14 tips how to transition summer pieces into fall

How to transition summer pieces to fall

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How to wear your summer pieces in fall

Interested in summer-to-fall outfit ideas? Then continue reading how to transition summer dress for fall. I thought that 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 are the inspirations listed 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

Summer to autumn transition outfit ideas and inspirations

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 constanze bag, statement silver belt, BCBGMAX ankle studded pumps, Anne Klein sacrf, 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 hoodiemidlife woman in monochromatic autumn outfit with matching hat Fedora c/o Tenth Street with own Tee, Aerostrophale sequin detail jeans, Kieselstein Cord belt and buckle, Nine West plateau loafers, Longchamp bag, and brooches (all own), and ruby zip-front herring bone jacket c/o Whistle River

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)
over 40 style fall work outfit with tweed and floral top Eddie Bauer tweed skirt, Cable and Gauge floral print top, BCBG Maxazria belt, and Valentino Rock Studs (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, statment suede with gemstone buckle belt, Hermes collier de chien bangle, Coach bag, amethyst earrings, Chartier 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, statment 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

To elongate the time you can wear summer pieces (i.e. 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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Photos of me: G. Kramm

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