7 Style Rules All Timeless Dressers Follow

There are some people who, despite their age, have a quality about them that feels effortless and ageless. You get the impression that they were dressing the same way 20 years prior and likely looked just as sartorially relevant during that decade as they do today. Their sense of style has more to do with knowing what works for them and sticking to it than it does their age. That's not to say they don't dress for their age, but they don't let what they're "supposed" to wear dictate how they present themselves to the world.

Intrigued by what goes into achieving this timelessness that some people seem to naturally possess, we set out on a mission to study them with the purpose of honing in on specific tips. Ultimately, we narrowed it down to seven "rules" that they all follow. Curious?

Keep scrolling to find out what they are, and shop a few timeless pieces while you're at it.

Wearing pieces and outfit combinations that never go out of style (e.g., a black turtleneck, straight-leg jeans, and ankle boots) ensures you'll never look like you're trying too hard. Effortlessness is key for timeless style. 


(Image credit: Szymon Brzóska/The Style Stalker)

#2: They avoid oversize silhouettes.

Although oversize looks are a current trend, tailored pieces are the number one way to achieve polish, which timeless people typically have.


(Image credit: Getty Images )

#3: They stick to classic shoe styles.

Look at any timeless person's shoe collection, and you'll find an array of chic, classic footwear such as loafers, Chelsea boots, and block-heel pumps.


(Image credit: Szymon Brzóska/The Style Stalker)

#4: They have a go-to outfit formula.

You'll never hear a timeless person complain that they have nothing to wear. The reason? They have a go-to outfit formula that works for a variety of occasions and always makes them feel confident.


(Image credit: Getty Images )

#5: They don't over-accessorize.

Wearing too many accessories at once can ruin a look, but timeless people stick to a select few sleek options that will only enhance their outfits.


(Image credit: Szymon Brzóska/The Style Stalker)

#6: They invest in outerwear.

Since we wear outerwear on repeat and it's the first thing everyone sees, timeless people know to focus their wardrobe budgets on this all-important piece—and it shows. Gorgeous, versatile outerwear makes any outfit look more expensive and pulled together.


(Image credit: Szymon Brzóska/The Style Stalker)

#7: They stick to what they know.

Timeless people seem to know what works for them and tend to stick to those pieces. 


(Image credit: Getty Images )

This post was previously published on an earlier date and has been updated.

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Allyson Payer
Senior Editor

Allyson is a senior editor for Who What Wear. She joined the company in 2014 as co-founder Katherine Power's executive assistant and over the years has written hundreds of stories for Who What Wear. Prior to her career in fashion, Allyson worked in the entertainment industry at companies such as Sony Pictures Television. Allyson is now based in Raleigh, North Carolina, and is originally from Baton Rouge, Louisiana. She holds a BFA in theater. Her path to fashion may not have been linear, but based on the number of fashion magazines she collected as a child and young adult, it was meant to be.