How to Style a Henley Shirt

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I think that, like white tees, henley shirts can sometimes get a bad rep. Also, it get categorized as a lazy option to pick. After all, when you first picture a henley tee, what comes to mind? A guy it a loose top, with jeans who probably needs a good shave. He might look good, but it probably doesn’t look like he tried very hard. Now, white tees have finally made a comeback and we’ve figured out how to dress them up, so why not henley’s too?

Everlane The Long-Sleeve Waffle Tee c/o (Similar, Similar, Similar)
Old Navy Skinny Corduroy Pants (Similar, Similar, Similar)
L.L.Bean Boots (Similar, Similar, Similar)
L.L.Bean Camp Socks (Similar, Similar)

How to Style a Henley Shirt

If you don’t want to look lazy though, you’re going to have to put some effort into it. So let’s talk!

Pick a top that fits

So, now is not the time to grab your boyfriend’s oversized shirt. When you want to look put together, you wear things that fit. So go to the women’s section and pick a top that fits you. (But if you want to buy that oversized one for lounging later though, I totally understand.)

Sweatpants and ripped jeans are out!

I love them, but they are not going to help you look more put together when you’re wearing this top. Also, if you want to wear jeans, go for a pair of white or black jeans.

Skirts are totally in

Pairing your top with a skirt is a fun way to dress up your top without trying too hard. A midi or mini skirt can dress up your top and could make a great date night outfit. Either way, make sure to tuck in your shirt to complete the look.

Don’t forget about colors

If you have a colorful shirt, why not try pairing it with a skirt that has either that color in the pattern or a complimenting color. Or, you could go the opposite direction like I did, and opt for an all neutrals approach.

Remember though, a henley is still a henley

At the end of the day, as much as I love this top, you can only dress up your henley so much. It’s not really going to be your work-appropriate top (unless your office is casual). It’s also not going to be a top you can dress up enough for a fancy restaurant. But that doesn’t mean you can’t still have fun with it! It doesn’t need to just be reserved for lazy days at home. So, these tops are too comfortable for that. Wear your henleys in public and enjoy it!

Photos by Kimberly Graydon