Living in a city with seasons totally changed my concept of getting (extra) dressed. My SoCal upbringing gave me very limited range. For example, my middle school footwear oscillated from rhinestoned Rainbows in the spring/summer, tall Ugg boots in the fall/winter. But New York opened my mind, and my closet, to a new set of staples.
I love indulging in a new piece or two season over season, usually opting for a vintage coat or new cashmere sweater, but I realized I accumulated quite a nice stack of basics that continue to give structure to my colder weather outfits. They’re all under $100 and they’ve all been personally vetted. Plus, they’re also all light enough layers that they’re working well for a warmer California October, too.
Aritzia Olive Micro. My favorite thing to wear is a mini skirt and I have three of the Aritzia Olives. That’s when you know it’s good. It’s not too short (at least not on my 5’5 frame) and you can style it super casual with ballet flats and a baby tee or dress it up with tights, boots, and a cardigan. It comes in a lot of colorways this season, rejoice.
Old Navy SoSoft Cardigan. Speaking of cardigans… You cannot go wrong with the SoSoft from Old Navy. It comes in lots of colors and fits and feels like a much more expensive sweater. I find that Old Navy typically runs big, but I would take your normal size or size up if you want a more relaxed fit.
Calzedonia Sheer Essential Denier 20 Tights. My second favorite thing to wear is tights and luckily for me (and you) they pair well with mini skirts. But there’s nothing more furstrating than going to slip on a pair only to find it’s been ripped or torn. Not anymore, kids!!! I think I could run a marathon in these and they’d hold up. The hottest tip for tights: SIZE UP. Even two sizes! Makes putting them on effortless and doesn’t change much about the fit.
And I love tights, so you can trust me.
Calzedonia Soft Cotton Ankle Socks. While you’re shopping at Calzedonia for tights, get a pair of socks. So comfy cozy, great shade range, and the most ideal thickness and height to wear with loafers. You can even layer them over the tights if you want to be really prep school chic.
Peche Loafers. A favorite store of mine in NYC. They have an insane collection of loafers that are low profile and very cost effective. Most come in black and brown. My personal favorites are the Joyce.
Intimissi Boat Neck Modal Top. A sexy long sleeve. The sheerness of the fabric lets a bralette can peek through underneath and the boat neck shows off your décolletage. Soooooo soft, too.
Cou Cou Intimates Dress. I saw Christina Grasso wearing her and said she must be mine. Come to find out, all the it girls are big fans! Very 1960s in silhouette and ideal for fall layering. Throw on a trench coat and a pair of boots and you’re good to go.
Baggu Shoulder Pouchette. A new staple, but for good reason. One of the most frustrating things about wearing a coat is having to adjust your purse every five seconds because they strap is too short for the bulkiness of your coat sleeves. This shoulder bag from Baggu has extra long straps so that doesn’t happen! It holds the essentials: phone, keys, cards, lip combo and only costs $50 so you can toss her around.
Circus by Sam Edelman Shoes. A sleeper hit of a shoe brand. Circus is Sam Edelman’s funky younger sister. Cool shapes, unique prints, and a little more interesting all around. Buy your fall flats, heels or boots from here if you want to have a little more flair.
Abercrombie Gemma Satin Pants. The silk pants of 2026 are very reminisce of the (p)leather pants of years past. A “going out pant” if you will. I would opt for the blue grey or olive grey instead of black to give them a little more range.
OK, what is missing from the list? Rules are 1) you own the it, 2) you wear it every season and 3) it’s under $100.
SHOW ME TO ME RACHEL, lol.
xx, Caylee
PS, if you prefer videos you watch this deep dive on TikTok and IG.
Truly a perfect dress!