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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.

  • Feeling Good Faux Suede Block Heel Booties

    These booties bring major feel good vibes to your layered outfits! The booties feature an around the ankle fit, a back zipper closure, a pointed toe, and a low block heel. Complete look with a ribbed midi dress and moto jacket.

    Fit & Features

    • Around the ankle fit
    • Back zipper closure
    • Pointed toe
    • Low block heel
    • Faux suede material

    Style Number/Barcode: 07403-0526

    Category Name: Women’s Shoes

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Slay In Basics Faux Suede Block Heel Booties

    Slay in a basic bootie that elevates your layered outfits. The booties feature an around the ankle fit, a pointed toe, a thin block heel, and composed of a faux suede material. Complete look with a ribbed midi dress and moto jacket. 

    Fit & Features

    • Around the ankle fit
    • Pointed toe
    • Thin block heel
    • Inner zipper closure
    • Faux suede material 

    Style Number/Barcode: 07403-0525

    Category Name: Women’s Shoes

    Price: $12.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

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

    Lace-up in basic booties that bring the casual vibes. The booties feature a lace-up front, an almond toe, and a block heel. Complete look with a cardigan and distressed jeans. 

    Fit & Features

    • Lace-up front
    • Almond toe 
    • Block heel 
    • Faux suede material 

    Style Number/Barcode: 07403-1229

    Category Name: Women’s Shoes

    Price: $16.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Country Threads Western Microsuede Cowboy Boots

    Flaunt your country threads in these western microsuede cowboy boots with trendy western-inspired stitch detailing and a stacked block heel. Complete the look with a cowboy hat.

    Fit & Features

    • 2.5" stacked block heel, 7.5" leg opening, 9.5" shaft height
    • Pointed toe
    • Western-inspired stitch detailing
    • Below the knee fit
    • Smooth microsuede material
    • Runs true to size

    Style Number/Barcode: 07402-1128

    Category Name: Women’s Shoes

    Price: $19.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Basic Vibes Peep Toe Faux Leather Booties

    Fall back to basics in booties that are perf for your chic layered outfits. The booties feature an around the ankle fit, a peep toe, a block heel, and composed of a faux leather material. Complete look with a cardigan and high waist jeans. 

    Fit & Features

    • Around the ankle fit
    • Peep toe
    • Block heel
    • Inner zipper closure
    • Faux leather material

    Style Number/Barcode: 07403-1224

    Category Name: Women’s Shoes

    Price: $16.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Classy Chic Faux Suede Peep Toe Mules

    Keep it classy in chic mules to dress up your workwear outfits! The mules feature an open back, a wide strap over the toe, a peep toe, and a block heel. Complete look with a blouse and pencil skirt. 

    Fit & Features

    • Open back
    • Wide strap over the toe
    • Peep toe
    • Block heel
    • Faux suede material 

     

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

    Style Number/Barcode: 07401-2459

    Category Name: Women’s Shoes

    Price: $16.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • See Me Now Lucite Block Heels

    Get seen and noticed in chic heels that command attention. The heels feature an adjustable ankle strap, an open almond toe with a clear strap over the toe, and a lucite block heel. Complete look with a sweater dress for a casual date night. 

    Fit & Features

    • Open-back 
    • Adjustable ankle strap
    • Open almond toe
    • Clear strap over the toe 
    • Lucite heel

    Style Number/Barcode: 07401-2461

    Category Name: Women’s Shoes

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stacked On Basics Faux Leather Block Heel Booties

    Stack up on basic booties that add that chic touch to your fab outfits! The booties feature an around the ankle fit, a pointed toe, vertical line detail at the back of the ankle, and a block heel. The booties are composed of a faux leather material. Complete look with a boat neck sweater and high waist jeans. 

    Fit & Features

    • Around the ankle fit
    • Pointed toe
    • Vertical line detail at the back of the ankle
    • Block heel
    • Inner zipper closure
    • Faux leather material 

    Style Number/Barcode: 07403-0511

    Category Name: Women’s Shoes

    Price: $12.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • The Right Knit Block Heel Booties

    These booties are the knit piece that you need for your layered outfit! The booties feature an around the ankle fit, an almond toe, a knit material body, and a short block heel. Complete look with a bodysuit and jeans. 

    Fit & Features

    • Around the ankle fit
    • Almond toe
    • Knit material body
    • Short block heel

    Style Number/Barcode: 07403-0538

    Category Name: Women’s Shoes

    Price: $16.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cute And Cozy Faux Suede Booties

    Look oh-so-cute and cozy in these adorable faux suede booties! They feature a trendy pointed toe, a faux sherpa detail, strap detailing with a buckle accent, and a stacked block heel. Pair these booties with skinny jeans and a chunky knit sweater for the perf winter-time look.

    Fit & Features

    • Above the ankle fit
    • Pointed toe
    • Stacked block heel
    • Inner zipper closure
    • Faux sherpa detail
    • Strap detailing with a buckle accent
    • Faux suede material

    Style Number/Barcode: 07403-1206

    Category Name: Women’s Shoes

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Faux Suede Lace-Up Block Heel Booties

    Get an effortless, everyday stylish look in these block heel booties! They feature an ankle-high design with a pointed toe, a lace-up front, and a sturdy block heel. Pair these booties with denim for a casually chic vibe.

    Fit & Features

    • Ankle-high design
    • Pointed toe
    • Lace-up front
    • Block heel
    • Faux microsuede material

    Style Number/Barcode: 07403-0610

    Category Name: Women’s Shoes

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • So Cozy Faux Fur Slides

    Keep it so cozy in slides that bring the comfort! These must-have slides feature an open almond toe with a wide strap and composed of a faux material. Complete look with a matching lounge set. 

    Fit & Features

    • Easy slip-on design 
    • Open almond toe
    • Wide strap over the toe
    • Faux fur material 

    Style Number/Barcode: 07408-0049

    Category Name: Women’s Shoes

    Price: $11.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • So Cozy Leopard Print Slides

    Keep it so cozy in slides that bring the comfort! These must-have slides feature a leopard print, an open almond toe with a wide strap, and composed of a faux material. Complete look with a matching lounge set.

    Fit & Features

    • Leopard print
    • Easy slip-on design
    • Open almond toe
    • Wide strap over the toe
    • Faux fur material

    Style Number/Barcode: 07408-0050

    Category Name: Women’s Shoes

    Price: $11.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • So Fab Faux Suede Block Heel Booties

    Fall back on fab basics that complete your textured layered outfits. The booties feature an around the ankle fit, an almond toe, and a block heel. Complete the look with a cardigan and joggers for those low-key vibes. 

    Fit & Features

    • Around the ankle fit
    • Almond toe
    • Inner zipper closure
    • Block heel 
    • Faux suede material 


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

    Style Number/Barcode: 07403-0533

    Category Name: Women’s Shoes

    Price: $16.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Basic Babe Faux Suede Boots

    Bring it back to basics in boots that are pef for everyday! The boots feature a below the knee fit, a back tie accent, an almond toe, and composed of a faux suede material. Complete look with a ribbed mini dress and a moto jacket. 

    Fit & Features

    • Below the knee fit
    • Back tie accent
    • Inner zipper closure 
    • Almond toe
    • Faux suede material 

    Style Number/Barcode: 07402-0297

    Category Name: Women’s Shoes

    Price: $12.97 $31.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Lace-Up Glam Faux Leather Booties

    Lace-up in these cute booties that are perf to dress up your looks in. The booties feature a lace-up front, an almond toe, and an inner zipper closure. The booties are composed of a faux leather material. Complete look with a bodysuit and mini skirt. 

    Fit & Features

    • Around the ankle fit
    • Lace-up front
    • Almond toe
    • Low block heel
    • Inner zipper closure
    • Faux leather material 

    Style Number/Barcode: 07403-1225

    Category Name: Women’s Shoes

    Price: $16.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Gorgeous Glitter Mesh Block Heels

    Add a gorgeous and glam touch to your look with these glitter mesh heels! They feature a square toe, a thin block heel, and an adjustable ankle strap. Pair these heels with a luxe velvet dress for a chic holiday look.

    Fit & Features

    • Open square toe
    • Toe strap
    • Thin block heel
    • Adjustable ankle strap
    • Closed back
    • Glitter mesh material

    Style Number/Barcode: 07401-2450

    Category Name: Women’s Shoes

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • A Bold Move Stiletto Heels

    You'll make a bold, stylish move in these sleek stiletto heels! They feature a trendy pointed toe, a strappy design with stud detailing, and a sleek stiletto heel. Pair these pumps with a little black dress and layer on a faux leather jacket for an edgy-chic look.

    Fit & Features

    • Pointed toe
    • Strappy design with stud detailing
    • Closed back
    • Stiletto heel
    • Patent faux leather material

    Style Number/Barcode: 07401-2527

    Category Name: Women’s Shoes

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Major Must-Have Square Toe Block Heels

    These faux microsuede heels are a major must-have you need in your closet! They feature a trendy square toe, a sleek thin block heel, and a thin adjustable ankle strap. Pair these heels with a form-hugging pencil skirt and a boyfriend blazer to elevate your workwear look.

    Fit & Features

    • Open square toe
    • Toe strap
    • Closed back
    • Adjustable ankle strap
    • Thin block heel
    • Faux microsuede material

    Style Number/Barcode: 07401-2449

    Category Name: Women’s Shoes

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Glam Vibes Chrome Short Stiletto Heels

    Get major glam vibes in these gorgeous chrome short stiletto heels! They feature an open almond toe, a toe strap with rhinestone detailing in a chic greek key design, and an adjustable ankle strap. Pair these heels with a glitter dress for the perf NYE 'fit!

    Fit & Features

    • Open almond toe
    • Toe strap
    • Rhinestone detailing in a greek key design
    • Adjustable ankle strap
    • Closed back with zipper closure
    • Short stiletto heel
    • Chrome faux patent leather

    Style Number/Barcode: 07401-2534

    Category Name: Women’s Shoes

    Price: $16.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trend Alert Over the Knee Faux Suede Boots

    Set it off in trendy boots that are perfect to style your layered outfits with. The boots feature an over the knee fit, an almond toe, a block heel. a back tie accent, and composed of a faux suede material. Complete look with a ribbed mini dress.

    Fit & Features

    • Over the knee fit
    • Almond toe
    • Back tie accent
    • Back zipper closure
    • Faux suede material 

    Style Number/Barcode: 07402-0265

    Category Name: Women’s Shoes

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Edgy Girl Peep Toe Stiletto Booties

    Yes girl, showcase your edgy side in these trendy stiletto booties! They feature a pointed peep toe, a lace-up front, a sleek stiletto heel, and a faux leather material. Pair these booties with your fave pair of skinny jeans to elongate your legs for a flattering silhouette.

    Fit & Features

    • Above the ankle design
    • Pointed peep toe
    • Lace-up front
    • Inner zipper closure
    • Stiletto heel
    • PU material

    Style Number/Barcode: 07403-1211

    Category Name: Women’s Shoes

    Price: $22.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Get Spotted Faux Fur Slippers

    Get spotted in these cute slippers that are all too cozy to lounge in. The slippers feature an open almond toe, a cow print, a wide strap over the toe, and composed of a faux fur material. Complete look with a matching lounge set. 

    Fit & Features

    • Slip-on design
    • Cow print
    • Open almond toe
    • Wide strap over the toe
    • Faux fur material 

    Style Number/Barcode: 07408-0052

    Category Name: Women’s Shoes

    Price: $12.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Up To No Good Rhinestone Fishnet Booties

    Experience the ultimate in sexy sophistication with these statement stiletto booties! These pointed-toe booties feature sheer fishnet adorned with sparkling rhinestones, adding a touch of glamour to any outfit. 

    Fit & Features

    • 4" Stiletto heel, 4" leg opening, 5" shaft height
    • Pointed toe
    • PVC clear trim
    • Sheer fishnet with rhinestone embellishments
    • Back zipper closure, ankle-length shaft
    • Nubuck material
    • Runs true to size

    Style Number/Barcode: 07403-000014

    Category Name: Women’s Shoes

    Price: $15.97 $42.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK, WHITE

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

    Product Badge:
    • Sale