How To Transition Your Clothes From Summer To Fall

I get a lot of questions from clients about how to transition your clothes from summer to fall. And it’s a very good question. You’re not going to wear a summer dress one day and a turtleneck the next, right? So, here are some tips for extending your summer wardrobe while still looking chic and weather-appropriate.

Dresses transition well from one season to another. The color and pattern are important to determine whether a dress can make it or not. If it’s very light or white, it won’t work well going into fall. However if the colors and/or pattern are strong, there’s a good chance for success.

In the set below, I picked two fun summer dresses that will look great in the fall. When the weather is starting to cool down, you can wear both of them with a jean shirt tied at the waist. As it gets cooler, wear them with a cardigan, jean jacket or blazer. Use a belt for longer cardigans to give them (and you!) a shape. Otherwise, they will look frumpy. In the colder stages of fall, pair the dresses with a leather jacket. I love the juxtaposition between these feminine dresses and the biker jacket.

Jewelry is another way to make the move into fall. Add chunky jewelry to anchor the looks and make them more substantial.

Finally, swap out the sandals and flip flops for ballet flats in a fall shade and then change to tights and booties or boots as fall wears on. Both of these dresses will look great with boots!

There are a ton of biker jackets at so you’ll be sure to find one, if you’re looking. is always a great spot to find shoes or boots.

Transitioning from Summer to Fall


Shorts are another great transitional item. Again, if the pattern or color isn’t too summery, it is easy to carry them into the new season (I always try to buy some shorts that transition well). You can wear a cute hoodie or a cardigan in a fun color layered over a tank top or a T-shirt at the beginning of fall. When it gets cooler, wear the jean jacket or a super-cute military jacket. A leather jacket is perfect for chilly fall days.

Wear navy or dark brown tights (yes, you can wear brown and black together). All the footwear below, the flat and heeled oxfords and the boots up the chic factor of any of these outfits. Oxfords are very on-trend for fall. The colorful jewelry is fun, yet transitions well because of its chunkiness.

If you don’t have any shorts for fall but want to buy some some, check out They have some cute ones. You can find a huge selection of military jackets at and are good websites for reasonably priced denim jackets.

Transitioning from Summer to Fall

Other tips

  • Get your scarves out to wear with T-shirts or long-sleeve shirts when the weather gets cooler (I mean fashion scarves, not winter scarves!).
  • Make sure you have a cute trench. They are invaluable for fall and spring.
  • Tights are very, very versatile. Buy lots in fun colors to wear. If you are gun-shy about buying an item in cobalt blue or bordeaux, the hot colors for fall, buy a pair of tights in those colors. Even they  just a bit peek out from under a knee-length skirt and knee-high boots, you will look stylish.
  • Wear knee socks pushed down to your ankles with booties and cropped jeans.

Transitioning from summer to fall can be fun, and your summer clothes can be worn again and again if you know what to wear them with. Happy fall!

Thanks for reading!

Illysia Neumann-Loreeck

6 thoughts on “How To Transition Your Clothes From Summer To Fall

  1. This post is really helpful. I have a hard time during the fall when its hot one day and cool the next. It gives me ideas on how to transition.

  2. Of course I went right to the $3000 Donna Karan jacket. I can always pick the most expensive thing in the room.

    Great blog.

Leave a Reply

Your email address will not be published. Required fields are marked *