Some hairstyles from decades past make a triumphant return. Others… well, let’s just say they’re best left in the scrapbook. Case in point: Deb’s side ponytail in Napoleon Dynamite.
Granted, Deb’s hair was supposed to look goofy — it was part of the humor. We’d never crack on sweet Deb!–or ponytails in general. They’re a perennial favorite for many reasons. First of all, they can look great. Besides that, they keep you cool, solve a bad hair day, and are so versatile that you can dress them up, dress them down, or land anywhere in between. Nevertheless, just like the makers of Napoleon Dynamite understood when they made Deb’s sad pony so unflattering, there’s a way to do ponytails right and keep them current.
The Side Ponytail’s Redemption Arc
Like all great classics, the ponytail evolves. Placement, texture, and finish make all the difference between fresh and dated. For side ponytails especially, the key is keeping them current. Lowering the height and softening the style? This is the way. (A little Star Wars allusion for my husband, even though he will never, ever read this post.) Think shoulder- or collarbone-grazing, with gentle movement and a relaxed hairline. Add a little wave, a hint of curl–or even a loose braid for a boho, effortless feel– and suddenly your pony is modern, romantic, and completely wearable.
Hall of Fame vs. Hall of Shame Side Ponytails
Not all ponytails deserve equal treatment. Some belong in the Hall of Fame, others… the Hall of Shame.
- Hall of Fame: The low, romantic side ponytail that brushes your shoulder or collarbone — soft, flattering, and pretty from every angle.
- Hall of Shame: Deb’s original ear-height side ponytail, sticking out like it was trying to flag down a bus.
What the Pros Say
Celebrity hairstylist Jessica Ruby, owner of The Flamingo Lounge (NYC & LA), believes a ponytail should never be an afterthought — it’s a statement. She’s a fan of the high, snatched ponytail for its instant lift and face-framing magic — think J-Lo and Ariana Grande….
Also, she swears by the low, textured ponytail with soft, face-framing tendrils for an easy romantic vibe:
Her secret weapons? Volumizing foam for grip and lift, amethyst oil for serious shine, blow-dry cream plus shine cream for that polished slick-back, and a style-and-shine spray to lock in shape and gloss. Both the high snatched and low textured styles are timeless, wearable, and can be dressed up or down.
Additionally, her team also loves a sleek-braided ponytail, polished at the base but playful in texture — perfect for showing off color and adding just a bit of drama without going full editorial.
For the truly adventurous, master stylist Ruby Rainbow takes ponytails into punk-rock territory with safety-pin threading, layered ponytails at varying heights, and sculptural twists. These alternative ponytails are for the bold at heart — and probably much younger than this editor. My younger daughter loves the look of edgy, vivid hair, so I’ll just admire from a safe distance while she plans out her someday version. You can see their full range of creative work — plus the Flamingo by Ruby elastics, pins, and playful adornments — on Instagram at Flamingo Lounge Hair and Ruby Rainbow Hair.
Side Ponytails in the Wild
Technically, the side ponytail can work… but only in its modern form: low, soft, and a little undone. In very specific, high-fashion situations, a sleek side ponytail might appear — but most of the time, keeping it low and romantic is your safest bet for avoiding that “middle school dance” vibe.
Ditching the Side Ponytail…Forever?
Whether you’re rocking a sleek low ponytail, a textured high ponytail, or a loose, romantic ponytail over your shoulder, the moral of the story is this: nostalgia is fun, but your hair deserves better than to sprout sideways like an escaped unicorn horn. And if you do resurrect the side ponytail for a costume party? Just make sure you’ve got the Napoleon Dynamite soundtrack queued up.
P.S. For more hair inspiration, check out our article on Melrose Place style.
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