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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.

  • Trendy Chic Square Toe Stiletto Booties

    Trendy and oh-so-chic, these stiletto booties will amp up your fall and winter wardrobe! They feature an ankle-high design with a square toe and a triangle-shaped stiletto heel. Pair these faux microsuede booties with a curve-hugging pencil skirt and a fitted blazer for a stylish workwear look.

    Fit & Features

    • Ankle-high design
    • Square toe
    • Triangle-shaped stiletto heel
    • Back zipper closure
    • Faux microsuede material

    Style Number/Barcode: 07403-0564

    Category Name: Women’s Shoes

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • On to the Next Chunky Sneakers

    Let these sneakers take on to the next stylish moment! The sneakers feature a lace-up front, an almond toe, and a two-tone design. Complete your look with an oversized tee and biker shorts.

    Fit & Features

    • Almond toe
    • Pull tabs at the back 
    • Two-tone design 
    • Lace-up front
    • Chunky textured sole

    Style Number/Barcode: 07407-0177

    Category Name: Women’s Shoes

    Price: $18.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • On the Go Chunky Sneakers

    Throw on these sneakers for the girl on the go! The sneakers feature a lace-up front, pull tabs at the back, and a chunky platform sole. Complete your look with a tie dye matching separates to nail those casual vibes. 

    Fit & Features

    • Lace-up front
    • Almond toe
    • Pull tabs at the back 
    • Chunky platform sole
    • Faux leather material

    Style Number/Barcode: 07407-0181

    Category Name: Women’s Shoes

    Price: $12.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Keep on Moving On Basic Sneakers

    Move on to the next big thing in these basic sneakers that keep it chic and casual. The sneakers feature a lace-up front, an almond toe, and a jelly insole detail. Complete look with biker shorts and an oversized tee. 

    Fit & Features

    • Lace-up front
    • Almond toe
    • Jelly insert within sole

     


    Please be advised that these sneakers run 1 size too small.

    Style Number/Barcode: 07407-0183

    Category Name: Women’s Shoes

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Faux Suede Stiletto Sock Booties

    Looking to amp up your everyday basic 'fit? These faux suede sock booties are a definite must-have. Featuring a trendy pointed toe and sleek stiletto heel, they will elevate any look. Pair them with a curve-hugging midi dress for a chic vibe.

    Fit & Features

    • Pointed toe
    • Inner zipper closure
    • Stiletto heel
    • Sock bootie design
    • Faux suede fabric

    Style Number/Barcode: 07403-0368

    Category Name: Women’s Shoes

    Price: $14.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Faux Leather Quilted Heeled Mules

    Slip on these chic faux leather heeled mules to add a trendy vibe to your workwear look! They feature an open square toe, a wide strap with quilted detailing, and a short thin heel. Pair these mules with tapered paper bag pants for an adorable work from home 'fit.

    Fit & Features

    • Open square toe
    • Wide strap with quilted detailing
    • Open back
    • Short thin heel
    • PU material

    Style Number/Barcode: 07401-2447

    Category Name: Women’s Shoes

    Price: $14.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • A Clear Choice Stiletto Heels

    These chic clear stiletto heels are clearly the right choice for you! They feature an open pointy toe with a clear PVC adjustable ankle strap and a sleek stiletto heel. Pair these with a curve-hugging bodycon dress for your next date night.

    Fit & Features

    • Open pointed toe
    • Clear PVC toe strap
    • Clear PVC adjustable ankle strap
    • Open back
    • Stiletto heel

    Style Number/Barcode: 07401-2485

    Category Name: Women’s Shoes

    Price: $12.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Faux Suede Platform Lace-Up Booties

    Elevate your chic everyday style with these faux suede booties! They feature a chunky platform and an adorable lace-up back detail. Pair these booties with dark wash skinny jeans for an elongated look.

    Fit & Features

    • Ankle-high design
    • Almond toe
    • Inner zipper closure
    • Chunky platform
    • Tall block heel
    • Lace-up back detail
    • Faux suede material

    Style Number/Barcode: 07403-0345

    Category Name: Women’s Shoes

    Price: $20.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Step Out In Style Faux Leather Combat Booties

    Slay each step in these stylish faux leather booties! They feature an ankle-high design with a trendy lace-up front, a lug sole, and a stacked block heel. Pair these booties with a basic little black dress to make a chic statement.

    Fit & Features

    • Round toe
    • Lace-up front
    • Inner zipper closure
    • Pull tabs
    • Lug sole
    • Stacked block heel
    • PU material

    Style Number/Barcode: 07403-0600

    Category Name: Women’s Shoes

    Price: $16.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sleek And Sassy Over The Knee Block Heeled Boots

    Sleek and sassy, these over the knee boots will make any 'fit all the more chic! They feature a faux leather material and a sturdy block heel. Complete your fall-ready look with a sweater dress and gold hoops.

    Fit & Features

    • Over the knee design
    • Almond toe
    • Block heel
    • Inner zipper closure
    • PU material

    Style Number/Barcode: 07402-0225

    Category Name: Women’s Shoes

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Peep Toe Platform Block Heels

    Showcase your adorable pedi in these classic peep toe block heels! They feature an added platform and a sturdy tall block heel. Pair these chic heels with your fave workwear look and you'll be a total boss babe.

    Fit & Features

    • Almond shaped peep toe
    • Closed back
    • Platform
    • Block heel

     

    Please be advised that these heels run 1/2 size small. 

    Style Number/Barcode: 07401-2478

    Category Name: Women’s Shoes

    Price: $12.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Heart Eyes Only Slide Sandals

    These comfy-cute slides feature a clear strap topped with a bold heart charm—perfect for pool days, park hangs, or running errands like a style icon.

    Fit & Features

    • Round toe
    • Clear PVC strap with heart cutout
    • Comfortable footbed
    • Platform sole
    • Runs true to size

    Style Number/Barcode: 07404-000005

    Category Name: Women’s Shoes

    Price: $9.97 $20.90

    On Sale: Yes

    Availability: In Stock

    Available Color: CLEAR

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

    Product Badge:
    • Sale
  • Bold Lace-Up Platform Block Heels

    Be brave and bold with your style in these fab platform block heels! They feature a front lace-up design with a tall sturdy block heel. Pair these statement shoes with a faux leather mini skirt to bring some edginess to your look.

    Fit & Features

    • Open almond toe
    • Thick toe strap
    • Front lace-up design
    • Open back
    • Platform
    • Tall block heel
    • Faux suede


    Please be advised that these heels run 1 size too small.

    Style Number/Barcode: 07401-2474

    Category Name: Women’s Shoes

    Price: $12.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Add Some Edge Faux Leather Combat Boots

    Add an effortless edge to your everyday look with these combat boots! They feature a patent faux leather material with a lace-up front and a chunky platform. Pair these boots with destructed denim and a graphic tee to go chill with your squad.

    Fit & Features

    • Round toe
    • Lace-up front
    • Pull tabs
    • Inner zipper closure
    • Platform
    • Lug sole
    • Patent faux leather material

    Style Number/Barcode: 07403-0353

    Category Name: Women’s Shoes

    Price: $36.90

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Lace-Up Faux Suede Over The Knee Boots

    Give your 'fit a trendy vibe in these faux suede over the knee boots! They feature an adorable side lace-up detail, an inner zipper closure, and a low heel. Pair these boots with your fave cozy sweater dress for a must-have date night look.

    Fit & Features

    • Over the knee design
    • Round toe
    • Low heel
    • Inner zipper closure
    • Side lace-up detail
    • Faux suede material

     

    Please be advised that these boots run small. Fit model recommends one size up.

    Style Number/Barcode: 07402-0204

    Category Name: Women’s Shoes

    Price: $12.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Lead The Way Faux Leather Over The Knee Boots

    Lead the way in in these of the moment faux leather over the knee boots! They feature a trendy pointed toe with a sturdy block heel and inner zipper closure. Pair these boots with an adorable plaid mini skirt for a total it-girl vibe.

    Fit & Features

    • Over the knee design
    • Pointed toe
    • Block heel
    • Inner zipper closure
    • PU material

    Style Number/Barcode: 07402-0211

    Category Name: Women’s Shoes

    Price: $12.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Faux Nubuck Strappy Stiletto Heels

    Elevate your stylish look in these sexy stiletto heels! They feature a strappy design with an open almond toe and a sleek stiletto heel. Pair these shoes with a satin bodycon dress for a gorgeous night out look.

    Fit & Features

    • Open almond toe
    • Thin toe strap
    • Strappy design
    • Adjustable around the ankle strap
    • Open back
    • Thin stiletto heel
    • Faux nubuck material

     

    Please be advised that these heels run 1 size too small.

    Style Number/Barcode: 07401-2457

    Category Name: Women’s Shoes

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Make A Statement Faux Leather Combat Boots

    Yes girl, make a stylish statement in these trendy combat boots! They feature an allover patent faux leather material with bright multi-colored laces and stitching. Pair these boots with a basic mini dress for an edgy vibe.

    Fit & Features

    • Round toe
    • Multi-colored lace-up front
    • Pull tabs
    • Inner zipper closure
    • Platform
    • Lug sole
    • Patent faux leather material

    Style Number/Barcode: 07403-0352

    Category Name: Women’s Shoes

    Price: $17.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fierce And Fab Faux Suede Combat Boots

    Keep your everday look fierce and of course so fab in these combat boots! They feature a faux mircosuede material with an allover cheetah print, a lace-up front, and a chunky platform. Pair these boots with a simple little black dress to add some edge to your girl's night out look.

    Fit & Features

    • Round toe
    • Lace-up front
    • Pull tabs
    • Inner zipper closure
    • Platform
    • Lug sole
    • Faux mircosuede material with an allover cheetah print

    Style Number/Barcode: 07403-0351

    Category Name: Women’s Shoes

    Price: $17.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortlessly Edgy Block Heel Booties

    Get an effortlessly edgy look in these faux nubuck block heel booties! They feature an ankle-high design with a chunky lug sole and a tall, sturdy block heel. Pair these booties with dark wash skinny jeans and an oversized sweater for major fall vibes.

    Fit & Features

    • Ankle-high design
    • Round toe
    • Inner zipper closure
    • Lug sole
    • Block heel
    • Faux nubuck material
    • Partial elastic detail at ankle

    Style Number/Barcode: 07403-0386

    Category Name: Women’s Shoes

    Price: $12.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Faux Fur Greek Key Slides

    Give your stay at home look a trendy vibe in these faux fur slides! They feature an open toe with a wide strap with faux fur detailing and a thin clear rhinestone and jeweled greek key design. Pair these adorable slides with you fave comfy loungewear set for a cozy-chic look.

    Fit & Features

    • Open toe
    • Wide strap with faux fur detailing and a thin clear rhinestone and jeweled greek key design
    • Open back
    • Flat faux leather sole

    Style Number/Barcode: 07408-0068

    Category Name: Women’s Shoes

    Price: $15.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So Basic Faux Suede Booties

    Lace-up in these basic booties that go with all your fab layered looks! The booties feature a lace-up front, an almond toe, and wedge heel. The booties are composed of a faux suede material. Complete look with a cozy cardigan and skinny jeans. 

    Fit & Features

    • Around the ankle fit
    • Lace-up front
    • Almond toe
    • Wedge heel
    • Faux suede material 

    Style Number/Barcode: 07403-0550

    Category Name: Women’s Shoes

    Price: $15.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Total Glam Girl Strappy Kitten Heels

    You'll be a total glam girl when you add these gorg kitten heels to your outfit! They feature a square toe, a strappy design, and a metallic gold hue. Pair these heels with a pair of mom jeans to level up your everyday look.

    Fit & Features

    • Open square toe
    • Strappy design with a thong strap
    • Around the ankle adjustable strap
    • Open back
    • Kitten heel

    Style Number/Barcode: 07401-2246

    Category Name: Women’s Shoes

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Basic Fuzzy Thong Strap Slippers

    Bring it back to basics in slippers that are so cozy to lounge in! The slippers feature a faux fur material, a solid hue, and a thong toe strap. Complete look with the matching separates.

    Fit & Features

    • Faux fur material
    • Multicolored pastel print
    • Thong toe strap
    • Flat footbed

    Style Number/Barcode: 07408-0041

    Category Name: Women’s Shoes

    Price: $10.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free