How to Transition from Trendy to Timeless Fashion

January 19, 2024

Forget everything you think you know about timeless fashion. Erase those invisible rules you’ve given yourself:

  • People are just BORN with timeless style.”
  • “I could never dress like my favorite celebrities who never get caught on the worst dress list.
  • I’m not some Parisian cool girl, I don’t know where to start with creating timeless outfits.”

All of that goes in the trash because none of it is true. 

Anyone can learn how to transition from trendy to timeless fashion. All it takes is knowing exactly what defines timeless style, what sets it apart from the endless march of trends, and having a stead-fast rule of tips by your side.

Thankfully, we’ve gathered all of that for you right here. No more looking frumpy in outdated pieces. Keep scrolling to enter a new chapter of your life.

What is Timeless Style and Why Does Your Closet Need it

Timeless style refers to a mode of dressing that transcends time. These are outfits with classic silhouettes, core colors, and impeccable fit that you can get at least five outfits out of.

For example, a fire-engine red statement dress has limited use versus a navy sweater. With a red dress, you’re much more limited in the items you can pair with it, and the occasions it suits.

But a navy sweater goes with countless options–way more than a meager five.

In short, people with timeless style can look back at photos of themselves in 20 years and love what they see. If you depend too much on trends, you’ll like to look back at your old photos and feel embarrassed and sloppy.

That’s why your closet needs a timeless twist. You get more wears per item, more pride in your looks, and more people take you seriously. (Especially if you work as a CEO! Execs and CEOs should always have a top-notch wardrobe to make good impressions and show off their personal brand.)

What’s the Difference Between Trendy and Timeless Style?

Trendy vs Timeless

To review, the difference between trendy and timeless style is:

Trendy tends towards…

  • Bright colors and prints. Think accent colors like Barbie pink or a fad pattern like zebra. 
  • Items that come and go seasonally. Before the start of summer, you can’t get away from psychedelic prints and disco bell bottoms. But as soon as autumn creeps up these pieces mysteriously disappear.
  • Pieces the press is always covering. Trends dominate your social media feeds, favorite fashion magazines, and runways. Why? Because retailers love “newness” and want to encourage you to buy, buy, buy. Even if you don’t need it.

Timeless clothing leans into…

  • More classic styles and silhouettes. How many times do people STILL reference Audrey Hepburn’s style all these years later? Yet some of her most iconic looks are a black turtle neck and cigarette pants. Classic.
  • Core Colors. Black, white, grey, and navy go with everything. You’ll never see the day when these neutrals stop going together and with everything else.
  • Subtlety. You don’t see as many Instagram ads and press coverage for a grey crew neck or medium-wash straight-leg jeans. These pieces don’t need the hype, and you can almost always find them stocked at your favorite stores.

4 Tips for Building Timeless Outfits

4 Tips For Building Timeless Outfits

Starting to feel more confident about achieving a timeless style?

Good, Now it’s time to show you how you can build timeless outfits, no matter your experience level. Even if you have zero time to get ready in the morning, you can follow these tricks,

1. Do a Closet Edit

Cassandra after a closet edit

At Next Level Wardrobe, a  great wardrobe begins and ends with a great closet. 

A stylish, functional wardrobe…

  • Doesn’t stress you out in the mornings.
  • Doesn’t take away time from the things you really care about.
  • Doesn’t hold you back from your potential. 

A phenomenal closet…

  • Simplifies your routine.
  • Feels organized.
  • Reflects who you are TODAY, not who you were 10 years ago.

To get the wardrobe of your dreams, you need to conduct a closet edit. That means taking everything out. Yes, even those pieces you always shove to the back and pretend you didn’t buy.

Then, you try everything on. Seriously. If it doesn’t fit, match your work or lifestyle, or doesn’t boost your confidence, get rid of it. Create a donation pile for these pieces and cut until you’re left with pieces you actually need and wear.

Now that you’ve cut the fluff, you can see the actual gaps in your wardrobe so you can shop with purpose.

2. Focus on Core Colors

Outfit Focused On Core Colors

We mentioned core colors earlier, but they are the bread and butter of timeless fashion.

Core colors are part of NLW’s Style System. This is the holy grail that we use for styling every single client we work with. 

What we do is tell them to make core colors the focus of your closet. Black, navy blue, grey, and white never go out of style. They act as a way to ground bolder pieces and keep your outfits looking polished and professional.

That’s why we say they should make up the biggest section of your clothing selection. Somewhere between 35 – 45%. You should always buy your wardrobe basics in core colors because you’ll be wearing them the most. Versatility over everything!

Next, designate a smaller third of your apparel to fall in the “tonal colors” category. These are colors that are variations and textures of those core colors. Think brown, tan, light blue, beige, etc. 

These pieces are slightly less versatile than core colors, but you can still wear them with all core colors and some accent shades and patterns. This is also a prime opportunity to add texture to your rotation.

Ribbed knits, cable knits, leather, satin, and more all add visual interest to a timeless outfit.

Lastly, the smallest part (no more than 10 or 15%)  of your clothing should be accent pieces. We’re talking about those trendier pieces, mega-watt colors, and even some of those “trend” patterns. 

The key here is to be intentional about what bold pieces you pick. And, to remember that they’re accent pieces. That means they add a literal accent to your look. Please avoid wearing three different accent pieces at once. This isn’t Coachella.

3. Prioritize Quality over Quantity

This is your sign to grow out fast fashion. When you go to the mall or scroll online, stores like H&M, Zara, and Forever 21 shouldn’t even cross your mind.

Why? Besides the major environmental and ethical impact, fast fashion looks bad. And it’s much more likely to live in trend-world. 

Retailers often make trendy items very quickly and in astronomical quantities. These pieces fall apart after a few washes or if they don’t, they look like they’re about to.

If you want to take yourself seriously and have others take you seriously as well, invest in quality. Find one amazing natural-fiber sweater from a verifiable brand rather than 20 in a million colorways.

This will help you create more of a capsule wardrobe where you get more use out of fewer clothes. 

4. Don’t Sacrifice on Fit

We can’t emphasize this enough. So say it with us:

Just “good enough” isn’t good enough. Almost fits isn’t the same as fits like a glove.

So many people don’t realize this but most clothes don’t fit most people straight off the rack. That’s why you have to try on a wide range of brands and styles before making a purchase. 

(Or you need to work with someone who can do that heavy lifting for you. One of the benefits of working with a personal stylist is they research and pull clothes for you ahead of time.)

This is also why you shouldn’t count out tailors. We know getting your clothes altered is an extra expense. It also takes more time than just grabbing something from a hanger. But it’s so much more rewarding to have a piece that’s made for you. 

Most people need three common alterations: their sleeves, body, and hem fit. That’s how celebrities and top CEOs get the perfect fit. 

If you find a high-quality item that you love and know you will get thousands of wears out of, and the fit needs a small adjustment? Call up a trusted alterations expert.

How To Know if Something Is Trendy or Timeless: A Style Pop Quiz

Think you’ve got a firm grasp on what makes clothing timeless? It’s time to test your knowledge! 

We’ve grabbed five items that are either the epitome of timeless fashion or a trend piece. Make your guesses at each picture and then scroll down for the answer.

La Doublej’s Geometric Print Shirt

La Doublej’s Geometric Print Shirt

Product by La Doublej, shop here.

Answer: Trendy

The bright colors and prints put it automatically in the trend column. Seasonality dictates what patterns and hues are in fashion. 

Though this is a higher-quality piece thanks to the 100% silk fabrication, you’re still likely to see knockoffs and similar styles to this in fast fashion. Those retailers are trying to “capture the moment”.

Gabriela Hearst’s Grey Mock Neck

Gabriela Hearst’s Grey Mock Neck

Product by Gabriela Hearst, shop here.

Answer: Timeless

A grey mock neck returns to closets and stores every year without fail. In colder climates, they never leave. That’s because this is a necessity: a women’s cashmere sweater.

You can wear it with black slacks, wide-leg jeans, a floral skirt, or anything in between.

Marant Étoile’s Slogan Crew

Marant Étoile’s Slogan Crew

Product by Marant Étoile, shop here.

Answer: Trendy

Obvious logos automatically go into the trendy column. 

If you want to have a timeless outfit, stay away from over-the-top logos. After all, remember the era of rhinestone BEBE shirts? 90s kids are still trying to recover from that faux pas. 

The Row’s Black Leather Belt

The Row’s Black Leather Belt

Product by The Row, shop here.

Answer: Timeless

What more can we say? A minimalistic accessory like a black belt with a gold or silver belt is absolutely classic. It goes with pants of every shade. Plus, it’s an easy hack to make an outfit look more polished.

One thing to keep in mind, however, is that it’s an accessory, not a necessity. That means that even though it’s timeless, not every person needs it. For example, if you don’t wear separates or you don’t like defining your waist, this may be a skip for you.

Always consult your closet before buying an accessory. (And always start with black!)

The Row’s Lace-Up Wide-Legs

The Row’s Lace-Up Wide-Legs

Product by THE ROW, shop here.

Answer: Trendy

Just because something comes in a core color doesn’t mean it’s timeless.

Even though these pants are black, they have clear markers of a fad. From the zippered knees, the the pull-tie hem, to the lace-up front, this screams trend.

You may get more use out of it than other louder trendy pieces, but they’re still not classic. And they’re definitely not work-appropriate for 99.9% of offices.

Coachella attendees: you’re the exception.  

Achieving timeless style is only a click away. Apply for Next Level Wardrobe’s women’s styling services to take the hassle out of building outfits. Our team of experts has years of experience in the fashion industry and working one-on-one with high-achievers like yourself. We’ll revolutionize your closet, change your shopping habits, and simplify timeless fashion.

About the Author - Cassandra Sethi
About the Author - Cassandra Sethi

Personal Stylist & Image Consultant

Cassandra Sethi is a Personal Stylist and Founder of Next Level Wardrobe, a luxury Personal Styling and Shopping Service that helps successful professionals of all ages and sizes. After working in the fashion industry for over 25 years, she used her expert knowledge to create a proprietary styling system called ‘The Next Level Wardrobe Style System' which guarantees clients more outfits with less items in their closet. NLW has been featured in The Wall Street Journal, The Tamron Hall Show, NY Mag, Huffington Post and more.

*Disclosure: Next Level Wardrobe only recommends products that we’d suggest to our clients or personally wear ourselves. All opinions expressed here are our own. This post may contain affiliate links that at no additional cost to you, Next Level Wardrobe may earn a small commission. Read the full privacy policy here.

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Cassandra Sethi

is a NYC Personal Stylist and Image Consultant. She is the Founder of Next Level Wardrobe and 'The NLW Style System' that guarantees clients more outfits with less items.

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