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. 

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

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.

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.

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.

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.

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

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

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