How to Ditch the Rules and Wear Gaucho Pants 5 Days Straight

YouTuber and brand consultant Kellie Brown is all about the gaucho pant this summer. “I’ve mostly been wearing the soft jersey stretchy kind and pairing them with just about anything,” she said over email. The latest person to be tapped for our Five Days, Five Ways series, Kellie was asked to select an item to style for (you guessed it) five days in a row, and she went with the ASOS gauchos you see here. She loves their slouchy fit, tie waist and khaki color. Well, same. Scroll on down to see how she put that love to the test five different ways (bet you also could have seen that coming), from a “no f*cks” approach to embracing her inner romantic. And in the comments, let me know what you’re wearing over and over.

1. Monday

Torrid bandeau, ASOS stripe shirt, Vans sneakers, street vendor sunglasses -- similar here Torrid bandeau, ASOS stripe shirt, Vans sneakers, street vendor sunglasses -- similar here

One of the reasons I love this outfit so much is because it’s a part of my current no f*cks approach to dressing my body. Though I live by the idea of total fashion freedom today, I was a victim of more than a decade of working in the “industry,” married to clean, straight lines – which is near impossible when your body is, in fact, round(er).

I’ve had this bandeau top for actual ever but didn’t wear it for the first year. It’s now a regular part of my summer wardrobe and looks so slick with the green pants and striped shirt.


I can’t say yellow is my favorite color (I’m non-committal) but it’s certainly my happy color. This “T-shirt” is actually an oversize T-shirt dress that fell victim to my overzealous laundry mat and can no longer serve my 5’10” body as a dress. Tying the tee at the waist and tucking the belt of the pants gives it a cool feel.


Dresses over pants again! Not sure if this is still a thing but here it is, and shall remain. Definitely one of my favorite silhouettes. The dress came with a removable lining and since sheer things are the best things, I opted to leave the slip at home. I feel like this dress works kicking around the city but I could wear it on a tropical vacation after a whirlwind four-hour romance where we’d need to leave same day.


This gray tank has seen better days but it’s one of the few articles of clothing that I own to which I am emotionally attached. Not sure why; it has no significant moment or meaning, it’s just perfect and I love her. I added heels and a hat to balance out the fact that my beloved tank has holes in it.


Oh, I’m just a romantic at heart. I love this top and the white earrings. I’d wear both again with just about anything. What works best for me is when I feel casual and comfortable but a little more dressed up. This is one of those outfits I can run around in, have back-to-back meetings in and and still wear for drinks later in the evening. The gauzy top is also perfect for the 700% humidity that New York City is currently experiencing. It dries really quickly.

Follow Kellie Brown on YouTube and Instagram

Photos by Emily Malan.

Amelia Diamond

Amelia Diamond

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

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