12 Classic Basics Never Going Out of Style

As we enter our 40s, there’s a newfound confidence in truly knowing who we are, and our wardrobes should reflect that.

Gone are the days of chasing every trend. It’s about building a closet full of essentials that last and feel authentic to us.

Once those foundational pieces are in place, it’s easy—and fun—to experiment with trends. With the right basics, you’ll get more out of your wardrobe, and the outfit possibilities are endless.

Personally, I’m starting fresh with my wardrobe after shedding the last of my ‘baby weight’ (the baby is almost six!) and the extra pounds I picked up during COVID.

Now that my body feels familiar again, I’m rebuilding a wardrobe that reflects that. It’s exciting but also overwhelming at times. I want to share this journey with you to show that it’s normal to feel overwhelmed and that taking it one step at a time is okay.

As a professional, this reset has been eye-opening. I’ve been exploring new brands, discovering some fantastic pieces, and rethinking how to invest in what matters most. I can’t buy it all at once, so I’m learning to be intentional about each choice.

With that in mind, I want to share the 12 basics that will set the foundation for a versatile, timeless wardrobe.

Here’s what every woman over 40 should have in her closet that won’t go out of style.

12 Classic Basics Never Going Out of Style

1. The Perfect White Button-Down

This is the quintessential wardrobe staple. A crisp white button-down works for practically any scenario, whether tucked into jeans for a casual look or paired with a pencil skirt for a meeting. And when you find the one that fits you just right? It’s like magic.

Megan’s Pick: Garçon Classic Shirt in Cotton Poplin from J.Crew, $98

2. A Tailored Blazer

A well-fitted blazer instantly elevates any outfit. Whether you’re wearing it with jeans and a tee or over a dress, it adds structure and polish. I’m always surprised at how a great blazer can make even the most casual looks feel pulled together.

Megan’s Pick: Both in either black or navy The Diana Blazer from Tuckernuck, $298 / or Banana Republic Captains Blazer, $250 plus 40% off up to size 20.

3. High-Quality Jeans

The relationship we have with jeans changes over time. By now, we’ve probably kissed goodbye to low-rise cuts (thank goodness!). A good pair of mid- or high-rise jeans in a dark wash or classic blue can take you from errands to dinner.

Find a pair with stretch and structure, so they move with you but still hold everything in place.

I still very much love an affordable pair and wear them happily. The Gap Factory Mid Rise Baby Bootcut Jeans are a 10/10 for only $35, and I recently bought THREE pairs of the Old Navy WOW High Waisted Straight Leg Jean in light, medium and dark wash for $20.

But sometimes a great fitting, high quality jean that hugs in all the right places can take your outfit to the next level. And for me, I’m a super fan of Mother Denim.

Megan’s Pick: Mother Denim The Mid Rise Hiker Hover, $258

4. A Classic Trench Coat

You can never go wrong with a trench coat. It’s lightweight enough to be worn in transitional seasons, and it has a way of making you look effortlessly chic, even if you’re just running to the grocery store. Whether in beige, black, or navy, it’s a timeless piece that every wardrobe benefits from.

I would spend a little here, but I don’t think you need to go to Burberry prices. For longevity and versatility I would opt for a tailored cut with a mid length – avoid anything long and oversized.

Megan’s Pick: Greta Belted Water Resistant Twill Trench Coat by Barbour, $375

5. A Go-To Little Black Dress (LBD)

The little black dress has been a style savior for decades, and for good reason.

It’s simple, flattering, and can be dressed up or down with the right accessories. If you haven’t found your perfect LBD yet, take the time to invest in one that makes you feel amazing.

Often we think that the LBD needs to lean formal but I like to have one that, sure, I can wear with heels, but I want to be able to pair with a flat, or sneaker, take to dinner, or wear traveling.

Megan’s Pick: Catalyst Dress by J.McLaughlin, $238

6. Comfortable Flats

As much as I love a good heel, the reality is that I often reach for my flats. A pair of stylish, comfortable flats are a must for those days when we’re constantly on the move. Opt for a neutral color like black, nude, or even leopard print if you want to add a little edge.

And THIS MORNING I found the deal of the season so far …

Megan’s Pick: Stuart Weitzman Gabby Ballet Flat, ON SALE $158

7. A Soft Cashmere Sweater

Cashmere is one of those fabrics that feels as luxurious as it sounds. A soft cashmere sweater in a neutral tone like grey, camel, or navy is not just a cozy companion but a versatile one. Wear it with your jeans, layer it over a dress, or pair it with your tailored trousers for a more sophisticated look.

Megan’s Pick: NAADAM The Original Cashmere Sweater, $98

8. Tailored Trousers

When it comes to trousers, a tailored pair in black or navy is a wardrobe essential. They’re ideal for work, dinners, or anytime you want to look polished without going overboard. The fit is key—make sure they sit perfectly at the waist and hips, with a flattering drape down the leg.

This is also the perfect time to assess your lifestyle and how often you’ll wear certain pieces. For example, I wear jeans almost every day, so I’m happy to invest in a great pair, knowing I’ll get plenty of use out of them. But for me, trousers are more of a “nice to have” item, so this pair from BRF—under $60 with an excellent fit—is just what I need without overcommitting.

Megan’s Pick: Banana Republic Factory Sculptured Straight Pant, $58

9. An Everyday Leather Bag

There’s something to be said about a great leather bag—one that’s both functional and stylish. I like to invest in bags that will last for years and have the right amount of room for everything I need, from my laptop to my makeup essentials. A structured tote or crossbody in a classic color like black, tan, or cognac will never go out of style.

Coach is killing it lately, and while $400+ for a bag is an investment, the quality is outstanding.

Megan’s Pick: Coach Carry Bag, $395

10. A Great White Tee

A white tee might seem basic, but it’s a workhorse in any wardrobe. Whether layered under a blazer or worn with jeans for a classic look, it always feels effortlessly stylish. Invest in one that holds its shape and isn’t too sheer. Trust me, you’ll reach for it more often than you think.

Megan’s Pick: Clean Cut T Shirt by COS, $35 / I also like their Shrunken Tee, $45

11. A Pair of Heels You Can Actually Walk In

Notice I didn’t just say “heels”—I said ones you can walk in. As much as I loved them, my days of teetering on sky-high stilettos are behind me. Opt for a lower block heel or a kitten heel that gives you that extra boost of confidence without the blisters.

Megan’s Pick: INEZ Lola in Nappa Leather, $268/ I’m going to do a full review of these in an upcoming post.

12. A Simple Belt

Finally, never underestimate the power of a great belt.

Whether you use it to cinch a dress at the waist or add definition to a relaxed look with jeans, a stylish belt can completely transform an outfit. Invest in a high-quality leather belt in a neutral color with hardware that works back to your go-to jewelry.

Megan’s Pick: The Favorite Belt by Favorite Daughter, $88