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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.

  • Faux Suede Over The Knee Flat Heel Boots

    Get ready for the cooler months in these adorable over the knee flat heel boots! They feature a smooth faux suede material and a tie back detail. Pair these chic boots with a sweater dress for that total fall vibe.

    Fit & Features

    • Over the knee design
    • Almond toe
    • Flat heel and sole
    • Inner zipper closure
    • Faux suede material
    • Tie back detail

     

    Boot runs small. Size a half size up.

    Style Number/Barcode: 07402-0202

    Category Name: Women’s Shoes

    Price: $17.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Faux Suede Pointed Toe Sock Booties

    These faux suede sock booties are essential to have for this fall and winter season! They feature a trendy pointed toe, an ankle-high sock bootie design and a sturdy block heel. Pair these booties with distressed denim for a casual everyday slay.

    Fit & Features

    • Ankle-high sock bootie design
    • Pointed toe
    • Inner zipper closure
    • Block heel
    • Faux suede material

    Style Number/Barcode: 07403-0539

    Category Name: Women’s Shoes

    Price: $16.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Slip On Stretch Knit Sneakers

    Slip-on these sneakers to create a casually cute streetwear outfit with matching separates. The sneakers feature an easy slip-on design, a ribbed ankle, a stretch knit body, and a textured chunky sole.

    Fit & Features

    • Slip-on design
    • Ribbed ankle cuff
    • Stretch knit body
    • Almond toe
    • Textured chunky sole

    Style Number/Barcode: 07407-0178

    Category Name: Women’s Shoes

    Price: $20.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Golden Hour Spiral Stiletto Heels

    These stiletto heels shine brighter than your favorite filter. The metallic finish + spiral strap = instant golden goddess vibes, perfect for dressy occasions or date nights!

    Fit & Features

    • Stiletto heel
    • Almond toe
    • Spiral straps
    • Metallic faux leather material
    • Runs true to size

    Style Number/Barcode: 07401-000351

    Category Name: Women’s Shoes

    Price: $35.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: 7.5, 8

  • Slip On Stretch Knit Sneakers

    Slip-on these sneakers to create a casually cute streetwear outfit with matching separates. The sneakers feature an easy slip-on design, a ribbed ankle, a stretch knit body, and a textured chunky sole. 

    Fit & Features

    • Slip-on design 
    • Ribbed ankle cuff
    • Stretch knit body
    • Almond toe
    • Textured chunky sole 

    Style Number/Barcode: 07407-0179

    Category Name: Women’s Shoes

    Price: $7.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Level Up Colorful Chunky Sneakers

    Level up your everyday look with these trendy colorful chunky sneakers! They feature a lace-up front, a textured sole and pull tabs to easily put on. Pair these adorable sneaks with high waist denim and a simple tee to elevate your basic 'fit.

    Fit & Features

    • Round toe
    • Lace-up front
    • Side zipper accent
    • Textured sole
    • Pull tabs
    • Multi-colored

    Style Number/Barcode: 07407-0176

    Category Name: Women’s Shoes

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Keep It Trendy Pastel Chunky Sneakers

    Keep your look trendy with these of the moment pastel chunky sneakers! They feature a textured sole, lace-up front and pull tabs to easily put on. Pair these adorable sneaks with biker shorts for the perf athleisure vibe.

    Fit & Features

    • Round toe
    • Lace-up front
    • Textured sole
    • Pull tabs
    • Multi-colored

    Style Number/Barcode: 07407-0180

    Category Name: Women’s Shoes

    Price: $12.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stylish And Sleek Embossed Block Heels

    These stylish and sleek block heels will make your everyday 'fit all the more chic! They feature a faux leather material with an allover embossed print to add some texture. Pair these heels with high rise boyfriend style jeans for an elevated look.

    Fit & Features

    • Open almond toe
    • Thin toe strap
    • Around the ankle strap
    • Closed back with zipper
    • Thin block heel
    • PU material with embossed print

    Style Number/Barcode: 07401-2452

    Category Name: Women’s Shoes

    Price: $14.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Faux Nubuck Banded Block-Heeled Mules

    These banded block-heeled mules are perf to elevate your everyday 'fit! They feature a dual banded design with a sturdy block heel and a faux nubuck material. Pair these mules with distressed denim for a cute and casual vibe.

    Fit & Features

    • Open square toe
    • Dual banded design with thin toe strap and second wide strap
    • Open back
    • Block heel
    • Faux nubuck material

    Style Number/Barcode: 07401-2490

    Category Name: Women’s Shoes

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Faux Suede Over The Knee Block Heel Boots

    Get a chic, stylish look in these faux suede over the knee boots! They feature a pointed toe with a sturdy thin block heel. Pair these trendy boots with a ruched mini dress for a fall or winter date night.

    Fit & Features

    • Over the knee design
    • Pointed toe
    • Thin block heel
    • Inner zipper closure
    • Faux suede material

    Style Number/Barcode: 07402-0209

    Category Name: Women’s Shoes

    Price: $20.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Strut and Stun Faux Leather Block Heels

    Strut it out in these chic heels that will level the right impression! The heels feature an ankle strap, a zippered back, an open almond toe, and a block heel. Complete your look with a ribbed midi dress and a blazer. 

    Fit & Features

    • Ankle strap
    • Zippered back 
    • Open almond toe
    • Block heel
    • Faux croc-embossed pattern
    • Faux leather material 

    Style Number/Barcode: 07401-2451

    Category Name: Women’s Shoes

    Price: $16.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Shine A Lil' Brighter Rhinestone Stiletto Heels

    Shine a little brighter than the rest when you have rhinestones on your side! What we love about these stiletto heels is that they just just the right amount of bling to accent any look!

    • Open square toe
    • Single narrow band over the toe
    • Shiny patent faux leather
    • Velcro rhinestone ankle strap 
    • Skinny stiletto heel

    Please be advised that this style runs 1/2 size big

    Style Number/Barcode: 07401-2207

    Category Name: Women’s Shoes

    Price: $16.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Faux Suede Fishnet Ankle Stiletto Booties

    Give your look a trendy vibe in these faux suede stiletto booties! They feature a pointed toe, a fishnet ankle design, and a sleek stiletto heel. Pair these chic booties with a basic mini dress for fab 'fit.

    Fit & Features

    • Pointed toe
    • Fishnet ankle design
    • Stiletto heel
    • Partial faux suede material


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

    Style Number/Barcode: 07403-0392

    Category Name: Women’s Shoes

    Price: $14.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Caged Pointed Toe Pumps

    Get a chic, of the moment look in these trendy pumps! They feature a closed pointed toe, caged detailing with adjustable buckles and a sleek thin heel. Pair these pumps with a curve-hugging bodycon dress for your next girl's night out.

    Fit & Features

    • Closed pointed toe
    • Caged detailing
    • Adjustable buckles
    • Inner zipper closure
    • Thin heel
    • Faux suede material

    Style Number/Barcode: 07401-2491

    Category Name: Women’s Shoes

    Price: $12.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cozy Comfort Sherpa Slides

    Slip into comfort with these cozy slides. They feature an easy slip-on design, a wide toe strap, and composed of a sherpa material. Complete look with matching separates to lounge in style.

    Fit & Features

    • Wide toe strap
    • Slip-on design
    • Sherpa material

    Style Number/Barcode: 07408-0064

    Category Name: Women’s Shoes

    Price: $12.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cozy Moment Sherpa Slides

    Slip into comfort with these cozy slides. They feature an easy slip-on design, a wide toe strap, and composed of a sherpa material. Complete look with matching separates to lounge in style. 

    Fit & Features

    • Wide toe strap
    • Slip-on design 
    • Sherpa material

    Style Number/Barcode: 07408-0063

    Category Name: Women’s Shoes

    Price: $12.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • In the Clear Platform Lucite Heels

    Clearly stay on trend bby with these chic lucite heels! The heels feature an adjustable ankle strap, an almond toe with a clear strap over the toe, and a clear lucite heel. Complete look with a body-hugging bodycon. 

    Fit & Features

    • Clear adjustable strap
    • Open almond toe
    • Clear strap over the toe
    • Clear lucite block heel 
    • Platform

    Style Number/Barcode: 07401-2505

    Category Name: Women’s Shoes

    Price: $12.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Thigh High Faux Suede Stiletto Boots

    Stun in chic boots this season to create chic layered outfits. The boots feature a thigh-high fit, a tie back accent, almond toe with a wide platform, and a wide stiletto heel. The boots are composed of a faux suede material. Complete look with a chunky sweater with skinny jeans. 

    Fit & Features

    • Thigh-high fit
    • Tie-back accent
    • Almond toe
    • Platform
    • Stiletto heel
    • Faux suede material 

    Style Number/Barcode: 07402-0193

    Category Name: Women’s Shoes

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Faux Suede Pointed Toe Block Heel Booties

    Everyone need that basic pair of pointed toe block heel booties! These feature an ankle high fit with a smooth faux suede material. Pair these chic booties with a sweater dress and a faux leather jacket for a fall night out!

    Fit & Features

    • Ankle high fit
    • Pointed toe
    • Sturdy block heel
    • Inner zipper closure
    • Faux suede material

    Style Number/Barcode: 07403-0329

    Category Name: Women’s Shoes

    Price: $16.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Glitter Fishnet Stiletto Booties

    Get the extra AF look in glitter booties that glow up your look! The booties feature a mid-calf fit, fishnet body with glitter embellishments throughout, a faux suede trim, and a sleek stiletto heel. Complete look with a sleek bodycon. 

    Fit & Features

    • Around the ankle mid-calf fit
    • Fishnet body
    • Glitter embellishment 
    • Faux suede trim 
    • Pointed toe
    • Sleek stiletto heel

    Style Number/Barcode: 07403-0374

    Category Name: Women’s Shoes

    Price: $13.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So Rare Faux Leather Diamond Block Heels

    Show off your affinity for the luxe life with these chic heels! The heels feature a wrap-around strap, a square toe sole with a toe loop, and a diamond-shaped block heel. The heels are composed of a faux leather material. Complete look with a little black dress. 

    Fit & Features

    • Wrap-around strap
    • Square toe
    • Toe loop
    • Diamond-shaped block heel
    • Faux leather material 

    Style Number/Barcode: 07401-2419

    Category Name: Women’s Shoes

    Price: $14.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Crisscross Faux Suede Platform Heels

    Keep it chic in trendy crisscross heels that stun on your next night out! The heels feature a crisscross design, a wide platform, and a chunky block heel. The heels are composed of a faux suede material. Complete your look with a sleek bodycon.

    Fit & Features

    • Open-back
    • Adjustable ankle strap
    • Crisscross straps
    • Open almond toe
    • Wide platform
    • Block heel
    • Faux suede material 

    Style Number/Barcode: 07401-2499

    Category Name: Women’s Shoes

    Price: $12.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sleek and Strappy Stiletto Heels

    Keep it sleek in these lace-up heels that impress! The heels feature lace-up straps, a square toe with a thong toe strap, and a sleek stiletto heel. Complete look with a ribbed knit midi dress to create a stunning night out look. 

    Fit & Features

    • Lace-up straps
    • Square toe with thong toe strap
    • Adjustable ankle strap
    • Square toe sole
    • Sleek stiletto heel
    • Faux leather material

    Style Number/Barcode: 07401-2413

    Category Name: Women’s Shoes

    Price: $12.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sun Soaked Espadrille Strappy Wedges

    Step into sunny style with these espadrille wedges in a strappy design that elevates any look! 

    Fit & Features

    • Wedge heel
    • Square toe
    • Criss cross straps
    • Closed ankle, back zipper closure
    • Espadrille material
    • Runs true to size

    Style Number/Barcode: 07406-000011

    Category Name: Women’s Shoes

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free