Day 14

Holiday Shopping

The vibe

simple, comfortable, stylish

Styling tips

For a fun day of shopping with friends or family, you want a look that's equal parts form and function.  Find a dress that's comfortable for a long day of hitting the pavement and also make sure you can quickly and comfortably whip it on and off in a changing room!

Additional Favorites


30 Dresses in 30 Days

Fall / Winter 2017

Day 14

Holiday Shopping

The vibe

simple, comfortable, stylish

Styling tips

For a fun day of shopping with friends or family, you want a look that's equal parts form and function.  Find a dress that's comfortable for a long day of hitting the pavement and also make sure you can quickly and comfortably whip it on and off in a changing room!

Additional Favorites


105 Responses to 30 Dresses in 30 Days | Fall/Winter 2017

  1. anmituhime says:

    How can l get it??l live in Japan

  2. Natali says:

    Looking absolutely astonishing!!

  3. One of the most beautiful outfit I’ve seen combined with white booties 😉

  4. GORGEOUS! PS – you REALLLLLY need to share your workout! x

    chevrons & éclairs

  5. this dress looks so chic and pretty.

    Abigail Alice x

  6. Rach says:

    I’m so with ya that a LBD is a must-have! This LBD is so pretty!

  7. Natali says:

    Fantastic minimalistic dress! Your rocked this combo and those boots are just perfect to complete the look!

  8. Denise Y Ross says:

    Bring on the sweater dresses! Comfort at its best – minus the fabulous white boots though. Travel with my family means flats, flats, flats!

  9. Natali says:

    You are always looking absolutely incredible top to bottom! I’m in love with your dress, it’s so chic and elegant. 🙂

  10. Chi Chi says:

    Absolutely, fabulous and versatile look indeed. I Looove the shoes and belt.

  11. JulieUpdike says:

    This is so fun – I love a sweater dress, and the boots are a great update.

  12. Jill says:

    LOVE your style – always so chic, sophisticated, and polished!

  13. Rach says:

    This print is so fun! And those heels are gorgeous!

  14. Manita says:

    Loving the sleeves for fall/winter season and the print is just so gorgeous

  15. Sara K says:

    Love a wrap dress. This one is really fun.

  16. Felicia Thompson says:

    I love this dress. It looks so stylish AND comfortable! Are you planning to post any dresses that are more affordable? Maybe some holiday party dresses under $100?

    • Mary Orton says:

      Yes, there will definitely be affordable dresses in the mix! Also, keep an eye on the “Additional Favorites” section of every post because I always include affordable options there as well. : )

  17. Megan says:

    I bought these booties immediately after seeing them here! I’m excited to wear them with a midi suede skirt for a fun fall look.

  18. Carolyn says:

    Now this is a animal print I love! I also love the length, being over 5’8″ I love this length!

  19. Maria Samson says:

    While I do like animal print sometimes I feel like it’s too loud. How do you minimize the loudness of the print without sacrificing the look?! This looks awesome.

  20. Elena Robbins says:

    I absolutely love this project and feel as though you have given life to so many different beautiful dresses! I am excited and feel inspired to try new styles and colors for the fall and winter seasons coming up! Thank you for sharing your talents and creating an outlet for me amongst school and work haha. You truly make everything look incredible and I appreciate your creativity, classy style, and willingness to share!

  21. Jelena says:

    Such an amazing dress:)

  22. Anisha Chellani says:

    Great ideas!

  23. Kim says:

    Love all of these, Day 5 is my favorite. I need to order that for sure.

  24. Natalie says:

    I love it when you do the 30 days 30 dresses!! So many great items to covet!!

  25. Sophie Dawson says:

    I have to agree a sweater dress – particularly a neutral one with great details like this grey one! Great choice! Is perfect for travel.

  26. Natali says:

    Looking like a doll in this ladylike and beautiful styled outfit!

  27. Simply Sory says:

    Esta sección me parece una pasada, el look de entrevista no puede ser más acertado. Muy guapa.

    Te dejo mi último post, LDB

  28. wow the dress is absolutely gorgeous and I agree a perfect interview look!

    Abigail Alice x

  29. Cindy Benjamin says:

    Love this outfit, perfectly pulled together!

  30. Mari says:

    I like this very much!

  31. Emily Rabbitt says:

    I loveeee Ted Baker. He makes the best dresses. I love how you added the belt as well!

  32. Claire says:

    You make everything look so fabulous! You have a real eye for a gorgeous look!

  33. Shannon Benson says:

    Wow! This sweater dress is perfect. It’s form fitting yet cozy and warm – perfect for winter!

  34. Shannon Benson says:

    Love the Thrive Dress from Anthro… swoon. Teal and velvet. Perfection.

  35. Katie C. says:

    Love this feminine look! Agree with you that it might not be appropriate for interviews in more formal fields, but definitely would work for a client meeting or a panel presentation. Gorgeous!

  36. Carolyn says:

    I love a bow tie!

  37. Laura says:

    Hi there! I absolutely love the warmth and comfort of a sweater dress. Do you have any ideas on how a young professional (with a limited budge) might be able to pull one off in the office? I personally am in a business casual setting but have daily interactions with senior executives so I try to stay more towards the business side.

    Any suggestions are super helpful! Thanks!

  38. Laura says:

    OOPS!! I just saw my typo!! Budget** instead of budge.

  39. Morgan Davenport says:

    Last year I joined a live chat on Instagram to share that I had gotten an internship and wore an outfit to the interview inspired by things I have seen on the blog. Now that I am ushering into my professional career I am so excited to start pulling more inspiration from the blog in my everyday workwear. Whether I like it or not how I dress in the workplace says a lot and you have provided me with ideas on how to inject color and one of a kind cool pieces into a dull 9 to 5 day!

  40. Diane says:

    Love that it actually is a dress that just looks like separates! So convenient.

  41. Anna says:

    The sweater dress is super nice! Could you do a post about combining tights and dresses/skirts? I live in a colder climate and bare legs are definitely not an option here. I always end up with the same boring black tights (sheer or opaque, depending on the skirt), but it. Would be nice to try out something new. Still nothing too crazy, I don’t think I would be able to pull off a pair of “statement ” tights! Thanks xx

  42. Tierney says:

    Love these dresses, they look so comfortable. I usually wear pants and a big sweater while traveling but a dress would be even easier!

  43. Katherine says:

    Ah, this dress is magic!

  44. Love this dress and your style! <3

  45. Rach says:

    This dress definitely is perfect for a conference! Love it!

  46. Kim says:

    It’s been awhile since I’ve been on your site on my laptop – I love what you did with the pictures! It’s so nice to not have to scroll for 10 hours to get to the bottom of the post 😉 But I do love to see the outfits from different angles, so I appreciate that you still include a ton of pictures.
    PS. You look ravishing in red!

  47. Melanie says:

    I love this dress as office wear too!

  48. Katie C. says:

    Great advice for a business conference or day-long client meeting, Mary! I’ve definitely made the mistake of wearing my pointiest, most stylish pumps to day-long events and been in agony by early afternoon.

    Also LOVE the shade of red of this dress.

  49. Madeline Forcier says:

    Loving this color on you, elicits so much confidence! Really makes for a stand out look especially in the work place and when attending conferences where networking is necessary.

  50. Simply Sory says:

    Como me gusta el vestido de hoy, te queda espectacular.

    Te dejo mi nuevo post de travel

  51. Ambar Rosas says:

    Lovely dress, I can’t believe how well it matches with that jacket.

  52. Jelena says:

    So simple but elegant

  53. Katie C. says:

    Nobody does the sleeveless-dress-to-jumper styling better than you, Mary! Whenever I try to pull it off I look like a school marm! As you noted, this might not work for more conservative (cough cough banking and law) client meetings, but I would definitely wear this look to a meeting without the turtleneck and with a stylish blazer… love the tweed!

  54. Kathy says:

    The dress for the client meeting looks particularly professional with the jacket you are showing. It takes the whole outfit up a notch.

  55. Megan says:

    What brand of tights do you wear? It’s so difficult to find the perfect sheer in a sturdy tight!

  56. Catherine W. says:

    I love the way you are layering dresses with blouses and turtlenecks. Surely the jumper is back — but more fashion forward with the shorter length. Opens up all kins of possibilities in my closet!

  57. Kirby says:

    I love how you can take a dress from spring/autumn to winter with a layering turtleneck! Definitely need to add a few to my closet.

  58. Patricia says:

    The necklace you are wearing really compliments the outfit!

  59. Belen Jonker says:

    Such a classic! I’d also wear this w a black blazer and black boots! Timeless tweed!

  60. Speed Jahna says:

    Simply, classic and stylish.

  61. Natali says:

    Always a stunner! Perfect dress!

  62. bella says:

    Can you wear tights with this? I find it hard to do with dresses that aren’t lined. Any tips on this would be super helpful!

  63. Fabiana Zollo says:

    I live this outfit, the dress is elegant but those white boots are to die for!!!

  64. Anna DeHaven says:

    Thank you so much for showcasing two dresses less than $100!! I always LOVE you Banana Republic and Brooks Brothers looks!!

  65. Lukeria Efimoff says:

    I would like to purchase this dress how do I do that?

  66. Janice says:

    The velvet dress from Boden is sold out, along with the belt! Nooooo!

  67. xokimmy says:

    LOVE the business casual office party look! So fun and could definitely be reworn many times. Thanks for the inspiration!

  68. Tinisha says:

    I noticed that you paired a brown bag with black shoes. I am always worried that that is a faux pas. Is it okay to do that now? Please say yes, please say yes!

  69. Corinna Keeling says:

    I’ve bought three new dresses so far! 🙈 ugh I can’t help it I just fall in love. Thanks for helping me build my professional winter wardrobe!

  70. Keisha says:

    The blue sweater dress is stunning! Hmm, I wish I had a fabulous Hanukkah party to go to, but our friends have a tacky sweater dreidel party! Haha – it’s still fun but not worthy of a dress this great!

  71. Natali says:

    Need that coat, it’s so grand!

  72. Rach says:

    That jacket of yours is gorgeous!

  73. Josephina says:

    How do you be this fit? Always you are magnificent.

  74. Rachel says:

    Hi! I watched your insta stories live yesterday with Caroline and she asked a really great question. Something about what you wish you knew starting out when building you workwear wardrobe. And your response was “quality over quantity” for those key staple pieces which I agree with 100 percent. I believe that one key item is a white button down blouse but I have had difficulty finding a great one. Would you be willing to share any recommendations or go-to brands for white button down shirts? Thanks in advance!

  75. Jelena says:

    Perfectly matched colors

  76. Tamsyn says:

    Perfect look!! Its quite difficult to get looks that are both stylish and easy to change quickly…
    p.s. can you please share your workout?!

  77. Jess says:

    This is hands down my favorite installment of 30 Dresses because of the addition of similar options. It’s now 300 Dresses in 30 Days, and this is certainly a more the merrier situation. Also loving your live Q&A; it’s interactive and totally original, as far as I’ve seen. Not sure what is the best platform to ask or answer this question, but I was wondering where you and your husband found the inspiration and courage to become tech and fashion entrepreneurs. Going beyond why you thought Trove was needed in the marketplace, but more how you took that leap of faith to actually do it. I’m always inspired by those who change paths and take risks (as someone who is not a risk taker). I love what you two are doing and keep up all the amazing work! It’s evident you both work tirelessly on blog and Trove. Much love and respect.

  78. Hannah Rose says:

    Do you get your dresses tailored? They look like they fit you perfectly! I’m trying to knock it out of the park this Christmas for a boy I’ve been crushing on (*sigh* I know, female cliche) and I would definitely splurge on tailoring if it would help me look as sharp as you do . Please let me know 🙂

  79. Natali says:

    This velvet dress was made for you to wear it! You are looking show stopping here. 🙂

  80. Rach says:

    The velvet fabric and sweetheart neckline is gorgeous!

  81. This velvet dress is so darling! I love the color because while it is festive for the holidays – it can really be worn any time of year if accessorize the right way like you did! I so love this series and seeing the new incredible outfits you put together each and every day. I know it’s a labor of love and I want you to know we are all thankful you put in the time to do so. 🙂

  82. Lydia says:

    Looking forward to seeing what you showcase for a winter wedding! …Although I’m already drawing inspiration from your Night at the Theatre and Holiday picks! 🙂 Do you have any styling suggestions for repurposing a dress for an office holiday party and wedding?

  83. Jelena says:

    I’ll only say WOW

  84. Josephina says:

    Your dress is excellent and you look so beautiful in it.

  85. Rach says:

    Love the metallic gold dress with pop of red! It is so festive!

  86. Nadia says:

    You’re so beautiful! I feel like we’re friends because our style is so similar…Sometimes I cover my eyes whilst looking at your posts! How Tall are you? I love this look, and all of your looks are so effortless and tres chic!!

  87. Love the holiday hustle & bustle outfit! So true. Nothing worse then leaning over to get something out of the oven and showing everyone the girls!! And I love how you paired it with red pumps to tie the whole look together.

  88. Nikki says:

    The one shoulder look is just so gorgeous.
    I tried one out on my blog too, take a look:

  89. Shannon says:

    I love your combinations, you inspire me to look at my wardrobe differently.

  90. Theresa says:

    Absolutely stunning – the perfect Christmas dress! 🤗

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Welcome to the Fall/Winter 2017 edition of 30 Dresses in 30 Days!  As the name suggests, for the next 30 consecutive days, I’ll be sharing a favorite dress specifically geared towards every possible occasion the fall and winter seasons may bring your way.

In addition to providing a fun collection of my favorite dresses, my hope is that this 30 Dresses portal will serve as a resource for navigating all of the season’s occasions in style.  Whether you’re preparing for an upcoming job interview, a fall date night, a winter wedding or the onslaught of holiday parties, I’ve got you covered with dress suggestions, styling tips and etiquette info!

Hit the arrow to the right or click below to dive in!

All product selections, opinions, endorsements and styling choices are 100% my own and 100% genuine. This site does contain sponsored content and Memorandum is also a member of several affiliate networks which means that I may make a commission on clicks and purchases from some links contained on this site and related social media platforms (including Instagram, Twitter, Facebook and Pinterest).
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