The Olsen Twins’ Best Styling Tricks Were Made for Fall
Consider this your crash course in getting dressed like fashion's most famously unbothered sisters.
Mary-Kate and Ashley Olsen have never met an enormous coat, suspiciously long trouser, or an aggressively practical flat they couldn’t make look wildly expensive. And while their wardrobes may include plenty of The Row, the real appeal of Olsen-twin style has less to do with price tags than proportion, restraint, and an almost supernatural ability to make “I just threw this on” look like a legitimate fashion philosophy.
This fall, I’m taking notes. The best Olsen twins fall outfits tend to rely on deceptively simple styling tricks: oversized outerwear tempered by sleek shoes, generous layers, tonal color palettes, beautifully boring basics, and accessories that quietly do all the work. Consider the tips ahead a guide to channeling Mary-Kate and Ashley Olsen’s fall style—without requiring a Manhattan-sized The Row budget or sunglasses large enough to conceal your identity.
Invest In The Button-Up Shirt:
The button-up shirt is the cornerstone of almost every coveted Olsen twin look, and it's how they wear them that makes it so inspiring. Their preferred versions are oversized, slightly rumpled, and styled with a studied disregard for conventional proportions—collars left unbuttoned, sleeves pushed or rolled, and hems hanging loose over equally generous trousers.
Have fun with the “Wrong Shoe Theory”
The Olsen twins were practicing the Wrong Shoe Theory long before TikTok gave it an official name. Think polished trousers with beat-up sneakers, elegant coats with casual flip-flops, or jeans with shoes that feel like they belong at the beach—high and low, formal and casual, always slightly at odds.
Go Wild For Crocodile Handbags:
Our favorite stylish sisters have never been afraid of a bag with a presence, and their penchant for oversized, croc-effect styles is practically a calling card. Worn against slouchy layers and otherwise restrained outfits, a glossy, gargantuan bag adds just enough old-world polish.
Embrace a Touch of Bohemia
Minimalism may be their default setting, but the Olsens have never been complete purists. Their best looks often introduce a bohemian wildcard—an embroidered blouse, a trailing scarf, stacks of jewelry, or something wonderfully fringed—giving all that immaculate restraint a little undone, worldly charm.
Use Maximum Proportion for Minimal Separates
The Olsens treat proportion less like a rule and more like something to deliberately distort. A voluminous white poplin blouse—long in the sleeve, generous through the body, and decidedly un-tucked—becomes even more compelling paired with equally languid trousers or an oversized coat, proving that sometimes the chicest silhouette is simply more.
Go tried-and-true with a turtleneck + stirrup legging pairing
One of my personal favorite Olsen outfits is anything that involves a lush cashmere turtleneck. The chicness of something so luxurious teamed with a casual, off-duty pair of leggings is exactly what makes their outfits work. Tension!!!
Collect The Classics: The Samba Sneaker
Both Mary-Kate and Ashley have a love for one classic, affordable sneaker. You guessed it—it's the OG Adidas Samba. Practical with just enough detail, you'll see them sporting theirs with everything from puddling trousers and oversized coats to leggings and off-duty layers.
