Celebrity Julia Roberts Julia Roberts' 'Ugly' Shoes and Skirt Combo From 'Runaway Bride' Still Confuses Me I mean, it's not what I would wear to confess my love to an ex, but ok. By Samantha Sutton Samantha Sutton Instagram Samantha is InStyle's senior fashion editor. She joined the brand in 2019 and oversees the site's fashion coverage, including trend reporting, fashion exclusives, celebrity style interviews, and Fashion Week coverage. InStyle's editorial guidelines Published on February 15, 2021 @ 10:00AM Pin Share Tweet Email Photo: Getty Images Every so often, I'll turn on a '90s movie in hopes of feeling that same dose of joy and excitement I felt as a child — only to end up overanalyzing every little detail. I'll cringe at the offensive lines, find easily solved plot holes, and lose myself in a spiral about whether the characters' jobs are even a little bit realistic (as a reminder, Kate Hudson is 23 in How to Lose a Guy in 10 Days). As a fashion editor, I also inspect the style, and I have to say: Julia Roberts' love-confessing outfit in Runaway Bride is still very confusing to me. In case you need a refresher on the 1999 film, Roberts plays Maggie Carpenter, a woman who has left three different grooms at the alter on three separate occasions, causing her to develop a reputation. Richard Gere (of course he's in this) plays Ike Graham, a reporter who initially exaggerates a story about Maggie's relationship history, then tries to save his career by fully investigating the situation himself, traveling to meet her, her family, and all her ex-fiancés. Of course, she's engaged (again), but unsurprisingly, the two fall in love. Also unsurprisingly, they decide to get married. And still unsurprisingly, she leaves him at the altar and then, later, after she gets to know herself, finds him and wins him back. Julia Roberts Has Been Following This One Fashion Rule Since the '80s We could probably find a million problems with that storyline (oh great, the rude guy wins again), but what I'm focusing on today is Maggie's shoes. Please don't ask me why some of Roberts' most iconic movies are full of questionable footwear (never forget her Notting Hill flip flops). But, those brown, slipper-like loafers that Maggie wears while meeting Ike at his apartment are nearly just as bad. Paired with a simple, solid turtleneck, a midi-skirt, and black tights, it comes across as business-casual office attire. My mom likely wore this to commute to and from her job that year. I won't say the look is bad, but it's also not a "I haven't seen you in a while, but I made a mistake and we should actually get married this time" kind of look. It's just...meh. Paramount Pictures I know from interviews Roberts has done about her Notting Hill flip flops that she really enjoys it when her characters have realistic wardrobes, aka outfits she thinks us normal people might wear in everyday life. And, it's also true that Maggie comes from a small town, is new to the big city (where she recently began selling creative lamp designs), and is possibly experimenting, trying to figure out her cool, new, city girl style. Her preppy ensemble does sort of feel like it's been ripped from the pages of an old J.Crew catalogue. But, in any decade, if I, a normal person, were going to propose or confess my love to someone, I wouldn't pick your average comfy work outfit. I'd aim for something slightly sexier, swap out the midi for a mini, or at the very least trade my brown slipper-like loafers for...literally anything else. However, I will admit that I'm also that person who has panicked before events or nights out, even going as far as dipping out of the office early to find something cuter than I what I had on. And that's just for friends and coworkers — not life-changing moments. So, it's possible I'm overthinking this, and maybe Maggie was just trying to show Ike that she's more mature now. Now she's the type of person who wears sensible shoes and turtlenecks. I'm a Fashion Editor with a Closet Full of Shoes — But These Are My 8 Favorite Pairs If you've started to reflect and wonder "Well, is it possible people just wore this kind of stuff in 1999?" I'm telling you, no. 1999 Julia Roberts dressed just like modern day Emily Ratajkowski, so there were definitely other options. Maggie chose the safe route. Anyway, if you're in the mood for a '90s rom-com, Runaway Bride is on Netflix. Not all the fashion in the film will make you feel this judgey, either. Maggie's second-to-last wedding dress, for instance, is retro and dreamy (and definitely worth the commotion Ike caused when he bought it for her).