October Weekend Outfits

As the crisp autumn breeze sets in and the leaves begin to change, October is the perfect month to embrace the cozy vibes of the season. And what better way to start than by curating fabulous weekend outfits? Midlife women, it’s time to step into your closets with a fresh perspective and revamp your style without splurging on new items. Let’s explore a range of outfits suitable for various activities, ensuring you look and feel amazing this October!

NOTE: I am 5’1, 26” inseams, and generally wear 4P. All items fit true to size (TTS) unless noted otherwise.


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Crewneck Sweater (no tucking – I have the hem turned under with fashion tape) + Jeans (wearing 26 REGULAR cut to custom length) + Crossbody / Hobo Bag + Ballet Flats = Errands Outfit

Errands Outfit

Running errands doesn’t mean compromising on style. Combine comfort and chicness by pairing your favorite denim jeans with a cozy crewneck sweater. Complete the look with a pair of feminine ballet flats or sneakers for a touch of effortless cool. Accessorizing with a casual crossbody bag…and head out the door!

Crewneck Sweater + Puffer Vest + Jeans (Petite Length / Regular Length) + Boots = Fall Festival Outfit

Fall Festival Outfit

When it comes to dressing for a fall festival, comfort and style go hand in hand. Embrace the season’s cozy vibes with a fabulous outfit that perfectly captures the essence of autumn. Start with a timeless camel crewneck sweater, a versatile piece that exudes warmth and sophistication. Layer it with a camel puffer vest for added insulation and a touch of modern flair. Pair this combination with classic straight leg jeans, providing a flattering silhouette that complements any body type. Complete the ensemble with a pair of chic ankle boots, adding a trendy edge while keeping your feet comfortable throughout the day. With this effortlessly stylish and practical outfit, you’ll be ready to enjoy all the festivities the fall festival has to offer, while turning heads with your impeccable taste.

Sweater Dress + Knee High Boots (Regular / I am wearing Wide Calf Version) + Amazon Handbag = Winery Outfit

Winery Outfit

Midlife women, if you’re planning a visit to a winery this October, it’s the perfect opportunity to embrace a sophisticated and elegant ensemble. Opt for a luxurious cowlneck cashmere sweater dress, as it effortlessly combines comfort and style. This dress will keep you cozy while exuding a touch of refinement. Pair it with knee-high brown boots, adding a touch of warmth and sophistication to the outfit. Complete the look with a designer handbag, which will serve as the perfect accessory, elevating your entire ensemble. With this chic and polished outfit, you’ll be ready to indulge in the winery experience with grace and style, making a lasting impression wherever you go.

Cableknit Sweater + Jeans (wearing 26 REGULAR cut to custom length) + Crossbody / Hobo Bag + Boots = Apple Picking Outfit

Apple Picking Outfit

Heading to the orchard for apple picking? Embrace a playful yet practical outfit. Opt for a timeless cableknit sweater with straight leg jeans or corduroy pants. Complete the look with comfortable ankle boots or sturdy sneakers. This outfit will ensure you’re prepared for any outdoor adventure while staying stylish.

Crewneck Sweater + Black Pants + Crossbody / Hobo Bag + Ballet Flats = Brunch Outfit

Brunch Outfit

Enjoying a leisurely brunch with friends calls for an ensemble that exudes effortless style. Opt for flowy wide leg black trousers in neutral colors like gray or black. Layer it a white tank and gray crewneck sweater. And as always…NO TUCKING HERE! I have the hemline of this sweater secured with removable fashion tape to make it appear it is tucked. Complete the look with feminine ballet flats or casual fashion sneakers. You’ll be the epitome of autumnal effortless style!

Lounge Set – Bra – Shoes = Stay at Home Outfit

Stay at Home Outfit

As the temperatures drop and the leaves start to fall, there’s no better time to create a cozy lounge set from your existing wardrobe for those relaxing days at home this October. Begin by rummaging through your closet for a soft, oversized sweater or a chunky knit cardigan that you can pair with your favorite pair of leggings or joggers. Seek out comfortable yet stylish options like fleece-lined leggings or joggers for an extra touch of warmth. Complete the look by slipping into a pair of fluffy socks or plush slippers to keep your feet toasty. Don’t forget to accessorize with a cozy blanket scarf or a soft beanie for added comfort and style. With a little creativity, you can transform your existing wardrobe into a snug and stylish lounge set that will make staying at home this October an absolute pleasure. So grab a book, light some candles, and snuggle up in your curated cozy ensemble, enjoying the tranquil moments of the season.

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5 thoughts on “October Weekend Outfits

  1. I did some shopping in my closet this week and can’t believe how many things looked great that I thought I didn’t have a use for! Thanks! Also, I recently reorganized my closet. So now I’m curious how you organize your closet. Type of clothing -> (sleeve) length -> color? (My current layout) Or color first? Something else? I looked through some pages of your posts but didn’t see this; if you’ve written about it already just let me know! TIA

    1. I was actually just thinking about this yesterday! Did reorganizing your closet help you to look at your existing wardrobe with fresh eyes? (Closet organization is on my weekend to-do list…)

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