What to wear in 40 degree weather + cute outfit ideas | TeriLyn Adams (2024)

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It’s officially cool here in Winston-Salem NC! Well, sort of. It’s cool in the mornings, but by the late afternoon, it’s warm again. These are the days where I have the hardest time picking out an outfit (and that doesn’t take into account the fact that I’m 7 months pregnant, so picking out an outfit is already a challenge!).

So that’s what I’m talking about today in this post: the awkwardly cold days that aren’t quite cold enough to elicit a full blown winter ensemble, but still won’t allow for shorts because it’s officially fall. You know when it’s freezing in the morning but then by the afternoon you’re sweating in your sweater? Yes, those are the days I’m talking about.

So, let’s say the temperature when you’re getting ready for the day is 47 degrees and in today’s post, I’ll share tips to help you get dressed. I’m also going to share a roundup of practical outfits that I’m actually wearing these days that keep you warm when it’s cold and that are easy enough to take off when the temperature rises.

What To Wear in 40 Degree Weather

First, let’s talk about some basic wardrobe needs for fall fall/early winter.

Denim

Denim is a no brainer for confusing weather. It can be worn year round, and (if you have the right pair!) it’s comfortable and flattering. I find that I wear jeans almost any time I’m not in workout clothes, at least in the cooler months. For weather that’s unpredictable, you can feel confident that a pair of jeans will be the right choice almost 100% of the time.

I have lots of jeans in my closet (you can see a peek at all my jeans in my closet cleanout post), but the most versatile pair I own is by MOTHER. They’re stretchy and comfortable, a versatile wash (not too casual and not too dressy) and they’re cropped at the ankle, making them easy to pair with all sorts of shoes. If you want jeans at a lower price point, check out my favorite Madewell jeans and Abercrombie jeans.

For 40 degree weather, I usually opt for Vejas sneakers or laid back loafers with jeans.

Leggings or Joggers

On the off chance that I’m not wearing jeans (which, if we’re honest, is most days now that I’m in my third trimester), I’m wearing a dress, leggings or joggers. While I was turned-off of athleisure outfits for many years, I’m appreciating them much more these days. Comfort is king, especially while chasing a toddler around the house.

I’ve learned that if I still do my makeup and style my hair, I can feel pulled-together, and even polished, in workout clothes, despite how comfy they are. I’ve also starting buying athleisure that’s a little more “fun” than just a basic pair of black running leggings. In 40 to 60-degree weather, leggings are always a warm enough, but still breathable option. Amazon has some great athleisure finds lately.

Side note if you’re a runner: Leggings and a short sleeve top or tank is also my preferred 40 degree weather running outfit since it helps keep the moisture away from your body while still keeping you somewhat warm.

Layers

Layers are KEY for awkward weather. This usually means a lightweight sweatshirt for me – I love this cream sweatshirt from Nordstrom because it’s oversized (great for a bump) and cozy but not sloppy. I like knowing that I have an extra layer to throw on if I feel cold, but my outfit is complete without it if I don’t wear it. There’s nothing worse than warming up and having to keep a sweatshirt on because you didn’t wear anything underneath! I’m sweating just thinking about that scenario.

For days that start out cold and warm up throughout the day, I like to dress for the warmer weather that I’m expecting at the end of the day, and layer on top of that warm weather outfit. Then I’m prepared for either.

Lightweight jackets

Lightweight jackets definitely fall under the “layers” category above, but I felt like they deserved their own spot. In the late fall/early winter, I generally don’t like to pull out my heavier down puffer coats or insulating jackets just yet, and I appreciate having a lighter weight option.

I recently ordered this quilted puffer coat from Amazon in the green color. It’s lightweight but (hopefully) warm enough to wear with the AC running, and the color is fun and happy, which is so appreciated in a sea of muted fall tones. I got a size medium in hopes that it will fit my bump. I’ll report back! I also own a quilted jacket from Amazon (mine is unavailable now, but this is similar) that I wore non-stop last fall.

Sneakers

Shoes are slightly less complicated in weather like this since sandals and flip flops are out of the question, and you just need something that keeps your foot comfortable all day. I opt for a cute pair of sneakers 85% of the time. I wear them year round, and they’re great with jeans, leggings, shorts, and even dresses.

40 Degree Weather Outfits

Now that we’ve broken down the basics, let’s get into some outfit inspo. I’ll share a handful of outfits I’ve worn recently, and a few that are in my head to wear soon. I hope these help inspire you to make outfits out of things in your own closet.

Here’s what to wear in 40-degree weather that warms up to 50 degrees or even 60 by the end of the day. Keep in mind that I’m 7 months pregnant, so you’ll have to use your imagination when planning outfits sans-bump.

Jeans and a sleeveless sweater

The simplest way to dress for confusing cool weather is with a great pair of jeans and sleeveless sweater. This outfit says, “I know it’s fall and I’m participating, but I will not sweat.” The jeans I’m wearing are Abercrombie maternity jeans, but the same style comes in a regular fit as well. I have the non-maternity version in the Curve Love fit (which has a tiny bit more room in the hips and glutes). Both the maternity and non-maternity options are SO good. (I have an entire blog post dedicated to Abercrombie jeans since I love them so much.)

My sleeveless sweater is an older Nordstrom find, but I linked a few similar options in this LTK post.

A shirt dress and tall boots

Another favorite outfit combo of mine in the awkward fall/winter weather is a shirt dress with tall boots. I love this combo for a few reasons, the main being that you can easily roll the sleeves on a shirt dress when it warms up. I’ve been loving this olive green mini shirtdress from Madewell for the last few weeks because the color is very appropriate for fall and winter, and the material is on the thicker end, but it’s still relaxed and loose enough that I’m comfortable as it warms up.

Tall leather boots are also perfect for fall weather because they’re on trend and add another aspect of coverage for the cooler part of the morning. My boots are by Madewell as well and are comfortable right out of the box. (I always go up 1/2 size in boots.)

If the temps stay cool and you need another layer, try styling a blazer on top of the dress. And while you’re shopping from Madewell, add this chocolatey brown tote to your cart and thank me later. BEST. BAG. EVER. It fits a laptop.

Leggings and a tshirt

Like I mentioned above, if I’m not wearing jeans, I like to wear leggings. And of course, a sweatshirt (actually the same sweatshirt I mentioned above in a different color because I love it so much), so that I have a layer. The leggings I’m wearing are a GREAT Amazon find. They’re about 90% as good as Lululemon and crazy affordable. I bought an XS pre-pregnancy and they’re still working at 28 weeks pregnant but I’ll size up to a Small if I buy another pair.

And a quick note about the New Balance sneakers: if you can find them in stock, snag them as fast as you can. They’re the most comfortable sneaker in my closet right now. I got a half size up from my normal shoe size.

A knit dress

While this knit dress from Madewell is short sleeve, the material and pattern is perfect for fall. It’s comfortable and stretchy (great for a growing bump), but feels very pulled together and cute. I styled it with clogs, which are my go-to heeled shoe in the fall. And everything I’m wearing is from, you guessed it, Madewell. If it’s truly too cold to leave the house in short sleeves in the morning, throw a solid colored blazer on top. I have an XS in the dress and blazer.

Bottom Line

I hope these outfit ideas help inspire you when you’re getting dressed in this weird in-between weather! You can see what I’m wearing everyday on the LTK app (follow @terilynadams), and shop and save my outfits. I always share sizing details as well. You can also bookmark this page if you prefer to shop without an app!

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