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.)