Creating Outfits Is Easy With Your Wardrobe Essentials: Cold Weather Edition

We stand in our our closets and have nothing to wear–sound familiar? Are you stuck in the vicious cycle of buying and returning, or worse, buying and never wearing something? In 2024, we’re taking control of our wardrobes (and spending) with these wardrobe essentials. Wardrobe essentials are the building blocks of every outfit–once you have these in place it’s easy to get dressed. Adding a few trends each season (more of about trends coming SOON!) is like the icing on the cake. Today we’re sharing the timeless classics that make building a stylish outfit effortless.

Basics Don’t Need to be Boring!

It all starts with having the right wardrobe essentials in our closets, the building blocks for every outfit. Use them as a foundation, and then each season you add carefully chosen, on-trend pieces that match your style and budget. Think of this as a mini capsule wardrobe.

As women over 40, many of us have amassed a collection of timeless basics that form the backbone of our wardrobes. However, do you have the right ones? Let’s start today with wardrobe essentials that have stood the test of time. If you need to update your basics, never fear, we’re sharing our favorites to help you get started.

This is a savvy approach for those of us in a stage of life where financial prudence takes center stage, especially as we envision what retirement is going to look like. It’s buying smarter, buying less, and loving what we have. Embrace the art of blending the old and the new to create outfits that reflect YOUR timeless style.

Your assignment: Head into your closet and find your wardrobe essentials! Do they fit well? Are you in love with them? Are they in good repair (nothing needs a hem or button)? If you answered no to any of that, then keep reading for our recommendations. To help, we’ve created this checklist for you (we love a list!).

We’re here to help make getting dressed easier! Each month, we’ll be sharing blog posts to help you add a few on-trend pieces to update your essentials for the new season. Focusing on wardrobe basics with a few trendy items added in is helping us get dressed every day AND we’re making smarter shopping decisions.


Favorite Denim

MEGAN: Denim is my #1 wardrobe essential and the foundation of 90% of every outfit I wear. For my petite height (5’1) and curvy body J.Crew’s Curvy Vintage Straight and Lil Mother Mid Rise Dazzler are my best fit. I’m currently staying away from distressed and skinny jeans (unless I’m wearing tall boots!).

CHRISTA: These are the two pair of denim I reach for again and again and again (Kut from the Kloth and Wit & Wisdom). With a darker wash or a flare leg, you can wear them almost anywhere. A pair of flare or boot cut gives you a dressier option.


Black Bottoms

MEGAN: Two pairs of black pants see me through every scenario, year round. My trusty Liverpool Kelsey knit trousers are like sweatpants that look like dress pants. Talbots makes a really traditional flat front wide leg trouser that is easily dressed up. Both slacks are appropriate in any season, in the office or at a cocktail party.

CHRISTA: The black Wit & Wisdom pants were my holiday hero this year! Wearing them on repeat was probably the lightbulb moment when I realized that with good basic pieces, the rest of my outfit falls into place easily and getting dressed isn’t a struggle. The black corduroy pants (on sale) are another great option, especially if your lifestyle is more casual. They look and feel like velvet, but wear like your favorite pair of jeans.


Versatile Blouses/Tops

MEGAN: Little known fact–I’m addicted to button down shirts. Without a doubt a white button down shirt is a closet essential. She can be worn as a blouse (remember Sharon Stone in that GAP shirt at the Oscars? Iconic), a cardigan, a layer under a sweater, a beach cover up, a robe, a sexy nightgown… the list is endless. Add to that a denim chambray button up (or western style!), and you have endless combinations of outfits. Also essential as a layering piece is a silk or satin cami, can be worn alone or under any of your sweaters.

CHRISTA: I love a good, solid blouse as a staple piece. This short sleeve blouse from Ann Taylor comes in lots of colors and patterns, both long and short sleeve. The red one was a favorite during the holidays, but in black or white it’s a great staple and layering piece. The other top from Old Navy was also a go-to piece this fall, available in several solid colors and some patterns, too. Grab this top now – huge sale and it’s in most sizes in both black and cream. With a few blouses you love in your closet, you can mix and match with your bottoms for virtually endless looks.


Classic Sweaters

MEGAN: Timeless wardrobe essentials, this is my answer 20 years ago, now and 2044. A black cashmere turtleneck sweater and a gray cashmere crew neck sweater.

CHRISTA: These two sweaters are staples for me because they can go with everything. The solid black sweater (available in lots of colors) has dressier balloon sleeves and a very subtle v-neck, and when paired with the black pants/black slingbacks it creates a very chic column of color. The stripe sweater is another great basic, the stripes giving it a little more interest; this one is a great option with dark denim and dresses up or down nicely. It’s also thin enough to be a great layering piece. And having a cardigan in a classic color gives you extra options for layering different looks.


Go-With-Anything Neutral Shoes and Boots

MEGAN: Two colors, beige and black and you can pretty much make anything in your wardrobe work. If I were to add a third shoe to this line up it would be a neutral “fashion” sneaker. Pro tip: we are too old to mess with uncomfortable shoes. Forget the mole skins, blister tape and stretchers. Go to the department store and try on as many pairs as it takes to find the pair that works for you.

CHRISTA: With a nice pair of slingbacks and a pair of neutral booties (under $40), I can go anywhere! The booties are probably the shoe I wear most in the colder weather and the lower height hitting at my ankle makes them work with most length pants.


Blazers, Jackets and Coats

MEGAN: I’ve had this Liverpool blazer with a hoodie zip in for four years. She dresses up leggings and makes a suit with my Liverpool Kelsey pants (see above). It’s the only blazer I own and although I don’t wear it every week, I’m always glad it’s there when I need it. My go to winter coats are a long line black quilted Zella jacket (casual) and a wool wrap dress coat.

CHRISTA: I have two winter coats that are on repeat for me all season – a black puffer jacket (under $100) for everyday and a classic wool camel coat for something a little dressier. You can’t go wrong with these two basics, and they’ll definitely get the most wear.


Dress/Skirt

MEGAN: If you have an hourglass body, a wrap dress accentuates and if you don’t have curves, they give the illusion of curves. Kinda perfect AND thanks to Diane von Furstenberg they NEVER go out of style. My second wardrobe essential is the dress category is the beloved slip skirt. I struggled to add this because I’m on the fence as to whether this is a trendy item or not. Final decision is in, I’m adding it as a wardrobe basic because it is so versatile and I think they will be around for a long time.

CHRISTA: If you don’t have a black dress you love, I think that is one essential you NEED to own. A black dress isn’t just for funerals! You’ll find yourself grabbing that black dress for date night, cocktail parties, work functions, you name it. And your black dress will be your best friend–it’s elegant, slimming and forgiving, so you’ll feel and look great. The first dress below, by Kensie, is MY FAVORITE dress. I have it in two colors plus a velvet for the holidays because I love it that much! The little slit isn’t too high, but just high enough to feel extra feminine. And if you’re bigger on top, this blouson style is perfect to accommodate the girls.


Bonus: Finishing Touches

MEGAN: Ahhh, the third piece, my favorite. You’ll rarely catch me without gold hoops dangling from my ears. Sunglasses are the magical item that take me from exhausted car pool mom to glamorous ingenue. The one piece that ties all of the others together is a silk scarf. . A silk scarf is the Grace Kelly piece you didn’t know you were missing. A classic black leather bag can be used in any season, dressed up or down. Always splurge for real leather.

CHRISTA: These are my four favorite accessories that I wear most days. When I travel, I don’t really bring any other jewelry with me because these work with everything. And, of course, a black crossbody works with all my outfits. I love the size of this one, big enough to use everyday.


Megan’s Essentials Look: denim // sweater // white button down

Christa’s Essentials Look: sweater (similar) // black pants // slingbacks


Shop the Post for Your Wardrobe Essentials

Shop Megan’s Wardrobe Essentials

Shop Christa’s Wardrobe Essentials

Not sure where to shop for your non-athleisure wardrobe essentials? Our favorite go-to retailers for timeless, quality pieces includes: Nordstrom, J.Crew and Ann Taylor.


For more style inspiration, you can find many of our essentials styled in 3 Ways to Style Our Favorite Fall Finds.


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