Age doesn't matter.

How to Transition Your Outfits in the Fall

Early Fall is still tinged with Summer. Then as it gets colder, nature surrounds us in brilliant color. So let’s enjoy this beautiful season! Below I explore the many ways to transition your outfits in the fall, followed by outfit ideas.

While we’re in between hot and cold, we need to stay comfortable.  And that means finding ways to layer, first over our summer clothes and then adding more and more warmth.  Besides layering, you can add certain other touches that signal Fall.

We can all dress between the seasons and look good doing it.  Age doesn’t matter!

I hope you enjoy this update of my post on the fall transition.

Ways to Transition Your Outfits in the Fall

Fall transition FP
Celestial Skies Midi Dress from Free People in a fall color with animal-print sneakers
  • Even if the weather is still hot, you can wear your light and cool summer clothes in fall hues, such as:  orange, red, rust, mustard yellow, and earth-tones like chocolate brown, and burgundy.
  • Wear white jeans with jewel tones or traditional fall colors.
  • Just add shoes and accessories to your summer outfit in autumnal textures, colors and prints.  Some examples are:  tortoise shell, leopard print, snake print, fall florals.
  • Add layers to your summer outfits.  The magical number of three layers creates the perfect look.  If it’s still warm out, use light, floaty layers; or leave something bare, like legs or arms.
  • Wear tights or leggings to warm up a summer skirt or dress.
Millie Velvet Smoking Jacket from Johnny Was with a cami and jeans
  • Add a velvet piece to a basic outfit.  It could be a velvet camisole, tank, top, joggers, leggings, pants, skirt or topper.
  • Throw on a jacket or cardi over a summer tee.
  • Add a long-sleeve lace top under a dress.
  • Summer maxi dresses are still usable:  layer with a tank, t-shirt, sweater, leather or suede jacket.

Long Open Cashmere Poncho with a white tee and joggers
  • Throw a poncho over your basics.
  • Wear bright, lightweight dresses into fall by layering a cotton turtleneck underneath.  Look for paper-thin versions in neutral colors that will look natural as a base layer.  Don’t force summer prints or wintry turtlenecks into the equation.
  • Add a dark layer (black turtleneck, tee, etc.) under a summer dress.
  • Sundresses are still usable with warm layers, a blazer, or a cover-up. Or, top your sundress with a black (faux) leather jacket.
  • A summer top, tunic or sun-dress over pants (even corduroy or leather).  You may want to add a long vest as well.
Solid Turtleneck Rib-knit Sweater from Shein with belted trouser shorts and boots
  • Shorts are still usable with tights or tall, over-the-knee boots or both.  You may want to add a long-sleeve top, a 3/4 length coat, etc.
  • Between seasons, a scarf will update and warm up any outfit:  A light scarf for temperate days, a warm scarf for chilly days.
  • A sleeveless  or short-sleeve sweater or mock-neck, or other partially-exposed sweater worn alone or layered with other knits.
  • Layer your favorite summer tops under a cardigan or vest.
  • Add a faux suede or leather vest to summer pieces to warm them up for fall.
Starlight Mongolian Vest from Free People over a graphic tee and white jeans
  • Use a faux fur vest as a jacket when it’s not too cold yet. At the end of fall, if it gets very cold, add a jacket or coat over your fur vest outfit.
  • A long vest over a summer outfit.
  • A t-shirt over a thin hoodie top, or a hoodie over a t-shirt.
  • Add a jean jacket to a summer dress.
  • Add a jean jacket to a summer maxi-skirt and tee.
Denim Seamed and Structured Jacket from Free People with a graphic tee and jeans
  • Wear a jean jacket over or under an olive utility jacket.
  • A blazer in place of a jacket, with a sweater or hoodie underneath.
  • Now is the perfect time to wear a faux leather jacket as outerwear.
  • Wear a fleece vest with a turtleneck or under a coat.  This vest offers versatility in unpredictable autumn weather.
BIRKENSTOCK Arizona suede sandals
Birkenstocks from Net-a-Porter with jeans and a cozy cardigan

Transitional Outfits

Here are outfit ideas based on the general guidelines as listed above. You’ll find outfits to bridge the seasons using dresses, skirts, pants, jeans and other bottoms.

Dresses:

Filipa Jacket from Free People over a floral-print dress
  1. A summer maxi dress + a moto jacket.  Add flats.
  2. Drape a lightweight scarf around your summer shirts and dresses to keep the chill off.
  3. A printed dress + bomber jacket.  You might like to add pumps.
  4. A dark floral (such as navy) dress + a jean jacket.  Add ankle boots + colorful layered bracelets on one hand + rings on the other.
  5. A turtleneck + a summer dress + a faux leather jacket.Long cardigan from H&M
  6. A short-sleeve midi dress + a chunky sweater, a cardigan, a leather jacket, or a jean jacket.  You might like to layer on some cool accessories.
  7. A favorite summer dress + tights.  You might like to add a tailored shirt underneath + a faux leather or suede jacket.
  8. A summer dress or tunic + pants.  Add boots.
  9. Add a lightweight jacket over a sleeveless dress.
  10. A maxi t-shirt dress + cut-out booties.  You might like to add a long, gold, tassel necklace and a bracelet.  If cold, add a sweater, tights, boots.

    Smoke & Mirrors Maxi Slip Dress from Free People with an earth-color cardigan
  11. A little black dress (LBD) + over-the-knee boots.  Add pendants + bangles.
  12. An LBD + an olive utility jacket.
  13. An LBD + a jean jacket + boots.  You may want to roll up the sleeves, add a cuff and a necklace.
  14. An easy tee dress + a jean jacket + slip-ons or mules.  Add a chunky chain necklace.
  15. When going out, throw a faux fur jacket over a summer dress.
    Lolita Bomber Jacket from Sundance over a floral dress
  16. A cool-weather blazer + a summer dress.  You might like to belt the dress or blazer.
  17. Wear a velvet kimono to warm up a summer maxi dress.  You may also like to add boots, an ethnic bag.
  18. A maxi dress + a toned kimono or duster.
  19. A short dress or skirt + over-the-knee boots + a slouchy cardigan or jacket.
  20. Add bold accessories + heavier layers on top of a beach dress (i.e., a cardigan, jacket, etc.)Velvet Midi Dress from Free People over a floral thermal top
  21. Wear a thermal top under a summer dress.  Try adding chunky boots or menswear brogues with warm socks.  Then add your favorite jewelry.
  22. Layer a flannel shirt over a t-shirt dress.
  23. A slip dress + a plaid flannel shirt worn open as a jacket.  Add ankle boots + long necklaces + bracelets.  You might like to add a beanie for extra warmth.
  24. A slip dress + a suede vest.  Add bracelets.

    Sun Child x Free People Long Caftan over jeans worn with a cap on a casual day
  25. A dress over skinny jeans. You might like to wear heels with this.
  26. A slip dress + a cardigan. You might like to layer necklaces. Add sneakers.
  27. Warm-weather dress + leggings + boots.
  28. A suede jacket + a floral dress.

Skirts:

Fall transition SS outlet
A rust shirred jersey-knit top over a black burnout velvet skirt with boots – from Soft Surroundings Outlet
  1. A white tee under your most madcap, bright-color blouse over a neutral (navy, gray, brown or black) pencil skirt.  Add black tights + ankle boots.
  2. A short-sleeve t-shirt over a pencil skirt + a jean jacket.  You may want to add tall, flat boots.
  3. A boyfriend cardigan buttoned over a scoop-neck tee over a pencil skirt.  Add flats + neck chains + a bangle.
  4. A long-sleeve ivory t-shirt tucked into an earth-toned maxi-skirt (such as taupe) + a colorful infinity scarf.  Add an earth-toned cuff bracelet + snakeskin sandals (or other neutral leather sandals).

    Printed A-Line Knit Maxi Skirt from J.Jill with a silk-knit sweater, a corduroy jacket and boots
  5. A short-sleeve black sweater + a brown midi-skirt or maxi-skirt.  Add leopard slip-ons.
  6. A cozy Fall sweater + a summer skirt or dress. You might like to add ankle boots, tassel earrings.
  7. A cashmere sweater + a floral dress or skirt.
  8. A short-sleeve knit shirt over a long white or beige skirt.  A drawstring skirt is good here.  Sling a big belt over it + mixed metal bangles.
  9. A short-sleeve turtleneck + a short faux suede skirt.

Pants:

Fall transition Johnny Was
A t-shirt with teal velvet pants, a statement necklace & sneakers – from Johnny Was
  1. A camisole over gray trousers.  May add peep-toe booties.
  2. Wide-leg trousers + a long-sleeve tee or fine-knit sweater + a blazer.  Add sneakers.
  3. Wide-leg trousers + a warm sweater + sneakers.  Add an oversize coat or trench.
  4. A cozy cardigan + a Henley or a top with pretty cuffs  + skinny corduroy pants.  Add a pendant + rings.
  5. A feminine top + cargo pants.  Add a lightweight scarf looped around your neck.
    Annabella Jean Jacket and cargo pants from Sundance
  6. A jean jacket + a t-shirt + cargo pants.  Add sneakers.
  7. A jean jacket + a white tee + stone-color pants.  Add flat sandals.
  8. A utility jacket + brown pants or jeans.  Add a printed scarf in toned colors twisted around neck with ends in front.
  9. A rust boyfriend cardigan + a rust tank top over brown skinnies.  Add a rust printed scarf looped loosely around neck with the ends tucked in front center + gold ballet flats + a gold bangle + small gold earrings.  Push back sleeves.
  10. A white or tan cashmere sweater + pants in any shade of white or tan + a ruana or poncho in any shade of white or tan.

Jeans:

white-pants-after-labor-day
White pants after Labor Day.
  1. A silky button-down + white jeans.  Add bright sandals or wedges.
  2. A gray leopard shirt (or solid gray or solid black) + white jeans.  Add black jewelry.
  3. A white shirt +skinny blue jeans.  Add crystal stud earrings + a printed scarf.
  4. An indigo cardigan over an indigo t-shirt over blue jeans.  Add sneakers + hoop earrings with blue beads.
  5. A teal or other color sweater + blue jeans + any ethnic bag slung across body.  Colors don’t have to match.
    Teal Poncho by SerenityoftheSouth at Etsy with a white top, blue jeans and boots
  6. A t-shirt, either graphic or solid + blue jeans + any topper.  Try a poncho, a blazer, a leopard-print jacket, a snakeskin cardigan, a rust-color duster, etc.
  7. A chunky cardigan + a metallic tank top over blue jeans.  Add a lightweight printed scarf tied European style (fold lengthwise, then thread ends through loop.)
  8. A lace-up t-shirt unlaced enough to show a camisole beneath + jeans.  Add a cardigan toned to the colors you are wearing or a chambray shirt worn open as a jacket.  Add peep-toe booties + a few necklaces + a few bangles.
  9. A chambray shirt over a Henley top + jeans.  If you like, button just one button on the Henley to show layers.
  10. A bomber jacket + a striped tee + blue jeans.  Add a long, fuzzy scarf looped around neck with ends in front + pendants on cords + sneakers.

    Fall transition Sundance
    A plush duster cardigan over a white blouse inside blue jeans with brown belt and layered necklace – from Sundance
  11. Skinny jeans + an oversize sweater.  Add ankle boots.
  12. A cardigan over a plaid shirt + skinny jeans + ankle boots.
  13. A long-sleeve plaid shirt + jeans + motorcycle jacket.  Add flat ankle boots.
  14. Top a black t-shirt & blue jeans with a black bomber jacket. Add sneakers.
  15. A tank top + blue jeans + a kimono.
    Aziza Shirtdress from Soft Surroundings with a burnout top and blue jeans
  16. A duster or a shirtdress worn open as a duster + any top + jeans.  Add clogs or boots.
  17. A flannel shirt worn open as a jacket over a lace top + jeans + a biker jacket.  Add socks + sandals (match or tone them.)
  18. A short-sleeve plum tunic + skinny jeans.  Add an olive jacket.
  19. An olive jacket + a black scoop-neck top + blue jeans.  Add peep-toe booties + a long chain necklace & bracelet.  Roll up sleeves.
  20. A long-sleeve gray t-shirt + skinny jeans + olive utility jacket.  Add ballet flats.
    Dolan Demi Bootcut Jeans from Free People with a long shirt, a vest and a duster.
  21. A long shirt + blue jeans + a vest + a velvet duster.  Add a chunky chain necklace and ankle boots.
  22. A faux leather jacket + a longer-length t-shirt + coated jeans.  You may like to add a gothic pendant + combat boots.
  23. A faux black leather jacket + a black peplum top + coated jeans.  Add heels.
  24. A black blazer + a black top + coated jeans.  Add a statement necklace + black heels.
  25. A buffalo plaid shirt + skinny jeans + a moto vest.  You may like to add tall black boots over the jeans + a leopard-print coat.

Other Bottoms:

Fall transition DVF
High Waisted Culotte with a long-sleeve top and ankle boots – from Diane Von Furstenberg
  1. An animal-print top + cropped trousers.  Add boots.
  2. Start with a maxi-skirt or culottes + one of your dressy tops.  Add a thermal, tall boots, leather jacket, and a scarf for chilly weather.
  3. A long-sleeve white t-shirt over black culottes.  Add big colorful earrings + multi-color bangles + flat black sandals.
  4. Start with any style of bottoms + a tank top + ankle boots.  Add a hat, lightweight cardigan + jacket.
  5. A long-sleeve top + denim shorts.  Add black tights + black boots.  If cold, add a 3/4-length coat.
    Stevie Fringed Knit Kimono from Anthropologie with printed joggers
  6. A warm knit kimono belted over jogger pants.  Add neutral mules + layered necklaces.
  7.  Top a t-shirt & olive leggings with a sage-color duster.  Or use a different-color duster and leggings.  Or use a different topper and/or different bottoms.
  8. A black tunic + brown leggings.  Add flat brown boots + a brown cord or cuff bracelet.
  9. A black tunic + black faux leather pants or leggings.
  10. Wear a sweater over track pants. Layer a couple of gold pendants (one short and one long.) You might like to wear sandals!
  11. A sleeveless tunic + black skinnies (denim or not) + a long black cardigan.  Add black heels.

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