While I like to get a bit wild and wacky with my looks, I equally respect and love timeless, classic outfits. Yes, I am like a moth to a flame when it comes to colorful outerwear or a quirky midi skirt. But I also treasure my favorite pair of straight-leg jeans, the perfect ballet flats, and simple, chic everyday outfits. Today, I am diving into all things classic fashion — from my go-to timeless pieces to tips on shopping for quality investment items. If you’re ready to embrace timeless style with confidence, this one’s for you!
Must-Have Classic Fashion Staples
When it comes to timeless staples, the “must-haves” will vary for everyone. They depend on your lifestyle, budget, location, and personal style. However, there’s always some overlap — that’s the beauty of classic fashion!
If you’re looking to build a timeless capsule wardrobe, start by thinking about your needs with these three questions:
- What are your most-worn pieces? Do you already have timeless staples in these categories? Are they in good condition, or do they need a refresh?
- What are you comfortable wearing all day long? For example, you might be tempted to buy a variety of classic dresses because they’re beautiful. But if you’re not comfortable wearing them regularly, they’re probably not practical pieces to invest in.
- What occasions do you dress for most often? Are you looking for classic workwear? Are you a stay-at-home mom seeking timeless basics for daily wear? Do you attend a lot of formal events?
Keeping these questions in mind will help you create a wardrobe that’s both functional and stylish. Once you’ve identified what you need, it’s time for the fun part — shopping! Here are my top classic fashion items that I own, love, wear often, and highly recommend.
1. Straight-Leg Cropped Denim
Personally, I’ve found that a great pair of straight-leg cropped denim is the fit that works best for my lifestyle and styling preferences. This classic cut pairs well with many of my wardrobe staples, making it a very versatile piece. It’s also the most comfortable yet flattering fit, and it can easily transition from super casual to slightly dressy with just a few styling tweaks.
My absolute favorite pair is the Tomcat Straight-Leg by MOTHER — they have the perfect balance of structure and softness. Another great option is the Pistola Ally Jean, which offers a timeless bootcut silhouette. Both styles are incredibly practical and can be worn with a variety of classic outfits, from crisp button-downs to cozy knits.
2. A Great Pair of Ballet Flats
In my opinion, ballet flats never go out of style — which is why they’ve always had a place in my closet! Their timeless silhouette always looks polished and put together. Plus, they’re easy on the feet, offering both style and comfort!
If you’re willing to splurge, the Chanel Cap-Toe Ballet Flat is the classic fashion holy grail. The Margaux Demi is another favorite, which comes in so many rich, beautiful colors. And for a more modern take on this timeless shoe, I also love these ballet flats. I actually adore this pair so much that I own it in multiple colors!
3. The Perfect Striped Sweater
I probably sound like a broken record, but when it comes to classic style, it doesn’t get much more timeless than a striped sweater. Specifically, I love a classic crewneck. This style is incredibly versatile and easy to mix and match with everything from jeans and joggers to skirts or even layered over dresses.
This one is by far my most-worn striped sweater. I love the slightly chunky knit, slightly oversized fit, and slightly longer length. It’s available in both neutral and “pop” color combos, which I appreciate. I recently added this lightweight, solid version to my closet, and I adore it just as much. This silhouette is one that will forever be in style!
4. A Classic Bag
Again, if budget weren’t an issue, the Chanel Medium Double Flap Bag is as timeless as it gets. This purse is the chefs kiss of classic fashion. Plus, it can be worn as a crossbody, a long shoulder bag, or carried by the top handle—making it such a handy piece.
When it comes to materials, I prefer the caviar leather over lambskin. I’ve found that it holds up much better over time and is far superior when it comes to hiding scratches. And for the price of this one, you want to make sure it maintains its polished, classic look for many years to come!
5. Simple Tees
Every closet needs a few great simple tees. However, all tees are not created equal. I’ve tried countless styles at different price points in hopes of finding a few that are durable and flattering. In fact, I even wrote an entire blog post last year about my hunt for the best women’s tee!
While I have quite a few that I rotate depending on my needs, this crewneck tee is my overall number one pick. I love that it feels a bit more substantial—no sheer fear here! It features a tighter crewneck, a more fitted silhouette, and a length that fully covers your torso without riding up. This simple tee is a year-round classic fashion staple for me. I actually just ordered two more last week!
6. A Navy Blazer
Every timeless wardrobe needs a navy blazer—this is simply a fact! A well-tailored blazer is flattering, effortlessly chic, and instantly elevates any outfit, from simple everyday looks to polished workwear. Plus, if you choose a classic silhouette, the blazer will never go out of style!
Whenever I talk blazers, the Veronica Beard Miller Blazer is always in the mix. Sometimes I feel bad recommending the same item again and again because I want you to find fresh, new content here. But the reality is, classic fashion isn’t about new, new, new. That’s not how the typical woman shops—and it shouldn’t be! My goal is to offer a balanced mix of new finds and trusted favorites because that’s honestly how I approach my own wardrobe.
So again, when it comes to blazers, the Miller will always be on my list. My previous posts on how to style blazers and the best blazer brands are great resources if you’re looking for some outfit inspiration!
7. A Midi Skirt
Remember when I mentioned earlier that “what’s classic to one may not apply to all”? Well, the midi skirt is a great example of this. But, these skirts are classic fashion pieces to ME! I love to casually dress this style down as much as I enjoy dressing it up for more formal occasions.
Ever since Tibi stopped making their classic midi, I’ve been on the hunt to find similar styles. I think this affordable cotton skirt is a suitable alternative. Sadly, I no longer have a go-to midi brand, so it’s always a hunt. But if you’re looking for some fun outfit inspiration, I have plenty of ideas in my post on how to style a midi skirt.
8. A Classic Shirtdress
On the flipside, I would venture to say that almost any list of timeless style staples would include a classic shirtdress. Whether it’s a mini, midi, or full-length cut, there’s just something about the chic, button-down design that will forever be in style.
When I teamed up with Tuckernuck, we created the Chloe Dress, and the rest was history. This dress became an instant bestseller, and now you can get it in so many beautiful colors and prints! It’s a versatile short-sleeve style with a nipped-in waist and a great midi length. Plus, it easily transitions to any season—you can see how I styled it for cooler weather here!
9. Classic Accessories
This might be one of the only times I’ll ever say “less is more”! When styling a classic look, I tend to pare down my accessories and wear more streamlined, minimal pieces.
Some items that I’ve been wearing in heavy rotation for the better part of the last year include my Longines watch, this classic belt, these pearl studs, and all things Dorsey. These accessories elevate my classic outfits without overwhelming them.
How to Shop for Classic Fashion Investment Pieces
Once you identify which classic fashion pieces your closet is missing, the next step is to think about how to shop for those pieces. Below are a few tips and tricks I use!
Identify Quality Items
This is easier said than done, but the key is to identify quality pieces that will hold up over time. Timeless staples are meant to be worn for years to come, so you want them to last. This doesn’t necessarily mean everything you buy has to be expensive (for example, this tee is only $35), but it’s important to choose items from brands and labels you trust—ones that stand behind their products. However, I am more prone to splurging on classic pieces rather than trendy ones because of my “cost per wear” rule!
Choose the Right Fit
When it comes to classic outfits, fit is so important. Not only do you want to invest in timeless pieces that will last, but you also want them to fit you impeccably. Items that fit well and are tailored to your body look more expensive and elevate any outfit. Plus, they’re more likely to become wardrobe favorites because, let’s be honest, we all avoid items that aren’t comfortable or don’t fit properly!
Don’t Go Label Blind
Most of the classic pieces I’ve outlined, outside of the Chanel bag, are not logo-centric. Timeless wardrobe staples can come from anywhere, so don’t fall into the trap of always gravitating toward trendy labels. This is similar to the misconception that the most expensive item is the highest quality. Do your research and try on as many styles, labels, and fits as you can! It is all about what works best for your personal style and needs.
Choose Quality Over Quantity
It is better to have one incredible navy blazer than three mediocre ones. Focus on finding high-quality pieces that fit the bill, and only buy multiples if they serve a distinct purpose in your wardrobe.
Care for Your Clothes
Once you’ve found the pieces that work for you, make sure you maintain them by reading care labels, cleaning them properly, and storing them correctly. Great staples will last, but you have to take the time to care for them. I’m constantly spot cleaning, de-pilling, and dry cleaning my classics so that they will have a longer lifespan!
A Guide to Classic Fashion
If you’re looking to build a timeless, classic fashion wardrobe, I hope this post serves as a helpful starting point. For even more style inspiration, be sure to check out my posts on basic outfit ideas, how to wear blazers, white pants outfit ideas, and how to style a midi skirt.
