5 Classic Hairstyles That Never Go Out of Fashion

October 10, 2021 at 06:00AM

While we pride ourselves on being ahead of the curve when it comes to the latest trends, there’s something to be said for forgetting about what’s cool and embracing the classics. When it comes to hair especially, the mix of trending haircuts and celebs undergoing colour transformations can make visiting the hair salon feeling like you’re about to sit an exam. After all, what if you go for a daring new chop only to regret it a couple of weeks later? To help, I’ve done a little research into the hairstyles that have stood the test of time and come up with an edit of five that always look timeless. From Alexa Chung’s bob to Jennifer Aniston’s long, layered locks, there are certain tried and tested formulas that never seem to go out of style.

Keep scrolling to find out what the five styles are and for plenty of inspiration from the celebrities and fashion girls who wear them best. You can thank me next time you’re at the hairdressers.

I’m not sure that there could actually be a style more classic than a bob. Always elegant and decidedly chic, this simple hairstyle is made famous by A-listers like Anna Wintour and Alexa Chung. Yes, it does require a bit of upkeep, as you’ll need to get your hair trimmed every four to six weeks, but you’ll always look polished and pulled together with this classic hairstyle—whether you wear it tousled, straight or blowdried to have extra volume.

From Jennifer Aniston to Rosie Huntington-Whiteley, a long, layered hairstyle is definitely one for girls that are glam at heart. It’s the layers that are key here and prevent the look from dating. One-length, centre-parted strands tend to look a little ‘90s, but adding different lengths into the mix adds volume and texture to your style.

I’m not talking about a micro fringe or blunt bangs here. The secret to making a fringe look timeless is to go for piecey strands that look like you might have woken up like that (in a good way, of course). Trust me—a fringe needs some serious styling to make sure that it always looks good, but if you’re up for a challenge, then a feathery fringe will always look cool.


More low maintenance than a bob and a hairstyle that looks good on everybody, a lob is a one-length cut that sits around shoulder height. Even if you have naturally straight hair, wearing it slightly tousled or with beachy waves keeps the lob always looking modern and relaxed.

While a pixie cut is definitely a hairstyle for the brave, this is one style that you really can’t pin down to any one era or time. It’s utterly timeless, always chic and seriously stylish. One for fashion girls with attitude.

Up Next: 3 French Haircuts That L.A. Girls Are Asking for Right Now.

Author Mica Ricketts | Whowhatwear
Selected by CWC

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