Texture decides most of this list: the Natural Curly Hair Look and the Drew Barrymore Bob work with the curl you already have, the Relaxed Curls Perm gives fine, straight hair some body, and the Cindy Crawford Blowout takes a round brush and a good dryer.
The list runs from a hat-and-curls look that needs no heat to a short Halle Berry pixie, and the Relaxed Curls Perm is the one commitment you grow out rather than wash out.
Curl pattern and how much daily effort you’ll put in decide which of the 6 fits.
1. Drew Barrymore Bob
A curly bob sitting around chin length lets the natural texture do the styling, and that’s why this one feels so easy. Short hair shows every curl pattern, so the shape of the cut matters more than any product.
I’d ask a stylist to cut it dry or curl by curl, since curls spring up once they dry and a wet cut can land shorter than planned. Wavy or loose-curly hair suits it best.
A plaid shirt keeps the Drew Barrymore bob casual, and flannel or soft cotton in a loose fit suits the shape best.
2. Natural Curly Hair Look
Ringlets pulled into a loose updo, with a few left out around the face, are the easiest way to wear natural curls without fighting them.
Skip the brush. Detangle with your fingers or a wide-tooth comb on damp hair, then let it dry without heat.
A V-neck, like the black one visible here, balances the volume on top. I’d pin the updo loosely so the curls keep their shape.
3. Relaxed Curls Perm
Modern perms use looser rods, so you get bounce and body without the tight, springy curl people remember. For fine, straight hair that falls flat, that texture is the whole appeal.
A relaxed curls perm is a real upside over daily curling irons, though it’s a commitment, and you grow it out rather than wash it out.
Bring photos and ask for large rods if you want relaxed curls. I’d book a consultation first.
4. Voluminous Curls with Hat
Big curls and a structured hat make a better pair than you’d expect: the stiff brim contrasts with soft, full hair. Choose a hat with a crown wide enough to sit on top of your volume instead of squashing it.
Set the hat on last, after the curls are dry and shaped. Pressing it down on damp hair flattens the root lift.
A bright blazer, like the yellow one visible here, keeps the 90s mood going. Under that bright blazer, a neutral top keeps the color in one place and leaves the curls and hat as the focus.
5. Cindy Crawford Blowout
Rounded, bouncy volume with ends that curve under is the point of this blowout, and a round brush plus a good dryer does most of the work. Dry in sections, rolling each one around the brush from root to end.
Lift at the crown for height. Setting the hair in large hot rollers while it cools helps the bounce last longer.
It’s a polished look, so I’d save it for dinners and events rather than daily wear. A ruffled top suits the softness of a Cindy Crawford blowout; white or cream keeps the volume as the focus.
6. Halle Berry’s Pixie
A short curly pixie puts the cheekbones, eyes and jaw front and center, which makes it the boldest cut here. Since curls shrink as they dry, I’d ask for a little extra length on top.
Keep the sides and back tight and let the top hold its curl. A light styling cream, scrunched in on damp hair, is enough.
Expect regular trims to hold the shape. Statement earrings, or a ring like the one visible here, finish it.
Frequently Asked Questions
What were some popular hairstyles for women in the 1990s?
The Rachel, bouncy blowouts and a range of curly looks were the big ones.
Among the curly styles I like: a chin-length curly bob, natural ringlets pinned in a loose updo, a relaxed perm done on large rods, a Cindy Crawford blowout with rounded ends that curve under, and a short curly pixie like Halle Berry’s.
Each one gets its shape from either the cut or the volume, which is why they still read as 90s.
Do curls make you look older or younger?
Neither, on their own. How the curls are shaped matters more than the curls.
Soft, bouncy curls like a relaxed perm or a loose blowout read as playful and youthful, but a cropped pixie leaves the cheekbones, eyes and jaw fully exposed, and that comes across sharper and more confident.
Pick the cut that suits your face and your hair’s natural pattern.
Is a side ponytail 90s?
I can’t say from what I know here, so I won’t guess.
For a 90s feel with curls, I’d go with a chin-length bob that lets the natural texture show, or ringlets in a loose updo with a few pieces left out around the face.
Both are easy to wear and don’t depend on heat.
