You are currently viewing 16 Tips 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.

    1. Why We Hang on to Our Summer Clothes
    2. List of Tips How to Transition Your Summer Pieces into Fall
    3. Try to Transition a Summer Look to Fall with a Motorcycle Jacket
    4. Summer Hoodie Shirt with Denim Jacket and Leather Joggers
    5. Wear a Jacket as a Top
    6. Change the Vibe of a Summer Outfit to Fall by Swapping the Shoes
    7. More Summer to Autumn Transition Outfit Ideas
    8. Summarizing How to Transition Summer Pieces into Fall
    9. Top of the World Style Linkup No. 321

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Why We Hang on to Our Summer Clothes

It’s normal to be 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. Since summer clothes ask for light fabric, they are much less expensive than winter clothes. Thus, shopping for summer clothes didn’t rib a big whole into our allowance. Having to buy a winter coat was the worst. It didn’t leave much wiggle room for the other Must-haves or any Lust items for the back-to-school shopping list.

And yes, the winter coat wasn’t the It of the season, but more a necessity. The statement coat was out of our budget to begin with! Not to mention an awesome coat wardrobe! Thus, our mother’s forbid us to wear our brand-new cold season clothes too early to not get into winter wardrobe boredom.

post banner of summer to fall transition outfit guide


The ease of summer and summer clothes! No wonder that we want hold on to them as long as possible. When your transition season is as short as it is up here in the Interior of Alaska, you may even get away without any fall clothes at all.

List of Tips on How to Wear Your Summer Pieces in Fall

A list is easy to print out. Therefore, I compiled a list of the tricks shown in the wear-it-now vs. wear-it-later examples. This way, you can hang it into your closet for some cute fall outfit ideas right at your finger tips.

  1. Summer dress with a leather jacket, tights, tan or black wood sandals
  2. 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 best accessorizing with belts in this guide
  3. Try wearing a denim jacket, black tights, open toe booties or fall sandals with a floral summer dress
  4. Dark cardigan worn open over floral summer dress with matching tights, fall sandals
  5. Summer dress with denim shirt and blazer
  6. Wear a sweater over a summer dress, add a jacket and tights when it gets even cooler
  7. Wear a summer mini-dress as tunic with leggings and pumps. See this post for 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 your summer dress with a faux fur vest or a long grandpa style cardigan, tights and fall sandals
  10. Transition the look by using a piece, shoes and accessories in fall colors
  11. Try adding leather items like a leather skirt, top, jacket or vest because they are associated with the cold season
  12. Add a plaid shirt
  13. Wear a floral summer top with a tweed skirt
  14. Go for a dark leather bag instead of a light or straw bag
  15. Wear a slip or underskirt, tights and halftee under a summer dress
  16. Use layering to create stylish looks and increase insulation for the best cold wet weather outfits.


Try to Transition a Summer Look with Motorcycle Jacket

In September even in mid-latitudes, the mornings get already chilly. When the weather forecast calls for temperatures in the lower 60s (15oC) in the morning, but 70s in the afternoon, a summer work outfit is still a Do. Just add a leather motorcycle jacket for the commute. At lunch, leave it in the office. On your way home, wear it as a cape like in the look below.


stylist in summer to fall transitional separates of skirt, shirt, pantyhose jacket

woman wearing a leather jacket as cape

Nicole in transion season outfit with silk skirt, shirt motorcycle jacket
Kieselstein Cord belt, Hipstik® Legwear pantyhose, Jones New York silk top, DIY silk skirt, barrette, Hermes collier de chien bangle, Graham and Spencer leather jacket, rough tourmaline earrings and Sam Edelman studded bucket bag (all own)


Summer Hoodie Shirt with Denim Jacket and Leather Joggers

In midlatitudes, leather is a favorite to keep the wind off. Thus, on a windy day, leather joggers or pants paired with your favorite summer hoodie and a denim jacket make a great look. The denim jacket keeps off the chill.

summer shirt hoodie denim jacket leather jogger transitional look
Salvatore Ferragamo pumps, Vince leather joggers, statement necklace, Hermes collier de chien bangle, Donney and Brooke top handle bag (all own), hoodie shirt c/o Coolibar

Wear a Jacket as a Top

outfit details with color palette


over 50 years old fashion blogger transitioning a summer skirt to fall by wearing a jacket as top

blogger Nicole in tulle skirt, utility camouflage jacket summer to fall transition outfit

mature woman stepping off a rock in skirt, heels, striped bag and camo jacket

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


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

Not only the colors of your clothes, but also the shoes are a great mean to style an item for different seasons. Sandals with chunky heels and/or wood soles work great as fall sandals. Open-toe booties in tan or black also can create a fall vibe when worn with tights. Dress shoes with chunky or sturdy heels also have a fall vibe. Dark pumps in black, brown, or burgundy add a fall vibe. Strappy sandals or slides with bare feet scream summer (and vacation).


More Summer to Autumn Transition Outfit Ideas

In the following some easy-to-recreate transitional outfit inspiration.

midlife fall transitional outfit with blue jeans, black blouse, floral bow, taupe coat, red bag and black heels
Hermes Constance bag, statement silver belt, BCBGMAX ankle studded pumps, Anne Klein scarf, Burberry London trench coat, statement cuff (all own), cropped pants c/o Ethyl Clothing, and blouse c/o Lily Silk


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 (all own), wooden watch c/o Jord


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

Always shop for clothes you can wear in more than one season when on a budget! #budgetfashionists #frugalshopper Click To Tweet


#styleover40 mature woman in faux twinset and floral skirt

#fashionover40 mature woman wearing an autumn work outfit

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


older woman in leather shell

style influencer in trench coat
Outfit details: Burberry trench coat with leather shell, L.K. Bennett wedge patent leather heels, silk scarf, Jaeger leather tote (own) and striped skirt c/o eShakti


Look at your clothes and ask yourself how you can wear them in more than one season. #budgetfashion #agelessstyle Click To Tweet



#accessories outfit details

fall work outfit with mixing stripes and floral pattern

fall work outfit with cardigan and floral skirt
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 (all own), and glasses c/o


Summarizing 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.

Pro tip: Add summer accessories and keep the look on the casual side. Summer is much more casual than all other seasons.


When you liked what you read in this post, you may also enjoy reading how to transition a summer dress for fall or how to create a working fall wardrobe.

You may be interested in reading my how to wear your great fall wardrobe already now.

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

Top of the World Style Linkup No. 321

Top of the World Style linkup party logo

Welcome to the Top of the World Style linkup party.

Tilden in shorts and a long sleeve sweater
Tilden from To be Bright became Top of the World Style Winner. Photo from her post


Jill in early fall outfit with jean and blouse
Jill from Doused in Pink became the Top of the World OOTD Readers’ Fav. Photo from her post.


Iris in lavender hat mint midi dress
Iris from Lamoumous became the Top of the World OOTD My Fav. Photo from her post


Congrats Ladies! Grab your award buttons.

Please invite your friends.

Come join me at the Top of the World Style #linkup party. #ffblogger Click To Tweet


Runway to the party


I invite all fashion and style bloggers to co-host the top of the World Style linkup party. Just send me an email with your request. Want to throw your own party?


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Photos of me: G. Kramm

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