Thoughts on "flattering"

Everlane wide leg crop pants in ochre — Cotton Cashmere Cat Hair
Striped tee fall outfit with tan wide leg pants — Cotton Cashmere Cat Hair
Leather jacket outfit with wide leg pants — Cotton Cashmere Cat Hair
Fall outfit with Everlane wide leg cropped pants — Cotton Cashmere Cat Hair
Fall outfit with leather jacket and wide leg pants — Cotton Cashmere Cat Hair

When you see an outfit or a garment that you would consider to be “flattering” on the wearer, what does that mean, exactly? Is the garment pleasing to the eye, or does it make the wearer more pleasing to the eye? According to the dictionary, flattering means to enhance one’s appearance. Who gets to decide what is and what isn’t flattering when it comes to clothing choice? Is it the person who chooses to wear a particular garment, or is it the people the wearer comes across during their daily life?

I often find myself struggling when it comes to trying new silhouettes, including wide leg pants, because I don’t consider them to be conventionally flattering like other pant silhouettes. I dipped my toes in the trend earlier this summer when I bought these chambray pants from J.Crew Factory. I always admired Everlane’s wide leg cropped pants from afar and especially the women wearing those pants on social media, but I never thought I would wear them myself. I didn’t think they would be flattering on me. (I even had a reader DM me on Instagram, telling me I needed to try them for myself.)

I couldn’t stop thinking about them months later, and when the short inseam was released, I knew I had to at least give them a shot. (This color sold out when they were released, but I think they got a few returns which is how I was able to snag a pair recently.) I put them on and didn’t take them off the rest of the night. Seriously—one of the most comfortable pairs of pants I own! That said, I wasn’t crazy about what I saw in the mirror. I’m not used to seeing my legs hidden; I’m used to seeing them being hugged by skinny jeans. They’re also cropped, which is how they’re supposed to look, but I thought: did the crop make me look even shorter than I already am?

I wore them to work the very next day with this outfit here. To keep the rest of the look in my comfort zone, I wore a simple striped tee, black ankle boots for a little height but also a little bit of drama, and my leather jacket for added edge. Even though the pants were new and somewhat nerve-wracking, the other garments in the outfit were old favorites that helped me get through the day without worrying about my outfit.

I still don’t think I’d consider these pants to be flattering on me, but as I’ve gotten older, I’ve started caring less about buying only items that I would deem to be flattering. At the end of the day, these pants are comfortable as hell, and that’s way more important to me right now. ;)


BlankNYC jacket / old; similar
LOFT tee / old; similar or similar by Brooks Brothers
Everlane pants / exact
Madewell boots / old; similar
Madewell earrings / old; similar from Aldo or Nordstrom
Le Specs sunglasses / exact style
Dior Addict Lip Glow in pink / exact