Fall Transition Outfits: 6 Looks That Go From Warm, Sunny Days to Chilly, Fall Nights

Who doesn’t love the weather this time of year? The days are often still warm and perfect for playing outside while the nights are wonderfully crisp and call for a scarf and a mug of hot chocolate. It’s the best of both worlds! Unfortunately, a thirty or forty degree temperature differential is a little challenging to dress for. How can you be comfortable in 80 degrees and 40 degrees without completely changing clothes?

Here are six fall transition outfits to help you take your outfits from Indian summer days to crisp fall nights.


  • Fall Transition Outfits 1 of 13
    Fall Transition Outfits

    Click through to see how I go from day to night during this time of year!

  • Outfit 1 | Day 2 of 13
    Henley and Cowboy Boots

    A long-sleeved henley goes super casual with lightweight leggings and rolled sleeves for warm days. Find a couple of updos that won't leave a weird dent. That way, you can have your hair up and off your neck during the day, but down (and a little warmer!) at night. A loose pony, a bun held up with bobby pins or a french braid are all good options.

  • Outfit 1 | Night 3 of 13
    Henley, leggings and quilted vest

    A quilted vest is a lot warmer than you'd think (I was sweating taking these photos) and even less difficult to carry around than your average jacket. Check thrift stores! I usually find a few good, warm vests every time I go. This one cost me $1!

  • Outfit 2 | Day 4 of 13
    Maxi Dress

    I'm a big fan of dresses in any season but I think they're perfect for the transition into fall. They're breezy enough for the days but offer some leg coverage for when it gets cooler in the evenings.

  • Outfit 2 | Night 5 of 13
    Moto jacket + maxi dress

    An edgy jacket with a pretty dress is hands down one of my favorite cold weather looks. Spiked flats complete the look. Booties and flats are perfect for this time of year. They keep your toes from freezing but don't provide quite as much warmth as traditional boots. Leave your knee-high boots for the REAL cold weather!

    Jacket from OASAP, $45.90

  • Outfit 3 | Day 6 of 13
    Scarf and Skirt

    A medium-weight scarf is great for keeping your hair out of your face while running errands or going on a fall bike ride.

    Tee from Headline Shirts, $24

    Skirt from Charlotte Russe, $14.99

  • Outfit 3 | Night 7 of 13
    Scarf and Skirt

    As soon as it gets cooler, pull your scarf out of your hair and use it for some extra warmth around your neck. Add a warm coat and you're ready for dinner out on the town. If you can't find a scarf you love then make one! This one came from a fabric remnant I couldn't pass up a few years ago.

  • Outfit 4 | Day 8 of 13
    Jeans and Tee

    I'm actually not much of a jeans-and-tee wearer but it's a standard mom uniform! Since jeans tend to be a little warmer and heavier, make sure you pair them with lighter-weight flats so your lower half doesn't get too warm during the day! There is nothing worse than sweaty feet. Ugh.

    Tee from Out of Print Clothing, $28

  • Outfit 4 | Night 9 of 13
    Jeans Tee and Beanie

    I feel like an idiot in a beanie, but my husband thinks they are super attractive (he buys them for me ALL THE TIME. Sadly, they are always too small. He has weird ideas about my head size, apparently). Regardless, they are super easy to stuff in your purse or glove box and make a BIG difference when temperatures drop!

  • Outfit 5 | Day 10 of 13
    Red Dress

    Red (or, if you're feeling fancy, SAMBA!) is one of the hot hues for fall. A long-sleeved dress is a perfect transition piece!

  • Outfit 5 | Night 11 of 13
    Leggings and Red Dress

    Confession time: I do not own any tights. They drive me nuts! I go for leggings instead. Pair jersey leggings with a jersey dress and you've got yourself a ridiculously comfortable ensemble that will also keep you toasty. Bonus points for a warm felt hat!

  • Outfit 6 | Day 12 of 13
    Sweater Skirt

    I thrifted this sweater skirt several years ago and it has become one of my go-to fall pieces. It's soft, comfy, and cozy.

  • Outfit 6 | Night 13 of 13
    Sweater skirt and leather blazer

    A leather detail blazer is office appropriate but also great for keeping you warm on cooler evenings!

    Blazer from H&M, $39.95

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Article Posted 3 years Ago

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