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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.

  • Cowgirl Off Duty Fold Over Western Boots

    These boots were made for compliments. The fold-over western boots mix chill slouch vibes with a pointed toe and block heel, perfect for taking your 'fit from casual to iconic.

    Fit & Features

    • 2.5" Block heel, 7" leg opening, 6" shaft height
    • Smooth faux leather material
    • Pointed toe
    • Below-the-knee height, pull tabs
    • Slouched fold-over design
    • Runs true to size

    Style Number/Barcode: 07402-000080

    Category Name: Women’s Shoes

    Price: $46.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • The New Classic Platform Block Heels

    Step up in heels that bring a classy chic vibe to your looks! Step out for that next bridal shower or dress up a workwear outfit in these block heels. The heels feature an open almond toe, a wide platform, and a sturdy block heel. Complete your look with a floral dress and duster earrings. 

    Fit & Features

    • Closed-back
    • Open almond toe 
    • Single strap over the toe
    • Adjustable ankle strap
    • Block heel 
    • Faux Nubuck material  

    Style Number/Barcode: 07401-2389

    Category Name: Women’s Shoes

    Price: $12.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Red Hot Faux Patent Leather Lug Booties

    Set off sparks in booties that bring the fire! These ankle booties feature an inner zipper closure, a round toe, a lug sole platform, and a block heel. Complete look with a mini skirt and bodysuit for your next date-night! 

    Fit & Features

    • Ankle-length
    • Inner-zipper closure
    • Round toe
    • Lug sole platform
    • Block heel
    • Faux patent leather material 

    Style Number/Barcode: 07403-0347

    Category Name: Women’s Shoes

    Price: $12.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Pretty In Peep Toe Faux Suede Booties

    Keep it pretty in booties that perfectly go with all your favorite fall outfits. We love a little peep-toe action, and these booties are all about it! Style with an oversized jean jacket and large hat!

    Fit & Features

    • Open peep toe
    • Ankle fit
    • Inner zipper closure
    • Block heel 
    • Faux suede

    Style Number/Barcode: 07403-0266

    Category Name: Women’s Shoes

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Making Bold Moves Lucite Block Heels

    You'll be making major bold moves in these trendy lucite block heels! They feature a leopard printed patent faux leather material to make your look all the more fierce. Pair with a little black dress and let your heels make the statement at your next party.

    Fit & Features

    • Open almond toe with a toe strap
    • Clear wide band over the top
    • Open back
    • Leopard printed patent PU material
    • Thin lucite block heel

     

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

    Style Number/Barcode: 07401-2416

    Category Name: Women’s Shoes

    Price: $22.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dazzle and Bling Stiletto Heels

    Bring the dazzle in these heels that command the room! The heels feature mini rhinestones throughout, a faux microsuede trim, an open almond toe, and a sleek stiletto heel. Complete your luxe look with a sleek satin dress and earrings. 

    Fit & Features

    • Closed-back 
    • Adjustable ankle strap 
    • Open almond toe with a single strap over the toe
    • Mini rhinestones
    • Wide platform 
    • Stiletto heel
    • Faux microsuede trim 

    Style Number/Barcode: 07401-2337

    Category Name: Women’s Shoes

    Price: $12.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Triple Threat Faux Nubuck Block Heels

    Bring more in heels that are perfect for every day looks and dressing up for a day out. The heels feature a triple row strap design, a wide ankle strap, an open almond toe, and sturdy block heel. Complete your look with a ribbed midi dress and hoop earrings. 

    Fit & Features

    • Open almond toe with a strap over the toe
    • Wide ankle strap
    • Triple strap design
    • Zippered back 
    • Faux nubuck material 

    Style Number/Barcode: 07401-2381

    Category Name: Women’s Shoes

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Glitter Rhinestone Platform Stiletto Heels

    Bring the dazzle in heels that bring the luxe and glamour. The heels feature mini rhinestones throughout, an adjustable ankle strap, an open toe with a single strap and a sleek stiletto heel. Complete your look with a heat stone dress and rhinestone earrings. 

    Fit & Features

    • Closed-back
    • Adjustable ankle strap
    • Wide platform
    • Rhinestones
    • Open almond toe with a single strap over the toe
    • Stiletto heel
    • Composed of a glitter mesh material 

    Style Number/Barcode: 07401-2334

    Category Name: Women’s Shoes

    Price: $12.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Pretty In Pastel Chunky Sneakers

    Keep it pretty in pastel sneakers to give your streetwear outfits a pop of color. The sneakers feature a multi pastel colored body, a lace-up front, a zippered accent, and a chunky sole. Complete your look with matching knit separates and a dainty necklace. 

    Fit & Features

    • Multi-pastel colors
    • Round toe
    • Lace-up front
    • Zippered accent
    • Pull tabs 
    • Chunky sole

    Style Number/Barcode: 07407-0172

    Category Name: Women’s Shoes

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Faux Leather Lace Up Lug Booties

    Lace-up in booties that bring the edge to your look! Create a stylish grunge outfit with these must-have booties! The booties feature an around the ankle fit, a lace-up front, and a lug sole with a block heel. Complete your look with a graphic tee and high waist pants.

    Fit & Features

    • Around the ankle fit
    • Lace-up front
    • Round toe
    • Lug sole
    • Block heel
    • Faux leather material 

    Style Number/Barcode: 07403-0366

    Category Name: Women’s Shoes

    Price: $22.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Lace Up Faux Nubuck Stiletto Booties

    Lace-up in these chic booties this season as you head out to grab a PSL or to go with your back to school outfit! The booties feature a trendy pointy toe, a lace-up front with small grommets, and a sleek stiletto heel. Complete your look with a cute cardigan and high waist skinny jeans. 

    Fit & Features

    • Around the ankle fit
    • Lace-up front with small grommets
    • Pointed toe
    • Stiletto heel
    • Faux nubuck material

    Style Number/Barcode: 07403-0316

    Category Name: Women’s Shoes

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Step Up Faux Leather Stiletto Heels

    Step up your heel game in these chic beauties! Perfect for glamming up your workwear attire or completing a date night look, these heels will become your go-to! The heels feature an adjustable ankle strap with a large buckle, criss-cross straps, a wide strap over the toe and a sleek stiletto heel. 

    Fit & Features

    • Closed-back
    • Adjustable ankle strap
    • Criss-cross straps
    • Wide strap over the toe
    • Stiletto heel
    • Faux leather material 

    Style Number/Barcode: 07401-2399

    Category Name: Women’s Shoes

    Price: $18.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • On Chic Criss Cross Faux Suede Block Heels

    Stay on chic girl in these heels that keep your look simply stunning! The heels feature an adjustable ankle strap, a criss-cross design, a double row strap detail over the toe, and a trendy block heel. Complete your look with a sweater dress and door knocker earrings. 

    Fit & Features

    • Closed-back 
    • Adjustable ankle strap
    • Criss-cross design 
    • Double row strap design over the toe
    • Open almond toe
    • Block heel 
    • Faux suede material 

    Style Number/Barcode: 07401-2408

    Category Name: Women’s Shoes

    Price: $16.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wildly Fierce Faux Suede Stiletto Booties

    Step out in these wildly fierce booties for your next girl's night out or for your next date night with bae! The booties feature an around the ankle fit, a lace-up front, wildly-inspired leopard print, and a sleek stiletto heel. Complete your look with dark wash denim jeans and a bustier.

    Fit & Features

    • Around the ankle fit
    • Lace-up front
    • Inner zipper closure
    • Pointed toe 
    • Leopard print
    • Sleek stiletto heel
    • Faux microsuede material 

    Style Number/Barcode: 07403-0319

    Category Name: Women’s Shoes

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Clearly Chic Lucite Block Heels

    Clearly these lucite block heels couldn't get any more chic. With their patent PU material and lucite swirl heel, you'll strut every step. Pair with a flirty skater dress and a sparkly clutch for a night out with your girls.

    Fit & Features

    • Open almond toe with toe strap
    • Adjustable around the ankle strap
    • Open back
    • Patent PU material
    • Clear lucite swirl design block heel

    Style Number/Barcode: 07401-2154

    Category Name: Women’s Shoes

    Price: $14.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Game On Bungee Lace Chunky Sneakers

    Keep it sporty in chunky sneakers that level up your streetwear style! The sneakers feature bungee laces, a round toe, a chunky textured sole, and a back strap accent at the heel. Complete your look with a matching lounge set and hoops. 

    Fit & Features

    • Bungee laces
    • Round toe
    • Chunky textured sole
    • Backstrap accent at the ankle
    • Pull tabs
    • Two-tone accent

    Style Number/Barcode: 07407-0166

    Category Name: Women’s Shoes

    Price: $12.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Stacked on Style Faux Suede Booties

    Lace-up in stylish booties this season! The booties feature an around the ankle fit, an outer lace-up design with small metal grommets, and a stacked block heel. Complete your look with cuffed mom jeans and a soft to the touch oversized sweater. 

    Fit & Features

    • Around the ankle fit
    • Almond toe
    • Outer lace-up design with small grommets
    • Inner zipper closure
    • Stacked block heel
    • Faux microsuede material 

    Style Number/Barcode: 07403-0364

    Category Name: Women’s Shoes

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sleek and Chic Lace Up Stiletto Booties

    Lace-up in sleek booties for your next night out to make a stylish statement! The booties feature an around the ankle fit, a lace-up front with small grommets, a pointed toe, and a low stiletto heel. Complete your outfit with a trendy sweater dress and door knocker earrings. 

    Fit & Features

    • Around the ankle fit 
    • Lace-up front with small grommets
    • Inner zipper closure
    • Pointed toe
    • Low stiletto heel
    • Faux nubuck material 

    Style Number/Barcode: 07403-0317

    Category Name: Women’s Shoes

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Faux Suede Lace Up Booties

    Lace-up this season in chic booties that perfectly go with your layered looks! The booties feature an around the ankle fit, a lace-up front with small grommets, and a trendy cutout design. Complete your look with skinny jeans and a faux leather moto jacket.

    Fit & Features

    • Around the ankle fit
    • Caged design
    • Cutout pattern
    • Lace-up front, peep toe
    • Zippered back closure
    • Block heel
    • Faux suede material 

    Style Number/Barcode: 07403-0320

    Category Name: Women’s Shoes

    Price: $12.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • The Everday Faux Suede Stacked Booties

    These booties are perfect for your every day chic outfits! Step out to grab your favorite latte or create a fab back to school outfit with these essential booties! The booties feature an around the ankle fit, goring panels for a comfortable fit, an almond toe and low stacked block heel. Complete your look with cuffed jeans and an off the shoulder top. 

    Fit & Features

    • Around the ankle fit with pull tabs
    • Almond toe 
    • Goring panels 
    • Low stacked block heel
    • Faux suede material

    Style Number/Barcode: 07403-0354

    Category Name: Women’s Shoes

    Price: $18.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • On Point Criss-Cross Strappy Mules

    Simple, sharp, and seriously chic. These strappy mules nail the vibe every time—with a luxe cushioned insole that keeps it comfy from day plans to PM plans.

    Fit & Features

    • Block heel
    • Faux leather material
    • Open square toe
    • Criss-cross strappy design
    • Open back, on-and-off styling
    • Luxe fit cushioned insole
    • Runs true to size

    Style Number/Barcode: 07401-000349

    Category Name: Women’s Shoes

    Price: $32.90

    Availability: In Stock

    Available Color: WHITE

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

  • Luxe Criss Cross Nubuck Block Heels

    Bring the luxe with heels that make a stunning statement! Complete your date night outfits or create a chic cocktail outfit with these platform heels. The heels feature a zippered back, an adjustable ankle strap with a large buckle, criss-cross straps at the ankle, matching cross straps over the toe and a wide platform. Complete your look with a curve-hugging bodycon dress and crossbody. 

    Fit & Features

    • Zippered back
    • Wide cross straps at the ankle
    • Wide cross straps over the toe
    • Open almond toe
    • Wide platform 
    • Narrow block heel
    • Faux nubuck material 

    Style Number/Barcode: 07401-2395

    Category Name: Women’s Shoes

    Price: $12.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Staying Out Tonight Black Point Toe Booties

    Stay out  all night long with sleek polished booties! Style with a leather jacket and skinny jeans for that effortlessly trendy finish!

    • Pointed toe
    • Block heel
    • Inner zipper closure
    • Faux leather
    • 50/50 Croc embossed | Smooth 
    • Cut out ankle fit

    Style Number/Barcode: 07403-0291

    Category Name: Women’s Shoes

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • On Point Lace Up Stiletto Booties

    Lace-up in chic booties to keep your look on point! Perfect for your next GNO or your next date night with bae. The booties feature a trendy lace-up front to create a customized fit, a pointed toe, and a sleek stiletto heel. Complete your look with a sweater dress and moto jacket. 

    Fit & Features

    • Around the ankle fit
    • Lace-up front
    • Inner zipper closure
    • Pointed toe
    • Stiletto heel 
    • Faux microsuede material 

     

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

    Style Number/Barcode: 07403-0318

    Category Name: Women’s Shoes

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance