In this near-perfect Lizzie McGuire episode, Lizzie sneaks onto the set of a Christmas-themed Aaron Carter (ugh) music video. The silver pants and red top she wears are fitting for the era, plus the fit is something I could totally see Duff’s HIMYF character, Sophie, modernizing and wearing on the Hulu show.

There’s perhaps a little too much embellishment on this ‘fit, but hey, that’s Lizzie McGuire for ya. White and denim are made to last and a boot helps toughen up every look.

They say first impressions count, and movie star Olivia Burke’s introduction to Manhattan’s elite is no different. Most of Duff’s outfits in Gossip Girl are painfully of the time — think: Herve Leger bandage dresses, statement necklaces, and spangly going-out tops. Still, the blue Mets T-shirt and fedora Olivia wears during her first meeting with Dan Humphrey (Penn Badgley) has cool-girl, off-duty actor appeal, making this her best outfit on the show — and the only Gossip Girl ensemble to grace this list.

As the saying goes, on Wednesdays we wear pink… and army pants. Three years before Lindsay Lohan rocked the look in Mean Girls, Duff gave this unexpected pairing a go.

This hot-pink Rebecca Vallance bow dress is perfect for a 30th birthday party, which is exactly what Sophie wears it to. It also gives strong Younger vibes, harking back to a dress Duff’s Kelsey wore on the show (more on that later).

This bright-yellow Tibi top became synonymous with Duff’s character throughout Younger’s run, mixing flirty feminine with business chic. By pairing it with jeans, the look signals Kelsey’s desire to forgive Liza (Sutton Foster) for lying about her age the whole time they’ve known each other.

This AFRM sheer, purple wave turtleneck paired with necklaces, a black leather skirt, and silver platforms wouldn’t have been out of place on Lizzie McGuire. All it’s missing? Butterfly clips. Here, Sophie wears it for a night out with new besties. The classic baby blue Vince coat modernizes the look.

I love pink on Duff, so this boardroom-ready Marni turtleneck is an instant fave. Paired with a plaid Gucci blazer, it reminds me of the coat Sophie wore in the HIMYF pilot. I’d like to wear something similar at work, for sure.

This Alice + Olivia jumpsuit and Western-inspired B-Low the Belt piece delivers major Samantha Jones from SATC energy. Considering Samantha was known for her power suits, this look could be a slight nod to Kim Cattrall, who plays an older version of Sophie in HIMYF.

Despite the fact that it was styled by legendary costume designer Patricia Field, I think about this ‘fit a lot simply because it’s so relatable.

Cher Horowitz’s plaid skirts and berets endure for a reason, so this striking Lizzie look also stands the test of time. I prefer the outfit without the Balmoral cap Lizzie wears in the episode, but I still think it’s a winner.

Younger costume designer Jacqueline Demeterio, who eventually replaced Field, was on a blue pants kick in this episode. Kelsey wore an effortless, sophisticated pair of Alice + Olivia pants paired with an Isabel Marant belt. In addition, she wore a flared floral Racil pair with a racing stripe.

For a fun scene in which Kelsey runs around Williamsburg, Duff wore a red and pink Gucci bomber jacket with a giant bow. “We used it on the street because I knew a paparazzi shot was gonna happen!” Demeterio said about the look. While Kelsey is often seen at work, Demeterio and Field often relied on fun pops of colors to let her personality shine outside the office.

Younger’s fashion was so on point in Season 4 that every outfit could honestly be on this list. However, I had to pick my favorite: the Gucci pink pleated dress. Kelsey wears it to a funeral (of all places) that called for a pink dress code. As always, she didn’t disappoint.