16 tips how to transition summer pieces into fall
Herve Leger silver leather jacket, Banana Republic abstract floral print dress, crocus petal Coach top handle bag (all own) and Ivanka Trump pink suede pumps c/o Wikibuy

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

Contents
  1. Dressing in the transition season is tricky
  2. Try a summer look with motorcycle jacket
  3. Wear it now – wear it later
    • Example: Summer dress with a jacket
    • Example: Silk skirt with jacket
    • Add a jean jacket to your fav warm season look
  4. List of tips how to wear your summer pieces in fall
  5. More summer to autumn transition outfit ideas
  6. In summary

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Dressing in the transition season is tricky

It’s normal to be attached to your summer clothes. Since our childhood, we associate summer with leisure, pleasure, freedom and fun. That were the times, 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 wardrobe. 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.

Try a summer look with motorcycle jacket

Around early September or so even in mid-latitudes the mornings get already chilly even though equinox and the official start of autumn isn’t before later in the month. 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 go. 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)

Wear it now – wear it later

Example: Summer dress with a jacket

This look is straight forward adopted from clear sky summer evenings. You added the cardigan when it turned a bit chilly after sunset. In fall, just wear the cardigan all day and add a light trench coat of windbreaker for the commute from and to work. Another great possibility is to wear a dress with a biker jacket instead of a cardigan like in the photo below. To keep your legs warm go for pantyhose or nude fishnets.

mature woman presenting the same dress styled for two seasons
Banana Republic gray purple abstract print sheath dress styled for two seasons (left) with Hermes H-bangle, Hermes collier de chien bangle, and purple Prada pumps and (right) Coach bag, silver Herve Leger leather motorcycle jacket (all own), and suede pink pumps c/o Wikibuy

Example: Silk skirt with jacket

Wear a short-sleeve cashmere sweater with a light skirt a blazer …

#fashionover50 woman donning the same shirt-skirt outfit styled for a warm and cool day for the office
Same DIY shirt-skirt as in the second photo collage styled for a warm (left), and cool day (right) with Brooks Brothers cashmere short sleeve sweater, statement belt, Anne Klein glencheck blazer, Hermes collier de chien bangle and leather bracelet, head band, and Celine tote (all own)

… or an utility jacket. Pantyhose or tights optional.

#styledover50 woman donning the same abstract print top in a summer (left) and autumn outfit
Shein abstract floral print short sleeve top with uneven hem line styled with Oliveo striped leather skirt, Michael Koers cork plateau sandals, Hermes collier de chien bangle (left) and Studio strappy sandals, Kieselstein Cord belt and buckle, Newport News pink leather jacket, Hermes enamel bangles (all own), and cropped pants c/o White House Black Market

Not a fan of pantyhose? Tip:
Pumps with socks are a great trend this autumn. #trends Click To Tweet

Add a jean jacket to your fav warm season look

In the outfits below, all it took was a different pair of shoes, adding a scarf and a jean jacket to make the look work in the transition season.

older woman wearing the same shirt and pants in a summer (left) and fall outfit
Dress pants c/o White House Black Market and own Carhartt gingham shirt (pocket cut off) styled for summer (left) with silk geometric print scarf, statement snake tail buckle belt, Hermes collier de chien bangle, Jord bamboo watch, statement bracelet (all own), suede fringe designer clutch c/o Uno Alla Volta, and Matisse embroidered mules c/o Soft Surroundings and for fall (right) with Fossil white jean jacket, and Vittora car shoes

midlife woman wearing the same dress in two different ways

Gap camouflage shirt dress with Left: pink statement belt, Winkwood sunglasses, Cartier juste un clou bangle (all own), and Ivanka Trump c/o Wikibuy. Right: Banana Republic floral coat, Hermes collier de chien belt, Winkwood mirrored sunglasses, statement necklace, Christian Louboutin pumps, and Longchamp pilage (all own)

mature fashion blogger wearing a shirt-skirt styled for different ambient temperatures
DIY shirt skirt made from a Vintage Silk men’s silk shirt styled with (left) Jones New York sleeveless top, Paloma Picasso sunglasses, statement chain belt, Jord bamboo watch, Hermes collier de chain bangle, and L.K. Bennett pumps (all own), and (right) Moda International short sleeve cashmere sweater, statement belt, Ray Ban sunglasses, Festina watch, Hermes collier de chien bangle, and Aerostrophe anklestrap pumps
style blogger wearing an Hawaiian print skirt in camouflage colors once styled for warm vs. cool conditions
Hawaiian camouflage inspired print DIY A-line shirt-skirt made from a Vintage Silk men’s shirt styled for warm weather (left) with Shein utility top, statement dagwood necklace, Chanel bag, Hermes enamel H-bangle, Hermes collier de chien bangle, and Ivanka Trump ankle strap pumps (all own), and cool weather with Great Northwest suede utility jacket, Loft silk sweater, American Meteorological Society neckerchief, statement belt, and L.K. Bennett open toe plateau snake print pumps

List of tips on how to wear your summer pieces in fall

I thought that compiling the tricks shown in the wear-it-now vs. wear-it-later examples may be helpful. A list is easy to print out and hang into your closet for some cute fall outfit ideas right at your finger tips. Thus, here a listicle of  these inspirations that should work with any style and at any age.

  1. Summer dress with a leather jacket, tights, tan or black wood sandals
  2. Summer dress with cardigan (ends wrapped over each other hold by a belt (wide belt for long torso, thin belt for short torso)
  3. Denim jacket, black tights, open toe booties or fall sandals with 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 summer dress as skirt by pulling a sweater over the dress, add a jacket and tights when it gets even cooler
  7. Wear a summer mini-dress as tunic with leggings and pumps
  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. Add a piece, shoes, accessories in fall colors
  11. Add leather items like a leather skirt, top, jacket or vest
  12. Add a plaid shirt
  13. Wear a floral summer top with a tweed skirt
  14. Add a dark leather bag
  15. Wear a slip or underskirt, tights and halftee under a summer dress
  16. Use layering to create stylish looks and increase insulation

What are your tricks you hold on to your warm season wear? How long is your transition season? Is it long enough to invest in special clothes for it? Or do you mix and match warm and cold season items? What is your biggest wardrobe challenge in autumn, I mean except money. I mean
Who wouldn't love to pay a million in taxes, when they have the respective income? #budgetfashionista Click To Tweet

Want a cheat sheet for dressing? Buy my book How to dress for success in midlife to get the stress out of dressing your best.

I wore the look below on a windy rainy day. We were lucky to catch a break between showers to take the photos. I wore my layered blush tulle skirt with mules and a utility jacket. The latter served as a top.

outfit details with color palette

 

over 50 years old fashion blogger standing on a rock in mules, midi skirt and military inspired jacket

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 camouflage with floral print jacket, statment suede with gemstone buckle belt, Hermes collier de chien bangle, Coach bag, amethyst earrings, Cartier just un clou, Bandolino kitten heel mules (all own) and double layer tulle skirt c/o Lookbook Store

More summer to autumn transition outfit ideas

mature style blogger in blue and white skirt and shirt Summer dress worn as skirt under Carhartt gingham shirt (pocket removed), Dr. Scholl wedge sandals, Coach bag (all own), and green wood watch c/o Jord
midlife woman wearing twill leggings with a dress at the onset of the cold season Victoria Victoria Beckham dress worn as tunic, DIY belt, Jaeger Tote, Burberry trench coat BCBG ankle strap pumps (all own), and twill leggings c/o No nonsense
eShakti motorcycle dress with GNW tights and snake print booties (all own)
over 50 years old fashion blogger in summer lace dress styled for fall with leather jacket eShakti lace dress, Graham and Spencer leather motorcycle jacket, Prada bag, and Salvadore Ferragamo pumps  (all own)
mature fashion blogger wearing a summer dress with sweater as a skirt in autumn Karl Jäger summer dirndl, Jeanne Pierre sweater, ethnic belt, L.K. Bennett pumps (all own) and India Hicks scarf c/o Tammy Gray
over 50 years old style blogger in a summer dress and quilted leather jacket for a fall outfit eShakti printed summer dress, Halogen quilted leather jacket, GNW tights, BCBG statement belt, and Steve Madden fall sandals (all own)midlife woman in Casual Friday 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 Silkover 50 years old style blogger with a galaxy print fit-and-flare dress Loula Roe abstract galaxy-like print fit-and-flare dress, statement belt, Very Fine sandals, Belorita fish bag, statement necklace with moonstone and citrin, Hermes collier de chien bangle (all own) and c/o Tricia Tanaka cape hoodie
fashion blogger over 40 wearing a cardigan over a dress for a separates look GNW leopard print cardigan worn as top over eShakti floral print dress with H-belt, Michael Kors plateau sandals, Jaeger tote (all own) and wood sports watch c/o Jord
wear It Now Wear It Later Denim dress with J Brand skinnies Denim summer dress worn over J Brand skinnies, DIY necklace, belt, Anne Klein pumps, Jaeger tote (all own) and wood sport watch c/o Jord
mature style getting more wear out of my closet by styling summer items for fall eShakti fit-and-flare dress worn under Sofie cardigan worn as top, Nicole fall sandals (all own) and wood watch c/o Jord
over 50 style summer dress with cardigan for fall Isaac Mirzahi cardigan, eShakti abstract print summer dress with GNW tights, Nicole fall sandals, and Prada bag (all own)
transit Summer to Fall mature fall outfit with summer dress Lookbook Store motorcycle leather jacket over Jeanne Pierre sweater, eShakti floral summer dress, GNW tights, Steve Madden sandals, shawl, and Jaeger tote (all own)style book author in camo top, tulle skirt, striped bag, belt and mules Orvis utility camouflage with floral print jacket, statement suede with gemstone buckle belt, Hermes collier de chien bangle, Coach bag, amethyst earrings, Cartier just un clou, Bandolino kitten heel mules (all own) and double layer tulle skirt c/o Lookbook Storeblogger in fashion week inspired fall style with biker jacket, scarf, hat, jeans and sandals Vienna Scala hat c/o Tenth Street styled with own James & Graham biker jacket, wrapped twice knotted Oscar de la Rente scarf, Loft sweater, Oliveo Italian style jeans, Nicole plateau high heel sandals, and Celine shoppermature woman in polka dot dress with denim jacket fall wardrobe Great Northwest denim oversize jacket, Zaful polka dot dress, statement belt, Michael Kors fall sandals, DIY amber bangle, statement necklace that picks up the shades of the look, Hermes collier de chien bangle (all own), wood sports watch c/o Jord, and blue fish clutch c/o Bellorita

When you like the above fall outfit ideas for work and play, you may like my style book How to Dress for Success in Midlife with outfit ideas for all kind of situation in midlife. Buy the book now.

In summary

This post featured ideas and examples how to use pieces from summer to create outfits for the transitional season and to elongate the time you can wear inexpensive summer pieces. Whether your reason is to procrastinate on admitting or being on denial that it is early fall, shop your closet for

  • maxi skirts (you can even wear cropped leggings underneath
  • 3/4 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 that in early fall already cools down substantially over night, and
  • make that a summery look.

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

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

Photos of me: G. Kramm

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