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Unless otherwise specified, all sizes in this post are listed in women's.
1. A cushy quilted jacket that'll allow you to roll through your day as if you never got out of bed. (AKA my absolute dream.)
2. A pair of essential fall booties with a stacked heel so comfortable and easy to walk in, you *won't* look like a newborn baby giraffe the first time you wear them out.
3. A chunky oversized sweater guaranteed to keep you snug as a bug in a rug even though you're a human who exists exclusively in Spanx faux-leather leggings.
4. A batwing sweater dress you can layer over tights for extra warmth, dress down with trendy sneakers, or dress up with sexy over-the-knee boots. With this dress, the world is truly your oyster.
5. An oversized knit cardigan if watching Sex Education and Derry Girls (on repeat) has you channeling academia vibes.
6. A pair of crisscross faux fur slippers with memory foam insoles that'll have you feeling like you're walking on a literal cloud. Since they have a waterproof and slip-proof sole, you can even show 'em off while running errands.
7. A one-and-done sweatshirt dress because sometimes, just having to change out of PJs and then pick out undergarments is already more than I can handle.
8. A silky satin midi skirt with a silhouette that says "chic" and an elastic waistband that says "I'll give your most comfortable sweats a go."
9. Or a rib-knit skirt you can wear at your natural waist or hike up for a shorter silhouette. It's like getting two skirts in one!
10. A faux-fur purse that has enough room for your phone, wallet, and keys, and will resurface treasured memories of your favorite pillow pet.
11. A long-sleeve boho maxi dress with balloon sleeves and a faux wrap design that gives you the look you're after without having to babysit your boobs all day.
12. A graphic crewneck sweater you can throw on over jeans, wide-leg trousers, or a midi skirt for maximum pattern clashing. If you need further outfit inspo, a quick look through Harry Styles' fashion archive should also help.
13. A faux suede moto jacket that you can *literally* wear with anything. There was a time when my mom told me to stop using the word literally 'cause I said it every two seconds, but mom, I swear it's justified in this case!
14. A pair of head-turning Steve Madden sneakers for the maximalist who'd never even *dream* of stepping outdoors in plain white footwear.
15. A relaxed button-down dress — with ultra-comfy cotton construction — that can be worn two different ways sooo really...it's like spending $44 on two different dresses and not $88 on one, if ya think about it!
16. A pair of versatile, non-see-through biker shorts you can layer under an oversized crewneck in true Princess Di fashion. Sure, shorts won't take you all the way through fall but for those three days when it's warm enough to wear them and cool enough to wear a sweatshirt, they'll be a real moment.
17. A hand-knit mohair cardigan — the shade maple syrup, no less — with gorgeous oversized sleeves that are really the only thing people will be paying attention to. Accompanying skirt, shirt, overalls, who cares — those cozy cuffs are stealing the show!
18. A color-blocked cardigan dress (you can style alone or throw on over jeans) for those looking to exude serious main character energy with little added effort.
19. A cozy sweater dress that, as you can see below, looks fan-freaking-tastic with thigh-high boots but can also be belted or worn with tights. (Unpopular opinion: I LOVE wearing tights and would happily do so year-round if it was cool enough out.)
20. A pair of knit Amazon Essentials jeggings with ~thousands~ of 5-star reviews that almost unanimously state they feel like leggings but look like jeans.
21. A fuzzy sherpa jacket ready to keep you warm no matter what you're wearing underneath. Teddy coats really don't have to adhere to any fashion "rules," and, btw, neither do you!
22. An off-the-shoulder knit duo so sleek and expensive-looking, it's exactly what I imagine Hailey Bieber is hanging out in at home. Even if you do have unlimited funds to throw at your matching loungewear, why waste $$$ when you can look this good for 30 bucks.
23. A pair of high-waisted joggers with a comfy elastic waist that sure beats nonstretch denim. In the words of RuPaul, "Can I get an amen?"
24. A cozy jacquard cardigan that goes way down past your butt so you don't have to do that thing where you go into every public bathroom you pass just to make sure your leggings aren't suddenly see-through. Yes, you checked them before you left the house but who knows what they're up to now.
25. A beige trench you can plop on over anything and immediately look like an incognito celeb — especially if you throw sunglasses into the mix.
26. A simple but versatile merino wool sweater with a half-zip design you can make use of when you forgot to match the shirt you're wearing underneath. Just zip that bad boy up and no one will be the wiser.
27. A casual shift dress that really gives you a blank slate to build off of. Pair it with your chunkiest lug-sole boots, wide-brim felt hat, croc-embossed faux-leather cross-body — you name it. Then, do a Stevie Nicks twirl so you really start your day off on the right foot.
28. A tie-front cargo jumpsuit so stunning, you *will* be stopped by a streetwear Instagrammer on your otherwise boring run to Whole Foods.
29. A crisscross backless sweater that's all business in the front but party in the back because despite the fact that you only wear neutrals, you're never one to be boring.
30. A pair of corduroy pants with an elastic waist that gives you an excellent range of motion. You never know when you're gonna want to show off how well you can do the worm, after all.
31. A pullover puff-sleeve sweater you can pair with jeans, wide-leg pants, or a midi skirt depending on the temperature and your mood.
32. An oversized plaid shacket that my family back in New Hampshire would really get a kick out of cause they've been wearing them for function, not fashion (and since before I was born), but here we are!
33. A pair of faux-leather Spanx guaranteed to give you the confidence of Sandy (AKA the late Olivia Newton-John) at the end of Grease. Unfortunately they don't come with a drive off into the sunset courtesy of the Greased Lightnin' car, but they are pretty dang comfortable.
34. A popcorn-knit cardigan for days when they want to look pulled together but also feel like they're wrapped up in a throw blanket your grandma knit just for you. And who wouldn't want that?
35. A pair of Birkenstock's ultra-popular Arizona sandals lined with ~fall-friendly shearling~ for those who can't bear to put away their Birks even once temperatures start dropping.
36. A classic blanket scarf that'll soon be the most versatile piece in your closet. You can wear it as a regular ol' scarf, unfurl it into a shawl, fashion it into a travel pillow, or use to trap your cat/dog in a burrito-style swaddle.
37. An oversized vegan leather blazer if your outfit could use some textural OOMPH.
38. A pair of thigh-high boots with soft, stretchy suede and a chunky block heel that prevents blisters and knee and back pain. Finally, a chic and affordable boot you can confidently purchase without an accompanying box of Band-Aids.
39. And a Hackwith Design House shirt that can be worn ~six~ different ways because you've reallyyyyy been toying with the idea of a fall capsule wardrobe but that's easier said than done.
Me @ fall weather:
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