I feel like you’re either a shorts person or you’re not. As for me, I love a good pair of shorts. They’re my go-to for spring and summer. And I can’t wait to pull them out as soon as it warms up. But come fall and winter, these all get stored and I forget about them until the warm weather returns again. Not anymore. After spending some time in Paris, one of the things I saw on the streets from everyday women was shorts with tights for fall. And no, we’re not taking our summer shorts and wearing them for fall. Instead, it’s all about leather shorts and heavier wool shorts.
I loved the combination so much that I had to grab a pair of shorts to wear while I was there. I found these at a little boutique for around $40 and love them so much. You can wear this type of outfit out to dinner with friends or drinks, or make it a bit more casual for the day time depending on how you style it (more on that below). Either way, I love the option of a fall or winter short for those warmer winter days when you don’t know what to wear. Insert fall and winter shorts! Here’s how to wear shorts in cold weather and look fashion-forward.
How To Wear Shorts In Cold Weather
Choose Fall And Winter Appropriate Shorts
Let’s start with the foundation of your outfit. The shorts. As I said, we are not wearing our summer shorts in the fall. Those are tucked away for next year. This includes your lightwash denim shorts, linen shorts and cotton twill ones. Instead, it’s all about the fall and winter fabrics. Think leather, suede, wool, or any sort of woven knit that’s heavier. And the same with colors! Let’s say you have a pair of trouser-style shorts, but they’re pastel, I’d keep them for spring and summer. But if you have a black or brown pair, or something in an earthy fall colorway, let’s try it! There are always exceptions to this rule, but I think you can feel safe and confident in more earthy tones if you’re not 100% sure if a piece of clothing is a go for the season.
PS this entire vibe can also work with a mini skirt too! So if you’re anti-shorts, or don’t want to add more to your closet, you can 100% apply today’s tips to a leather mini skirt, a wool one like this and more.
Shorts With Tights
The whole point of rocking shorts in the winter is to pair them over tights. I love this combination and it’s a fun and more edgy update to a skirt and tight combo. Plus, it helps to stay warm in the colder months. For this pairing, I would go with sheer tights or ones with a slight pattern. Think polka dot tights or a minimal print. Doing an opaque tight just feels a bit 2010 these days (learn more about that here). If the weather is warm enough in the fall, you can also ditch the tights and go without. I recently did this in Paris on a really warm fall night. So long as the whole outfit is fall-appropriate, it works!
For wearing shorts in winter months that are really chilly, you can try the fleece-lined tights option. They even have sheer-style ones like these.
Choosing And Layering Tops
Just as with any outfit we pull together for a season, we want to match the seasonal energy! You can do a cotton tee and denim jacket for early fall. And then for cooler temps, lean into knitwear and blazers. I love a blazer paired with high waist leather shorts, I think it’s the perfect combination of fabric and texture. A long trench coat would be nice too to layer over a cable knitted sweater.
Where you plan to wear this outfit will also determine which tops and layers you choose. This blazer and shoe combination feels a bit more dressy to me. But you can easily dress this down with a more oversized relaxed blazer, or just a sweater, and style it with a flat shoe to make it more day-time and casual appropriate.
A few other outfit ideas if you’re wearing wool or tweed shorts is to pair them with a leather jacket. This is a great third piece to add to your outfit for fall and winter. Y
The Best Shoes To Wear With Shorts In Cold Weather
While in Paris, I saw a lot of sneakers with shorts for fall. I’m going to be honest, I hated the look. I don’t think it works and I think it was more of a comfort thing, than style move. I would maybe do a cool leather sneaker that maybe had some fall colors and textures in it. But a plain white sneaker I’d personally skip. A good shoe choice would be any good ankle bootie (western-inspired, lug sole Chelsea boot and more), chunky loafer a fun mary jane or Dr Marten boot.
I think this is part of the reason why I love this leather short trend much, the shoe choices that work best are the ones I love the most in my closet right now. And depending on where you’re wearing this to, you can really adjust the shoe to match the vibe. For date night, try a mary jane or high heeled bootie. If you want a more casual daytime look, try a flat lug sole loafer or Dr Marten boot. I’ve also worn mine with a flat lug sole knee high boot, but it would also be super cute with a high heeled knee high boot for a sexier take on this.
The Best Shorts For Winter and Fall Cold Weather Layering
Choosing season appropriate shorts for the winter season and fall is key to making this look work. If you’re wanting to try this trend, here are more of the best shorts for winter and fall to style.
