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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.

  • High Noon Western Cowgirl Booties

    Breaking news! These western cowgirl booties are all the rage this season. They feature a pointed toe, stacked block heel, inner zipper closure, and side elastic knit design, and are composed of faux leather material. Style with a fringe jacket for the country bar!

    Fit & Features

    • Pointed toe, stacked block heel
    • Inner side zipper closure
    • Side elastic knit design
    • Western-inspired styling
    • Pull tabs on each side
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07402-0867

    Category Name: Women’s Shoes

    Price: $8.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Strides Of Sass Satin Platform Pumps

    Stride into the party looking sassy in these satin platform pumps! Catch all the attention in these heels featuring a square toe, chunky design, block heel, and an ankle strap with adjustable buckle closure. Complete the look in a daring party dress.

    Fit & Features

    • Square toe
    • Platform chunky sole
    • Block heel
    • Ankle strap with adjustable buckle closure
    • Satin material
    • Runs true to size

    Style Number/Barcode: 07401-4054

    Category Name: Women’s Shoes

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Smokin' Babe Thigh High Boots

    You'll look and feel smokin' hot and like a babe in these glossy patent leather boots featuring a square toe, block heel, side zipper closure, and a thigh-high shaft length. Complete the look in a sultry LBD for a night on the town! 

    Fit & Features

    • Square toe
    • Block heel
    • Side zipper closure
    • Thigh-high shaft length
    • Glossy patent leather material
    • Runs true to size

    Style Number/Barcode: 07402-0875

    Category Name: Women’s Shoes

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Lady In Rhinestone Stiletto Heels

    Strut walking down the red carpet in these stunning rhinestone stiletto heels featuring an open almond toe, cutout strappy design, stiletto heel, and a closed ankle with zipper closure composed of micro faux suede material. Complete the look with a chic clutch.

    Fit & Features

    • Open almond toe
    • Cutout strappy design
    • Rhinestone embellishments
    • Stiletto heel
    • Closed ankle, zipper closure
    • Micro faux suede material
    • Runs true to size

    Style Number/Barcode: 07403-1597

    Category Name: Women’s Shoes

    Price: $17.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Off Duty Chunky Platform Sneakers

    Elevate your off-duty streetwear vibe in these chunky platform sneakers boasting high fashion inspiration! They feature an almond toe, front lace-up closure, faux leather and mesh knit detailing, and a rubber grip sole. Complete the look in a cool puffer jacket for a day out with friends!

    Fit & Features

    • Almond toe
    • Front lace-up closure
    • Faux leather and mesh knit detailing
    • Chunky platform design
    • Rubber grip sole
    • Runs true to size

    Style Number/Barcode: 07407-0213

    Category Name: Women’s Shoes

    Price: $12.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Double Take Mesh Sling-Back Pumps

    A little sheer, a little sassy—these pumps were made for double takes. The kitten heel keeps it comfy while the sling-back strap serves all-day, all-night vibes.

    Fit & Features

    • 2" Kitten stiletto heel
    • Closed pointed toe
    • Sheer mesh material
    • Adjustable sling-back strap, buckle detail
    • Luxe fit cushioned insole
    • Runs true to size

    Style Number/Barcode: 07401-000337

    Category Name: Women’s Shoes

    Price: $12.97 $30.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK

    Available Size: 6

    Product Badge:
    • Sale
  • Bold Strut Faux Leather Thigh-High Boots

    Show off a bold strut in these sleek faux leather thigh-high boots! They feature a square-shaped toe, a trendy platform, a tall block heel, a form-hugging fit throughout the leg, and a tie-back design. Style these edgy boots with a corset top and a mini skirt for a night out.

    Fit & Features

    • Thigh-high silhouette
    • Square-shaped toe
    • Platform, block heel
    • Inner zipper closure
    • Form-hugging fit
    • Tie-back design
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07402-0861

    Category Name: Women’s Shoes

    Price: $18.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Never Not Fab Over-The-Knee Boots

    In these slouchy boots, you'll never not be fabulous walking all over town! They feature a pointed toe, stiletto heel, inner zipper closure, and an over-the-knee shaft length on faux suede material. Style with a short sweater dress to complete your chic look! 

    Fit & Features

    • Pointed toe
    • Stiletto heel
    • Inner zipper closure
    • Over-the-knee shaft length
    • Slouchy design
    • Faux suede material
    • Runs true to size

    Style Number/Barcode: 07402-0828

    Category Name: Women’s Shoes

    Price: $14.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sleek Energy Over The Knee Boots

    Embody a sleek fashion sense in these over-the-knee boots perfect for elevating your fit! They feature an almond toe, block heel, inner side zipper closure, and an adjustable drawcord. Complete the look in a trendy sweater dress.

    Fit & Feature

    • Almond toe
    • Block heel
    • inner side zipper closure
    • Over-the-knee length shaft
    • Adjustable drawcord
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07402-0833

    Category Name: Women’s Shoes

    Price: $4.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Playful Icon Chunky Platform Pumps

    Doll it up as the playful icon we all know and love! These chunky platform pumps feature a square toe, ankle strap with buckle closure, and block heels, on patent faux leather material. Complete the look in a printed mini dress and earrings for a fun night out!

    Fit & Features

    • Square toe
    • Platform sole
    • Block heel
    • Ankle strap with buckle closure
    • Patent faux leather material
    • Runs true to size

    Style Number/Barcode: 07401-4055

    Category Name: Women’s Shoes

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Runway Ready Legging Stiletto Boots

    It's time to strut in style and treat every street like your runway in these bold legging stiletto boots! Channel iconic celebs in these pants featuring a high-rise elasticized waist, a curve-hugging silhouette, and attached pumps with a pointed toe and a sleek stiletto heel. The silky-smooth nylon fabric offers a high amount of stretch making it super flexible for comfortable wear. Complete your look with a sparkly rhinestone bustier and statement earrings.

    Fit & Features

    • High-rise elasticized waist
    • Pull-on design
    • Form-hugging silhouette
    • Attached pumps, pointed toe, stiletto heel
    • Smooth lightweight nylon fabric
    • High amount of stretch, super flexible
    • Runs true to size

    Style Number/Barcode: 07402-0858

    Category Name: Women’s Shoes

    Price: $12.97 $76.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Total Grudge Lug Sole Loafers

    These faux leather loafers are giving major grudge 90s babe vibes! They feature a round toe, chunky lug platform sole, and heel, and are composed of faux leather material. Complete the look in a trendy plaid matching set.

    Fit & Features

    • Round toe
    • Chunky lug platform sole and heel
    • Classic loafer style
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07405-0036

    Category Name: Women’s Shoes

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Crash The Party Satin Lace-Up Heels

    Go ahead, crash the party looking so stunning in these satin platform heels featuring a closed almond toe and ankle, block heel, lace-up straps with self-tie closure, and chunky silhouette. Complete the look in a sassy skater dress.

    Fit & Features

    • Closed almond toe and ankle
    • Platform chunky sole
    • Lace-up straps, self-tie closure
    • Block heel
    • Satin material
    • Runs true to size

    Style Number/Barcode: 07401-4124

    Category Name: Women’s Shoes

    Price: $4.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Casual Cool-Girl Vibes Knit Sneakers

    Style up these on-trend knit sneakers for a casual cool-girl vibe! They feature a lace-up front with adjustable drawcords, a textured sole, a lightweight knit design, and faux leather accents. Pair with a ribbed knit mini dress and your fave denim jacket.

    Fit & Features

    • Lace-up front, adjustable drawcords
    • Textured sole
    • Pull tabs
    • Knit design
    • Faux leather accents
    • Runs true to size

    Style Number/Barcode: 07407-0214

    Category Name: Women’s Shoes

    Price: $4.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Babe At The Party Stiletto Booties

    Walk tall babe in these stiletto booties at the party! They feature an almond peep toe, back zipper closure, closed ankle, and cutout sides with rhinestone trim on nubuck material. Complete the look with a necklace and earrings.

    Fit & Features

    • Almond peep toe
    • Stiletto heel
    • Closed ankle, back zipper closure
    • Cutout sides
    • Rhinestone trim
    • Nubuck material
    • Runs true to size

    Style Number/Barcode: 07403-1563

    Category Name: Women’s Shoes

    Price: $4.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Mixed Signals 50/50 Knee-High Boots

    Don't get your signals crossed, these knee-high boots are just what your closet needs! They feature an almond toe, low-block heel, side zipper, and are half faux suede and knit compression. Style with a chic handbag. 

    Fit & Features

    • Almond toe
    • Low-block heel
    • Side zipper
    • Knee-high length
    • Half faux suede, half knit compression
    • Runs true to size

    Style Number/Barcode: 07402-0696

    Category Name: Women’s Shoes

    Price: $8.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Always Chic Over-The-Knee Slouch Boots

    Your look will always be chic in these bold over-the-knee boots! They feature a slouched design, a pointed toe, a sleek stiletto heel, and an inner zipper closure. Pair with a corset top and a faux leather skirt and strut in style!

    Fit & Features

    • Over-the-knee fit
    • Slouched design
    • Pointed toe
    • Stiletto heel
    • Zipper closure
    • Faux leather material, smooth lining
    • Runs true to size

    Style Number/Barcode: 07402-0830

    Category Name: Women’s Shoes

    Price: $30.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sleek Story Over The Knee Boots

    Create a sleek and sophisticated outfit with these over-the-knee boots featuring a pointed toe, stiletto heel, and a pull-up/off styling. The boots are composed of faux suede material. Complete the look in a chic trench coat.

    Fit & Features

    • Pointed-toe 
    • Stiletto heel
    • Over-the-knee shaft length
    • Pull-up/off styling
    • Faux suede material
    • Fits true to size

    Style Number/Barcode: 07402-0835

    Category Name: Women’s Shoes

    Price: $6.97 $40.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • My Scene Lace Up Over The Knee Boots

    Steal the scene in these sassy over-the-knee boots featuring a trendy pointed-toe, stiletto heel, side bungee lace-up sides, and inner zipper closure, composed of smooth faux suede material. Complete the look in a short dress for a night on the town!

    Fit & Features

    • Pointed-toe
    • Stiletto heel
    • Side bungee lace-ups
    • Inner zipper closure
    • Over-the-knee shaft length
    • Faux suede material
    • Runs true to size

    Style Number/Barcode: 07402-0827

    Category Name: Women’s Shoes

    Price: $4.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stacked On Style Lace-Up Boots

    Stack on the style with boots that dare to go bold! The faux suede boots feature an over-the-knee shaft length, a sexy bungee strap lace-up back, an inner zipper closure, a pointed toe, and a sleek stiletto heel. Complete the look with a sweater and mini skirt for a dinner date!

    Fit & Features

    • Over-the-knee shaft length
    • Lace-up bungee strap back 
    • Inner zipper closure
    • Pointed toe
    • Stiletto heel
    • Faux suede material 
    • Runs true to size

    Style Number/Barcode: 07402-0825

    Category Name: Women’s Shoes

    Price: $4.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Femme Edge Platform Lug Booties

    Play up your edgy female energy in these faux leather booties featuring a trendy utility design, a round toe, block heel, chunky platform lug sole, knit side panels, and inner zipper closure on an ankle-length shaft. Complete the look in a cool moto jacket!

    Fit & Features

    • Round toe
    • Block heel
    • Chunky platform lug sole
    • Side knit panels and inner zipper closure
    • Ankle-length shaft
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07403-1559

    Category Name: Women’s Shoes

    Price: $12.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cutie In A Lug Bootie

    Hey, there cutie rocking these lug sole booties! They feature a round toe, chunky block heel, and rib-knit upper design on faux leather material. Complete the look in a flannel shacket for cold-weather vibes. 

    Fit & Features

    • Almond toe
    • Lug sole
    • Chunky block heel
    • Rib-knit upper design
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07403-1584

    Category Name: Women’s Shoes

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Walk This Way Strappy Block Heels

    Certified showstopper status. These strappy block heels were made to turn heads—perfect for nights out or leveling up your everyday slay.

    Fit & Features

    • Smooth faux leather with light padding
    • Multi-strap open design
    • Open square toe
    • Block heel
    • Runs true to size

    Style Number/Barcode: 07401-000238

    Category Name: Women’s Shoes

    Price: $12.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Edgy Sole Lug Knee High Boots

    Turn the edge in these knee-high boots featuring a round toe, lug platform sole, and side zipper closure, composed of faux leather material. Complete the look in a cool moto jacket.

    Fit & Features

    • Round toe
    • Lug platform sole
    • Side zipper closure
    • Knee-high shaft length
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07402-0863

    Category Name: Women’s Shoes

    Price: $4.97 $40.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale