The Ultimate Guide to Rocking Fashionable Ankle Boots This Season

Ankle boots are having a major moment right now. These booties are huge on fashion blogs, Instagram feeds, and city sidewalks for good reason – they’re versatile, comfortable, and seriously chic. Ankle boots go with everything from floral dresses to skinny jeans, adding a little edge or vintage vibe to any outfit.

With so many ankle boot styles in stores, it can be tricky to figure out how to choose the right pair for your personal taste and body type. Some are better for dressing up, others for casual wear, and the wrong shape or height can do your legs or feet no favors!

This in-depth guide covers everything you need to know to find your perfect pair of ankle boots. We’ll explore the top fashionable styles making waves, tips for choosing flattering and comfortable booties, and all those burning questions you may have about wearing and styling them.

Put away the sandals and get ready to step into autumn and boot season with confidence!

Top 5 Fashionable Ankle Boot Styles to Try This Season

Ankle boots come in so many styles these days, it’s hard to figure out where to start. From chunky platforms to pointed-toe slouchy boots, different silhouettes and details give each pair its own vibe.

The five boot trends below are huge right now, pairing well with all your casual to dressy fall and winter outfits. Consider these fashionable ankle boot styles as you shop around and find your new go-to pair!

1. Block-Heeled Booties

Block-heeled booties are classics that have staying power. Set on top of a chunky, block heel 2-3 inches high, these booties are comfortable enough to wear all day while elevating your outfit with a subtle boost.

Pros: The block heel provides more stability than a skinny stiletto, so you don’t have to worry about wobbling. You can find block-heeled booties in every style, from western-inspired to modern chic. They’re easy to dress both up and down.

Cons: The chunky heel lends a heavier feel than slimmer heels. Not the most lightweight or packable travel option.

Examples: Everlane Day Heel, Madewell The Forever Bootie, Thursday Boot Company Captain.

Styling Tips: Balance the chunky heel with flowy dresses or skinny jeans. Block heels with almond-shaped toes elongate the leg. Wear them to the office with trousers or skirts, out to dinner with leather leggings, and around town with oversized sweaters.

Summary: With their sturdy heel and endless versatility, block-heeled booties are a wardrobe staple. They’ll stay on trend for seasons to come.

2. Western-Inspired Booties

Channel your inner cowgirl with western-detailed ankle boots. Featuring decorative stitching, embroidered patterns, metal toe detailing, Cuban heels, and other southwest style elements, these boots make any outfit feel a little bit country.

Pros: Western booties are bold and eye-catching. The mid-heel Cuban style heel provides stability for walking around all day. You canfeel like a badass in these sassy boots.

Cons: The western aesthetic isn’t for everyone. Heeled western boots take some practice to walk in gracefully. They read more casual than dressy booties.

Examples: Frye Veronica Combat, Dolce Vita Graham boots, Steve Madden Carrson Booties, Schutz Ludi Booties

Styling Tips: Lean into the western vibe by pairing these boots with cropped flared jeans, denim cutoffs, or prairie dresses. Alternatively, balance out the country look by wearing them with sleek black trousers or edgy moto jackets.

Summary: Western-inspired ankle booties are fun, retro, and on-trend. For those who love embellished details and a cowgirl vibe, these boots were made for walking.

3. Chunky/Lug Sole Booties

Platform and lug sole booties are everywhere right now. With their thick rubber soles, these boots add major height and make a statement.

Pros: You get a boost without tight high heels. Extra traction makes them great for all-weather wear. They have a very cool, modern, street style vibe.

Cons: Heavy and clunky. Can feel bulky on petite frames. The casual soles don’t work for formal occasions.

Examples: Dr. Martens Jadon and 1460 boots, Prada Monolith Lug Sole Bootie, Alexander McQueen exaggerated sole boots, Jeffrey Campbell chunky sole booties

Styling Tips: Balance chunky soles with skinny jeans, leggings, or mini skirts. Wear them with oversized sweaters or leather jackets for casual cool vibes. Stick to solid colors rather than prints or brights.

Summary: If you love a platform heel but want more comfort, lug sole booties are made for walking in serious style. Just beware of tripping over those thick soles!

4. Pointed-Toe Booties

For an elegant, elongating style, you can’t go wrong with pointed-toe ankle boots. The sharp point visually slims the feet and legs.

Pros: Flattering tapered toe suits many foot shapes. Looks dressy and pulled-together with dresses or trousers. Versatile enough for work or weekends.

Cons: Narrow toe feels constricting for wide feet. Not the most stable or comfy for all-day wear. Point can look severe or dated if style leans very narrow.

Examples: Everlane Day Boot, Sam Edelman Petty Bootie, Coach Lena Pointed Toe Bootie, Vince Camuto Astan Bootie.

Styling Tips: Choose low vamps or rounded points to balance wider calves or ankles. Pair with skinny bottoms like jeans or leggings to create a long vertical line. Works with shorts, dresses and trousers.

Summary: Few boot styles elongate the leg like a pointed toe. This classic silhouette keeps boots feeling refined and flattering season after season.

5. Chelsea Booties

Chelsea boots are ankle boots with elastic side gore panels rather than zippers or buckles. This sleek style is currently trending.

Pros: The stretch panels make them easy to slip on and off. Streamlined, clean look goes with everything. Refined vibe dresses up casual outfits.

Cons: Elastic could lose its stretch over time. Not adjustable for wider calves. Less ankle support due to minimal shaft.

Examples: Everlane The Modern Chelsea, Franco Sarto Carolinna bootie, Blondo Villa Waterproof Chelsea Boot, Timberland Brooklyn Chelsea Boot.

Styling Tips: Pair Chelsea boots with jeans, leggings, or trousers for an effortlessly cool look. The elastic sides complement skinny bottoms. Wear them to the office or out on weekends.

Summary: Chelsea boots bring together comfort, convenience, and style. Their sleek silhouette makes any outfit look polished yet laidback.

How to Choose Fashionable Ankle Boots for Your Style

With so many trendy ankle boot styles to choose from, it can be tricky matching the right pair to your personal taste and lifestyle. Here are tips for picking fashionable booties tailored just for you:

Consider Your Personal Style

Do you lean toward an edgy, rock n’ roll vibe? Or prefer a girly, feminine aesthetic? Are you a preppy lover of classics or boho chic? Your personal style should guide you toward ankle boots that align with the look you love.

Girly styles tend to have shorter block heels, rounded toes, bows and buckles. Edgy booties feature spikes, chains, slouchy silhouettes and lug soles. The western and Chelsea boot trends work well for casual, laidback aesthetics. Sleek pointed-toe boots have a refined, elegant vibe.

Choose booties that jive with your go-to wardrobe and the image you want to project to the world. Don’t just follow trends – find ones that express your unique style.

Choose Boots that Flatter Your Body Type

Ankle boot silhouettes and heel shapes can complement or clash with your body’s shape. Keep these guidelines in mind:

  • Hourglass figures – Booties with heels that are 2-3 inches (a comfortable mid-height) are great for defining your waist. Pointed toes or almond shapes elongate curvy legs beautifully.
  • Pear shaped bodies – Lean toward heels 3+ inches high to add length to the legs. Rounded or square toe boxes help balance curvy hips.
  • Rectangle figures – Go for extra-high heels and pointed toes to mimic curves. Try Chelsea boots – the elastic sides enhance legs.
  • Petite frames – Avoid overly chunky block heels or platform soles to keep booties proportionate. Low vamps visually cut off legs while higher ones elongate.

The right bootie shapes will highlight your best assets and create the illusion of balance in your proportions.

Consider Heel Height

Heel height impacts comfort, walkability, and style. Here’s an overview:

  • Low, flat heels – Most comfortable for walking all day. Very casual vibe best for weekends and travel.
  • Kitten heels 1-2″ – Added stability from a subtle lift. Dress them up or down easily.
  • Block heels 2-3″ – Hit the sweet spot between comfort and dressiness.
  • Chunky, lug soles – Towering height with rock n’ roll edge but heavy to walk in.
  • Stilettos 3.5″+ – Dramatic lift, not meant for all-day wear. Ultra-glam and sexy.

Choose the right heel height for your lifestyle. Commuting all day? Opt for low heels. Want serious style cred? Lug soles make a statement. Adding a flirty flair to your look? Try an ultra-high but less stable stiletto.

Choose Quality Materials

The material ankle boots are made of impacts looks, care, and durability:

  • Leather – Most expensive, but ages well over time. Requires polishing and weatherproofing.
  • Suede – Rich color and texture, but stains easily. Needs waterproofing spray and frequent brushing.
  • Textile – More budget-friendly. Watch for pilling of knit fabrics with wear.

Consider investing in real leather, especially for black or brown neutral booties you’ll wear often. Well-made materials hold up better in the long run.

Find the Right Fit

Ankle boot shafts come in different heights and widths:

  • Ankle-height – Covers just above ankle bone. Allows pants to be tucked in.
  • Calf-height – Extends over the calf muscle. Stylish with skirts or bare legs.
  • Knee-high – Expands versatility of outfits. Hardest to fit off the rack.

The width of bootleg openings should fit smoothly around your ankle and calf without gapping or squeezing. Extended sizes accommodate wider calves. Take measurements for online ordering.

A bootie’s construction impacts comfort. Seek padded insoles, rubber soles and slight platform heels for all-day wear.

Mind Seasonal Appropriateness

Some tips for integrating ankle boots year-round:

  • In winter, chunky lug soles or warm sheepskin linings are cozy. Waterproof styles work in rain or snow.
  • For spring, try open-toe bootie styles to allow air flow as temperatures warm up.
  • In summer, opt for lighter colors like white. Low stacked heels keep feet cooler.
  • For fall, ankles boots pair perfectly with tights, midi skirts and trousers in rich autumnal colors.

With the right seasonal adjustments, you can wear versatile ankle boots nearly any time of year. They add stylish flair to any outfit!

Your Top Ankle Boot Questions, Answered

Booties may look great, but wearing the wrong pair can wreak havoc on your feet. Never fear – we’re tackling all the need-to-know intel so your boots fit and feel fantastic. Read on for answers to those burning bootie questions:

How do I break in stiff new leather or suede booties?

Stiff leather will soften up and mold to your feet over time. But you can speed it up! First, apply leather conditioner inside the shaft. Wear the boots on carpet for an hour, then walk on hard floors in short increments. The friction helps break them in faster.

For suede, use a shoe stretcher and wear thick socks to expand snug spots. Turn to your trusty hair dryer: Apply 20 seconds of heat on tight areas and the seams while the boots are on your feet. Repeat until the suede expands.

Can I wear ankle boots in warmer weather?

Absolutely! Transition to open-toed, cut-out or perforated bootie styles once temperatures warm up. Opt for versions with less structure that are made of breathable textiles or leathers.

Chelsea boots and short shaft styles easily slip on and off if your feet overheat. Stick to muted colors which stay cooler than black boots. Just avoid heavy, bulky styles with extensive coverage in summer.

What socks work best with ankle boots?

No show “footie” socks prevent blisters while keeping boots airy. For added cushioning, try lightweight mid-calf socks that don’t peek out the shaft’s top.

Knit knee-high socks layered under skinny jeans peek out the top of boots for a cute layered look. Thick patterned socks add visual interest when paired with simple dark booties.

How can I make booties more comfortable to walk in?

  • Wider widths prevent pinching toes. Take measurements to find your best fit.
  • Proper heel height for your arch distributes weight.
  • Chunky, low block heels offer stability when walking.
  • Cushioned insoles – replace flimsy ones with memory foam inserts.
  • Rub on moisturizer before wearing – it cuts friction.

Slowly break them in to loosen stiff materials. Visit a cobbler to stretch tight spots.

What pants are most flattering with ankle boots?

Ankle boots look best with slim, close-fitting bottoms:

  • Skinny jeans tuck cleanly into shafts without bunching fabric.
  • Leggings show off boots against your leg’s shape.
  • Pencil skirts taper for a streamlined silhouette.
  • Trouser pants get tucked or neatly cropped above the ankle.

The slimmer the pant, the better it balances an ankle boot’s chunky or sleek lines. Avoid wide leg pants or shorts that overwhelm dainty booties.

How do I prevent booties from rubbing my heels or feet?

  • Wear moisture-wicking footie socks without seams.
  • Apply petroleum jelly or a friction stick on potential hot spots.
  • Place cushioned heel pads or bandages on tender areas.
  • Choose suede over stiff leather which moves with the foot.
  • Have a cobbler install soft suede heel counters inside the boots.
  • For severe rubbing, opt for boots with elastic gore panels.

How do I clean suede or nubuck ankle boots?

  • Remove stains immediately with a suede brush or eraser.
  • Use a suede protective spray regularly to repel dirt and moisture.
  • Allow wet boots to fully dry at room temperature away from heat.
  • Gently brush the nap up with a suede brush once dried.
  • Avoid using cleaners with chemicals that could discolor or damage the material.

How can I wear booties if I have larger calves or ankles?

  • Look for wide-calf, wide-width or extended size offerings.
  • Opt for stretchy Chelsea boots or those with zippers or elastic/buckle closures.
  • Shoes sized up a half-size accommodate thicker socks to fill out the shaft.
  • Boots without pronounced ankle notches or detailed seaming fit larger ankles better.
  • Try mid-calf heights – they’re more forgiving than rigid ankle-height boots.

Are platform booties still in style?

The platform shoe trend is going strong for boots this season! Lug-sole booties from Prada, Miu Miu’s exaggerated platforms, and Saint Laurent’s disco diva styles prove this flashback fashion is here to stay.

Just keep platform boots proportional – avoid overdoing it with both a very high heel and sole. Chunky soles look best balanced with skinny jeans or sleek mini skirts. Scale down for day and save those sky-high platforms for night looks.

What are the best heels for ankle boots – block, chunky, or stiletto?

It depends on your preferences! Here’s how the heel types compare in ankle boots:

  • Block heels offer casual versatility, comfort, and just enough lift. A 2-3 inch height is ideal.
  • Chunky, lug soles make a bold, on-trend statement for serious height. Just know they’re heavy to walk in!
  • Stilettos instantly dress up any look with their staggering height. Not made for all-day wear or lots of walking, however. Save them for special occasions or nights out.

For all-around wear, stick with block heels. But trendy platforms and skinny stilettos each serve their time and place, too!

Rock Those Booties With Confidence!

There you have it – everything you need to know to find stylish, comfortable ankle boots tailored just for you. Trends come and go, but a quality pair of booties is a closet staple for seasons to come.

Follow these guidelines to pick the perfect pair. Look for ones that complement your individual style and body proportions. Consider heel height, materials, fit and seasonal versatility when shopping around.

Most importantly, choose ankle boots that make you feel amazing each time you slip them on. Flaunt your fabulous boots with any outfit. Step out in confidence and style!

We hope this guide gave you lots of great tips and food for thought on your bootie search. What are your favorite ways to wear ankle boots? Which trends are you eyeing this season? Share your thoughts and must-have styles with us below!

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