You are currently viewing 22 Tricks How to Transition Your Summer Pieces into Fall
Salvatore Ferragamo pumps, Vince leather joggers, statement necklace, Hermes collier de chien bangle, Donney and Brooke top handle bag

Interested in summer-to-fall outfit ideas? Then continue reading. This post provides a list of easy-to follow stylist tricks how to transition summer pieces into fall in a stylish way.



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Outfit details of first photo: Salvatore Ferragamo pumps, Vince leather joggers, gemstone necklace, Hermes collier de chien bangle, Donney and Brooke bag, hoodie shirt c/o Coolibar.


Why We Hang on to Summer Clothes in the Transition Season

We are  all attached to your summer clothes. Since our childhood, we associate summer with leisure, pleasure, freedom and fun. Summers were the time of no duties, no homework, just living into the day. Because summer clothes ask for light fabric, they are much less expensive than winter clothes. Therefore, shopping for summer clothes didn’t rib a big whole into our allowance. Having to buy a winter coat was the worst. Its cost meant small wiggle room for the other Must-haves and no Lust items for the back-to-school shopping list.

Of course, a new winter coat wasn’t the It of the season, because such a statement coat was out of our budget to begin with! Not to mention an awesome coat wardrobe!



Tip: Look at your warm and cold season clothes and ask yourself how you can combine them to increase insulation or acknowledge the vibe of the transition season.


creating extra insulation with a tunic and skirt for late summer early fall
Long-sleeve tunic dress c/o Coolibar. Left: Nordgreen sunglasses, DIY skirt, Coach bag, sandals c/o Newbella. Right: Very Fine Dance sport Shoes sandals, pendent necklace, skorts c/o Coolibar.



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. Sign up for my email list for more 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

transferring a lace skirt with T-shirt look the warm season for in between season with athleisure jacket
eShakti lace skirt, Rebecca Colins necklace, Studio fall sandals, Hermes collier de chien bangle, athleisure jacket c/o Vshred, watch c/o Nordgreen, and bag c/o R. Riveter. More on styling athleisure,



Try a Mini-Dress over Pants

summer to autumn transitional outfit with mini dress over pants and denim jacket
Oliveo jeans, Levi’s oversized denim jacket, Hermes collier de chien bangle, bag c/o R. Riveter (Use the code HIGHLATITUDESTYLE at checkout to save 10%), hoodie mini-dress c/o Coolibar, and pointy-toe flats c/o Vivaia


Wear a Vest

summer tunic and jeans with fall sandals
Moda International leather vest, amber pendant necklace, Musse and Cloud sandals, watch c/o Nordgreen (Get 15% off with my discount code HLSTYLE), Hermes collier de chien bangle, jeans c/o Ethyl Clothing, tunic c/o Coolibar, and bag c/o R. Riveter.



Don a Leather Motorcycle Jacket with Summer Separates

two summer looks transitioned to fall via a biker leather jacket
Left: Leatherskin motorcycle jacket, T-shirt and jeans c/o Femme Luxe, Nine West pumps, Nordgreen watch (Use code HLSTYLE to save 15%.), SUNGAIT sunglasses, and bag c/o R. Riveter (Use the code HIGHLATITUDESTYLE to save 10%). Right: Kieselstein Cord belt, Hipstik® Legwear pantyhose, Jones New York silk top, DIY skirt, barrette, Hermes collier de chien bangle, Graham and Spencer leather jacket, rough tourmaline earrings, and Sam Edelman bucket bag.


Layer with a Halftee or Light Trench Coat

transitional look with layering of a halftee and trench coat
Burberry trench coat, lace halftee, leather shell, L.K. Bennett wedge patent leather heels, silk scarf, Jaeger leather tote, and striped skirt c/o eShakti.


Pair Your Summer Look with a Cardigan

summer floral skirt with short-sleeve top and cardigan for the 1st chilly days
Jones New York striped cardigan with Brooks Brother sweater, statement necklace, Hermes collier de chien bangle, Loft floral print skirt, Kate Moss for Longchamp satchel, and Liz Claiborne pumps, and glasses c/o


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

over 50 years old woman in summer dress with cardigan for fall
Isaac Mirzahi cardigan, eShakti dress, GNW tights, Nicole fall sandals, and Prada bag, wooden watch c/o Jord.



Add Insulation with a Blouse

season transitional looks created by wearing a blouse over a dress, or capri with blouse
Left: Hermes Constance bag, statement silver belt, BCBGMAX ankle studded pumps, Anne Klein scarf, Burberry London trench coat, statement cuff, cropped pants c/o Ethyl Clothing, and blouse c/o Lily Silk. Right: Lula Roe short-sleeve dress, L.K. Bennett open toe pumps, Hipstik pantyhose, Nordgreen watch, Hermes collier de chien bangle, LilySilk blouse, and bag c/o R. Riveter.


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.

Combinations to try:



style book author in camo top, tulle skirt, striped bag, belt and mules
Orvis utility jacket, suede gemstone buckle belt, Hermes collier de chien bangle, Coach bag, amethyst earrings, Cartier just un clou, Bandolino mules, and tulle skirt c/o Lookbook Store.




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

The type of footwear is a great mean to style an item for a different season. Sandals with chunky heels and/or wood soles, dress shoes with chunky or sturdy heels as well as booties and open-toe booties create a fall vibe when worn with tights.


#fashionover50 mature woman in fall work outfit
Loft sweater, Hermes Collier de Chien belt, Talbot skirt, GNW cardigan, Longchamp bag, Hermes collier de chien bangle and belt, and Calvin Klein block heel pumps



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 MidlifeBuy the book now.



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

Learn how summer-to-fall transitional looks differ with climate region.

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

When you bought already the first cold season clothes read how to wear your great fall wardrobe already now.


Photos: G. Kramm

© 2013-2023 Nicole Mölders | All rights reserved

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This Post Has One Comment

  1. I like to wear a denim or faux suede moto jacket over a T-shirt when it turns cooler. A shacket is another great option. The weather is so unpredictable in the UK so layering is a must!

    Emma xxx