After spotting Madewell Balloon Jeans everywhere online, I finally cracked and decided to grab a pair last month. Heard they were super comfy with that loose thigh-to-tapered-ankle vibe. Figured sizing would be straightforward – just pick my usual Madewell size, right? Wrong.

First Attempt: Following My Gut
I grabbed my regular size 28 online since all my other Madewell jeans fit fine in that size. When they arrived, I yanked them up expecting magic. Damn things felt like I was swimming in them – extra fabric pooling around my hips and thighs. The waist gaped enough to fit two fingers sideways. Total balloon fail.
Figuring Out the Mess
Checked reviews obsessively after that disaster. Tons of people warned these run big. Some said size down once, others insisted twice. Got super confused. Even measured my waist with a tape measure like it was 1998. Turns out Madewell’s sizing charts are useless – they suggested size 28 should fit my measurements, which it clearly didn’t.
The Fitting Room Showdown
Drove to the store and grabbed three sizes: 27, 26, and 25. Locked myself in the fitting room. Tried the 27 first – better, but still loose around the waistband. The 26 felt snug initially but weirdly baggy through the knees. Then the 25… bam. Snug waist without being tight, the balloon silhouette actually showed up right, and the ankle taper looked intentional instead of sloppy.
What Actually Works
- Size down twice if you want that fitted waist. My usual 28 fit like garbage – 25 ended up perfect.
- Ignore the waist measurement on tags. These stretch like crazy after 3 wears. Snug is good initially.
- Check thigh room when squatting. Balloon cut means space there, but avoid knee-bagginess.
Now they’re my favorite jeans, but sizing them felt like solving trigonometry in the dark. Moral of the story? Never trust your usual size with balloon fits. Just swallow the pride and grab two sizes smaller than normal.