There is nothing more relaxing than taking Kirra for a walk to admire the bright blue skies and colorful leaves of fall, but California’s ‘fall’ weather doesn’t always mean pants and a jacket. The weather is going through an awkward stage as we hold onto the last bit of summer heat, and this is the perfect opportunity to experiment with seasonal styles!

Dresses are my go-to style for summer, and fall boots are a girl’s best friend — Why not combine the two? A dress doesn’t always go hand-in-hand with a pair of boots, but this trend is worth a try before moving into full-blown winter mode. The key to nailing this look is to select a boot style that complements the style of the dress! See below for 5 of my favorite dress & boot combos, and get some transitional style inspo before it is too late!

1. Flare Dress + Over the Knee Boots

Theory Marah Dress
Marah Dress
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2. Shift Dress + Combat Boots

Bella Dahl Shift DressBella Dahl Lace Back Shift Dress
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3. Midi Dress + Ankle BootsJust Like Honey Midi Dress

Just Like Honey Midi Dress
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4. Maxi Dress + Lace-Up Boots

Butterfly Skies MaxiButterfly Skies Maxi
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5. Sweater Dress + Fringe Boots

Bodycon Sweater DressKnit Body Con Dress
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