Autumn always feels like the season of reinvention, and boots are my favorite. It’s funny how a single pair can change the way you walk, the way you feel about facing a cloudy Monday or a spontaneous night out.
Over the years, I’ve collected boots in every shade and silhouette, but styling them for each part of my life has become my favorite creative challenge each fall.
Whether you’re pulling on well-loved Chelsea boots for errands or zipping into croc-effect heels for an evening with friends, every day brings a new opportunity to experiment.
Before we step into all the possibilities, below is a cheat sheet you’ll want to save. Classic autumn colors and favorite brands, so you can mix and match according to your mood.
| Occasion | Boot Style | Outfit Idea |
|---|---|---|
| Everyday Errands | Lug-sole ankle boots | Cuffed jeans, cozy cable-knit, classic trench (Dr. Martens or Ganni) |
| Office-Ready | Knee-high riding boots | Slim-leg trousers, oversized sweater, sleek belt (Sam Edelman, Tory Burch) |
| Girls’ Night Out | Croc-effect or pointed Chelsea | Mini skirt, silk blouse, statement coat (Vagabond Shoemakers, By Far) |
| Weekend Plans | Chunky combat or biker boots | Leather jacket, slim jeans, vintage tee (AllSaints, Frye, Steve Madden) |
| Autumn Brunch | Western/cowboy boots | Flowy midi dress, denim jacket, layered necklaces (Isabel Marant, Free People) |
| Creative Meetings | Chelsea boots & Chelsea-inspired | Pleated skirt, cropped sweater, tailored blazer (Everlane, & Other Stories) |
| City Strolls | Slouchy (paper-bag) boots | Cropped wide-leg pants, ribbed turtleneck, slouchy coat (Paris Texas, Schutz) |
| Date Night | Croc-effect & animal-print boots | Slip dress, boxy blazer, delicate jewelry (Stuart Weitzman, Mango) |
| Minimalist Days | Tucked-ankle boots | Straight-leg jeans, crisp white shirt, chunky cardigan (Aeyde, Dear Frances) |
Experiment with rich hues like oxblood, caramel, moss green, and classic black. The beauty of fall boots is how they make each day feel a little more like your own runway.
Chunky Combat & Biker Boots
Some mornings call for a little attitude, and nothing answers better than chunky combat or biker boots. This season, combat boots appear in everything from classic black to bold hues like olive or burgundy. Straight-leg or skinny jeans work beautifully tucked into the boots for a sharp finish, or let the hem graze the top for a relaxed approach.
Oversized knit sweaters and moto jackets deliver that effortless, tough-chic vibe. For softer moments, pair combat boots with a floaty midi dress or a floral skirt—the contrast keeps the look playful and unexpected. Patterned socks peeking out above the boots can add a flash of personality, while a wide belt cinched over a sweater shapes the silhouette. Seek out modern takes from Ganni or classic styles from AllSaints to refresh your collection.
Classic Knee-High Riding Boots
Equestrian-inspired knee-high riding boots bring polish to any fall outfit, especially in shades of chocolate, bone, or classic black. For busy office days or lunch meetings, try tucking slim-leg trousers or skinny jeans into knee-high boots, then add an oversized sweater and a sleek belt for a streamlined, subtly preppy effect.
Mini and midi skirts also pair well with riding boots, particularly when styled with cozy knee-high socks in tonal hues. Monochrome outfits—think head-to-toe taupe or charcoal—create a lengthening effect under a tailored wool coat. For refined designs, explore brands like Sam Edelman and Tory Burch.
Western & Cowboy Boots
Western boots introduce a little rebellious energy and instantly update classic fall looks. Modern pairs range from distressed brown leather to glossy metallics, often finished with a comfortable stacked heel. Cowboy boots complement flowy floral dresses or denim cut-offs for that Midwest-meets-Parisian edge.
Straight-leg jeans also work beautifully with these boots, especially when layered with a longline cardigan or a faux shearling jacket for extra warmth. Add a vintage-inspired bandana or a concho belt to complete the look. Unique styles from Isabel Marant and Free People deliver authentic Western flair in autumn’s richest colors.
Chelsea Boots & Chelsea-Inspired
Chelsea boots are the answer for days when both comfort and polish are non-negotiable. Their ankle-length shape and signature elastic side panel fit seamlessly with most outfits. Slim trousers, pleated midi skirts, and tucked-in knits give Chelsea boots a classic, effortless finish.
Look for pairs with a patent or metallic twist to add edge, or try western-tinged Chelseas with subtle pointed toes and detailed stitching. Cropped pants highlight the boot’s sleek lines, and playful socks can provide a personal touch. For timeless options, Everlane and & Other Stories are favorites, while Ganni offers standout colors and prints.
Chunky Lug-Sole Ankle & Platform Boots
Chunky lug-sole boots are perfect for brisk autumn days, bringing both style and a little extra height. Rugged soles pair well with cuffed jeans or mini skirts and chunky knits, grounding the outfit with confidence.
Play with proportions by adding oversized blazers, balloon-sleeve sweaters, or wide-leg cropped pants. For a cheerful twist, choose boots in unexpected shades to brighten up neutral outfits. Try styles from Dr. Martens, Ganni, or Vagabond Shoemakers for a blend of comfort and standout design.
Slouchy (Paper-Bag) Boots
Soft leather or suede slouchy boots bring movement and a relaxed touch to any look. Let them peek out from beneath wide-leg corduroys or culottes, paired with a ribbed turtleneck and a cozy coat for an effortless feel.
A chunky knit dress belted at the waist with slouchy boots creates textured depth, while delicate anklets or chain jewelry grazing the top add a subtle glimmer. Explore slouchy boot options in soft neutrals and fall shades from Paris Texas and Schutz.
Croc-Effect & Animal-Print Boots
Croc-effect and animal-print boots deliver instant glamour, elevating outfits from simple jeans and sweaters to silk slip dresses. For evening, croc boots in rich brown or deep burgundy pair beautifully with a slinky dress and an oversized blazer, merging sophistication with ease.
Mix animal prints for added intrigue—a snakeskin boot with a leopard scarf, for example. Gold jewelry and a structured bag echo the boots’ luxe vibe. Look for wearable statement pairs at Stuart Weitzman and Mango.
Tucked-Ankle Boots
Tucked-ankle boots, or short booties that peek from beneath straight-leg or flared jeans, create a minimalist, chic silhouette that’s quickly regaining popularity. Soft bone and caramel leathers work especially well for this look.
Pair these boots with straight-leg jeans, a crisp white shirt, and a chunky cardigan. A boxy, cropped jacket brings balance, while barely-there pop-color socks add a touch of personality. Consider elegant options from Aeyde and Dear Frances for a versatile finish.
