Madison is a huge fan of Kim Kardashian's Skims and admits that she bought a full set after her best friend convinced her.
"She was like, 'You have to get it. You have to get it.' Sure enough, I finally did, and it's like a cloud. It's so comfortable," she says.
Madison loves pieces that she can wear all of the time, like one of her favorites from NakedCashmere.
"If I could just live in this I would," she adds.
She even owns a cardigan from Taylor Swift's merch line for Folklore because she wanted to match the pop icon: "I wanted to twin with her. Who wouldn't?"
We can't argue with that.
Madison has also started collecting statement purses that happen to be designed by her friends. One of her recent acquisitions is a timeless white Longchamp bag.
"I'm now becoming a [handbag] girl because my friends, who are really talented, are sending me pieces of theirs, and I love celebrating them," she says.
Madison is ahead of the curve when it comes to fall shoe trends. Her black Stuart Weitzmanloafers have a special place in her heart—and a good story behind them.
Ahead of her first trip to the UK, Madison felt like she had to get a good pair of loafers to bring with her, but she forgot to break them in before she landed."Cut to about an hour later, blisters walking all around London," she says.
Don't worry. They're broken in now.
"No blisters, they feel great, and they've got some rain stains on them. I love them," she adds.
Madison also loves to rep her home state of Florida. Most of Madison's siblings went to The University of Florida, so when she spotted a T-shirt with the school's logo on it in an unusual location, she couldn't pass it up.
"I was in the UK again, and my flight was delayed, so I was walking around and stepped into Urban Outfitters, and they had a Gators shirt there," she says.
Madison has even more cozy—and collegiate—items in her closet.
Get a full look at her wardrobe below!
Keep scrolling to shop some of our favorites from Madison's cozy wardrobe.