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.

Amelia Diamond

Amelia Diamond

Amelia Diamond is a writer, creative consultant, and Man Repeller alumnus living in New York City.

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