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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.

  • Chic Chrome Rhinestone Ankle Wrap Stiletto Heels

    Elevate your style with these chic chrome stiletto heels! They feature an almond toe with a thong strap, a rhinestone adorned ankle wrap design with a tie closure, and a stiletto heel. Pair these shoes with your fave little black dress to add a touch of glam to your night out look.

    Fit & Features

    • Almond toe with a thong strap
    • Rhinestone adorned ankle wrap design with tie closure
    • Open back
    • Stiletto heel
    • Sleek chrome material

     

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

    Style Number/Barcode: 07401-2548

    Category Name: Women’s Shoes

    Price: $16.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stylish Diva Lace-Up Booties

    You're such a stylish diva, and these block heeled booties are perf to elevate your everyday style! They feature a trendy pointed toe, a lace-up front, and an inner zipper closure. Pair these fab booties with your favorite ribbed knit mini dress and distressed denim jacket.

    Fit & Features

    • Above the ankle design
    • Pointed toe
    • Lace-up front
    • Block heel
    • Inner zipper closure
    • Lycra material

    Style Number/Barcode: 07403-0498

    Category Name: Women’s Shoes

    Price: $19.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Glam Diva Rhinestone Ankle Wrap Block Heels

    Yes babe, showcase the glam diva you know you are in these gorg block heels! They feature an almond toe with a thong strap, a rhinestone adorned ankle wrap design with a tie closure, and a short block heel. Pair these shoes with faux leather joggers for a trendy vibe.

    Fit & Features

    • Almond toe with a thong strap
    • Rhinestone adorned ankle wrap design with tie closure
    • Open back
    • Short block heel
    • Faux microsuede material

    Style Number/Barcode: 07401-2542

    Category Name: Women’s Shoes

    Price: $16.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Rhinestone Queen Ankle Wrap Stiletto Heels

    Showcase some major style like the fashion queen you are in these dazzling heels! They feature a pointed toe with a thong strap, a rhinestone adorned ankle wrap design with a tie closure, and a stiletto heel. Pair these shoes with high rise mom jeans and a cute crop top to add some glam to your everyday look.

    Fit & Features

    • Pointed toe with a thong strap
    • Rhinestone adorned ankle wrap design with tie closure
    • Open back
    • Stiletto heel
    • Faux microsuede material

     

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

    Style Number/Barcode: 07401-2547

    Category Name: Women’s Shoes

    Price: $16.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Buckle Up Lug Sole Block Heel Booties

    Buckle up in these bold booties for a chic 'fit! They feature an ankle-high design, a trendy lug sole, sturdy block heel, and a buckle accent. Pair these booties with your fave pair of skinny jeans for an elongated look.

    Fit & Features

    • Ankle-high design with back pull tabs
    • Almond toe
    • Lug sole
    • Block heel
    • Inner zipper closure
    • Strap and buckle detail
    • Faux nubuck material

    Style Number/Barcode: 07403-1219

    Category Name: Women’s Shoes

    Price: $12.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • On the Move Jelly Sneakers

    Slip-on these sneakers to keep on moving, girl! The sneakers feature a lace-up front, an almond toe, knit body, and a clear jelly sole. Complete look with a matching crop top and leggings set.

    Fit & Features

    • Lace-up front
    • Almond toe
    • Knit body
    • Textured sole
    • Clear jelly sole

    Style Number/Barcode: 07407-0185

    Category Name: Women’s Shoes

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fall For Faux Suede Stacked Heel Boots

    Fall for these stylish boots to dress your layered looks in. The boots feature a below the knee fit, a pointed toe, a low stacked heel, and composed of faux suede material. Complete your look with a cardigan and cabby hat. 

    Fit & Features

    • Below the knee fit
    • Pointed toe
    • Inner zipper closure 
    • Low stacked block heel
    • Faux suede material 

     

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

    Style Number/Barcode: 07402-0239

    Category Name: Women’s Shoes

    Price: $12.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • All About Ruched Faux Suede Ankle Booties

    We're all about ankle booties that slay this season. These stylish booties feature an around the ankle fit with ruched detailing, an almond toe, and a sturdy block heel. The ankle booties are composed of a faux suede material. Complete look with a cardigan, high waist skinny jeans, and a cabby hat.

    Fit & Features

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



    Please be advised that these boots run one size too small.

    Style Number/Barcode: 07403-0399

    Category Name: Women’s Shoes

    Price: $22.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So Sleek Faux Leather Ankle Booties

    Let these ankle booties complete your sleek and stylish outfit! The ankle booties feature an around the ankle fit, a pointed toe, an inner zipper closure, and a block heel. The booties are composed of a faux leather material. Complete look with a ribbed midi dress. 

    Fit & Features

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


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

    Style Number/Barcode: 07403-0461

    Category Name: Women’s Shoes

    Price: $16.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Edgy Vibes Lug Sole Block Heel Booties

    Get major edgy vibes in these stylish booties! They feature an ankle-high design with a gore detail, a trendy lug sole, and a sturdy block heel. Pair these booties with your fave pair of dark wash skinny jeans.

    Fit & Features

    • Ankle-high design
    • Almond toe
    • Gore detail
    • Lug sole
    • Block heel
    • Faux microsuede material

    Style Number/Barcode: 07403-0531

    Category Name: Women’s Shoes

    Price: $12.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • She's A Gem Rhinestone Block Heels

    Shine like the gem you are in these heels that bring the glamour. The heels feature a rhinestone embellished adjustable ankle strap, back strap, an open almond toe with a strap over the toe, and a block heel. Complete look with a sleek LBD.

    Fit & Features

    • Rhinestone embellished adjustable ankle strap
    • Back ankle strap
    • Open almond toe
    • Strap over the toe 
    • Block heel 
    • Faux nubuck and suede material  

    Style Number/Barcode: 07401-2198

    Category Name: Women’s Shoes

    Price: $12.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Weekend Getaway Lace-Up Espadrille Wedges

    These chic espadrille wedges are the perfect excuse for a weekend getaway! They feature a trendy closed square toe and lace-up ankle straps that let you customize the look.

    Fit & Features

    • Espadrille wedge heel
    • Closed square toe
    • Lace-up ankle straps
    • Runs true to size

    Style Number/Barcode: 07406-000025

    Category Name: Women’s Shoes

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: In Stock

    Available Color: TAN

    Available Size: 7.5, 8, 8.5, 9, 10

    Product Badge:
    • Sale
  • Keep It Trendy Tie Dye Sneakers

    Keep your everyday look trendy in these adorable sneakers! They feature a lace-up design with back pull tabs, a tie dye knit fabric, and a clear insert at the sole. Pair these sneakers with biker shorts and an oversized tee for that casual and cute vibe.

    Fit & Features

    • Round toe
    • Lace-up design
    • Back pull tabs
    • Tie dye knit fabric
    • Clear insert at the sole

    Style Number/Barcode: 07407-0189

    Category Name: Women’s Shoes

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Glitzy And Glamorous Glitter Mesh Pumps

    Complete your glamorous formal look with these glitzy pumps! They feature a closed pointed toe, a closed back, and a short stiletto heel. They are composed of a glitter mesh material with a clear PVC insert with all-over rhinestone detailing for major sparkle. Pair these heels with a floor-sweeping specialty gown with a high slit.

    Fit & Features

    • Closed pointed toe
    • Closed back
    • Short stiletto heel
    • Glitter mesh material
    • Clear PVC insert
    • All-over rhinestone detailing

    Style Number/Barcode: 07401-2523

    Category Name: Women’s Shoes

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Trendy Babe Lace-Up Block Heels

    Hey babe! Showcase your bold and trendy side in these fab block heels. They feature a pointed toe with a clear PVC strap, a block heel, and a lace-up design that ties at the back. The heels are composed of a faux microsuede material with an all-over leopard print. Pair these heels with a little black dress for a girl's night out.

    Fit & Features

    • Pointed toe
    • Clear PVC toe strap
    • Closed back
    • Block heel
    • Lace-up design
    • Faux microsuede material
    • All-over leopard print

    Style Number/Barcode: 07401-2539

    Category Name: Women’s Shoes

    Price: $12.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Basic Faux Leather Square Toe Block Heels

    These basic faux leather block heels are a perfect addition to your everyday workwear 'fit! They feature a trendy square toe, a thin adjustable ankle strap, and a stacked block heel. Pair these shoes with an oversized blazer for a chic and stylish look.

    Fit & Features

    • Open square toe with strap
    • Thin adjustable ankle strap
    • Closed back
    • Stacked block heel
    • PU material

    Style Number/Barcode: 07401-2504

    Category Name: Women’s Shoes

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Faux-Ever Fashionable Block Heel Booties

    Keep your look forever fashionable in these adorable booties! They feature an ankle-high design with a chic faux fur cuff, a back zipper closure, and a block heel. Pair these booties with a simple little black dress and layer on a faux leather moto jacket.

    Fit & Features

    • Ankle-high design
    • Faux fur cuff
    • Back zipper closure
    • Almond toe
    • Block heel
    • Faux microsuede material

    Style Number/Barcode: 07403-0486

    Category Name: Women’s Shoes

    Price: $18.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Lace Up Glamour Stiletto Boots

    Girl, it's time to make a statement! These boots are composed of a faux suede material and hit over the knee, they have a pointed toe, and a zipper at one side. They have a lace-up detail at the back. They are a perfect addition to your wardrobe for the cold weather! Complete look with a sweater dress.

    Fit & Features

    • Over-the-knee fit
    • Pointed toe
    • Lace-up back
    • Faux suede material
    • Zipper closure

    Style Number/Barcode: 07402-0235

    Category Name: Women’s Shoes

    Price: $12.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Feline Fierce Block Heel Combat Booties

    Make a fierce impression in leopard booties that command the room! The booties feature an around the ankle fit, a trendy leopard print, a lace-up front, an almond toe, and a stacked block heel. Complete look with a black dress. 

    Fit & Features

    • Around the ankle fit
    • Lace-up front
    • Leopard print
    • Almond toe 
    • Lug sole 
    • Stacked block heel
    • Faux microsuede material


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

    Style Number/Barcode: 07403-0416

    Category Name: Women’s Shoes

    Price: $18.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Faux Leather Stacked Block Heel Booties

    These faux leather block heel booties are the essential shoes you need this winter season! They feature an ankle-high design, a flattering almond toe, a stacked, sturdy block heel, and a back zipper closure. Keep it more casual by pairing these booties with skinny jeans, or elevate your look with a sweater dress.

    Fit & Features

    • Ankle-high design
    • Almond toe
    • Stacked block heel
    • Back zipper closure
    • Smooth faux leather material

    Style Number/Barcode: 07403-0436

    Category Name: Women’s Shoes

    Price: $16.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Faux Leather Basic Pointed Toe Booties

    Fall back to basics in a bootie that goes with all your layered looks this season. The booties feature a mid-calf fit, a pointed square toe, an inner zipper closure, and a block heel. The booties are composed of a faux leather material. Complete look with a plaid scarf.

    Fit & Features

    • Mid-calf fit
    • Inner zipper closure
    • Pointed square toe
    • Block heel
    • Faux leather material 


    Please be advised that these booties run one size too small.

    Style Number/Barcode: 07403-0497

    Category Name: Women’s Shoes

    Price: $18.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Faux Suede Studded Glam Stiletto Booties

    Make your look edgy-chic in booties that command attention! The booties feature a mid-calf fit, a pointed toe, a studded trim, and a sleek stiletto heel. Complete look with a sweater dress. 

    Fit & Features

    • Mid-calf fit
    • Pointy toe
    • Studded trim
    • Inner zipper closure
    • Stiletto heel
    • Faux suede material 

     

    Please be advised that these booties run one size too small.

    Style Number/Barcode: 07403-0488

    Category Name: Women’s Shoes

    Price: $16.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Feeling Trendy Faux Suede Lug Booties

    Tap into your fashion instincts in these booties that bring the fierce factor to your look. The booties feature a mid-calf fit, a leopard print, a lace-up front, and a lug sole. The booties are composed of faux suede material. Complete look with a black ribbed dress. 

    Fit & Features

    • Mid-calf fit
    • Leopard print
    • Almond toe
    • Lace-up front
    • Block heel
    • Lug sole
    • Faux suede material 

    Style Number/Barcode: 07403-0412

    Category Name: Women’s Shoes

    Price: $18.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Over the Knee Faux Suede Leopard Print

    Step out and make a chic statement in boots that bring the drama to your night out looks. The boots feature a trendy animal print, an over the knee fit, an inner zipper closure, a round toe, and a sleek stiletto heel. The boots are composed of a faux suede material. Complete look with a black ribbed mini dress.

    Fit & Features

    • Animal print
    • Over the knee fit
    • Round toe
    • Inner zipper closure
    • Stiletto heel


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

    Style Number/Barcode: 07402-0252

    Category Name: Women’s Shoes

    Price: $22.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale