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Unless otherwise specified, all sizes in this post are listed in women's.
1. An off-shoulder blouse to wear with a pencil skirt or jeans — either way you're gonna look BOMB in it. 💣
2. A striped sweater, because the best time to wear a striped sweater is alllll the time (SpongeBob knew what he was talking about), and that includes date night.
3. A pair of printed pull-on flare pants to channel some '70s vibes for a ~far out~ fall look that's both super comfy and super trendy for a day of crunching through the leaves at the park with your partner.
4. A tie-waist sweater dress for a simple, yet cute look sure to have you feeling like a ~snack~ on your next lunch date.
5. A pair of chic paper bag–waist pants so fabulous you'll probably want them in multiple colors so you can wear them all the time. They'll pair perfectly with your fave frilly top or style up your go-to solid shirt.
6. A floral ruffle top, because flower prints aren't only meant for spring. This boho-style silhouette and the warm color scheme makes this the perfect top for a fall outing.
7. A skater dress available with short- or long-sleeve options, front button details, and pockets. It's an easy piece to jazz up with different shoes and statement earrings. Throw this on with some booties and a tote bag and you're ready for your date.
8. A shaggy open-front jacket to dress up a plain T-shirt and jeans. It'll turn a simple look into a total style moment that your date will def be complimenting you on.
9. A pair of black heeled booties that are comfortable and versatile. Pair them with skinny jeans or a flowy dress and you're good to go.
10. A pair of bell-bottom jeans, because pretty much anything nostalgic is on trend right now and these are no exception. Wear these with heeled booties and a cute sweater for a hayride with your sweetie.
11. A tie-dye maxi dress that's just as comfy as it is stylish. You could add a jacket and brimmed hat to this for a day at the pumpkin patch...and then take a nap in it immediately after you get home.
12. A pair of opaque tights you won't have to worry about snagging before you've even left the house. These are durable, available in tons of colors and designs, and they'll keep your legs warm so you can keep on wearing those mini dresses.
13. Or a pair of polka-dot thigh-high stockings for anyone who loves the look of tights, but hates when they go all the way up to your bust. This sassy addition to your wardrobe will pair perfectly with everything from lingerie to skirts and dresses.
14. A knit sweater dress you can effortlessly style up or down however you please. Flats, heels, a jacket, a belt — it'll all look good.
15. An oversized vegan-leather blazer that's basically the perfect layering pieces for all of your upcoming fall activities. You can wear it with a dress for a dinner date or with jeans for a more causal look.
16. An asymmetric long velvet jacket to add some texture and layers to your ensemble. Whether you and your person are attending a wedding or grabbing cider at the local brewery, this will keep you warm and fashionable.
17. A high-waisted faux-leather wrap skirt, because leather skirts were *made* for fall. And this silhouette will have your date checking you out all evening long.
18. An organza scrunchie perfect for spooky season — it'll take that messy bun from slept-in to fabulous in seconds. Your date will have no idea you took too long doing your makeup and ran out of time to do your hair.
19. A lace-trimmed tunic for an easygoing, yet cute way to jazz up a pair of jeans or leggings.
20. A lightweight sweater dress begging you to take adorable fall-themed couple photos in. Pair it with some knee-high boots and you're a fall fashion icon.
21. A fringe blanket scarf perfect for chilly days of running around town with your love. This will keep you looking effortlessly chic and, most importantly, feeling toasty warm.
22. A ruffle maxi dress you'll feel like an absolute queen in for your upcoming brunch date. It's easygoing, but still has that major "wow" factor.
23. A cable-knit two-piece set perfect for a scary-movie night at home, when you want to feel cute and "put together" while being cozy and cuddling with your boo.
24. A sparkly, sheer mock turtleneck for a witchy-meets-glam look you'll want to rock while sipping Halloween-themed cocktails at that trendy bar you've both been dying to try.
25. Or a solid mock-neck sweater great for a more sophisticated look. Tuck it into some trousers or layer on a cute jacket with a miniskirt — this baby has endless possibilities.
26. An off-shoulder bodycon dress that I can pretty much guarantee will have your date's jaw on the floor.
27. A knee-length open cardigan so cozy you will feel like you're being hugged every time you wear it. Throw it on over jeans and a tee and your look is automatically elevated.
28. An adorable pair of pumpkin earrings for adding a festive touch to your lewk. Just pop these on with whatever you're wearing and you'll feel totally on theme for carving pumpkins with your pumpkin.
29. A stylish wrap sweater to make you feel sassy and fashionable without sacrificing one bit of comfiness.
30. A versatile off-the-shoulder wrap top perfect for wearing with any style bottoms — from sneakers and high-waisted pants to pumps and a midi skirt.
31. A fuzzy popcorn sweater ideal for fall picnics with bae. Pair this with some jeans or leggings for an effortlessly adorable look.
32. High-waisted faux-leather leggings you'll want to pair with all of your cute tops for a sleek look that screams, "Yes, I know I look good."
33. A faux-layered sweater for a very Sabrina Spellman–esque look — and what could be better suited for fall than that? Imagine wearing this with some platform loafers on your next coffee date. 😍
34. An oversized knitted sweater-vest for a preppy outfit piece that'll make you look like a fashionable extra in Gossip Girl. Perfect for strolling through the city with your Dan Humphrey.
35. A Panama hat available in tons of color options — it'll be the ultimate finishing touch to your apple picking attire.
36. An oversized turtleneck sweater dress so you can be cute, cozy, and confident in knowing that you absolutely slayed it on your first date.
37. And a puff-sleeve blouse, because it'll dress up any simple bottoms. This with some silver accessories and black heels? Prepare to have your date drooling!
Your date when they see you:
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