Usually When You Roll Something This Good, It's Illegal
The smallest adjustment, the biggest reward.
As Snoop Dog and perhaps Martha Stewart would agree, some of the best things in life are rolled. Usually with cinnamon and sugar.
Second only to cinnamon rolls, is a rolled sleeve. A rolled sleeve is a compulsive styling trick I use nearly daily in my own wardrobe; I can’t wear a shirt without zhuzhing up the sleeve in some way. To me, it’s what makes or breaks an outfit. It’s how you make the formal, informal.
Because it’s finally spring (after what felt like an eternal winter) I’m defrosting some of my favorite ways to wear a rolled sleeve.
Unbothered Uniform
How To Wear:
I wear some variation of this weekly. My favorite (non-denim) pants right now are from Donni — I think they’re exceptional and incredibly comfortable. I’m also a big fan of flip flops right now, mostly because I wore so many pairs of wool socks this past winter that I started to hate them.
You could obviously sub any ball cap you currently own, although I think it’s a particularly great time to support journalists.
White Tee / Button Down / Pants / Flip Flops / Sunnies / Ball Cap
Covert Nonchalance
How To Wear:
The thing I love most about an oversized, boxy t-shirt is it’s ability to shape shift. Rolling the sleeves gives you a hint of shape without making it look like you’re trying to give yourself shape. There’s nothing worse than looking like you’re trying to look skinny in something several sizes too big in the first place, you know? Just wear it oversized or don’t. Not everything needs to be figure flattering. This is my lukewarm hot take.
Sporty Romantic
How To Wear:
This is genuinely one of my favorite shirts. It’s long sleeve but really lightweight so it’s great for transitional weather. I wear mine pretty often, though I have the brown and green color. Looks fab with the sleeves rolled!!
This is your reminder that long sleeve t-shirts go great with shorts. I periodically forget this and rediscover the combination to find that it really is the most comfortable, temperature regulating outfit. It’s the only spring outfit you actually need, to be totally honest.
American Prep
How To Wear:
Wow, what can I say about my love affair with denim on denim. Of course, we’re talking all about outfits you can roll your sleeves up in, so denim fits right in here. You can wear it in every season and it fits right in. Fantastic outfit for bopping around town on a Saturday as well. Looks great with a matcha, if that’s your thing.
Button Down / Jeans / Bag / Flip Flops / Sunnies
Thank you so much for reading Gatekept! Gatekept is now six months old, can you believe?? I certainly cannot — I’m thrilled to write for you every single week. Stay tuned for the upcoming articles this week and enjoy your spring! <3
-Morgan



















Obsessed with all these outfits! I am so bad at looking nonchalant lol.