Cooler Weather Wardrobe Basics


If there’s one thing that’s predictably unpredictable here in the Lowcountry, it’s the weather. Cooler temperatures in the morning may fool you into thinking you can pack away all of your summer clothes, but a walk outside in the afternoon will quickly remind you that the only true sign of fall here is the ads for pumpkin spice everything.

So, layers is what it’s all about for the early part of fall here in Charleston. Finding a few basic tanks and tees that fit well and that you love are key (and stocking up on them in multiple colors!) I’m sharing some of my favorite wardrobe items for cooler weather.

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Cooler Weather Wardrobe Basics

  1. Kicking it off with the very basics are these Target tanks that are perfect on their own (in warm weather) as well as for layering under a flannel or cardigan. The tan color is gorgeous (it’s more mauve in real-life) but you can never go wrong starting with black and white.
  2. Another basic I love that can carry me from summer through fall are the Madewell Northside Vintage tees. I love the crewneck and find that they’re fitted without being tight. Again, starting with the basic colors is great, but they also have some beautiful fall colors like the distant surplus green one. Tip:-I sized down in these shirts and like the fit of them better.
  3. Now that you’ve got your basic underlayers, let’s move on to some other tops. A chambray shirt is classic and can be worn all year long. I have a lightweight Target one from years ago but this one looks to be a similar color and fit. to wear with leggings or black jeans. To dress it up a bit, knot it at the bottom and wear it with a fun skirt!
  4. Shackets have been all the rage the past few years, and this sweater/jacket from Amazon is a great starting point if you’ve been unsure of how to wear this trend. I love that I can wear it as my top for the day or even as a light jacket. On my petite frame, it’s just the right length so I don’t feel like I’m swimming in it. Tip: I got the color apricot, but it reads more mauve in real-life.
  5. I love the oversized fit of this sweater. It’s just long enough for leggings on me, but would also be cute with jeans. I love the half-zip shawl collar, especially for chilly mornings! I have it in the coffee color, but there are a bunch of different colors to choose from!
  6. I have a love affair with sweatshirts. The right sweatshirt is cozy, comfy, and let’s not forget, this. This one from H&M in the light beige color (hello neutrals!) is one of my favorites. It’s the perfect length for leggings and the metal at the end of the hood ties elevates it just a bit. Plus, you can’t beat the price. One other place I love for sweatshirts, and fellow geriatric millenials might be surprised to see this one in here, is Abercrombie. I have to admit, they have some good sweatshirts, especially their half-zips. Tip: Try to grab Abercrombie stuff on sale as I find their regular prices a little high for basics. Also, watch out for their cropped sweatshirts if you’re taller than 5’1.
  7. Being from Chicago, I’m a sweater girl through and through. If you’re a Marshalls fan like me, you can sometimes hit the sweater jackpot there. But it’s always good to have a few go-to’s for any type of occasion. I recently got this one from Madewell and love that the ruffles add just a little bit of something extra. It can easily be dressed up (hello family pictures) or down. Tip: Sign up to be a Madewell insider and they’ll send you $25 to use the month of your birthday. They also have sales all year long so I definitely would wait for your favorites to go on sale. I also have and like this sweater from Amazon.
  8. Aside from regular blue jeans, I love a washed (read, slightly faded) black jean. I have been dipping my toes into the non-skinny jean trend and took a gamble on this high-rise kick-fit pair from Gap and I’m not lying when I said my mind was blown. I absolutely love these jeans, they have some stretch but hold their shape, and the kick flare looks great with all shoes but will be especially great with ankle booties. They’ve got a little bit of a raw hem and can definitely be dressed up or down. And they come in regular, petite, or tall lengths, so plenty of options!
  9. As a work-from-home mom, next to leggings or joggers, jeans are my most worn bottom for cooler weather. I know I’ve talked about the Madewell Perfect Vintage jeans in the spring edition of my wardrobe basics, but as a shortie, I’ve finally accepted that paying the higher price tag, for me, is worth it to get the right length. I have these in a lighter wash for early fall and spring, and also a more medium wash for year-round. Tip: Again, keep an eye out for Madewell sales, they have them all year long!
  10. I’m not a total monster, of course, I’m going to give you non-jeans options for pants. I had heard great things about Zella joggers and finally bit the bullet during the Nordstrom half-yearly sale. I have to admit, I can see the hype. They’re lightweight, are a good length, and don’t get all saggy in the back (iykyk). Nordstrom Rack also has a great selection of Zella activewear!
  11. Time to round out your cooler wardrobe with some shoe options. You already know about my love for these Sam Edelman sneakers which I wear all year long. It took me a long time to get on the mule trend, but once I did, I’m not getting off anytime soon. A neutral-colored mule is a great transition shoe in between sandal and boot weather, especially here in Charleston. This pair from Amazon looks great and will go with everything!
  12. Gone are my days of high-heel wearing, so a great pair of (low) block-heel ankle booties are my go-to’s when I want to dress up an outfit slightly (you’d be surprised at how much a slightly pointed toe elongates the leg!) I snagged some Vince Camuto ones from Marshalls a few years ago that I still wear, but these booties from Amazon look similar.
  13. Warm, heavy boots aren’t really necessary here in Charleston, so these Caslon Chelsea boots from Nordstrom (another thing I snagged from the Nordstrom half-yearly sale!) are perfect. They are so comfortable, water-resistant, and the pebbled leather just gets better as I wear them. And best of all, they don’t make my feet look huge! Tip: I’ve heard that Target has a similar pair this season!

Honorable mentions:

  • Everyone has a pair of leggings that is their absolute favorite, and I’ve loved my Amazon Colorfulkoala ones for years. I also have their joggers and love them as well.
  • On those especially warm fall afternoons, you’ll find me quickly changing from jeans to these H&M sweat shorts. Flattering isn’t a word I would normally use to describe lounge shorts, but I absolutely love these. The inside is a terry material so not super warm, and the cut doesn’t give you that “I look like I’m wearing a diaper”  from behind look. Just trust me, at $12.99, get these in every color.
  • Elastic waistband jeans. Need I say more? The Wit & Wisdom brand is new to me, but I’m already in love with how comfortable (and cute!) these jeans are.
  • Because I’m such a neutrals person, I keep my jewelry pretty much the same year-round. You can check out some of my favorites here.

Whew! Hope this was helpful for you and feel free to reach out if you have any questions about styling any of these items!

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Jody Vitali
Jody and her family made the change from big city life in Chicago to the suburbs of Charleston and couldn't be happier! With an undergraduate degree from Elon University, and a Masters in Counseling from DePaul University, Jody's career path took a different turn when given the opportunity to take over ownership of Charleston Moms. This new adventure has left Jody with so much excitement for continuing the great work that CM has already started, and also very little free time as any business owner knows! In between balancing the responsibilities of being a WAHM, Jody enjoys spending time/keeping up with her two young daughters, date nights with her husband Rob, practicing yoga, exploring Charleston, and indulging in some retail therapy.