Fall boots, historically my favorite of all the “shoe” drops, are dang good this year (if not more expensive due to what I think is tariff inflation). But man, do I wear them a lot, even my over-the-knee boots that I’ve had for three years (which takes any winter outfit from basic to date night so fast). Here’s what I’m into this year.
Classic Brown Mid-Calf Boot
Outfit #1: Sweater (Small) | Top (Small) | Scarf | Shorts (Size 27) | Belt (Medium) | Boots (Size 7) | Outfit #2: Jacket (Small) | Sweater (Small) | Scarf | Shorts (Size 2) | Belt (Medium) | Boots (Size 7)
These were my main purchases, and I struggled to find them for under $300, but boy, are they great. They are comfortable, have enough of a heel, and are the perfect color of leather that goes with everything and makes something basic look more polished. They have a stitching detail that makes it look a little more designer. I’m fearful of faux leather not lasting, but there are definitely more budget-friendly options in that category.
Tall Riding Boots | Campus Knee High Boot | Riggs Boots
Go-To Black Leather Mid-Calf Boots
Slouchy Cable-Knit Cardigan Sweater | Jeans (similar) | Boots (similar)
I found these at American Eagle for much less (but they aren’t real leather, should you care about that). They are definitely more of a moto vibe, but for the price are pretty great. I returned them and now they aren’t available for Jess found some great, better quality dupes for you 🙂
Terryy Round Toe Tall Boots | Sajan Riding Boots | Milah Platform Boot
Awesome “To The Knee” Suede Boots
Scarf (Similar) | Long-Sleeved T-Shirt (Large) | Sweater Vest (Small) | Skirt (Size 2) | Belt (Medium) | Boots (Size 38)
I LOVE these boots, and if I had an office job where I wanted to impress (and not wear the same boots daily), I would have absolutely kept these. I love the suede, the pointy toe is so flattering, and the little heel gives you that lift. They are wider in the calf, which I loved the look of, but didn’t slouch. Definitely a more polished vibe that really elevates an outfit.
Kendr-a Western Tall Boots | Kiki Kitten Heel Boots | Erena Kitten-Heel Boots
The Best Over-The-Knee Boots
Jacket (Small) | Long-Sleeved Tee (Medium) | Necklace (Unavailable) | Skirt (Size 2) | Boots (Size 7)
These are my over-the-knee boots I’ve had for years that come in a lot of different colors and are for sure an investment, but they are excellent and frankly hard to find for less in real leather. But Jess found a few that are also awesome.
Logan Over-The-Knee Boots | Linger Boots | Wide Fit Carter Over-The-Knee Block Heel Boots
The Very On-Trend Western Boot
Flannel (2 Extra Small) | Jeans (Size 27) | Boots (Size 7)
I haven’t gone full cowboy boot yet, but these are a great intro into it, just being a bootie. They are comfortable, look great with both jeans, skirts, and shorts, and are perfect for any festival vibe or just as a casual going-out boot.
West Ankle Boot | The Sadie Western Boot | Wesley Ankle Boots
The Go-To Heeled Booties
Outfit #1: Jacket (Small) | Jeans (Size 26) | Favorite Boots (Size 7) | Outfit #2: Knit Sleeve Crop Chore Jacket | Jeans (Size 26) | Boots (Size 7)
These are my favorite heeled booties that I wear most days. They are Korkease, so extremely comfortable, but with a heel that looks good with all the wider pants that I’m sporting. Stylistically, they are just simple and easy to mix with every vibe, up or down. They are super high quality and wear really well (I should know, I had them last for months that I wore every day until Buttercup ate one). Just rebought them and so happy that I did.
Carmine Waterproof Bootie | Downtown Chelsea Boot | Norfolk Staked Heel Ankle Boot
The Perfect Kitten Heel Boots
Outfit #1: Denim Trench | Kitten Heel Boots (Similar) | Outfit #2: Jacket | T-Shirt | Jeans | Boots
I wouldn’t have thought I would wear these kitten-heeled booties so much (from 2 years ago), but y’all, I’m so surprised how often I reach for them and how flattering they are. The pointy toe elongates you, and that little heel says, “I’m a delicate lady, but I don’t need to wear crazy high heels”. Big fan.
Wide-Leg Kitten-Heel Tall Boot | Liora Kitten Heel Boots | Quinley Pointed Toe Bootie
The Weather-Proof Cool Boots
Denim Blazer | Striped Top (Similar) | Jeans (similar) | Sorel Boot | Bag (similar)
These Sorrel waterproof leather boots are my favorites for when it rains. I don’t even wear rain boots up here, just these. I like the chunky rubber sole, and these look GREAT with cute socks and leggings. The perfect PNW boot for any occasion.
Joan FRWD Chelsea Boot | Bend Chelsea Boots
Happy boot season, y’all. xx
*Photos by Kaitlin Green