The Three-Question Method to Figure Out If Something Is Timeless or Trendy


(Image credit: @tylynnnguyen)

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TikTok has opened up a fresh space to discuss a range of topics in new ways—among them is fashion. Creators are touching on fashion in a range of ways, but stylist and TikTok "fashion teacher" Allison Bornstein's conversations about style and shopping have especially resonated. Earlier this year, we spoke with Bornstein about her "three-word method" to find your personal style (an approach that boils down to finding three words that describe your current style and the style that you aspire to have) as it went TikTok viral. 

Now, the stylist has a new method that's gaining attention on TikTok that dissects pieces to figure out if they're trendy or timeless. Her "three-question method" involves asking yourself three key questions to decide whether something is a fleeting trend or if it is a piece worth purchasing that has staying power. "I advise clients on a lot of purchases and they often will ask me if something is just a trend or if it is worth purchasing," Bornstein tells Who What Wear. "I like to try to help them make smart shopping decisions and avoid buying things that they will tire of or won't wear, so I usually walk them through these questions."

Ahead, see more on her three-question method that can help you make smart purchases—whether it's a new pair of sneakers or the right loafer silhouette.

The Three-Question Method

Ahead, Allison Bornstein dives into her "three-question method," explaining the key things to ask yourself about a specific piece to figure out if the purchase is timeless or trendy.


(Image credit: @fakerstrom)

Question 1: Would you have worn the piece last year?

"Essentially, this is meant to help us understand if we are just seeing this a lot on Instagram and are being influenced to purchase it or if it is something that you would have wanted before seeing others wear it," Bornstein explains. "I feel like with Instagram, we will see a specific bag or shoe or pieces a ton, and then it sort of gets into our subconscious and we can convince ourselves that we need it, when in fact, we never really wanted it until we were influenced. This also helps us look back and see if this is something that has been around or if it is a trend."


(Image credit: @pernilleteisbaek)

Question 2: Will you want to wear it next year?

"This is a big one. And sometimes I phrase it to clients like this, 'Even if no one else is wearing it anymore, would you still want to wear it?'" say Bornstein. "This helps us take a beat and reflect if we will actually want to commit to wearing this piece or if it's just an impulse."


(Image credit: @jordanrisa)

Question 3: If the trend returns later, will you wear this exact piece?

"Basically, if you don't wear the item for a while and it comes back in fashion (everything does eventually!) will you want to wear this exact piece? Or will you want to get a more 'updated' version. If you would want to get an updated version, then maybe it's a sign that the silhouette or color is not timeless," Bornstein shares. "I like to call this 'minting our own vintage' because we are holding onto things that we will want to wear again. It is sustainable and helps create a functional and timeless wardrobe."

Case Studies

After explaining how the three-question method works, I was interested to see how it would work in practice. Ahead, Bornstein applied her method to some specific fashion items to figure out if purchasing them would feel timeless or trendy. It's worth noting, however, that she points out everyone will arrive at a different conclusion, based on what works for their personal style. The items here are pieces Bornstein thinks would be timeless buys for her wardrobe. For example, a teddy jacket didn't make the cut since it's a piece she doesn't envision in her wardrobe five years from now.


Cowboy Boots
(Image credit: @tylynnnguyen)

Would I have worn them last year?

For me, I think I would! I like a Western influence and I feel like I could have gotten a pair at a vintage shop which is also a good sign of timelessness. They have been worn and recycled for years!

Would I want to wear them next year?


Will I keep these exact ones?

Yes! I think if you get a pair that is plain and simple you will definitely be inclined to keep them in your closet for when they come back around. In fact, I have a pair of shorter black Luchesse cowboy boots that I have had for at least eight years! I have to break those out.


Cat-Eye Sunglasses
(Image credit: @sophiaroe)

Would I have worn them last year?

Yes! And I can pull up a bunch of images of icons throughout the years wearing them 

Would I want to wear them next year?

Yes! I think they will not look out of place if I am wearing cat eye sunglasses even if everyone else has moved on to a different shape!

Will I keep these exact ones?

Yes. I have my Saint Laurent black cat eye sunglasses that I have had for years and although I don't wear them much, I break them out and don’t feel like I need new cat eye glasses because these still feel relevant aka they are timeless! 


Leather Blazer
(Image credit: @iliridakrasniqi)

Would I have worn them last year?


Would I want to wear them next year?

Yes, I love leather and love blazers and even if other people aren't wearing them as much, it feels like it goes with my vibe and my three words, so yes, I will wear. 

Will I keep these exact ones?

Yes! Leather gets better with age too so I think it would be the perfect thing to put aside and revisit in a few years if I get sick of it for now.

Shop More Timeless Fashion Pieces

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Associate Director, Special Projects

Kristen Nichols is the Associate Director, Special Projects at Who What Wear with over a decade of experience in fashion, editorial, and publishing. She oversees luxury content and wedding features, and covers fashion within the luxury market, runway reporting, shopping features, trends, and interviews with leading industry experts. She also contributes to podcast recordings, social media, and branded content initiatives. Kristen has worked with brands including Prada, Chanel, MyTheresa, and Luisa Via Roma, and rising designers such as Refine and Tove, and her style has been featured in publications including, Vogue France, WWD, and the CFDA. Before Who What Wear, Kristen began her career at Rodarte, where she worked on assistant styling, photo shoots, and runway shows, and at Allure, where she moved into print and digital editorial. She graduated from the University of Southern California, where she studied art history and business, and currently lives in New York.