Last updated on December 27th, 2021 at 10:16 pm

Updated 9/22/21

Summer to fall outfits: it’s transition time. For me, this can be one of the most difficult times of the year to get dressed, especially if you’re going to be gone all day. The days are warm and the nights are cool, so you’re always carrying a sweater or a jacket. And, if you don’t want summer to end (who does?) then you’re also probably trying to wear that favorite summer outfit just one more time.

But fall is coming. It’s actually my favorite time of year, but even I don’t want to rush it. Before we get into oversized sweaters, boots and coats, there’s still time to add a few new pieces that work in warmer weather. These will also give you a head start on upcoming fall trends.

We updated this post to include some of the upcoming trends from the Spring/Summer 2022 fashion shows – so you can get an early start on what’s new and exciting. To read the recap of the shows and see what trends are coming your way, click on the link below.

**Please Note: This post contains affiliate links and we will be compensated if you make a purchase after clicking on our links.

The List: Summer to Fall Outfits

Sweater Vests

If you’ve started looking into fall trends, you will see sweater vests at the top of the list. And they are the perfect piece for summer to fall outfits. Wear them now, by themselves, and when it gets cooler, add a layer underneath. Many that I’ve seen are cable knit, but they there is also an “academia” trend for fall. So you’ll also see some very preppy looks as well.

Trench Coats

Trench coats were all over the New York Fashion Week runways and it looks like they will be huge for Spring. So, why not get a head start on this trend, that is also a classic. It’s a piece to pick up now that will last for years. And you’ll be ahead of the trend come spring.

Sticking with a neutral trench coat is always a good idea, especially if you want to invest in one that’s a little more expensive. Here is another option, an A-line coat that is on a great sale as of this writing at Saks Off Fifth.

Color Trend: Lavender

Lavender/Lilac is also on the list as the “it” color for fall. It’s also a perfect transition color. You can wear it right now in a summer dress and soon you can wear it as a sweater. (I already picked up a great lavender sweater in the Nordstrom sale). I picked this denim jacket as my transitional piece. I’ve actually owned one for a couple of years and it was hard to find back then. But with lavender becoming so popular, they are much easier to find.

Gingham

If you read our recap on the Spring/Summer 2022 fashion trends, then you know that gingham is right at the top of the list. Again, if you want to be an early-adopter, these gingham sweats will be perfect right now and again in early spring.

Animal Print Part 1: Zebra

Animal print goes in and out of popularity, but it seems to coming back with a vengeance this fall. While leopard (see next item) is a fall staple, zebra is making its comeback this season. The reason I love it as a transitional item is because it’s black and white – one of my favorite summer color combinations. So, for your summer to fall outfits, it’s a perfect addition. I also love to accent black and white with red. Add a red handbag, and you’ve got the perfect transitional look.

Animal Print Part 2: Leopard

From what I am reading, leopard coats are going to be huge this fall. But wearing a coat in August is probably not something you’d want to do. So I found this leopard wrap that will be perfect for cool summer nights and chilly fall days. (But now would be the time to start shopping for leopard coats if you want to jump on that trend.)

And don’t forget this Leopard cardigan that we recently shared in our latest “How to Wear It At Any Age” series. You can read it HERE.

Color Trend: Pistachio

Another great summer to fall outfits transitional color. I love this dress from a company I just found, Fehrnvi (based in Idaho). It’s great how they already have it paired with booties for fall, but you could easily wear this right before the weather turns colder with sandals

I have a couple of items on order from them, so I will share on social media soon what I think of them after they arrive. You can get 15% off the entire site with the code HARPERGIRLS15, so check them out.

Don’t forget to use HARPERGIRLS15 at checkout for 15% off your total purchase at Fehrnvi.

I shared this t-shirt dress from Old Navy on social media – if you want to check it out – there’s a link below.

Handbag Trend: Puffy & Quilted

The latest trend for handbags are similar to a puffer coat! This is an easy way to add a trend to your existing wardrobe. When adding a new handbag to my collection, I tend to go with a classic color. In this case, I selected black for this new look. I have two options; the first from Mango is affordable, but a little more expensive. The bag from H & M is very affordable is you don’t want to spend a lot of money on something trendy.

Bold Color Trend

Bright, bold colors will also be trending this fall. I’ve even read that the “Miami Vice” colors will be back in style. I chose this one shoulder top for two reasons: 1) its bold color and 2) it easily transitions from summer to fall. It’s also available in navy and green, but I love this pink color.

The Classics Part 1: T-Shirt Dress

No summer to fall outfits list would be complete without the t-shirt dress. Wear it now with sneakers or sandals and then add a sweater or jacket and boots when it gets cooler. You can’t go wrong! I chose red because it’s a good all-year color and I like its boldness. It also would look great with a denim jacket.

The Classics Part 2: Cargo Pants

Yes, I wrote “cargo pants”. They are back for fall. What I love about this pair that I selected are the color options. The olive green is really a neutral that you can wear all year long. But I really loved this pumpkin color as we transition into fall. I don’t think you can go wrong with either color.

The Classics Part 3: The Sweatshirt

I will close out this post with the true summer to fall classic: the sweatshirt. At this time of year, I really like to wear sweatshirts in summer colors. It makes me feel that summer is not gone yet while still keeping me warm. This sweatshirt is from Draper James, which is Reese Witherspoon’s company. You can see her southern roots in the collections. All of the items are very feminine, like this pink magnolia sweatshirt. I do own this sweatshirt and I did size up as they recommended for a looser fit.

See below how I am styling it for both late summer and early fall.

What are your favorite transitional looks? Please let me know in the comments below!

Looking for more outfit ideas? Check out our recent posts on “back to work outfits:

Jen’s Post: The Best Business Casual Outfit Ideas for Back to Work

Dianne’s Post: Fashion Goes Back to Work: The New Office Essentials