Amber Wainwright, who worked as a VIP tour guide at the theme park, explained that guests are left with a sense of regret if they are not appropriately attired for a long day at the California attraction.
Writing for Business Insider, Wainwright said: "Seeing people dressed in Disney-themed attire is one of my favourite things. In fact, I love coordinating my outfits and taking photos in the parks.
"However, I've noticed that many park guests fail to remember that their outfits should also be functional. People often regret wearing heels, flip-flops, and brand-new shoes to Disneyland.
"I once heard a man who was wearing dress shoes say he wanted to go home halfway through the day. To help his aching feet, he had tennis shoes delivered to him via Uber."
Wainwright also explained how many guests are left to rue spending lots of time on sit-down dining experiences as it denies them the chance to go on their favourite rides.
She said: "If guests have limited time to explore the parks, spending two to three hours at a costly dining experience might not be worth it.
"I've seen the look of disappointment on people's faces when they finish an expensive dinner and realise they no longer have time to ride the No.1 attraction on their list.
"Instead, I always told guests to grab some quick snacks or limit their time in restaurants during their visit."