Monday, August 31, 2026

How to Style On The Loose Work Pants Classically




Late last year, I was gifted these viral On The Loose Work Pants in black. I saw them everywhere on social media and admired them on everyone. Truly, every person I saw wearing them looked good in them. I kept thinking, what kind of Sisterhood of the Traveling Pants magic is that?! Well, as I look ahead to fall, which has unofficially started since we have passed Labor Day, but doesn't officially begin until September 22, I'm so excited to rewear these pants again in fall and into winter. 

Though a barrel leg is not inherently classic, I questioned whether I would like them enough or wear them enough to justify the price tag. One day, I came home to a package, and the pants were inside, gifted to me by the brand. I was thrilled but still unsure as to how I would style them and unsure that they were 'me.' I love trying trends here and there and putting my own classic spin on them, but it's also important to me that what I wear feels like 'me.'

As I slipped them on for the first time, I realized that they really are not as 'barrel' as they seem. Not only that, but they are much easier to style than I thought. The best part, though? They are SO incredibly comfortable and don't really wrinkle. They are the perfect travel pants. The fabric feels almost like an 'athletic' piece of clothing. They are almost swishy, but they don't actually make that sound we all remember from those Starter pants from the '90s.

I absolutely LOVE them and could not recommend them more. Are they trendy? Yes, a bit. Are they worth the price tag? I think they are worth it when they go on sale, for sure, and they do at a decent rate. Last winter, I actually had to hold myself back from wearing them because I felt like I was wearing them too much. In black, they are, dare I say, slightly dressy-looking because of the way the fabric drapes. Pant silhouettes change on a dime these days. It's hard for me to keep up, and sometimes I don't even want to. These, though, feel enough like me without feeling outrageously trendy, and they even make me feel cool. Quite frankly, I am the least cool person!

I think the black ones, particularly, are dressier than the other colors. I think the 'Deep Sea' and 'Coffee' shades could also be dressed up a touch, but otherwise, the lighter shades skew much more casual. To me, the black pair looks almost like a dress pant! They don't look like athletic material, though I think you can tell that they are in the lighter colors.

All that said, if you have been on the fence about these pants, I would highly recommend them, and you'll see me in them a lot this autumn. You don't even have to take my word for it. The majority of reviews are glowing.

As for sizing, I wear a size 4 with a 'standard' length. They recently introduced different lengths, which is great. I am 5'6", and the standard length is perfect. This is one of those styles where you really want to make sure the length is right. They run roomy, and the size 4 is generous!

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