a maternity dress, but I love it! It’s so comfortable and has a bohemian vibe to it.
    Also, I hope you don’t mind, I used your blog as a topic on my latest “inspiration” post. :)

  13. I was distracted by how awesome her hair is (1st photo)! I stopped cutting my hair super short and I see I will have a similar style in a few months. Now I know what my hair will sort of look like lol.

    On the topic of dresses, I have become dress-obsessed lately. I would be skirt-obsessed too but good ones are much harder to find. I prefer minidresses to maxis but this black floral model is exceptional!

  14. yael steren says...

    Another great dress is this maxi dress by Lush and it’s only $39! I’ve worn it a few times on my blog and I still don’t understand why it’s as inexpensive as it is! Here is a link to one of the posts where I am wearing it (!! You should definitely check it out, it’s one of my best finds to date! xoxo yael

  15. I love the Fit + Flare Dress and the Abstract Pleated one. This is a really fun post because I like look at dresses that I wouldn’t necessarily be down to right away on my own. I also love your blog Joanna! So many insightful things and I’m often lost on it for hours.
    x Tali

  16. The batik dress is awesome. Beautiful design. Plus, I’m always on the lookout for summer dresses that have good sleeves.

  17. Laurel says...

    I want the one in the top picture!! Is there is link to that dress?

  18. Kerstin says...

    Love the blue and white print on the first dress! Boden always has a lovely collection of summer dresses along with free shipping and free returns. I love their “casual jersey dress” and have it in both navy and a sweet floral print. It’s one of their classic dresses that they repeat every year in different prints. So easy to wear and packs like a dream. Just roll and go!

  19. Love this selection! I recently went to Greece and Turkey (which – shameless plug – I’ve been blogging about), and blue summer dresses as well as maxis were my staples for those couple of weeks. These are great options! I’m going to Paris in a couple months, and I think either that red striped boatneck dress or that mixed pattern black & white one at the bottom would make a stellar outfit!!

  20. I’m so in love with the shirt dress and the butterfly skater dress! I’ve been on a hunt for some cute, affordable shirt dresses actually. Lovely picks for summer! <3


  21. Ali Kitchener says...

    Of course I love, love, love the first image! Desperate to find out where that one is from!

  22. Dee says...

    Love the denims!! But can I just compliment Miss Moss for the layout of this post? So clean I love it! :)

  23. Love the light blue polka dot maxi. And of course it’s Ann Taylor…I’ve been mooning after several of their dresses. Now this one is on the list too! Nice roundup!

  24. I agree. Love dresses for anytime of the year, but most esp during summer. I can’t pick a fave but the maxi dresses are sure faves for me :)

    Abby of Life in the Fash Lane

  25. I love, love, LOVE the fit and flare dress! As a lady with a booty – I always tend to like longer dresses in case, you know – it’s windy outside or I ever have to sit down, haha.

  26. Amanda Goad says...

    Love the fit and flare dress. The link isn’t working though, any ideas?!

  27. I normally don’t go for bright pops of colours but i do like the batik dress, a lot!

  28. Kelly says...

    Beautiful dresses – but any interest in expanding in the future to include plus size options? I love the inspiration, but would also love to see a few dresses mixed in that I could wear. Thanks!!

    • ashley says...

      I second this!

  29. ashley says...

    not that this is at all relevant, but i love the couple getting their picture taken BEHIND the model in the top picture. ;)

    • haha, agreed!

  30. I love the look of the fit and flare dress.

  31. Ah, I love this. I’m currently nursing…it’s wonderful, but i’ll miss wearing summer dresses this year, as they are not very nursing mama-friendly! Skirt round-up!? :)

    • Me too. The floral maxi could work if the girls were a little smaller and I were a pull-down breastfeeder, but no dice. Milk Nursingwear has a cute striped sleeveless nursing dress!

  32. CC says...

    I’m torn between the flit and flare dress and the abstract pleated dress. I feel like the abstract better fits my personality/style but I like the flit and flare because I love wearing colors and I could totally rock that at the office. I’d probably wear the abstract one to work too but it’s a little short for a frequent wear to work dress.

  33. Sarah H. says...

    I love that boho maxi, but I’m not sure what I’d do with with my boobs in it! Ha! Perhaps that one is best left to lovely smaller-chested ladies. :) The boatneck mini is great too.

    • Joanna Goddard says...

      hahaha me too.

  34. Oooh, I love the Batik and Denim Mini dresses especially! I am sporting a 30-week baby bump at the moment, so some of these will have to wait ;-)

    Joanna, do you have a link to the top dress? It’s stunning.

  35. The girl in the midi shift dress looks like she has to wear clothes and shoes donated by someone bigger than her.

    My favourite is the abstract pleated!

  36. Allie says...

    Where is the dress in the main photo from? Thanks!