My love for classic style started at a very early age. I grew up watching old movies with my mom and grandma. I remember being fascinated with the classic fashion icons and outfits from other eras as far back as middle school.
I’m often asked about the best way to build a wardrobe and put together outfits that can stand the test of time. So today, I am excited to build upon one of my most-read articles about timeless staple pieces. I’m going to reveal some of my favorite classic fashion icons, share some tips for putting together a timeless outfit, and highlight some classic style outfit ideas. Be sure to bookmark or Pin this post. My hope is that it will be just as relevant five years from now as it is today!
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What is Classic Style?
While there is no singular definition of classic style, in my opinion, it is synonymous with timeless silhouettes, effortless outfits, and enduring appeal. I believe that classic fashion can span different ages and stages of life. For example, a 25 year old and a 45 year old could both wear a pair of high-rise jeans with a white button-down shirt and look equally as great. And a timeless black shift dress hanging in my closet today will still be as chic and fashionable 10 years from now. To me, classic style is the cheat code to always looking stylish and put together.
Classic Style Icons Throughout History
When it comes to classic style icons, most of mine are from another era. For as long as I’ve loved fashion, I’ve loved the personal style of Grace Kelly, Katherine Hepburn, Audrey Hepburn, and Elizabeth Taylor, both on and off screen. I remember watching To Catch a Thief (with Grace Kelly) when I was 11 years old. Even at this young age, I couldn’t get enough of her wardrobe! Around the same time, I watched Sabrina (with Audrey Hepburn). I’ve been chasing that classic Sabrina style ever since. If you haven’t yet watched these movies, run and do so!
Classic Style Icons of 1990s-Today
In the 1990s, more of my classic fashion icons came on the scene, including Princess Diana and Carolyn Bessette-Kennedy. If I’m feeling in a rut, I like to look back to outfits these women wore in the 1990s and put my own spin on them! Most recently, Sofia Richie Grainge has been added to my style icons list. At the young age of 25, I am so impressed with her elevated, chic, and classic style.
The women of San Sebastian, Spain have also recently become style icons of mine. The boys have been attending a Spanish immersion school in San Sebastian for the past few summers. When we’re abroad, I find myself marveling at the women who are always coiffed and classic, with perfectly ironed clothes. They seem to invest in beautiful pieces that they take care of year after year. If you are traveling overseas, be sure to check out my Europe packing list, which is full of classic staple pieces perfect for mixing and matching!
How to Embrace Classic Fashion
Finding your own personal style is such a fun journey! My friend Blair Eadie of Atlantic-Pacific recently wrote an article discussing how to find your style. I think it’s worth checking out if you’re trying to decide whether or not classic style is the right fit for you. Obviously, it didn’t take me long to hone in on timeless fashion, but making it my own and putting a modern spin on it can be a bit trickier.
In order to do this, I like to reflect on my fashion icons, and think about what I really love about their specific looks. Then, I try to replicate it, but in my own, updated way. Additionally, mom has always been such a wonderful example of timeless fashion. Many of the classic looks that I put together are a mix of basic pieces and flattering silhouettes, influenced by my mom, mixed with my own sense of fashion.
Classic Style Tips & Tricks
While everyone will put their own twist on an outfit, I have learned some classic style tips and tricks over the years. These have helped guide me in putting together looks that are effortless, timeless, and chic.
1. Know what works for your body
While I love trying out trends, I’m in my forties now, and the gift of that is knowing what flatters and suits me, and what does not. I think knowing what makes you look and feel your best is so important, no matter what type of personal style you gravitate towards. For example, I typically prefer a higher neckline because I think it best suits me and makes me feel the most comfortable. However, these preferences will be different for everyone.
2. Opt for a tailored fit
The way a piece fits can make such a difference. If you buy something you love, but it doesn’t quite fit, then it’s time to see a tailor. Getting clothing altered can go a long way in making you feel comfortable and confident in an outfit. An inch taken in or let out, here and there, can do wonders!
3. Choose high quality fabrics
I’m always on the hunt for nice linen, cashmere, tweed, and silk. The great thing about classic style is that it’s easy to recreate. You can easily find elevated pieces, even from a thrift store, as long as you know what style, fit, and fabric to look for.
4. Don’t be scared to invest
On the flip side, sometimes it’s worth spending a little extra money to invest in timeless staple pieces. You certainly don’t have to spend a ton, but, you can build up high-quality basics over time. I’ve found this to be worth the investment.
5. Keep it simple
Simple doesn’t mean boring! While many classic staples are focused on the basics (a white tee, a great pair of jeans, a timeless shift dress, etc.), you can add fun jewelry, bags, and shoes to give these outfits your own twist!
Classic Style Staples
When you’re ready to start building out your wardrobe and creating timeless looks, there are a few classic style staple pieces that I recommend investing in. You certainly don’t have buy all of these at once, nor do you need these exact pieces. However, I do think versions of all of these will help you build out a wonderful collection of classic fashion items to choose from!
Timeless Tops
Let’s kick it off with classic tops! Whether I’m dressing up or keeping it casual, these are the tops that I always reach for. Many of them also make their way onto most of my packing lists and capsule wardrobes. All of these pieces are versatile and can be worn in so many different ways!
1. Linen Button-Down
At the top of my classic style list is a good linen button-down, and the Britt shirt is my go-to. They last forever and come in tons of great colors. While I don’t dryclean mine, I do have someone press them. There’s nothing like a nice pressed linen shirt! These look great with jeans, shorts, or pants.
2. Classic Cardigan
Every closet needs a classic cardigan or two! I wore this striped lady jacket sweater on repeat all summer last year. This cream cardigan is another great option that will match everything. If you want a little more warmth and structure, this tweed cardigan is a good option. And if you’re looking to add a luxury staple to your wardrobe, this blue tweed lady jacket is such a dream!
3. Simple White Tee
This classic white tee is only $15 and excellent quality for the price! I own it in a few different colors. I love the fit, but I do want to note that I recommend sizing up one size in this one.
5. Fitted Blazer
A fitted blazer is without a double a classic style staple piece. I own and love this navy blazer and I instantly feel put together and chic when I wear it!
6. Timeless Trench
A timeless trench coat is a piece that will be as stylish five years from now as it is today. It’s so easy to throw on and instantly elevate any outfit. This is a great piece to purchase in neutral colors, so that it matches lots of different looks in your closet.
Classic Bottoms
Now let’s talk about the perfect bottoms to pair with your classic tops. The good news is that you don’t need to have an abundance of bottoms. You can create many classic fashion outfits by mixing and matching a few different pairs. While I’m going to focus on jeans and pants below, if shorts are your thing, I linked a beautiful and timeless pair in this casual resort wear post!
1. Elegant Trousers
These wide-leg linen trousers are absolutely gorgeous! I love the natural color, it will match everything in your spring and summer wardrobe. A piece like this is definitely worth getting perfectly tailored. They’re truly the epitome of classic style!
2. Linen Pants
A great pair of linen pants will never go out of style. I love this wide-leg pair in French blue, and they come in lots of other beautiful colors as well. Plus, it’s a great price for a classic fashion staple piece!
3. Feel-Good Denim
Time and time again, a great pair of denim will never let you down! The AGOLDE 90’s pinch waist jean continues to be my favorite pair. I’ve had this style for over a year, and I continue to reach for it on a regular basis. I love the flattering high-rise waist and the slightly cropped fit.
4. White Denim
Not only do I recommend a pair of blue jean denim, but also a great pair of white denim. I know sometimes this can be a bit trickier, but there are so many different pairs of white jeans to choose from nowadays, making it much easier. This high-rise cropped pair is a favorite of mine.
Chic Dresses
No classic style guide is complete without a few favorite dresses! When choosing dresses for my closet, I tend to opt for timeless silhouettes and flattering styles that make me look and feel my best. If I find a dress that I particularly love, it’s not unheard of for me to buy it in more than one color, especially if it’s a one that I know I can wear for many years to come. Here are some of my go-to dresses!
1. Timeless A-Line
In my opinion, a chic a-line dress is a classic style that flatters every figure. Two of my favorites in this silhouette are the Tuckernuck Chloe dress and the Staud Wells dress. I love them both so much that I own each of them in more than one color! This timeless white shirtdress also looks like a great a-line option for summer.
2. Everyday Romper
Okay, obviously this isn’t a dress, but it’s close! This chic black romper is so good that I own it in three colors! It’s such an easy everyday piece to pair with heels or sandals. And the great news is, you can use code “sarahtucker25″ to take 25% off!
3. Lovely Linen
A go-to linen dress is a classic fashion staple piece. This chambray linen shirt dress has been one of my most-worn pieces for the past few years. It makes for such an effortless, yet elevated, outfit. This neutral a-line linen dress is another that I have reached for over and over again. Classic dresses like these make getting dressed so easy!
4. LBD
I’m not sure it’s possible to put together a list of classic staples and not include a little black dress! Every closet should have at least one that you feel great in. One of my personal favorites is the Calista dress from Mestiza. I often reach for it for a fun night out.
5. Belted Maxi
The vintage-inspired Millie dress from Staud is a classic style that has been a favorite of mine for years. Once again, I own this dress in two different colors. While it is no doubt an investment, I truly believe it is a timeless dress that will stand the test of time. I could easily see myself wearing it ten years from now, and loving it just as much. This new blue and white version just might become my third Millie dress, it’s so pretty!
Trusty Shoes
When it comes to shoes, I think it’s worth it to invest in quality staples that will not only match everything in your closet, but also last for years. There’s nothing worse than walking around in uncomfortable shoes or having them become damaged after only a few wears due to poor quality. I believe you only need a handful of great shoes to build a classic fashion wardrobe.
1. Comfy Ballet Flat
Jeans, pants, shorts, dresses…a comfy ballet flat pairs with almost everything! I own and love this neutral pair, they’re extremely comfortable. This fun Loeffler Randall pair is another great option that I own in two colors!
2. Classic Loafers
I don’t think you’ll find a shoe more classic or comfortable than Stubbs & Wooton. Each pair is so luxurious and beautiful, and their comfort is worth every penny!
3. Easy Sandals
If you’re putting together a classic style outfit in the spring or summer, an easy pair of sandals is a must. I love the rich color and croc-embossed leather on these handmade sandals. And for an affordable option, I love these $20 woven sandals from Target!
4. Pump it Up
Last, but certainly not least, a timeless pump is a classic fashion “must”! I love the subtle low heel on these tan and black color-blocked slingback heels. The color combination matches everything, and they look great with so many different bottoms and dresses!
Simple Accessories
For the most part, I really love simple accessories. A pair of pearl earrings, a gold pendant necklace, or a diamond bracelet are all classic fashion accessories that will never go out of style. However, on occasion, I do like to wear a fun pair of statement earrings! Most of my new jewelry comes from Susan Shaw, Julie Vos, or Tuckernuck. However, the pieces that are the most special to me are the ones that have been passed down through generations. Heirlooms will always be in style!
1. Cinched With a Belt
A good belt can pull a whole look together. I think J.McLaughlin does a great job with classic belts that still feel modern. If you browse my daily looks, you’ll most likely find me sporting a belt or two around my waist.
2. Pretty Handbags
My current favorite handbag is this dark brown leather mini bag, it’s such a classic style! I do like to change it up and carry different bags with different outfits, so there are always a few options in my closet. A straw bag and a bamboo clutch are two staples I reach for often. My favorite everyday bag and travel bag is my Longchamp tote. And when it comes to a timeless Americana staple bag, an LL Bean Boat Tote will always been the winner. I love all of these!
3. Chic Sunnies
When it comes to sunglasses, my personal motto is “the bigger the better”! I typically reach for classic style tortoise sunnies, as they look great with everything. My current favorites are my Krewe Olivia pair, my $12 Amazon sunglasses, and my Le Specs Air Hearts.
Favorite Classic Style Brands
As a girl who loves to shop, I’m always on the hunt for new classic styles to add to my closet. While I do enjoy playing with trends every now and then, for the most part, I like to shop at stores and boutiques that carry timeless pieces. These are a few of my favorite modern, but classic, places to shop (click on each brand to browse)!
Classic Style Forever
I’ve said it before and I’ll say it again, classic style will never go out of style! I think this is always reassuring to hear, as we all know how frustrating it can be to buy a “trendy” piece only for it to go out of style the following year. I love leaning into my favorite fashion icons and putting together looks that make me feel my best. If you’re also wanting to embrace timeless fashion, I hope you’ve found some inspiration from this post! For additional classic outfit ideas, check out my favorite timeless staples, my mix-and-match packing list, and my fall capsule wardrobe.
Shop the Classics
