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Trendy Shoes to Flex All Season Long

Hot Picks for Your Main Character Moment

Step into your spotlight with trendy shoes that make every outfit pop. From sun-soaked hangs to formal soirées, Windsor’s shoe collection is stacked with heels, sandals, boots, booties, and more—basically, every style you need to go from “getting ready” to “it girl energy” in a snap. Whether you’re that always-put-together friend, the spontaneous social butterfly, or somewhere in between, your next obsession starts here.

Dress Heels That *Do the Most*

This season’s edit? Total main character. Lace-up heels with 3D butterfly and flower details bring flirty vibes, while rhinestone-covered stilettos turn heads from every angle. For weddings or big event energy, dress heels in metallic finishes and platforms with trendy hardware give instant glam. Bridesmaid heels and wedding dress shoes stun in sleek satins, mesh, or glittery faux leather—and they’re all made with Windsor’s comfort-first insoles so your feet feel as good as you look.

Everyday Shoes with Main-Character Energy

On casual days, keep your cool in mules, flats, or low-block heels that go with everything from joggers to jean shorts. Into a bold boot moment year-round? We got you. Knee-high boots, cowgirl boots, and lug sole boots bring that unexpected edge to your festival ‘fit or rooftop vibe. And yes, they come in everything from classic neutrals to dopamine-bright colors made for selfies.

The Details That Make a Difference

With almond, square, pointy, peep toe, and open-toe styles, there’s a toe shape for every mood. Adjustable straps, metallic sheens, and textures like patent faux leather and all-over rhinestones make it easy to build your look from the feet up. And because we know you’ve got places to be (and pics to post), most styles come in multiple heel heights so you can slay your day—comfortably.

Trendy Shoes = Your New Flex

Scroll less and slay more with Windsor’s must-have shoes. These trendy shoes are ready to upgrade your rotation, one click, tap, or store trip at a time.

What Shoes Can I Wear With Jeans?

Honestly? Anything from Windsor. Pair your straight-leg denim with block heels or heeled mules for that low-effort, high-style vibe. Craving something cooler for cropped jeans? Try pointed-toe stilettos or trendy neutral-toned booties to elevate your look.

For casual slays, strappy sandals or flats are perfect for brunch or running errands with style. Want to dress up your fav dark-wash jeans? Go for a glitter heel, bold platform, or clear mule—you’ll be out the door and dressed to impress in seconds.

What Shoes Can I Wear With Jeans?

The best shoes to wear with jeans depend on your denim style, wash, and overall look. Black ankle boots or heeled mules pair effortlessly with straight-leg jeans for a sleek, polished vibe. For cropped denim, opt for pointed-toe heels, strappy mules, or neutral-toned boots to elevate your outfit for work or date night.

Keeping it casual? A stylish yet comfortable sandal adds an effortless edge to your everyday look. If you're dressing up dark-wash jeans with a bustier or statement-sleeve top, go for trendy clear mules or block heels that are easy to wear for hours.

  • Simply Polished Cutout Stiletto Pumps

    The kind of heels that instantly pull a look together. With a sleek cutout shape and classic stiletto lift, these pumps bring chic confidence and a touch of edge to any outfit—from office 'fits to dinner plans.

    Fit & Features

    • 4" Stiletto heel
    • Pointed toe
    • Side cutout design
    • Faux leather material
    • Luxe fit cushioned insole
    • Runs true to size

    Style Number/Barcode: 07401-000389

    Category Name: Women’s Shoes

    Price: $34.90

    Availability: In Stock

    Available Color: WHITE, WINE

    Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10

  • Retro Revival Faux Leather Mary Janes

    A classic with a twist—these slingback Mary Janes bring vintage vibes into the now with a block heel and sleek faux leather finish. Perfect with trousers, minis, or tights for that polished-cool look.

    Fit & Features

    • 3.5" Block heel
    • Closed square toe
    • Slingback strap with adjustable buckle closure
    • Mary Jane silhouette
    • Luxe fit cushioned insole
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07401-000386

    Category Name: Women’s Shoes

    Price: $34.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 10

  • Chic Step Strappy Block Heels

    The go-with-everything heel your closet’s been waiting for. These strappy block heels bring that clean, minimalist vibe with all-day comfort—because chic shouldn’t come with a time limit.

    Fit & Features

    • Block heel
    • Square toe
    • Strappy design
    • Closed ankle
    • Adjustable ankle strap with buckle closure
    • Cushioned insole
    • Faux suede material
    • Runs true to size

    Style Number/Barcode: 07401-000387

    Category Name: Women’s Shoes

    Price: $30.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10

  • Party Edit Bow Mules

    Shimmer, shine, and step out. These metallic bow mules bring playful sophistication with a sleek pointed toe and stiletto heel—aka your new favorite way to add instant glam.

    Fit & Features

    • 3" Stiletto heel
    • Pointed closed-toe with bow accent
    • Cushioned insole
    • Metallic material
    • Runs true to size

    Style Number/Barcode: 07401-000388

    Category Name: Women’s Shoes

    Price: $34.90

    Availability: In Stock

    Available Color: SILVER

    Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10

  • Sweet Finish Satin Bow Heels

    Flirty from every angle. These satin stiletto heels bring sleek sophistication with a playful twist—square toes, glossy finish, and statement back bows made to steal the spotlight (subtly, of course).

    Fit & Features

    • 3.5" Stiletto heel
    • Square toe
    • Sleek straps
    • Back bow
    • Closed ankle, adjustable strap with buckle closure
    • Satin material
    • Runs true to size

    Style Number/Barcode: 07401-000390

    Category Name: Women’s Shoes

    Price: $32.90

    Availability: In Stock

    Available Color: BLACK, HUNTER

    Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10

    Product Badge:
    • New Arrival
  • Attitude Strut Patent Stiletto Boots

    When the outfit needs attitude—these boots deliver. With a glossy patent finish, sleek pointed toe, and knee-high silhouette, they’re basically confidence in footwear form. Perfect for days downtown, date nights, and everyday styling.

    Fit & Features

    • Stiletto heel
    • Pointed-toe
    • Side zipper closure
    • Under-the-length shaft
    • Glossy patent faux leather material
    • Runs true to size

    Style Number/Barcode: 07402-000060

    Category Name: Women’s Shoes

    Price: $64.90

    Availability: In Stock

    Available Color: WINE, IVORY

    Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10

  • Frontier Chic Moto Boots

    Bring the western energy into your fall lineup with these knee-high boots. Featuring harness buckle detailing, a pointed toe, and a block heel, they bring western flair to a city chic vibe, perfect for styling with any look.

    Fit & Features

    • Block heel
    • Pointed-toe
    • Harness buckle detailing
    • Knee-high shaft length
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07402-000056

    Category Name: Women’s Shoes

    Price: $65.90

    Availability: In Stock

    Available Color: BLACK, BROWN

    Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10

  • Totally Heart Flat Sandals

    Fall in love with these heart sandals perfect for everyday styling!

    Fit & Features

    • Almond toe
    • Wide band with heart
    • Flat faux leather insole
    • Trim accents
    • Runs true to size

    Style Number/Barcode: 07405-0228

    Category Name: Women’s Shoes

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sleek Intentions Slingback Heels

    Effortless sophistication, start to finish. These faux suede slingback heels blend a sharp pointed toe with a classic stiletto heel—perfect for elevating your day or night look.

    Fit & Features

    • 4" Stiletto heel
    • Closed pointed-toe
    • Slingback adjustable ankle strap, buckle closure
    • Faux suede material
    • Runs true to size

    Style Number/Barcode: 07401-000419

    Category Name: Women’s Shoes

    Price: $32.90

    Availability: In Stock

    Available Color: TAUPE, BROWN

    Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10

  • Radiance Rhinestone Metallic Stiletto Heels

    When the invite says “dress to impress,” these heels deliver. Featuring sleek metallic straps with rhinestone accents and a sky-high stiletto, they’re made for making an entrance at parties and events.

    Fit & Features

    • 4" Stiletto heel
    • Almond toe
    • Rhinestone-embellished straps
    • Adjustable ankle strap with buckle closure
    • Luxe fit cushioned insole
    • Metallic material
    • Runs true to size

    Style Number/Barcode: 07401-000399

    Category Name: Women’s Shoes

    Price: $34.90

    Availability: In Stock

    Available Color: SILVER

    Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10

  • Western Sleek Knee-High Block Heel Boots

    Flaunt your style in western sleek knee-high block heel boots. With a stacked heel, pointed toe, and pull tabs, these boots are your go-to for a chic, confident stride.

    Fit & Features

    • Stacked block heel
    • Distressed faux leather material
    • Knee-high
    • Pointed toe
    • Partial inner zipper closure
    • Pull tabs
    • Runs true to size

    Style Number/Barcode: 07402-1070

    Category Name: Women’s Shoes

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Season’s Sleek Thigh-High Stiletto Boots

    The definition of drama. These scrunch thigh-high boots strike the perfect balance of luxe and daring, with a pointed toe and sleek stiletto heel made to elevate all your fall outfits.

    Fit & Features

    • 3” stiletto heel, 9.5” leg opening, 23” shaft
    • Pointed-toe
    • Side zipper closure
    • Thigh-high scrunch silhouette
    • Sleek faux leather material
    • Runs true to size

    Style Number/Barcode: 07402-000062

    Category Name: Women’s Shoes

    Price: $58.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10

  • Polished Intent Patent Mules

    Serving sophistication with a side of attitude. These patent mules feature a sleek pointed toe and a sculpted heel that takes you from dinner to downtown without missing a step. 

    Fit & Features

    • Stiletto heel
    • Closed pointed-toe
    • Cushioned insole
    • Faux leather patent material
    • Runs true to size

    Style Number/Barcode: 07401-000414

    Category Name: Women’s Shoes

    Price: $34.90

    Availability: In Stock

    Available Color: BURGUNDY

    Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10

  • Glam Agenda Rhinestone Bow Pumps

    Classic, but make it extra. These satin pumps steal the spotlight with a sharp pointed toe and a statement rhinestone bow that brings pure “it girl” energy to every step.

    Fit & Features

    • 3.5" Stiletto heel
    • Closed pointed-toe
    • Statement bow with rhinestones
    • Adjustable ankle strap with buckle closure
    • Luxe fit cushioned insole
    • Satin material
    • Runs true to size

    Style Number/Barcode: 07401-000412

    Category Name: Women’s Shoes

    Price: $36.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10

    Product Badge:
    • New Arrival
  • Starstruck Rhinestone Block Heel Booties

    Turn every step into a spotlight moment. These rhinestone booties dazzle with all-over sparkle, a sleek pointed toe, and a block heel made for dancing the night away (or just stealing the scene).

    Fit & Features

    • 4" Block heel
    • Pointed toe
    • Side zipper closure
    • Ankle-length shaft
    • Rhinestone-embellished metallic material
    • Runs true to size

    Style Number/Barcode: 07403-000019

    Category Name: Women’s Shoes

    Price: $56.90

    Availability: In Stock

    Available Color: SILVER

    Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10

  • Wrapped in Radiance Stiletto Heels

    When your shoes are the outfit, these metallic stiletto heels flaunt a sleek almond toe and sparkling rhinestone spiral straps that wind up the leg for that head-turning, “don’t wait up” kind of entrance.

    Fit & Features

    • 4" Stiletto heel
    • Almond toe
    • Rhinestone-embellished straps
    • Rhinestone-embellished spiral ankle strap
    • Luxe fit cushioned insole
    • Metallic material
    • Runs true to size

    Style Number/Barcode: 07401-000410

    Category Name: Women’s Shoes

    Price: $42.90

    Availability: In Stock

    Available Color: SILVER

    Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10

    Product Badge:
    • New Arrival
  • The Night Is Yours Bow Mules

    Dress to dazzle in these rhinestone-studded mule heels featuring an oversized bow accent that steals the spotlight with every step. The sleek stiletto heel and slip-on design bring instant glam to your night-out rotation.

    Fit & Features

    • Stiletto heel
    • Square toe
    • Statement bow detail and rhinestone embellishments
    • Luxe fit cushioned insole
    • Faux suede material
    • Runs true to size

    Style Number/Barcode: 07401-000413

    Category Name: Women’s Shoes

    Price: $40.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10

  • Delicate Drama Stiletto Slingback Pumps

    Delicate meets daring. These sheer lace slingback pumps bring instant elegance with a pointed toe and sleek stiletto heel—made for occasions when you want to look soft but feel unstoppable.

    Fit & Features

    • 4" Stiletto heel
    • Closed pointed-toe
    • Slingback ribbon ankle strap with bow accent
    • Luxe fit cushioned insole
    • Sheer lace trim, faux leather material
    • Runs true to size

    Style Number/Barcode: 07401-000418

    Category Name: Women’s Shoes

    Price: $32.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10

    Product Badge:
    • New Arrival
  • Gloss Effect Patent Stiletto Boots

    The kind of boot that owns every room. These patent stiletto knee boots serve glossy drama with a sculpted pointed toe and sleek silhouette—made for statement looks and confident strides.

    Fit & Features

    •  3.5” stiletto heel, 7.5” leg opening, 15” shaft height
    • Pointed-toe
    • Inner zipper closure
    • Knee-length shaft
    • Glossy patent faux leather material
    • Runs true to size

    Style Number/Barcode: 07402-000063

    Category Name: Women’s Shoes

    Price: $49.90

    Availability: In Stock

    Available Color: WINE

    Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10

  • Studded Edge Pointed Kitten Pumps

    These pointed toe kitten pumps bring attitude with stud and grommet details. The low heel keeps them comfy while the hardware trim makes sure your look stays unapologetically bold.

    Fit & Features

    • 2.5" Kitten heel
    • Closed pointed toe, grommet and stud embellishments
    • Cushioned insole
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07401-000422

    Category Name: Women’s Shoes

    Price: $32.90

    Availability: In Stock

    Available Color: BLACK, WHITE

    Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10

  • Grit And Glam Studded Kitten Pumps

    A western twist on city chic—these studded pointed pumps bring just the right amount of grit to your polished fits.

    Fit & Features

    • Kitten heel
    • Closed pointed-toe with studded detailing
    • Cushioned insole
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07401-000424

    Category Name: Women’s Shoes

    Price: $32.90

    Availability: In Stock

    Available Color: WINE

    Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10

  • Night Luxe Faux Fur Stiletto Boots

    Statement boots, but make them cozy glam. These faux leather stilettos are finished with plush faux fur trim for a bold mix of edge and luxe—perfect for nights out when you want your shoes to do the talking.

    Fit & Features

    • Stiletto heel
    • Pointed toe
    • Faux fur cuff
    • Sleek under-the-knee length shaft
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07402-000064

    Category Name: Women’s Shoes

    Price: $56.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10

    Product Badge:
    • Best Seller
  • Autumn Muse Under-The-Knee Boots

    Classic, chic, and made to strut. These knee-high boots feature a sleek faux suede finish with a block heel that gives height without sacrificing comfort—perfect for everything from city strolls to dinners out.

    Fit & Features

    • 3.5" Block heel, 8" leg opening, 12" shaft height
    • Almond toe
    • Side zipper closure
    • Under-the-knee length shaft
    • Faux suede material
    • Runs true to size

    Style Number/Barcode: 07402-000068

    Category Name: Women’s Shoes

    Price: $49.90

    Availability: In Stock

    Available Color: CAMEL

    Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10

  • Sparkle Scene Rhinestone Strappy Faux Leather Block Heels

    Sparkle up the scene at your next formal affair in these rhinestone strappy faux leather block heels! They feature an open square-shaped toe, a glitzy rhinestone-adorned strappy design with a chic center knotted detail, a thin adjustable ankle strap with a buckle closure, a closed back, a padded insole for comfortable wear, and a sturdy block heel. Style with the matching clutch for a seamless glam look!

    Shop Matching Clutch: Sparkle Scene Rhinestone Foldover Clutch

    Fit & Features

    • 4.5" Block heel
    • Faux leather upper
    • Open square toe
    • Rhinestone strappy design with knotted detail
    • Adjustable ankle strap with buckle closure
    • Closed back, luxe fit padded insole
    • Runs true to size

    Style Number/Barcode: 07401-4790

    Category Name: Women’s Shoes

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free