"This morning when I was getting dressed, I realized it would be cold enough to wear my wool wrap coat and I did a literal happy dance to the delight of no one (I live alone). Fall dressing just makes me so damn happy. Cinching my wrap coat, hearing my boots click on the sidewalk, letting the wind tug tendrils out of my ponytail. The simplest pleasures. And since fall dressing is my one true nirvana, here are all the pieces I recommend investing in for peak fall and winter wardrobe success. Go forth and get cozy, friends. 
Honestly, at the end of a long work day the only thing I want to do is come home and fall into a pile of cashmere turtlenecks. They are just. so. damn. snuggly. I know what you’re thinking: “Kelly, do I really need to spend for real cashmere?” And in answer, I ask you this: Do you want to be itching inside of your sleeves all day or do you want to be surrounded in a cloud as silky soft as Chris Hemsworth’s hair? I think that really says it all, don’t you?
How to Wear It
Cashmere Turtleneck / Topcoat / Dark Skinnies / Gold Hoops Work Tote (I have this and adore it!) / Leopard Loafers
Cashmere Turtleneck / Cardigan / Girlfriend Jeans Combat Boots / Leather Belt / Twisted Hoops
When I was younger, I used to dream about dressing business casual — pencil skirts, sweater sets, a crisp blazer with a button-down underneath. I would pull out the J.Crew catalog and circle sky high heels and calf dusting coats and present it to my mom like “here’s what I would like to wear!” Her response: “Kelly, you’re nine.” Anyway, happily I have now made my childhood dreams come true with an inspiring array of silk button-downs. I cannot get enough of them — they are so incredibly versatile. Wear with jeans, with ponte pants, midi skirts, pencil skirts, joggers… the options are truly endless. I recommend investing in quality silk for a wardrobe staple that will last you forevermore.
How to Wear It
Blazer / Silk Button-Down / Ponte Pants / Snakeskin Mules / Mini Hoops
Denim Jacket / Silk Button-Down / Pleated Skirt / Ear Crawlers / Ballet Flats
I had a revelation earlier this year about jeans. My usual strategy was to buy one pair of jeans at any old place — usually a brand from T.J.Maxx called like “Great Jeans, Inc.” and you know what, they weren’t bad. But then I’d wear them basically every day and after two months they were pretty much kaput. So a few months ago, I rethought everything by investing in three pairs of higher quality jeans and rotating wears. Is this something everyone else has already realized is the easier way to live? Oh well.
How to Wear It
Puffer Vest / Cozy Sweater / Dark Skinnies / Scrunchie / Boots
Trench / Tee / Dark Skinnies / OTK Boots / Ear Crawlers / Plaid Scarf
Ponte pants are the little black dress of my wardrobe. They are the Jennifer Aniston of Instagram. Universally beloved. Classic but fun. Casual but elevated. Literal perfection. That is all.
How to Wear It
Leather Jacket (an editor fave!) / Lace Camisole / Ponte Pants / Ear Crawlers Black Booties / Croc Crossbody
Utility Jacket / White Tee / Ponte Pants / Windowpane Scarf Faux Leather Backpack / Sneakers
Just call me Meghan Markle because shirt dresses are all I want to wear lately. I’m not usually a dress person — I’m a pants gal all the way. But the casual coolness of a good shirt dress is out to change my mind. And I don’t want to jinx it… but I think I’m in love.
How to Wear It
Sweater Coat / Denim Shirt Dress / Snakeskin Mules Tote Bag / Twisted Hoops
Plaid Coat / Utility Shirt Dress / Tiny Hoops / Boots
You know this already: boots are the staple of a good fall wardrobe. Whatever kind of boot is your current jam (riding boots, OTK boots, low-heeled booties, sky-high ankle grazers), invest in a quality pair that make you feel like a thousand bucks but won’t shred when they hit water.
How to Wear It
Puffer Jacket / Flannel / Skinnies / Riding Boots / No Crease Hair Tie
Denim Jacket / White Tee / Satin Midi / OTK Boots / Gold Necklace
I splurged on the Cuyana tote for my 27th birthday this year and I’ve never been happier with a wardrobe decision. I instantly feel more pulled together and luxe — packing up for work in the morning is an actual delight. Bonus: the bag fits A TON and is great for travel or flights. Pro tip: I got it monogrammed (#classylady4lyfe) and did the “Mini” size, which gave it the perfect, subtle glint of gold.
How to Wear It
Wrap Coat / Paper Bag Waist Pants / Graphic Tee / Ear Crawlers Leather Zip Tote / Low Heels
Faux Fur Coat / Silk Button-Down / Faux Leather Mini Skirt / Black Tights Classic Leather Tote / Loafers
Another anecdote from my childhood, get ready! I used to wear my coats alllll the time, to the point where my family was like “hello, can you take your coat off and make yourself comfortable?” But honestly I didn’t want to. I just love coats that much. There’s something about the feeling of wearing them: mysterious, ready for adventure, literally warm. All my favorite things.
How to Wear It
Wool Coat / Graphic Tee / Raw Hem Jeans / Pearl Hair Clips Sneakers / Suede Crossbody
Carly Coat / Wide Leg Black Pants (bought these last year and wear them constantly!) Tie Front Top / Heeled Loafer / Matte Lip Pencil