The 2025 Fall Boot Guide
The best styles for your closet - from my favorite affordable riding boot to the splurge shoe on my wishlist.
Happy first week of fall! Writing to you from another 80 degree week in Los Angeles where I’m cranking the AC in my house just to wear a sweater and feel something. I’m itching for layers, jackets, all the things, and a lot of you were asking me for fall recs in early August, so I’m going to assume we’re all on the same page.
The most pressing question I get asked when fall rolls around: what fall boot are we getting? They’re the mascot of fall dressing and the one piece that I think grounds an outfit in the new season.
I firmly believe everyone should have the core four in their closet: a Chelsea boot, a low and high heel ankle boot, and a knee high boot. When finding your perfect pair, they should naturally slot into your wardrobe, not feel like something you need to style around. Think: a knee-high boot that extends the life of your summer dresses, and a low-heeled boot that feels as effortless as a pair of black flats. Below are the styles I come back to year after year, in a variety of price ranges, with some of my personal favorites from my closet.
Chelsea Boot
If you’re going to invest in any boot first — let it be a Chelsea boot. It will be your most lived-in shoe this season under jeans and trousers, especially when the weather gets cooler. I invested in the Loro Piana Kilda boot last season — I love the sleek look of them. When picking a Chelsea boot, I recommend paying attention to the sole because that’s a big personality point. Lug soles will have a chunky wide bottom with treads like the Reformation boots below, while rubber soles will appear sleeker. If you’re going to be in snow, highlight recommend getting ones with treads!
Heeled Ankle Boots
If you follow me on Instagram, you know I have a strong alliance to the STAUD Wally Boot. The low-heeled pair is probably my most recommended shoe — and definitely one of my most worn. A low heel is perfect for comfort while still giving you that little extra oomph.
And when the moment calls for something more elevated (no pun intended), there’s nothing like a high-heeled boot to make you feel confident on a night out. Between the two, you’ll always have a go-to for workdays, dinners, and everything in between.
Riding Boots
The riding boot has had a real revival over the past few years, thanks to the return of J.Crew-inspired prep and Ralph Lauren–style classics. It’s the kind of boot that feels timeless, think Princess Diana in her jeans and riding boots. I just found my dream pair of CHANEL riding boots on The RealReal, and I’m already counting down the days until I can wear them with leggings and an oversized sweater. Also… a knee high boot is really the only time I’ll condone a skinny jean.
PSA #1: Stuff your knee high boots in your closet and don’t let them slump down. It will help them keep their shape! I use a boot shaper like this one from Amazon.
PSA #2: These are the best boot socks.
Heeled Knee High Boots
There’s something about a heeled knee-high boot that feels instantly sexy. I love them with sweater dresses or minis, or under a coat like I styled in the image below.
I’ve been seeing a lot of looser fit knee highs lately — it’s definitely giving that slouchy oversized 70s feel. I like something right in the middle.
What’s on your fall wish list this season?
Would you say the Staud boots run TTS? I have wider feet and am wondering if I should size up.