Style

A Week of Outfits: Madeleine Dore

Week of Outfits: Madeleine Dore

Last year, Madeleine Dore quit her day job to focus on freelance writing and her own project — the interview series Extraordinary Routines. For further inspiration, she flew from her hometown of Melbourne to visit New York for three months: “It’s a place full of people I want to interview.” Here, Madeleine shares her tips for creating playful outfits and living out of a suitcase…

Week of Outfits: Madeleine Dore

Dress: ASOS. Shirt: COS. Shoes: Nine West. Lipstick: MAC.

“I came to New York with one suitcase and a small bag. The small bag was basically just for my pillow. I knew I’d be sleeping on couches while I found my footing, and I read that having your own pillow helps you sleep better in new environments. But that meant even less room for clothing! So, when packing, I looked at what I had been wearing the past few months — mostly pastel shirts under bright dresses. Bringing such a limited amount of clothing has given me a uniform, and it has made me get more creative with my wardrobe.”

Week of Outfits: Madeleine Dore

Dress: Lulamae, similar. Purse: Everlane. Shoes: Modcloth, similar.

“I’m not the best shopper; I find it exhausting. My favorite shopping method is just googling exactly what I want. I was obsessed with fruit prints a while back. I searched for ‘dress with lemons’ — and actually found the cutest one. I also found grape earrings and a watermelon bag. ASOS frequently comes up because their selection is so large. For basics, though, Uniqlo is great. Their shapewear shorts are comfortable and soft, like the material at the top of a stocking — and they aren’t as intense as Spanx. In the summertime, I put them under a dress and don’t have to worry about panty lines or cutting into my stomach.”

Week of Outfits: Madeleine Dore

Shirt: COS. Sweater: Modcloth. Gingham skirt: Target, similar. Shoes: Nine West.

“When I find something good-looking and comfortable, I buy it in bulk. All my shirts are from COS. I have them in white, blue and pink — the material is so light and stretchy. I’m drawn to dresses with ‘scuba fabric,’ because they never wrinkle, and they’re flattering on curves. Comfortable shoes are harder to find. The Australian company Bared Shoes sells my favorite lace-up brogues that are orthotic-friendly. And I like lower pumps or Mary Janes; they’re supportive and stay on your foot. When I find a nice pair, I hop on it and buy two or more.”

Week of Outfits: Madeleine Dore

Dress: ASOS. Shirt: COS. Purse: similar. Ballet flats: ASOS.

“For most of my life, I haven’t abided by fashion color rules, like ‘blue and green should never be seen.’ It’s more interesting to find colors that suit you, and I like wearing two or three together. People always comment on a good color combo — it’s such a flash. When I want to tie everything together, I’ll wear a craft-store ribbon around my collar. I like a red ribbon with my pink shirt, and a navy ribbon for my pale blue shirt. I have a black ribbon for miscellaneous outfits.”

Week of Outfits: Madeleine Dore

Dress: ASOS. Shirt: COS. Shoes: Modcloth, similar. Sunglasses: Shag, similar.

“I like to dress like how I envision myself dressing at 80 years old — you’ve lived your life and you don’t care what people think of you. You are your boldest self.”

Thank you so much, Madeleine! You are wonderful.

P.S. More women share their go-to outfits, and nine summer trends.

(Photos by Christine Han for Cup of Jo. Interview by Stella Blackmon.)

  1. What a gorgeous lady! This post was a delight to read, totally going to try the ribbon thing!

  2. Daynna Shannon says...

    She is a layering GENIUS. God, I love her.

  3. Congee says...

    Wow, she is adorable. Great post!!!

  4. Jean says...

    What a vision. Her outfits are so unique, never seen anything like it.

  5. Candice says...

    She looks amazing! Thanks for sharing

  6. Polly Hitchcock Sage says...

    Where do you find these cool people! I love this series, but I love these bright color people most, simply because they choose to do what they love more than what is normal or cool right now. I smiled through the whole article. Thank you.

  7. Jay says...

    The colors! The colors! LOVE IT.

  8. Leanne says...

    What an inspiring interview. Currently running to Michaels to find all the ribbons…!

  9. Jamie says...

    She is just glorious! LOVE her style and her megawatt smile. Total cutie.

  10. solje says...

    HUGE LOVE

  11. Abigail says...

    I just love this column! No matter their size, I think most women have to engage in a little creative problem solving when it comes to picking outfits. This column makes me feel like that process can be a real joy! Thank you to everyone who has contributed! Also, that button down/spaghetti strap dress combo – I’m stealing that idea!

  12. I have never seen a crop top and a pencil skirt look soooooo legit, before. This girl knows exactly what she’s doing! :D

  13. Thao says...

    I just love Madeleine’s style! So much sunshine in her step and her smile. Great feature, guys.

  14. Love these outfits, this is the exactly example how also a curvy girl xan wear bright colors and be wonderful:D

  15. Ciara says...

    This woman speaks to me!

    “I like to dress like how I envision myself dressing at 80 years old — you’ve lived your life and you don’t care what people think of you. You are your boldest self.”

  16. Lillian Wylie says...

    Soooooo beautiful!!! Both Madeleine and her sense of style! Feeling so inspired, and loving seeing someone who does a similar sort of uniform to me (albeit I live in Scotland so wear far fewer bright colours to avoid startling the natives :) I love the Design Files, so nice to see a snippet over on CoJ!

  17. Chris says...

    Have to agree that bared in Melbourne have the BEST shoes in the world, perfect for brogues, ballet flats and heels that let you stay on your feet for 10 hours with no pain! I got two two pairs 6 years ago and another two just recently and they are magnificent!

  18. ZM says...

    What a stunning woman, beautiful style! ?

  19. lucie says...

    this is amazing, she is amazing, her website is amazing! THANK YOU!

  20. Ah I love the pops of colours. Madeleine looks fantastic!

  21. Anna says...

    Please PLEASE keep it up with these curvy ladies Week of Outfits. So many of the things that look cute on blogs and on Pinterest are just not realistic for those of us with hips and/or boobs and/or belly so I love when you feature women like Madeline who are really nailing the personal style with curves.

  22. Kat says...

    Love the color and totally love her philosophy on how to dress!

  23. Carly says...

    So cute! Love the colour and the ribbons… Doesn’t she look kinda like Drew Barrymore?

  24. CG says...

    Gorgeous!!!! But how does one keep the shirt underneath from bunching up when you’re moving around?
    {head scratch}

    • Emily says...

      I would imagine she tucks it into her shapewear/tights! Or even into high-waist underwear…I’ve done that trick before!

  25. Elisha Ferguson says...

    Absolutely love your style!

  26. Rosemary says...

    Your style rocks, Madaleine…always has…an expression of your inner artist. Looking at you akways felt like looking at a living art installation-visually enjoyable and thought provoking.

  27. Kanga says...

    Just beautiful!

  28. I adore her sentiment about dressing like your 80 year-old self! Something for us all to live by : )

    • Robin says...

      Yes!

  29. Alix says...

    YES!!! I LOVE her website!! Its a dream. Aussies represent?

  30. mwana says...

    The fourth outfit is my favorite. I would have never thought to pair a wrap around cutoff sweater with a button down shirt, with a gingam skirt. Her colors make me feel so happy!

  31. Tiffany says...

    She has the cutest style! I loved this. Can’t wait to tie a ribbon around my neck.

  32. Her style is ADORABLE – that little signature bow she wears! And dressing for her 80 year old self? Love that sentiment. <3

  33. I love her style!!! She dresses way more stylish and fun than most fashion bloggers I follow.

  34. Laura says...

    How about a series on Maternity style by trimester? I’m 19 weeks pregnant and am really struggling with how to dress while still feeling like myself. Especially work appropriate ideas. Everything is either skin tight (not appropriate for work) or shapeless.

    • Maaike says...

      this would be very welcome!! 11 weeks along, and stuff is beginning to be tight already (one very helpful colleague in the know pointed out that she was ” beginning to see” – how is this okay, you are basically calling me fat?) I know Cup of Jo has featured some good maternity brands in the past! but it would be cool to see them on modelled and curated.

    • I just had a baby and know this struggle! If you don’t follow the blog Well-Rounded NY (wellroundedny.com), I would recommend it. It has a whole series on different New Yorkers’ pregnancy style and different style ideas by trimester as well as other helpful posts.

  35. Jade says...

    That Last Red Dress is Stunning! Just added it to my Wishlist! I love the idea of rewriting/styling a limited amount of clothing.

  36. Laurel says...

    Hello Madeline! I’ve followed The Design Files for a few years and love Extraordinary Routines! Very cool to put a face to a name.

  37. Miriam says...

    Madeleine is lovely and has such great style. But, this description of her current job status – “Last year, Madeleine Dore quit her day job to focus on her own project — specifically, the interview series Extraordinary Routines” – had me scratching my head. How does one support themselves and move to NYC on a blog that does not seem to have a very large presence/advertising etc.? I feel like Cupofjo (my favorite place on the internet) has been killing it recently with honest conversations and I’d love to see that honesty brought to discussions that touch on money – i.e. Dore saved up money for 2 years to be able to pursue her passion project in NYC for 6 months or Dore runs an interview series and does freelance xyz.

    • Joanna Goddard says...

      this post was focusing on fashion, but i definitely see your point! we’d love to chat more about careers/finance/money and will do more posts coming up.

    • Jill H. says...

      Yessss! I completely agree! I don’t know how these creative types do it!? Especially in some of he most expensive sixties in the world, or with children (which so many COJ subjects seem to be). I work in corporate America and I have just ONE kid and couldn’t fathom how to make that work if I “quit my day job” to work on a pet project – paying for food, housing, healthcare, childcare, going out, etc.

    • Lola says...

      Yes I agree. More women speaking honestly about money.

    • Madeleine says...

      Hi Miriam! Such a good question and something I’m more than happy to talk about candidly, but it didn’t come up during the interview process as it was a focus on style etc. My blog has helped me to build a profile as a freelance writer and therefore attract corporate clients as well as have my pitches to dream editorial publications be successful! I’m very clear about being a freelance writer utmost and foremost – the blog is a passion project!

    • AJ says...

      I’m reading a book that exactly talks about this: “So Good They Can’t Ignore You: Why Skills Trump Passion in the Quest for Work You Love” by Cal Newport (I think it might have been recommended in the most recent book post on COJ).
      Talks about the concept of career capital. It’s been a revelation.

      I look forward to more COJ posts about career / finance / money!

    • Miriam says...

      Thanks so much Jo, Madeleine & everyone for being so responsive and committed to honesty surrounding money. This is why Cupofjo is just the best – the comment section is really valuable and interesting. Madeleine – you are such a badass lady. How amazing you were able to leverage all your skills to also support your dreams. Thanks for sharing! Jo – really excited for additional conversations about money and finance. And AJ – that book sounds interesting, I’m going to pick it up. xo

    • Madeleine says...

      Thank you for the prompt – such an interesting discussion to have and your openness and curiosity is so refreshing Miriam!

  38. Nina says...

    Ha I love that motto, dressing like an 80 year old!

  39. Kelly says...

    Love the 40s vibe of her hair in the second picture. We don’t have Cos in SF, will have to check it out online, is it an H&M company? Getting it and & Other stories confused.

    • Jeanne says...

      I know right? Cos is the upscale brand of H&M. Massimo Dutti is the upscale brand of Zara. Madewell is the less expensive branding of JCrew. Also Club Monaco is a less expensive branding of Ralph Lauren. I know there are so many other connections but that’s about all I can keep in my head!

  40. Love her! Such a happy style!

  41. Mica says...

    I feel like the whole Internet is wearing neutrals right now and this woman is wearing COLOUR! I love it!!

  42. I love her style — and her site! Funny, I had been thinking of doing something like this myself after loving the parts of my new job where I get to interview creatives … of course someone’s already done something like what I want to do. Great minds! :)

  43. Love that she doesn’t shy away from a print and color! I wish I was this bold but the NYer in me always gravitates towards black and navy.

  44. Lauren E. says...

    I love the craft ribbon around the neck! What a sweet look.

  45. Kim says...

    Her last sentence is everything!

    • Morgan says...

      Yes to this!

    • caitlin says...

      Yes! Really want to keep this in mind. <3

  46. Lashley says...

    Love it! I appreciate how she has a “uniform,” but everything feels fresh with all that color and print. If you’re taking suggestions, I’d love to see a SAHM week of outfits!

  47. Tanith says...

    I love the idea of the buttoned shirts under a spaghetti-strap dress!

    Such great advice too! Color is all based on your skin tone and personal taste.

  48. Amy says...

    She looks like spring and sunshine. Love it!

  49. Well, aren’t you just the cutest thing ever? I, too, love the quote about being your boldest self. And I love the pops of color in today’s monochromatic world. Also, I hope someday I can rock lipstick as well as you.

  50. CS says...

    Cute! What color is her mac lipstick?

  51. Rebecca says...

    So fun! Love the lipstick too!

  52. Kay says...

    This girl’s SMILE! What a beautiful person. When I saw that first photo of her I instantly wanted to befriend her. Great style, too.

  53. Yes! This feels very different from the past week of outfits posts!

  54. Elizabeth says...

    I love that Madeleine hates to shop but has stilled carved out her fashion niche. I have only achieved the first part of that equation (hating to shop) as it’s so enervating and overwhelming — still working on the second part.

    Love this series!

  55. Taylor says...

    Please do a week of outfits that a school teacher wears!

    • Joanna Goddard says...

      great idea, taylor! we’re on it!

    • Kait says...

      and an Accountant! (Office wear without being too “corporate”)

    • michaela says...

      funny enough my friend Jessie is a school teacher and dresses a lot like this lady. So cute!

  56. Victoria says...

    I really LOVE interesting color combinations. Inspiring!

  57. S. says...

    She rocks!

  58. Nadine Hughey says...

    What if we all didn’t wait to be the best versions of ourselves? Love those trout & optimist sign.

  59. Amanda says...

    I am so thrilled to see someone with such cute, feminine style! Cup of Jo is a good blog but I have only seen very NYC minimalist fashion here until now.

  60. Sherri Rigby says...

    She makes me want to do a painting using some of her color combinations – I love her fearless and unique style (that shade of lipstick is bomb)! I was also excited to see that she interviewed one of my favorite Australian artists, Frances Cannon!

  61. Rachel Simmons says...

    She’s darling! I could never pull off half of those dresses because I have large breasts. But she’s a doll!

  62. Amelia says...

    Love this and especially her last comment about dressing like she’s 80! Reminds me of this great, oft-referenced statement on “toddler grandma style” – basically the idea of dressing at the ends of the age spectrum when women aren’t expected to dress in order to appeal to men. Very thought provoking even if the authors style isn’t quite your jam!
    https://theestablishment.co/toddler-grandma-style-the-fashion-approach-that-will-set-you-free-92f787202928

  63. AJ says...

    Brilliant! This approach to dressing is both amazingly practical and organised and at the same time gorgeously fun and joyous. You’ve nailed it! I want to take a leaf out of your book Madeleine!

  64. Kattia says...

    I love her! Her style & attitude is so refreshing & fun!!! She’s awesome!

  65. rachel says...

    craft ribbon under the collar? great idea!

  66. Kathryn says...

    “I like to dress like how I envision myself dressing at 80 years old — you’ve lived your life and you don’t care what people think of you. You are your boldest self.”

    YES, YES, YES!

  67. Myra says...

    First of thank you for the link to her interview series which looks so very interesting!

    Secondly : “I like to dress like how I envision myself dressing at 80 years old — you’ve lived your life and you don’t care what people think of you. You are your boldest self.” YES to this so much. <3

    I was wondering if you have considered featuring somebody who is chronically ill either in this series or in the beauty uniform? From a personal perspective I would find that really interesting. I was diagnosed with fybromyalgia last year and like many chronic illnesses it is one that (mostly) does not show on the outside. It took me a while but after hiding away in blacks and greys for months I have taken pride and strength in dressing more boldly than before. It sometimes feels counterproductive in an odd way. Looking 'good' does not equal feeling good. And people, though well meaning, often struggle to understand. 'but you are looking so good' is something that I hear and stupidly cannot take as a compliment anymore. (I am working on that :). Still, putting attention into the way I dress is something that gives me back a sense of power after feeling like I lost all power over and connection to my body.

    I love that your focus is on featuring a true diversity of women out there.

    • Rebecca Q says...

      I want to second this! As someone else with a chronic illness, I love hearing how other people’s conditions change their way of approaching clothing. For eg. I have a condition that means my hips partially dislocate a lot. I wear snug trousers and loose tops because the trousers make my hips feel more “secure”. I also only wear natural fibres usually, because polyester and the temperature fluctuations caused by heavy duty painkillers are not comfortably compatible. I have outfits that are easy but fabulous that make me feel brave when things are at their worst. I’d love to see how other people negotiate similar issues!

    • Mary says...

      I also second this!
      I have alopecia and have gone from a few bald spots to complete baldness multiple times. I have made some sartorial decisions based on what’s happening on my head: bolder eye glasses and lipstick, fancy knotted “up-do” scarves, etc. But I feel I’ve also had to steer away from more edgy or angular clothing when I’m bald, because it ends up looking too harsh or futuristic!
      Anyway, all that to say: it’d be lovely to see peoples’ take on their illness or what I like to call my “body’s idiosyncrasie”.

    • Joanna Goddard says...

      yes! what a great idea, thank you so much, everyone!

    • Kate says...

      I have FM as well, and when I’m feeling especially awful, I like to dress in explosive vintage prints and wear print lipstick. I figure if I look down at my clothes enough, the brightness will rub off somehow.

    • Kelly says...

      YES please! There are so many different types of chronic illnesses and health conditions that affect how people dress. I have fibromyalgia, chronic fatigue, and depression, all of which affect what I wear. A lot of times, if I’m having a particularly bad day, I’ll do my best to “dress well” (colorful dresses, bright scarves) to lift my own spirits, as well as hopefully mask my pain from others (maybe they’ll be too focused on what I’m wearing to notice how tired I look). Some days, though, it’s all I can do to put any clothes on and get myself out the door. Some illnesses (or medications for them) can cause weight gain/loss, which can be hard to manage both self esteem and fashion wise.

  68. Bethany says...

    I want to know everything about her. I instantly identify with this girl’s style and attitude.

  69. jeannie says...

    i love her style! It seems optimistic and confident. And I totally love that top dress on her. But what made me laugh is when she said she buys in bulk. I have learned to do the same! I bought 2 more pairs of the same pants when I loved the first pair and wore them almost every day and when I found a polo shirt I liked, I bought one in every color!

  70. june2 says...

    I love how you wear those green pumps almost as a neutral! The blue gingham skirt look is my favorite but also LOVE you in that last red one!

  71. Cali says...

    Love this! Her style is so happy and attractive.

  72. Alice Jones says...

    madeleine, you are beautiful! thank you for sharing.

  73. Louise says...

    Madeleine, your sense of style makes me so happy! Color, color is what this world needs! I love how you’ve taken fancier dresses and have made them daytime with the addition of a button down. And, look out, you are going to start a major trend with the ribbon around the neck. You look both modern and retro. Not an easy thing to pull off. I am so tired of all the nudes, pale pinks, and washed out creams. Bring on the color!

  74. Cynthia says...

    Love her smile and bright colored clothes!

  75. Amanda G says...

    By FAR my most favorite week of outfits, and there have been some great ones! Madeleine has some serious style and I love both the items and their hues. Such flattering pieces, and I especially adore that trout print. I wish I could incorporate her style into my closet, but the world of corporate accounting is not a big proponent of bright colors :(

  76. Kate says...

    Where is the lemon dress from? All I see is an image!

  77. Vanessa says...

    The ‘Week of Outfits’ is my favorite feature of this site. Thank you so much for the constant inspiration.

  78. Amanda says...

    Love, love, love! I am especially excited to pick up some craft ribbon myself to experiment with my own collars!

  79. Julie says...

    OBSESSED!

  80. Angela says...

    oh my gosh, i LOVE these outfits and color combos! i would have never thought to pair some of these colors!

  81. Gitty says...

    I like this! She looks like a pink lemonade kind of girl

  82. Mandy says...

    I loved everything about this! Madeleine, you are absolutely awesome.

  83. Stephanie says...

    She looks fantastic! Love the bright and chirpy style, and how her fashion is affordable. How inspiring!

  84. Carrie says...

    What a freakin’ cutie! Love her style!!

  85. Kathleen says...

    Oh my GOSH I love these colors and the modern retro feel! I also really love and appreciate how affordable everything is – sometimes the week of outfits are veeeeery out of my price range, hah! Madeleine seems so bright, fun and happy!

  86. Natalie S says...

    How wonderful and colourful! I especially liked her last quote about living as your boldest self.

    • Abby says...

      YES! Me too!!

    • Yes! She’s such a sunshine. Love her outlook!

  87. Katie Larissa says...

    Loooove those pink pumps from the first outfit….and love her twinkling smile! She looks like such a warm and cheery lady.