22 Tricks How to Transition Your Summer Pieces into Fall

We are all attached to our summer clothes. Since our childhood, we have associated summer with leisure, pleasure, freedom, fun, no duties, no homework, just living into the day. Because summer clothes ask for light fabric, they didn’t rib a big hole into our allowance and back-to-school shopping list budget like buying the coat wardrobe. If you like to hang on to your summer pieces a bit longer you are lucky. This post offers a list of easy-to-follow summer-to-fall outfit ideas. Read stylist tricks on how to transition summer pieces.

Disclosure: This post has affiliate links.

Incorporate the New Fall Trends

Check what’s trending this fall like the denim/jeans revival, leather bikers. Then riot your closet for such pieces from the cold season, and combine them to increase insulation or acknowledge the vibe of the transition season.

Easy Summer-to-Fall Transitional Tricks to Try (Downloadable List)

Download the summer-to-fall transition tricks complied in the following sections, and hang it into your closet for some cute fall outfit ideas right at your finger tips.

Best Tips to Transition Summer Separates to Fall

1. On warm autumn days, transition a summer outfit with shoes, bag, and accessories in fall colors.
2. When you live in the mid-latitudes, try adding a leather skirt, top, jacket or vest because these pieces are associated with the cold season. Furthermore, their material is great to keep the chilly fall winds off. More on styling leather in midlife.
3. Add a plaid shirt in a casual outfit.
4. Wear a floral summer top with a tweed skirt. More on looking great in tweed.
5. Try a plaid skirt with a T-shirt. More on creating great fall looks with a plaid skirt.
6. Swap your short sleeve shirts with long sleeve shirts.
7. Wear a maxi skirt.
8. What is underneath the clothes matters. Wear a slip, underskirt, pantyhose, tights, halftee to increase insulation.
9. Add an athleisure, denim, utility or baseball jacket as a layer for thermal comfort. More on styling utility jackets.
10. Use layering to create stylish looks and increase insulation for the best cold wet weather outfits.

Create a Transitional Look with Athleisure Jacket

Try a Mini-Dress or Tunic as Top to Increase Warmth around Your Bum

Wear a Tunic with Vest or Jacket

Layer with a Halftee or Light Trench Coat

Pair Your Summer Look with a Cardigan

How to Wear Your Summer Dress in Fall

1. Wear a summer dress with cardigan. You can wrap the ends over each other or vary the look with a belt (wide belt for long torso, thin belt for short torso). More on accessorizing with belts.
2. Try wearing a denim jacket, black tights, open toe booties or fall sandals with a floral summer dress.
3. Dark cardigan worn open over floral summer dress with matching tights, fall sandals.
4. Summer dress with denim shirt and blazer.
5. Blouse over your dress.
6. Wear a sweater over a summer dress, add a jacket and tights.
7. Wear a summer mini-dress as tunic with leggings or skinnies and pumps. More dress-over-pants outfit ideas.
8. Knot a shirt over a summer dress for some extra insulation on the first cool days of fall
9. Wear a vest or a long grandpa-style cardigan over your summer dress with tights and fall sandals.
10. Summer dress with a leather jacket, tights, tan or black wood sandals. More on how to transition a summer dress for fall.

Wear Your Summer Dress with Tights, Cardigan, and Fall Sandals

Add Insulation with a Blouse

Use Dark or Fall Colors to Acknowledge the Season

Shoes, bags and accessories in dark colors like black, brown, burgundy, olive, navy as well as the typical autumn colors like orange, amber, yellow, red, tan add the transitional vibe. Recall olive is the new black. This seasons trending neutral: Khaki.

Combinations to try:

• Pink or red with camouflage
• Black and white
• Brown and black

Change the Vibe of a Summer Outfit to Fall by Swapping the Shoes

Use footwear to style an item for a different season. Sandals with chunky heels and/or wood soles, dress shoes with chunky or sturdy heels, booties and open-toe booties create a fall vibe when worn with tights.

Summary of the Best Tricks How to Transition Your Summer Pieces into Fall

This post featured ideas how to use pieces from summer to create outfits for the transitional season. Its easy-to-recreate examples can elongate the time during which you can wear inexpensive summer pieces. To create summer-to-fall transitional looks shop your closet for

• Maxi skirts (you can even wear cropped leggings underneath)
• 3/4 sleeve t-shirts or shirts
• Jackets that permit layering and cover you up in the cool morning and evening hours
• Closed sandals to keep your feet warm or wood sandals for insulation from the ground. Note that in early fall, the ground already cools down substantially over night.

Don’t miss out on How to Dress for Success in Midlife. Buy the book now.

Further Outfit Inspirations for Summer to Fall transition for Women over 50

Learn how to create a summer-to-fall transitional for your climate region.

You may also enjoy reading how to create a working fall wardrobe.

Are you eager to wear your new fall wardrobe already now.

Photos: G. Kramm

© 2013-2025 Nicole Mölders | All rights reserved