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Are skinny jeans dated? How to wear skinny jeans without looking stuck in 2006

2/18/2026

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Let’s settle it: skinny jeans in or out? First of all, many trends cycle back into being more current every 20-30 years. Skinny jeans were current in the 2000’s so their big come-back may be imminent.
Secondly, social media influencers are forever trying to make you feel like your clothes are dated so that they can get affiliate commission when you buy from their links.  Don’t fall for it. Can your clothes look dated? Yes. But here’s the answer to the question I get everytime I step into someone’s closet and they say, “I know this is old, dated, etc. aka I’m so not cool.” The answer? 
   It’s not what you wear, it’s how you wear it.
The key to looking current in the dated piece (in question) is to wear it in a more modern or trendy way.
1.  Skinny jeans are wonderful with tall boots! Show off your gorgeous (and oh-so-warm) pair of boots with a great pair of skinny jeans. (Wear them with booties and you could risk looking dated.)
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2.  Add an oversized sweater. (Wear ripped skinny jeans with a long clingy cardigan and you could risk looking dated.)
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3.  Add a boxier jacket. (Wear them with a fitted jacket and you could risk looking dated.)
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4.  Wear with a longer button-up boyfriend shirt and bright-colored flats/sneakers. This look is even better if the skinny jeans are more slim-cut, meaning they aren’t painted onto your calves, (which can cause you to look dated).
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Here are a few more things to keep in mind when wondering if your favorite (fill in the blank) is dated.
A - The more simple in design, the more classic, and therefore less dated it will look.
B - When you know your figure type and how to create the illusion of the ideal, choosing the right clothing shapes for you will trump any influencer’s dated clothing report.
C - Your personal style is unique to you. What may be dated for some, is timeless for others.

If you are looking to dial-in on your personal style type, Dani can help.
Learn More

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    Dani Slaugh

    Image consultant and personal stylist.  Dani is happily married, the mother of 3 charming children, and an Aussie named Josey Wales.  

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