
Styling Timeless and Trendy Fashion: An Editorial Inspired by Drew Joiner
Nov 28, 2024
6 min read
Understanding Timeless Fashion
Timeless fashion embodies styles that endure beyond seasons and fads. Pieces such as linen shirts, polos, wool sweaters, and well-fitted jeans consistently look fresh in any setting. Timeless fashion also leads to consumers who invest in timeless pieces save money in the long run, as they do not fall into the trap of constantly chasing after the latest trends. Investing in these classics not only builds a unique wardrobe but also promotes an eco-friendly approach to fashion.
Drew Joiner's Perspective
The idea of timeless vs trendy fashion was first introduced to me by Drew Joiner, whose a fashion influencer focused on exploring the world of fashion through his discussion and vlogs videos. In Joiner's video series, "Trendy vs Timeless (How to build a timeless wardrobe)," He explains that timeless fashion are clothing that exist and thrives in all eras of history while trendy fashion is clothing that belongs in certain era and its the consumer interest rise and fall during a short duration of time in the fashion world. A good example of timeless clothes Joiner brings up is basics shirts like, plain t-shirts, hoodies, and crew necks. He also brings collard uppers like dress shirts, oxford shirts, polos, and quarter zips.
He also mentions how many sneaker models tend to fall into the category of trendy due to sneakers models having a drastic rise in popularity and immediately falling as soon as the newest sneaker becomes popular. Sneakers that fall under this category are models like the Nike Dunk and the Adidas Sambas. However, Joiner mentions that Jordan 1 is an exception to this idea because the sneaker has been the backbone of the sneaker world and is one of the most wanted pieces of street wear since the 80s.
While Joiner does prefer timeless over trendy fashion, he does believe that it is a good idea to mix the two ideas together. While you do not want to create a outfit that looks like you're only following trends on fashion media, you want to create a perfect mix between the two that shows off your own style and allows you to express one's uniqueness.
The Allure of Trendy Styles
Trendy styles often grab our attention with their novelty and excitement. A vibrant, oversized sweater may look great today but can quickly feel out of style. I find myself occasionally swept up in this cycle, especially during fashion weeks or social gatherings. However, the reality is that many trendy items end up being discarded. For example, a trendy item may only be worn a handful of times before it loses its appeal and takes up space in my closet.
The main era of trendy fashion that comes to my mind is the "hype beast" fashion era which consisted of limited Supreme clothing drops, Bape hoodies, Ultra Boost, and the Yeezy line. While I do not have interested in the "hype beast" style anymore, I used to have an obsession with the style that was an intersection with fashion, skating, and basketball. I admit that I was a supreme enthusiast myself who owned an all black hoodie which I took pride in wearing in my early years of high school. Now, the supreme hoodie just sits in my closet due to the evolution of trendy fashion. While Supreme was one of the top fashion brand in street wear, Supreme has lost its groove being seen as basic rather than unique.
Longevity vs. Temporality
Timeless fashion's most compelling aspect is its longevity. Classic pieces not only serve me well today but will remain relevant as styles evolve. This durability allows for a more personal expression through layering and mixing. The temporary allure of trendy fashion, in contrast, often leads to quick purchasing decisions driven by fleeting excitement. Choosing timeless garments offers a sustainable alternative, supporting a fashion movement that values quality over quantity.
Building a Timeless Wardrobe
Some people reading this might be thinking that they have to dress twice their age to have their outfits considered timeless, however that is not the case. You can still wear modern clothing from the brands you like but there are some criteria you should follow.
Similar to what Joiner said in his video, basic and colored uppers are a very elegant way to style your outfit without looking basic. While the idea of graphic t-shirts and hoodies fall under trendy, there are ways to rock the style while looking unique. I recommend going with a more vintage look of a graphic t-shirt. While brands who fall under trendy tend to make vintage graphic t-shirts, I believe its a style that blends well with other timeless clothing and accessories.
While some people may see some of the timeless clothing as plain or bland, I recommend adding accessories to the outfit like a necklace, bracelet or rings. Jewelry is an accessory that be seen in all eras of history. Adding a single piece of jewelry adds more flash to any outfit.
The Intersection of Timelessness and Trends
While I advocate for timeless fashion, I acknowledge that trends can inspire creativity. They offer opportunities to infuse new life into classic styles. As a lover of sneaker brands like Nike and Adidas, I have been able to connect timeless outfits with some of the most trendy sneakers. For example, pairing a classic linen button up and a pair of jeans with a Nike Dunk or Adidas Gazelle creates an intersection between timeless clothing and such a trendy sneaker.
As someone who is very fond of streetwear brands, I do struggle with trying to make my outfit look authentic rather than a copy and paste. I personally think the best way to indulge in the trendy styles in the fashion world without looking "basic" is through dissecting and picking accessories like hats, sneakers, jewelry, graphic t-shirts and hoodies and mixing them with with a timeless wardrobe to create your own authentic and unique style.
Personal Picks for Combining Timeless and Trendy Clothing/Accessories
Adidas: Gazelles, Sambas, Handball Spezial, Campus


While some people may consider the Adidas Gazelle as a trendy sneaker, the sneakers history and characteristics fit the idea of timeless fashion. Even though the Gazelle model has became popular in recent years, the sneaker was first released in 1960s. A sneaker being able to be relevant in the fashion world since the 60s proves to me that the model is timeless. The sneaker also has a simplistic design and flashy color-ways that can complement any outfit. I am currently rocking the Pink Gazelles on the left. I am personally obsessed with the sneaker and love wearing them with neutral colored outfits. They also complement a striped dress shirt and jeans very well.
Nike: Air Jordan, and Cortez

The Jordan 1 and Cortez are two sneakers that come into my mind when I think about timeless streetwear.
Since the 1985, Jordan 1 has became the face of the sneaker world through Micheal Jordan being the face of the sneaker. As popularity of the sneaker rose, the basketball shoe evolved more into streetwear which has became one of the most memorable product among groups like fashion enthusiast, basketball players, and skateboarders. While the Jordan 1s popularity does come and go with new color-way releases, the sneaker has also dominated in the street wear market.

Cortez has been an iconic sneaker since the 70s with their simplistic but slick design that grabs a buyers intention with the vibrant nike swoosh. The Cortez has varies color-ways that can complement any style fashion.
Hats: Rope Snapbacks, Corduroy

Personally I see corduroy hats and rope snapbacks as trendy fashion since the product became extremely popular last year. While walking around on campus at my college, I do not think a day went by where I did not see a corduroy hat or a rope snapback. However, I personally love them. As a hat collector myself, I have become obsessed with this style.
I am currently wearing the SunDaze California corduroy snapback which complements a vast majority of my outfits. I recommend corduroy hats because they bring more character to a outfit compared to any basic baseball cap.
Embracing My Personal Style
Ultimately, fashion is about confidence and self-expression. Timeless fashion empowers me to embrace my individuality while allowing for a bit of experimentation. I often reflect on which pieces resonate with my personality, and I choose those that make me feel both authentic and stylish.
As Drew Joiner demonstrates, fashion is more than mere clothing; it's about storytelling. Each piece I own narrates my journey and values, showcasing a personal elegance that feels genuine.
Reflecting on Timeless Fashion
By embracing timeless fashion, I recognize the importance of curating a wardrobe that resonates with my individuality. Drew Joiner inspires me to appreciate how classic pieces enrich my daily life, balancing both style and comfort. Fashion may evolve, but the allure of timelessness remains constant. By focusing on quality, versatility, and personal expression, I create a wardrobe that is not only enduring but deeply reflective of who I am. As I navigate the fashion world, I will always cherish the classics that resonate with my essence and withstand the test of time.
Any specific jewelry brands you'd recommend?