Style Challenge: A Fashion Editor Wears Red Boots 5 Days in a Row

The moment I get something new, I like to wear it immediately — and then I want to wear it forever, with every outfit, for all of eternity. I want to be that kid who wears a Spiderman costume from October 1st through July. The thing is that, when the item in question makes a statement, I get self-conscious and chicken out from doing it. I fear that if I wear the same bold thing too many times in a row, everyone on the playground will start calling me That Same Shirt Girl behind my back. That’s why I enjoy Man Repeller’s 5 Ways, 5 Days franchise so much. It reminds me that there is always a way to wear the same thing on repeat and still keep the outfit feeling new. You just have to be creative about it/not give a hoot because literally no one is calling you That Same Shirt Girl. Oh look, I’m talking to myself again.

In this round of 5 Ways, Lindsay Peoples, Fashion Market Editor of The Cut and New York Magazine, takes a pair of red knee high Aldo boots for a spin around the five-day block. Her outfits will send you on a hunt for all things red and polka-dotted. Because of her, you’ll want to put jeans under dresses and go vintage-hunting for a classic trench. There’s a stretchy black dress involved that feels like the solution to at least three of my wardrobe problems. Last but not least, you’ll want a pair of tall, slouchy statement boots; and the best part is…you can wear them with everything!

Day 1:

I’m not one to try to eloquently describe my style, but the one “rule” I follow religiously is to always incorporate red as much as possible. It has been my favorite color since I can remember, not just because it looks good against my melanin skin, but because red really embodies my personality: bold and defiant. I love this look because it looks really expensive but it’s literally a dress I bought on Amazon that looks like Valentino and under-$200 boots.

Day 2:

I really make an effort to avoid trendy-brand bandwagons, but when I saw this Vetements dress on Yoox, I fell in love with it. It’s so versatile and not the clichéd bright florals. I like that it doesn’t feel over-the-top ladylike. I’ve worn it on its own with Doc Marten combat boots, but it also works well with jeans, the addition of red, and some height (since I am height-challenged).

Day 3:

I’ve worn this combo probably a million times to work because it’s so effortless and works for meetings, appointments and everything in between. My husband and I were vintage shopping years ago when he picked up this trench coat and asked me, “Is Dior Homme a brand you like?” I think he only paid $100 for it, and clearly, it looks better on me. I’m a huge Sade fan so wearing this chunky Aritzia turtleneck and thick gold Laura Lombari hoops combo is something I always come back to. Also, everyone always thinks these earrings cost $300 — they’re $98!

Day 4:

I really enjoy how playful Jacquemus’ designs are and this shirt is the perfect example of that. The way it moves in the wind when you walk feels good, and even though it’s a very attention-grabbing polka dot print, it never feels like I’m trying too hard. It just feels fun.

Day 5:

I’m a size 8 with booty so it’s hard for me to find sweater dresses that aren’t incredibly short and ride up, but this Aritzia one actually hits the knee and is formfitting without being inappropriate to wear to work. And this Theory blazer is more than just a red blazer to me: the slim tailoring and the longer length are what make it worth the money. Overall, this is a modern Pretty Woman look in my book.

Lindsay Peoples is the Fashion Market Editor at The Cut and New York Magazine. Follow her on Instagram here.  

Photos by Edith Young.

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  • leahpapa

    Was literally just test-driving an outfit to wear on date night tomorrow with the hubs – a black-and-white polka-dot cropped sweater vest and red booties – and I was about to chicken out (“is red ‘over?'” “am i trying too hard?” “i’ll be that girl in the red boots”) but this has given me back my oomph, because what Lindsay is serving up here is full. confident. realness. Thanks, Lindsay and MR!

    • Amelia Diamond

      post outfit photo please!!

      • leahpapa

        Here goes…first time posting a mirror selfie and sharing an outfit idea publicly 😬

        • Amelia Diamond

          Oh man please please wear this tomorrow!

          • leahpapa

            Will do! And maybe my hair won’t even have peanut butter/banana mash/Play-Doh/assorted kid schmutz in it by then…

        • Rosemary

          YOU LOOK AMAZING. that top is everything and you styled it perfectly!

          • leahpapa

            Aww, shucks! Thanks 🙂 True story: the vest is reversible. Looking forward to wearing it with the black background side out in the future, maybe layered over something pastel?

          • Rosemary

            Ahhh yes! It would look awesome with light blue!

        • You look so cool! here’s hoping you did wear it!

  • Allegra

    These are incredible! And for someone who is not a maximalist, I’m happily surprised to see they are quite approachable too! Love it

  • pdbraide

    well done you! i love all but the 1st and 3rd most

  • Amelia Diamond

    Day 4 wins for me but now I want that trench

  • Jules

    LOVE THESE OUTFITS and love that I could wear them all to the office! you look amazing Lindsay! I want to recreate these!!

  • NVD

    there she is!! i studied abroad in London my senior year with Lindsay! so happy to see her doing so well!!! and red really is her color.

    • Rosemary

      omg this is so cute what a small world!

  • magiblin

    The thing I love most about this piece (besides defining the Same Shirt Girl – that’s me!!) is showing a well-known fashion editor wearing FAB outfits that aren’t 100% high-end. I would love to see content on this site, and others, where there is a mix of high and low. Great job! Her style is killer!

    • leahpapa

      Yes! Reminds me that great style/taste isn’t a matter of having a thick wallet.

  • I’m down with the red boots! I think the shake thing up and have the made-U-look factor. Who doesn’t want that?

  • Léa

    Day two 😍 what a perfect outfit Lindsay! I’ve never seen a dress/jeans combo look so fab!

  • Tahlia Burton

    Lindsay — the all red. Wow. You are my Red Queen and you’ve slain me.

    • Kiks

      Day 1 is perfect. I was all set to move on to head-to-toe lilac but now I need to keep wearing red.

  • Mollie Ward

    RED BOOTS! I just bought a pair of knee high red almost cowboy boots for $5. First MR wrote this:
    telling me my knee high red cow boys were a good buy. AND NOW THIS! I’m definitely not a style maximalist so I feel a little nervous but I’m excited, I CAN BE A RED BOOTS KINDA GIRL.

  • Leigh

    They really do look good with everything! And very flattering on you.

  • Casey McDermott

    Day 1!! Red looks amazing on you and I love your style.