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October is one of our favorite months here at Love, Olive Co. The air is crisp, the colors are warm, and weekends are filled with all things cozy and fun. Whether your plans include a trip to the pumpkin patch, brunch with friends, or a night in, we’ve got outfit ideas for every fall activity.
Here are some of our favorite October outings — and exactly what to wear for each.
Nothing says “October” like a visit to the pumpkin patch! Between hayrides, photos, and pumpkin picking, you’ll want something cute, comfortable, and fall-photo ready.
What to Wear:
Start with a midi dress in a fall floral or earthy tone. Add a shacket or denim jacket for layering, and finish with ankle boots or sneakers. A wide-brim hat adds a picture-perfect touch.
Love, Olive Co. Picks:
Style Tip: Bring a crossbody bag so your hands are free for pumpkins and hot cider. 🍎
October mornings call for warm drinks and cozy fits. Whether you’re meeting a friend or picking up your favorite latte, aim for relaxed and stylish.
What to Wear:
Try a lightweight sweater tucked into high-rise jeans, or go for a sweater dress with sneakers for a more feminine vibe. Add a shacket or oversized scarf if it’s chilly.
Love, Olive Co. Picks:
Fall family photos are the perfect excuse to get dressed up. Choose colors that complement the season and photograph beautifully.
What to Wear:
A neutral midi dress with subtle texture (like ribbing or smocking) always looks timeless. Layer with a cardigan or cropped jacket in earth tones like cream, rust, or olive.
Love, Olive Co. Picks:
Style Tip: Coordinate colors with your family, not outfits — complementary tones look best in photos.
Some of the best October plans are the simple ones. Whether you’re watching a spooky movie or baking treats, go for something soft, cozy, and easy to lounge in.
What to Wear:
Opt for a soft knit set or relaxed sweater and leggings. If you prefer dresses, a sweater dress with fuzzy socks is the perfect cozy combo.
Love, Olive Co. Picks:
Cooler weather calls for outfits that feel special but still warm. Whether you’re headed to dinner or a walk downtown, keep things feminine and layered.
What to Wear:
A floral midi dress paired with boots is romantic yet practical. Add a cardigan or suede jacket and a few gold accessories to complete the look.
Love, Olive Co. Picks:
Style Tip: Swap boots for block heels if your date night is a little dressier. ✨
From crafts to local vendors, fall festivals are all about fun and movement. You’ll want an outfit that’s easy to wear and comfortable all day long.
What to Wear:
Pair high-rise jeans with a graphic tee and layer with a shacket or corduroy jacket. Finish the look with sneakers or boots and a wide-brim hat.
Love, Olive Co. Picks:
Style Tip: Bring a tote or crossbody bag for all your market finds. 👜
If you’re spending the afternoon in an orchard, your outfit should be functional but still cute for photos.
What to Wear:
Choose a tiered midi dress with ankle boots and layer with a flannel or shacket. A wide-brim hat ties the look together.
Love, Olive Co. Picks:
Style Tip: Flat boots or wedges are best for walking on uneven ground.
October is full of cozy, memory-making moments — and your wardrobe should match the magic of the season. Whether you’re picking pumpkins, sipping fall drinks, or relaxing at home, Love, Olive Co. has the perfect pieces for every autumn plan.
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