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Cassie Brady

effortlessly chic style for the everyday woman

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in clothing, Fall, Fashion · November 10, 2026

Cupshe Party Season Collection

Products purchased through this post may earn me a commission. 

You guys liked the Cupshe pieces I posted in this blog post so much that Cupshe reached out and offered to send me several more pieces! This time from their Party Season Collection. It’s hard for me to believe the holidays are fast approaching, but here we are! I chose a variety of outfits from casual to more formal. Hopefully there’s something here that you can picture yourself wearing for one of your upcoming events. I can’t wait to here what you think of these outfits! And like before, I’ll link these pieces from Cupshe’s website as well as where you can find them on Amazon. I know several of you prefer to shop on there. Myself included!

brown and white plaid long sleeve mini dress

Outfit Details: Cupshe dress (also available on Amazon), Dooney & Bourke Bag (similar here) , Pierre Dumas Boots

How cute is this plaid dress? Love that it’s comfortable with its relaxed fit, yet still looks dressy and pulled together. I styled it with cowboy boots, but this dress would look just as cute with knee high boots, pumps, or even flats. An easy choice for a Thanksgiving meal where you might eat too much and prefer not to wear anything too tight, yet want to look nice. Also, breastfeeding mom approved with the buttons down the front.

red and orange midi long sleeve dress

Outfit Details: Cupshe Dress, Melie Bianco Purse (similar here), Express Pumps (loving these)

Another Thanksgiving dress option. This one has a smocked top and loose fitting mid length skirt. The long sleeves and slight puff at the shoulder is so pretty. Not to mention the orange and red combination is beautiful for fall. Wear it with boots, flats, or pumps like I did here. The stretchy smocked top is also great for breastfeeding moms like myself and the loose fitting skirt is comfortable enough for a day of relaxing and eating a Thanksgiving meal.

brown polka dot sweater

Outfit Details: Cupshe Sweater (also on Amazon), H&M Jeans (similar here), Dolce Vita Sandals (similar here)

This chocolate colored polka dot top with scalloped edges is too cute! Wear it with dress pants or a skirt for Thanksgiving dinner, or with jeans like I did here to go holiday shopping.

long sleeve striped polo with leather shorts

Outfit Details: Cupshe Polo, Express Shorts (similar here), Coach Purse (similar here), Restricted Loafers (similar here)

I’ve been seeing polos everywhere recently and I really like the color combination in this one. The light blue and chocolate brown pair so nicely together. This polo looks great with dress pants, jeans, or leather shorts like I’m wearing here. Great for casual get togethers with friends or holiday shopping.

Dark wash wide leg jeans

Outfit Details: Cupshe Sweater (also on Amazon) & Jeans, Michael Kors Purse (similar here), Jessica Carlyle Sneakers (similar here)

Dark wash jeans always read a little more dressy to me. If you have any get togethers this holiday season where you want to look casual, yet pulled together these jeans with attached bow are so cute! Pair them with this striped sweater where the blue stripes match perfectly for a fail safe combination.

Black and white knit set

Outfit Details: Cupshe Sweater (also on Amazon) & Pants, Dasein Purse (similar here), Birdies Sneakers (similar here)

This sweater set is so cozy and warm. Perfect for running errands, casual get togethers, or holiday shopping. Since it does run warm, this set will be great to wear all winter long!

Previous Post: « Cupshe Fall Try On Haul And Where I’ve Been These Past Three Years

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Hi there! I'm Cassie, a fashion and lifestyle blogger located in the Midwest. I love fashion, photography, & working from home with my dog on my lap. On this site you'll find fashion, travel, and home decor inspiration to help you feel more confident in the clothing you wear, trips you take, and home you create. Thank you so much for stopping by! x Cassie

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The Dark Plum

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My Mother’s Day started at 4am with a nursing baby My Mother’s Day started at 4am with a nursing baby in my arms, a toddler crawling into my bed and falling asleep on my shoulder, & a doggie sleeping across my legs. 💕 They have no idea what today is, but I’m feeling so blessed to be surrounded by all my babies on Mother’s Day 👶🐶👧 Even if it was at 4am 🥱

Not pictured our dog Sydney. 🐶 I’m so tired I didn’t even notice until after we got these pictures 🤪 I knew I was forgetting something! 🙈
Color coordinating with my son for a quick photo s Color coordinating with my son for a quick photo shoot before going home 📸🧸 His going home outfit, sign, & blanket are from @cadenlane & I bought a button front nightgown to match from @amazon in brown 🤎
He’s here! 🥲💙 Henry Patrick Brady April 7th, 2026 He’s here! 🥲💙
Henry Patrick Brady
April 7th, 2026 3:16am
7lb 9oz & 20 inches long
Exactly one week early

After laboring at home for 2 hours we JUST made it to the hospital maybe 45 minutes before he came out with 2 quick pushes! It all happened so fast my head is still spinning. 🥹 

So thankful my SIL @thedivinemissem77 answered her phone and came quickly to stay with Audrey & my hubby @npbrady9 taking care of everything else as we rushed to the hospital. ♥️ God is so good & we couldn’t be happier with the newest member of our family 🤗
Happy Easter 🐣 ✝️ So thankful for all of Gods’s bl Happy Easter 🐣 ✝️ So thankful for all of Gods’s blessings including this little boy on the way. We can’t wait to meet you little guy 👶 So hard to believe he will be here any day now! 🐰 This pregnancy has really flown by!🤰

Wearing a pregnancy/nursing dress from @amazon & The comfiest shoes for my swollen feet from @birdies 💕
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