Ankle boots are a timeless and adaptable fashion choice, offering both comfort and style. They’re a fantastic addition to any wardrobe, suitable for every season. Whether you’re considering your first pair, seeking advice on styling tan ankle boots, or simply need fresh ideas, this comprehensive guide provides essential tips for wearing ankle boots throughout the year.
Autumn/Winter Trends
With shorter days and dropping temperatures, ankle boots are back! They soften the blow of winter’s arrival. Struggling to style your winter look with ankle boots? Unsure what shoes complement skinny jeans? Ankle-height boots are flattering and perfect for the season.
Dark-hued boots in black, tan, and brown are perfect for transitioning from autumn to winter. As darker shades dominate wardrobes, footwear becomes a focal point for self-expression. Consider leopard prints, studs, velvet textures, frills, or intricate embroidery. These ankle boot styles pair exceptionally well with skinny jeans, a favorite look among celebrities in 2025.
A/W Inspo: Jeans and Boots
For a stylish look with skinny jeans and ankle boots, choose black or blue denim. These colors pair perfectly with brown shades. You’ll always know how to style brown ankle boots!
Considering boyfriend or bootcut jeans this season? Avoid tucking them into your boots – a fashion faux pas! Instead, try rolling up your jeans slightly. This reveals stylish, frilly socks peeking above the ankle. Alternatively, opt for frayed edges, a trendy choice right now. Both styles beautifully showcase boot embellishments or a cute, feminine heel. Perhaps even combine both elements for a stunning look! More on that in our top 15 style tips!
A/W Inspo: Boots to Wear With Dresses
Tan ankle boots paired with dresses and opaque tights are a perfect winter style. Consider warm, fall-inspired colors to match the season. If your top has a pattern, choose simpler, more understated boots.
A/W Inspo: What to Wear With Black Boots
The classic black boot remains a wardrobe staple. Wondering what to wear with black ankle boots this winter? They truly complement almost any outfit! The contrast between delicate floral patterns and robust boots creates a stylish look, even in colder weather. Feel confident knowing your favorite black boots, whether heeled or flat, pair perfectly with skinny jeans and oversized sweaters on weekends. They also work well with shirts and dresses for the workday (we especially love office ankle boots), and even for those after-work cocktail outings.
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Spring/Summer Trends
Spring’s arrival doesn’t mean you have to retire your ankle boots. Rest assured, your favorite boots are still perfectly stylish!
S/S Inspo: How to Wear Ankle Boots with Dresses
A dress and boots combo is a stylish and comfy choice for daytime wear. Many new boot styles feature sandal-like details, such as slingbacks, offering more breathability. Brown boots paired with summery outfits create a fantastic daytime look. Try a patterned spaghetti strap dress and denim jacket for a relaxed feel. Alternatively, high-waisted shorts and ankle boots are perfect for hot weather.
Floral embellishments on boots are trending now. They pair perfectly with dresses for any occasion. This style is especially fitting for spring 2025.
S/S Inspo: Evening Outfit with Boots
For nighttime ankle boot styles, consider heeled peep-toe or pointed boots. They pair perfectly with shorts or skirts. They also offer a chic, comfortable option with jeans and a leather jacket. Ankle boots are incredibly versatile, easily elevating or relaxing any look. The ever-stylish mid-heel ensures you can dance all night comfortably!
Heeled Chelsea boots create a stunning mini skirt and ankle boot pairing, if you’re up for it. They also look fantastic with dresses. Wondering what to wear with black skinny jeans? Problem solved! This is an ideal evening outfit.
S/S Inspo: Office Ankle Boots
Ankle boots in summer workwear? Absolutely! A pencil skirt paired with boots creates a chic look. Choose a mid-heel for leg elongation and all-day comfort. Flowy midi skirts are essential for warm workdays. They look effortlessly stylish when combined with boots.
Photo Credit: Pinterest
Our Top 15 Ankle Boots
Our curated top 15 boots are perfect for any season, style, or occasion. Each pair offers a unique touch. A black leather boot is a must-have, but many brands now feature colorful heels or delicate ankle embroidery. We especially adore the burgundy heel from Oasis shown below. It will instantly elevate your style.
Beyond classic leather, suede remains a top trend. We’re especially drawn to the fall-inspired reds, browns, and greens. The rich, deep blue hue of the Chloe ankle boots exudes luxury. The intricate scalloped stitching on the front adds a beautiful detail.
In 2025, our favorite floral patterns are styled with comfortable mom jeans and a cozy oversized sweater for daytime wear. They also pair perfectly with a classic leather skirt for an evening look. The same versatility applies to those bold leopard print boots!
This collection offers a variety of heel heights for every occasion. Planning a full day of shopping? Classic Chelsea boots are an excellent choice. Need ankle boots for the office or a dressier event? A mid-heel is the ideal solution.
Do you have a favorite one already?
