How To Dress Classic Without Looking Dated

How To Dress Classic Without Looking Dated

a classic style wardrobe doesn't have to be old-fashioned

i've always had a classic wardrobe

“You always look like such a little lady!” I remember being a little girl in a group of women who were crooning over my “grown up” outfit, but I wasn’t playing dress up, I was wearing what I liked.

For as long as I can remember, I have preferred, actually NEEDED classic, timeless, tailored clothing styles. Even as a kid I hated anything with a lot of fabric, anything loose or really casual. My sister lived in overalls all through middle school and high school, and she looked so cute and comfortable in them. They suited her. I would occasionally try them on and felt so uncomfortable and wrong. In those kinds of clothes I WAS playing dress up, even though it was a major trend for girls my age. I hated wearing flared skirts, baggy sweaters, ruffles, overalls, tunics, pleats, gathers, anything that didn’t skim my body. I got my first pencil skirt when I was 11 and it was true love. In my head I wanted to wear the cute, poofy styles that other girls my age seemed to love, but I felt ridiculous in them.

April from Stunning Style wearing a pencil skirt and stripes.

I have a few items in my closet that I’ve owned for 20 years. I’ve been drawn to classic clothing my whole life. It’s who I am. I have always purchased items that can be kept for decades, and for a long time I didn’t even realize what I was doing. It’s just what I naturally gravitated toward. Once I got my first black turtleneck sweater, I’ve never been without one since. Now I have it in multiple sleeve variations because it’s one of my favorites.

April from Stunning Style wearing a black turtleneck sweater, black skirt and patterned jacket.

The trouble I’ve had over the years with my classic, timeless clothes, is sometimes I felt dated and boring. I felt a little frumpy, a little stuffy, or a little too old for my age. So what is the trick to loving a classic style wardrobe without looking dated? I have a few secrets for you.

hair and makeup

My hair is my number one accessory. It’s piecey, sharp, angled, and pointy because I am Edgy Classic. That automatically adds an air of danger to me and my outfits. If my hair looked like Queen Elizabeth’s hair, it would age me dramatically, and it would automatically take my outfit from edgy classic to frumptastic. My hair keeps my timeless and classic outfits younger and fresher, and it changes over the years to reflect current trends…to a degree, which we will discuss below. If Queen Elizabeth had a more current hairstyle, she would look younger and her classic outfits would look updated. Her hair hasn’t changed since the 50s. What does your hair say about you?

April from Stunning Style with a pixie haircut.
April from Stunning Style wearing a black top with black jeans.
April from Stunning Style wearing a navy top with bootcut jeans.

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I also keep my makeup current (find my makeup tutorials here). I have items in my closet that are identical to items my mom has always worn. Black pencil skirt, white blouse, black shoes, etc. In the 80s, she wore the Barbie trend of blue eyeshadow, bubblegum pink lipstick, and heavy blush. It’s what everyone wore then. It was the style, and it’s what made her outfit look current then. If she had held onto the heavy, winged eyeliner and frosted lipsticks of the 60s, her 1980s look would have been dated. I wear the same items now with makeup that follows the current trends, and that keeps my pencil skirt, blouse and shoes looking updated. Is your makeup updated? Or are you stuck in another decade?


This is a biggie. The same pencil skirt and classic white blouse can be current and timeless or dated, based on the accessories.


I have a black shirt dress that I’ve had for 20 years. 20 YEARS. With a classic wardrobe that isn’t unreasonable. Below is a picture of me wearing it with a pair of black knee high boots when I was much younger. It was one of my favorite outfits. These boots were trendier and had a square toe box, small platform in the front, and a block heel. Styles changed enough that those boots were no longer fashionable, and when the styles changed, I got an updated pair to wear with my dress. Those boots aren’t really the right style anymore either, and I recently replaced them. By keeping my boots current, I am keeping the dress current. 

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The boots that were so perfect back then would make my classic shirtdress look outdated now. By changing the shoes, the dress stays current.

Shoes can also be super classic and timeless, but by wearing a shoe that is a little trendy, it keeps the clothing items fresh. If you take my boot example above, at the time they were very classy, elegant, and on-trend, but they weren’t timeless. There are boot styles that are, but most of the details change over the years. Heel shape, toe shape, heel heights, shaft heights, and colors come and go. I remember the day those boots I loved so much suddenly felt so outdated I couldn’t put them on again. Heel and toe box shapes had shifted. Platforms were over. I had to find a new pair.

Riding boots were everything for so many years, and they came in vogue because of the shift to skinny jeans. Over the last few years riding boots have taken a supporting role with mostly dresses and skirts, and booties are everything right now. My shoes are pretty classic, but most of them have details that keep them current.


Jewelry plays another role. The jewelry I choose sets a tone to my outfit the same way my shoes and hair do. I’m whispering details of who I am through my jewelry. Keeping it updated keeps my whole outfit updated. We’ll discuss it a little more below, but one item that comes to mind is the bubble necklace that was everywhere several years ago. It was so trendy it was duped by makers all over the world in every color imaginable. It’s such a trendy item wearing it immediately puts a time stamp on any outfit. 
Bubble necklace trend.

Jewelry is going through a major shift right now. For years it was all about the statement necklace, and now delicate necklaces and statement earrings are all the rage. I’m enjoying the shift and it keeps my timeless and classic clothes looking current and up-to-date. Gold has been the metal of choice for several years, and that tells me a change is coming sooner than later.

If I want to wear more classic jewelry and shoes, I will pair them with a top or pants that are a little trendier. By mixing and matching my classic pieces with current pieces, I keep everything looking fresh and updated without losing the classic look and feel I love so much.


There are some perpetually classic bags out there, like the Chanel double flap bag, and they tend to cost in the thousands. Purses go through trends in size, shape, materials, and colors. Larger bags were very popular a few years ago, and now smaller bags are. Structured bags are having a moment, but 15 years ago the hobo bag was the shape du jour. Keeping your bag updated in the size and shape is a great way to keep your look updated. Mine will always be structured, but when the time comes that is not the trend, I will rely on the other categories to keep me trendier, because a structured bag is a classic, and I love them too much to give them up.

it's ok to just pick one

You don’t have to wear trendy shoes, trendy jewelry and a trendy bag all in the same outfit, or ever. I can honestly say I would never, have never wanted or carried a hobo bag because…I just…can’t. I only carry structured bags. I know women who would do almost anything else before they wore a statement necklace. If you have problem feet, trendy shoes aren’t a possibility for you. Look at the categories and decide what does work for you. One trendier or updated item per outfit can be enough.

mix and match trendy and classic to keep a classic wardrobe update

Everything goes through trends, but there is always a classic version of it. Collars change in size and flare, but the classic collar will always be stylish. Sleeve lengths shrink and lengthen or flare and taper, but fitted wrist length will always be a good choice. Hemlines go up and down, but just above the knee is always perfect. Jewelry gets bigger and smaller, but a classic pendant or strand of pearls will never go out of style.

If every single item you are wearing is perfectly classic and timeless, you can look frozen in time or a little stale. By adding in a few trendy elements, your classic look will be updated instead of stodgy. I don’t mean you have to run out and buy flared, high-waisted sailor pants or an off-the-shoulder ruffled crop top if you don’t like those. I mean choose a few areas to be subtly up-to-date. My favorite place to do this is in shoes, jewelry, and handbags. My clothes tend to be pretty classic.

how the details can update a classic wardrobe

Let’s look at some examples between Princess Diana and Kate Middleton, who often lovingly emulates the style of the mother-in-law she never got to meet.

In these pictures Princess Diana and Kate Middleton are wearing nearly identical outfits, but what makes the outfits different is the hair. If Kate had that quintessential 80s feathered pixie she would look dated and out of style in her classic outfit. But with her au current hair and makeup, she could don the exact outfits Diana is wearing and look perfect. (Photo credit here)

In this picture it’s also the accessories dating the dress Diana is wearing. Back then matching the shoes and clutch to a formal gown was essential. It was so critical that stores sold white satin shoes and bags and custom dyed them to match the gown. On top of that she is wearing a super matchy set of jewelry that is distinctly dated. 

Kate, on the other hand is wearing black pumps and clutch with her purple gown, and while her jewelry is every bit as classic as Diana’s, she is wearing coordinating, instead of matching, jewelry, which is the current trend. The dresses are so timeless they are interchangeable. Kate could easily have stunned in Diana’s gown, and with her updated hair, makeup, and accessories, we never would have guessed the dress is at least 2 decades old. (Photo credit here).

You can see more examples of this in this post. I was inspired by Jackie Onassis and took her classic outfits and adapted them to the current styles.

stay true to your signature style

The final tip is to stay true to your own personal style. There are things that are so me. When people who know my style see it they say, “That is so April!” That’s not to say that my style isn’t always evolving or that I ignore trends. Trends are fun, and changing things up keeps fashion interesting. However, I’m very selective in the trends I adopt.

Gold jewelry has been very popular for several years, but I’ve stuck to silver because that is what I have always preferred, and always will. It also looks best with my skin tone. Skinny jeans are becoming less the thing to wear, but I switched back to bootcut jeans years ago because they flatter my body shape more, and they are a classic style of pants that are always stylish, even when they aren’t trendy. Skinny jeans are also classic, and if you prefer them, keep wearing them.

Statement necklaces are taking a backseat to delicate, layered jewelry, but I have some statement necklaces I occasionally enjoy wearing with very simple outfits when I need one standout focal point. A few years ago the trend with statement necklaces was to wear a colorful statement necklace with a colorful outfit. Lots of color, lots of big, attention-grabbing focal points in one outfit, like a rainbow attacked someone. I’ve adapted my statement necklaces to wear with simple outfits that on their own might be a little boring, but the necklace makes it interesting. Below I wore a classic fitted black turtleneck sweater, classic black ankle pants, which could be boring, but I added a bold, updated statement necklace to keep it current and interesting.


Bold hues were everything about 6 years ago, and the fashion scene has swung to the opposite extreme with everything being neutral, nude, naked, non-colors. Those colors look awful on me, and I’m not going to wear them. Instead, I stick to my mostly neutral color palette of  black, navy, white, cognac, leopard, and silver and mix them with splashes of bold color.

Florals and ruffles have never been right for my style, and you’ll never see me wearing them, even though they are all the rage, I leave them to those who love them. They aren’t me, and I would never feel comfortable following those particular trends. Even as the trends and styles shift, I stay true to my signature lady-like style, and that keeps my classic and timeless pieces looking current, and looking like me.

If you want to learn about the Classic Style Twists and which one might be perfect for you, you can read about Soft Classic, Edgy Classic, Sporty Classic, Minimal Classic and Cute Classic!

If you are not sure what your style is yet, take our Classic Style Twist quiz, and then read about the different Twists here to learn how to bring your own personality type through while still embracing classic style

In the Stunning Style Wardrobe Guide, everything is strictly modern classic, but in the shopping links I provide as many style options as I can find.  You’ll find edgy, cute, soft, and sporty options for many of the items so you can customize the wardrobe to your personal style, and 100 outfit options for 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.

Have you joined my FREE Facebook group? Classic Capsule Conversations is the perfect place to discuss capsule wardrobes and classic clothing style with a community of like-minded women!

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