Classic Clothing Items I've Had in My Closet for 15-20 Years

I’ve had certain clothing pieces in my wardrobe for 10, 15, and even 20 years. I’ve worn them consistently because they are so classic in style. Come see what to look for and what to avoid when buying classic pieces you want to keep for years, and what to avoid as we talk about classic versus trendy. I’m also sharing the items I’ve had for a decade or more that have truly stood the test of time!

20 years ago I was enjoying my stroll through the mall after living in a very rural part of Brazil for a year and a half. So many things were different, and so many things were the same. There had been a major style shift while I was gone, and it was interesting to see all of the changes. I walked into Banana Republic and saw these adorable tiny tweed blazers.

“Have you started selling children’s clothes?” I asked the sales associate. She looked at me like I was making a lame dad joke. “No,” she said curtly. “Cropped blazers are on trend right now.” And she turned her back and marched to the back of the store.

I felt…out of touch. I turned to inspect the mini Chanel-esque blazers again. The length came to my waist. The sleeves came just past my elbows. They looked like something that would fit Mary Kate and Ashley Olsen in their tween years. I quietly made a dignified exit while trying to wrap my brain around this new trend of child-size clothes for adults.

Classic Wardrobe Items I’ve had for Decades

I have several items in my closet that I’ve owned for 20 years, some for over a decade, and some that I’ve had a version of in my closet for as long as I can remember, but I’ve had to buy replacements for as they wear out. You would never know to look at them that I’ve had them that long. Inevitably someone asks me where I got these items in the hopes of finding one for themselves, and I must always disappoint them with my answer.

“I’ve had this for 20 years.”

Whenever I tell people that, they just can’t believe it! Jaws hit the ground. How can I possibly have and wear items for 20 years and they not go out of style, or stay in good enough shape? It’s because there is no trendy detail to give them away. Every part of it is timeless. And this is the very definition of a classic wardrobe item.

What are trendy versus classic details?

As you shop for items and consider how long you want to keep them in your wardrobe, keep these things in mind. This is a general list to give you an idea of things to look for.

Extreme widths or lengths

Think super wide or narrow lapels and collars.

Really short or really long hemlines, whether on a skirt, top, or jacket, like crop tops or tunics, mini or maxi skirts, cropped jackets or dusters.

Flared ends like the top or bottom of a sleeve (like a bell sleeve that flares at the bottom or a balloon sleeve that flares at the top).

Very voluminous or very tight tops and bottoms, like the current over-sized slouchy tops that would fit you and your whole family or the previous second-skin-this-top-is-so-tight-I-can-see-what-you-had-for-lunch tops, and skinny pants/jeggings and flares.

Extremely high-waisted or extremely low-waisted pants.

Extreme heel heights, toe box shapes and lengths, and platforms.

Extreme sizes like very large or very small handbags.

Colors

While my color palette doesn’t change with the trends, neutrals are the most classic colors when it comes to long-term wardrobe staples. You’ll notice most of my items are black or white. The ones I’ve had the longest are black because white does yellow over time.

Finishes

Appliques of any kind can date an item (but not always), like sequins, embroidery, cut outs (think cold shoulder tops), patterns, metallics, studs, etc.

The classic equivalents

Look for medium-width lapels and collars.

Skirt hemlines that hit anywhere from just above to just below the knee.

Jackets, blazers, and tops that hit at the hip.

Jackets like trench coats that hit just below your seat to mid-thigh.

Sleeves that are straight.

Jackets, skirts, pants and tops that skim the body shape.

Bootcut jeans, tailored tops, straight cut ankle pants, mid-rise pants.

Pointed, round, and almond toe shoes and boots. 2.5-3.5 inch heels and flats.

For more ideas and details, I wrote about Classic Style here, here and here.

Are trends a no no for a classic wardrobe?

Does this mean I never buy anything with trendy details? Absolutely not. Incorporating the right trends for me is how I keep my classic wardrobe from looking dated and stodgy. I enjoy adding trends in my wardrobe, and they are often a great way to incorporate the Classic Style Twists. The exposed zipper trend has been a favorite of mine for years because it feeds my Edgy Classic style. Flared bell sleeves are perfect for a Cute Classic. The oversized boyfriend trend brings in softness for a Soft Classic. The racing stripes on jeans are on many Sporty Classic wishlists. The dainty necklace trend is a Minimal Classic dream come true.

I grab the trends that work with my style, but my core items, the ones I want to have for years and years, and typically my favorite wardrobe items, those are always classics. They also tend to be the most expensive items in my closet, but not always. I’m willing to spend more on a classic item I will get years of wear from.

If I’m loving a super trendy detail, I keep it in the budget-buy category. Something that will last me a season or two, and after I’m tired of it, it’s worn out, or it’s no longer of-the-moment, I will have no guilt parting with it.

Even though I love to purchase quality items so they last forever, I can tell you that none of these items falls into the high quality category because I was in high school and college. I was broke. Though I believe that even the less expensive brands were of a higher quality two decades ago than they are now.

In the Stunning Style Wardrobe Guides, my goal is to help you build a classic wardrobe that can carry you from season to season and year to year without having to constantly replace new items. I help you incorporate your Classic Style Twist to personalize it. Each season I carry over items from previous seasons to maximize your wardrobe while introducing a few new things that will refresh your basics. I encourage you to shop your closet for as much as you can, and I provide shopping links for anything you may want to add. You can learn more about the Wardrobe Guides here, and get started on building or maximizing your classic wardrobe.

The Classic Wardrobe Items I’ve Owned for 15-20 years

I call this my Trinity coat. As in Trinity from the Matrix. It fits me perfectly, is super tailored, and is so amazing. 20 years ago I walked into Express at 10 a.m. when they opened, and they had just rolled out a rack of these coats with a big $15 clearance sign (They were $200 full retail). I tried this one on, swooned, turned around to grab one for my best friend as a birthday gift, and THE RACK WAS EMPTY (sorry, Amanda). That. Fast. This is my dressiest coat, and I love it. It’s still in amazing condition. It’s not an every day coat, so it hasn’t gotten as much wear, but it is still in mint condition. I never fail to get questions and comments about this coat.

I’ve had this pencil skirt for 20 years. Two decades. A very, very long time. And it is absolutely timeless. The hem line sits just below my knee, which works great for me, especially when I’m sitting. I hate fighting to keep my skirt down when I sit. Even more when I have kids on my lap. It is stretchy, but structured, fits me perfectly, and will continue to be a staple in my wardrobe. I bought it at The Limited (which was definitely higher quality back then than it is now).

This whole outfit is extremely classic with the fitted half-sleeve turtleneck (oh, how I want it in navy and white as well!), the pencil skirt, the knee high, high heel leather boots, and black, structured, medium-sized bag.

I’ve had a white button up shirt in my closet since high school. I have to get new ones periodically because they do yellow with age. This is my current favorite. I have 12 of these shirts in a variety of colors and patterns. I love the spread neckline. I love the relaxed, but not over-sized, fit. I love the roll tab sleeve. I do wish this one weren’t so sheer, although it looks more sheer in this picture than it is in real life because of all the lighting to take the pictures. And I wish it didn’t have chest pockets. Honestly there’s probably not a clothing item in the world I wouldn’t want to edit in some way. But still, I love these shirts. You can buy this shirt here. I’m wearing an XS in the regular fit. If you get the slim fit, size up one size.

I bought this red faux suede skirt 20 years ago, and I’ve worn this exact outfit every year since. I even wore it on my first Valentine’s Day date with my husband. I have always worn it with a black, fitted, ribbed turtleneck sweater, and high heeled, knee high black leather boots. I also have the skirt in black, but didn’t take pictures because it felt repetitive. I’ve always worn that one with a white turtleneck sweater, which I currently don’t own, but have been looking to replace for ages. My last one wore out. I bought this skirt at 5-7-9. Do you remember that store? Definitely not expensive. It was like the Forever 21 of the 90s. I guarantee this skirt was less than $20 at full price, and I probably got it on sale.

I also bought this black shirt dress 20 years ago. It’s a jersey knit, so it’s super comfortable and stretchy. It’s a classic cut, the three quarter sleeves make it wearable 3 seasons a year, and the length is perfect. I wear it often. I also bought this dress at 5-7-9. Possibly on the same day I bought those skirts. Similar here.

Ok, this outfit is a replica of an outfit my mom wore in the early 80s. This is her exact blazer from nearly 40 years ago. It’s velvet, and 100% classic in the length, fit, lapel width, sleeve length and tailoring. I’ve had this skirt for 15 years, and a high heeled, knee high black leather boot of some variety for 20 years. The blazer is a much better quality than the other items. It’s Koret. The wool skirt is Harve Benard (also a good quality brand), and I’ve had it for 15 years. The current white shirt is from Banana Republic (white shirts tend to yellow after a few years, so must be replaced periodically). The boots are from J. Crew and over 10 years old.

I have had a fitted, ribbed, black turtleneck sweater in my closet for probably 25 years. I haven’t been able to keep the same one because sweaters inevitable get holes in them or stretch out, but I never part with one without having another ready to replace it. Sometimes I keep two in my closet at a time just in case because it’s one of my most-loved, most-worn closet items. I also love to have a pure white one, and a deep dark navy blue at all times. I’m currently without a white one because my last one wore out, and it’s not easy to find pure white. I miss it. I wear this sweater all the time. This time I chose one with a button detail on the shoulders and sleeves that makes it a little more special.

I’ve had this particular denim jacket for 15 years, but I’ve had a denim jacket in my wardrobe since sixth grade. I clearly remember getting my first one, and I wore it on the first day of school. I love this one because it’s dark wash, has silver hardware, a tailored fit, and plenty of stretch. I wear it a lot in spring, summer, and fall. These are both favorite outfits that I love to wear. The denim jacket is from New York & Co.

Is your jaw on the floor? Here, let me help you pick that up. I bet I’m not the only one with items in my closet from a decade or two ago. What do you still have?

ARE YOU READY FOR SOME CLASSIC STYLE INSPIRATION?

If you’ve been nodding along with this article, you’re a woman with classic style. Check out these posts  to find more style inspiration. Or take our Classic Style Twist quiz here, and then read about the different Twists here to learn how to bring your own personality type through while still embracing classic style.

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