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Every month, I round up the best sellers from The Well Dressed Life, and October’s list feels like the perfect snapshot of fall style. These are the pieces our community loved most, the ones that made getting dressed feel simple, pulled together, and a little more special.
October always brings that sweet spot of the season. We’re starting to layer more, reaching for texture and warmth, and leaning into those easy, polished neutrals that make everything feel intentional. This month’s favorites reflect that balance perfectly, from soft knits and holiday-ready pieces to timeless accessories that elevate your everyday look.
As we turn the page to November, these are the pieces worth keeping close. They’ll carry you from cool fall mornings into the start of the holiday season with ease.
If you’re refreshing your wardrobe or just curious what everyone’s loving right now, start here. These best sellers are versatile, flattering, and made to last.
Italian Handwoven Leather Mini Shoulder Bag
This Quince bag continues to be a reader favorite, and I completely understand why.
I love this piece and am so glad so many of you do too. The quality is incredible for the price, and the woven leather gives it that elevated, designer look without the designer price tag. I have the small size, and it’s more than enough room for daily use.
Available in four colors, I went with the cognac.
Shop the Italian Handwoven Leather Mini Shoulder Bag →
Read: The Bags I’m Carrying This Fall
ThirdLove WonderKnit™ Classic Pajama Set
If you’re ready to upgrade your pajama drawer, this is the set to start with. The WonderKnit fabric is buttery soft, drapes beautifully, and feels luxurious without feeling precious. I love the Peacock color because it’s rich, elegant and perfect for fall. This set makes a lovely self-purchase to elevate your at-home style or a thoughtful, cozy holiday gift for someone special.
Shop the WonderKnit Classic Pajama Set →
Read: It’s Pajama Season, and I’m Not Mad About It
Chico’s Crewneck Cashmere Pullover Sweater
This sweater is the kind of classic piece that makes any outfit look effortless. The shorter sleeve and light gray color make it easy to layer under jackets or wear on its own for a polished but relaxed look. The cashmere is soft and lightweight, which makes it a great choice for fall and beyond.
Shop the Crewneck Cashmere Pullover Sweater →
Tuckernuck Merlot Embroidered Floral Frankie Sweater
This Tuckernuck sweater is one of those special pieces that feels classic and festive at the same time. The deep merlot color is perfect for fall, and the floral embroidery adds just the right amount of texture and detail. It’s ideal for pairing with jeans, trousers, or even a skirt for the holidays. I always size up in sweaters from Tuckernuck unless the description says it’s oversized.
Shop the Merlot Embroidered Floral Frankie Sweater →
See: The Best Tops and Sweaters to Wear on Thanksgiving with Jeans
Banana Republic Cotton Velvet Puff-Sleeve Top
This velvet top is such an elegant option for the upcoming holiday season. The deep burgundy color feels festive but refined, and the puff sleeves give it a beautiful, structured shape. It’s perfect with jeans and heels for a dinner out or dressed up with trousers or a skirt for a holiday gathering.
Shop the Cotton Velvet Puff-Sleeve Top →
Read: Chic and Comfortable: My Thanksgiving Edit
Avara Gabbie Navy Two Piece Dress
This dress is such a clever find. It’s a two-piece set with a lightweight knit top and tank dress with pleated skirt. The navy color keeps it classic, and the combination feels effortless while still put together. It’s an easy option for fall gatherings, school events, or dinner out when you want to look dressed without overthinking it.
Shop the Gabbie Navy Two Piece Dress →
Read: Chic and Comfortable: My Thanksgiving Edit
Mignonne Gavigan Emery Studs
These are the perfect everyday earrings when you want something simple but still special. The gold knot design feels classic and adds just enough shine without being over the top. They’re substantial but comfortable to wear all day, and instantly make any outfit feel a little more refined.
Athleta Coaster Luxe High Rise Jogger
Joggers are the perfect alternative to leggings, still casual, still active, a little more elevated. The Nirvana fabric is soft, breathable, and drapes beautifully. They’re perfect for travel, errands, or a casual weekend at home, and the high waistband makes them flattering and easy to wear with everything from a fitted tank to an oversized sweater.
Shop the Coaster Luxe High Rise Jogger →
Boden Cornelia Ottoman Dress
This is one of those versatile dresses that works for almost anything. The structured knit fabric and flattering shape make it easy to dress up or down, whether you’re wearing it to the office, a dinner, or Thanksgiving with family. The navy color keeps it classic and timeless, and the fit is comfortable without feeling too casual.
Shop the Cornelia Ottoman Dress →
See: Thanksgiving Dresses for Women over 40
Freie Liebe Pleated Clutch Bag
This clutch is such a great find from Amazon. The pleated fabric and gold clasp make it look far more expensive than it is, and the size is just right for an evening out. I carried it recently and couldn’t believe the quality for under $25. It’s perfect for weddings, parties, or holiday events when you need something elegant but affordable.
Shop the Freie Liebe Pleated Clutch Bag →
Read: The Bags I’m Carrying This Fall
Evereve Lottie Cardigan
This cardigan is the definition of easy style. The neutral plaid pattern goes with everything, and the structured fit gives it a polished, almost jacket-like look. It’s great for layering over a simple tee with jeans or trousers and instantly makes an outfit feel finished. A perfect piece for fall days when you want something cozy but elevated.
See: The Best Tops and Sweaters to Wear on Thanksgiving with Jeans
Away The Everywhere Bag
If you travel often, this is one of the smartest purchases you can make. The Everywhere Bag fits perfectly over a suitcase handle and has a surprisingly roomy interior that still looks sleek and minimal. It works just as well for a weekend away as it does for everyday errands or work trips. The quality and design make it feel timeless and polished.
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