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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.

  • Sleek Goals Over the Knee Boots

    Kick your style into a sleek direction with these patent leather boots featuring an on-trend, pointy toe, stiletto heel, side zipper closure, and an over-the-knee length. Complete the look in a sultry little black dress.

    Fit & Features

    • Pointy toe
    • Stiletto heel
    • Side zipper closure
    • Over-the-knee length
    • Patent leather material
    • Runs true to size

    Style Number/Barcode: 07402-0797

    Category Name: Women’s Shoes

    Price: $4.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sparkle Society Rhinestone Booties

    Slip into these sparkly rhinestone booties to add the perfect shine to your outfit! They feature an almond toe, block heel, side zipper closure, and a scrunched ankle fit. Complete the look in a chic trench coat for a day out & about.

    Fit & Features

    • Almond toe
    • Block heel
    • Side zipper closure
    • Scrunched ankle fit
    • Rhinestone embellished
    • Runs true to size

    Style Number/Barcode: 07403-1580

    Category Name: Women’s Shoes

    Price: $12.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Be Dazzled Rhine Over The Knee Boots

    These rhinestone over-the-knee boots will dazzle you! They feature an almond toe, block heel, side zipper closure, and a high shaft with an adjustable drawstring so you can customize the fit. Complete your glam look in a sleek LBD for date night or a concert!

    Fit & Features

    • Almond toe
    • Block heel
    • Side zipper closure
    • Over the knee length
    • Adjustable drawstring
    • Rhinestone embellishments
    • Runs true to size

    Style Number/Barcode: 07402-0816

    Category Name: Women’s Shoes

    Price: $12.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • In The Mood For Drama Stiletto Booties

    These chic stiletto booties will have you in the mood for drama! They feature a trendy pointed toe, a sleek fitted design, a tall stiletto heel, and a marabou feather trim at the ankle. Style with glitzy rhinestone jewelry.

    Fit & Features

    • Fitted ankle booties
    • Pointed toe
    • Inner zipper closure
    • Stiletto heel
    • Marabou feather trim at the ankle
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07403-1585

    Category Name: Women’s Shoes

    Price: $5.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Made For Struts Over The Knee Boots

    Made for stylish strutting down the street, you'll adore these faux leather over-the-knee boots featuring an almond toe, a stacked block heel, a side zipper closure, and a high shaft. Complete the look in a trendy sweater dress for a day in the city!

    Fit & Features

    • Almond toe
    • Stacked block heel
    • Side zipper closure
    • High shaft, over the knee
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07402-0843

    Category Name: Women’s Shoes

    Price: $4.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sleek Ambition Faux Suede Booties

    Sleek and chic, these faux suede booties make a bold statement! They feature a round toe, side zipper closure, block heel, and fit above the ankle. Complete the look in a duster trench coat.

    Fit & Features

    • Round toe
    • Side zipper closure
    • Block heel
    • Fits above the ankle
    • Faux suede material
    • Runs true to size

      Style Number/Barcode: 07403-1608

      Category Name: Women’s Shoes

      Price: $8.97 $36.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Just The Basics Platform Block Heels

      The perfect stylish PU basic heels to create all sorts of killer looks! They feature an open almond toe, wide toe strap, platform sole, block heel, closed ankle, and an adjustable ankle strap with buckle closure. Style with a chic jumpsuit for brunch.

      Fit & Features

      • Open almond toe
      • Wide toe strap
      • Platform sole, block heel 
      • Closed ankle
      • Adjustable ankle strap with buckle closure
      • PU material
      • Runs true to size

      Style Number/Barcode: 07401-4010

      Category Name: Women’s Shoes

      Price: $12.97 $28.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Western Roots Faux Leather Cowboy Boots

      Embrace your country roots with these trendy faux leather cowboy boots! They feature a below-the-knee length, a pointed toe, a short block heel, and a western-inspired embroidered design. Pair with a mini dress and a cute handbag.

      Fit & Features

      • Below-the-knee length
      • Pointed toe
      • Short stacked block heel
      • Western-inspired embroidered design
      • Faux leather material
      • Runs true to size

      Style Number/Barcode: 07402-0852

      Category Name: Women’s Shoes

      Price: $12.97 $52.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Lots To Love Block Heel Booties

      There is a lot to love about these nubuck booties and all the ways you can style them! They feature an almond toe, block heel, and side zipper closure, and fit above the ankle. Complete the look in a chic duster trench coat for a day in the city!

      Fit & Features

      • Almond toe
      • Block heel
      • Side zipper closure
      • Above the ankle length
      • Nubuck material
      • Runs true to size

      Style Number/Barcode: 07403-1570

      Category Name: Women’s Shoes

      Price: $12.97 $36.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Under Wraps Lace-Up Block Heels

      You'll be so obsessed with these lace-up heels perf for dressing up any outfit! They feature a square toe, thong toe strap, thin block heel, and a self-tie lace-up design. Complete the look in a satin midi dress for cocktail hour!

      Fit & Features

      • Square toe
      • Thin block heel
      • Thong toe strap
      • Self-tie lace-up design
      • Faux leather material
      • Runs true to size

      Style Number/Barcode: 07401-4120

      Category Name: Women’s Shoes

      Price: $12.97 $30.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Major Glow Rhinestone Chrome Heels

      These glamourous embellished chrome heels will give your formal 'fit a major glow! They feature an open almond-shaped toe, a clear toe strap, criss-cross adjustable ankle straps with mini rhinestone embellishments, a tall block heel, and an all-over metallic chrome sheen. Style with a sleek clutch.

      Fit & Features

      • Open almond-shaped toe, clear PVC toe strap
      • Criss-cross adjustable ankle straps, buckle detail
      • Heel strap
      • Rhinestone embellishments
      • Block heel
      • Chrome sheen, faux leather insole
      • Runs true to size

      Style Number/Barcode: 07401-3964

      Category Name: Women’s Shoes

      Price: $4.97 $32.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Babe Walking Platform Block Heels

      Walk that walk babe in these platform block heels! They feature an on-trend square toe, thin toe, and ankle strap with buckle closure, composed of shiny patent faux leather material. Complete the look in a marabou trim dress for a night out!

      Fit & Features

      • Square toe
      • Platform sole
      • Block heel
      • Thin toe and ankle strap, buckle closure
      • Patent faux leather material
      • Runs true to size

      Style Number/Barcode: 07401-4123

      Category Name: Women’s Shoes

      Price: $12.97 $32.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Glam Strut Rhinestone Lace-Up Heels

      Strut in these glamorous rhinestone heels into your dressy night! They feature an almond toe with strap, block heel, closed back, and a lace-up with tie closure. Complete the look with an embellished clutch.

      Fit & Features

      • Almond toe with strap
      • Block heel
      • Closed back
      • Lace-up with tie closure
      • Rhinestone embellishments
      • Nubuck material, faux leather insole
      • Runs true to size

      Style Number/Barcode: 07401-4121

      Category Name: Women’s Shoes

      Price: $22.97 $32.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Made For The Drama Platform Booties

      These sleek faux leather booties were made to bring the drama to your look! They feature a square-shaped toe, a tall platform and block heel, and an inner zipper closure. Style with glitzy rhinestone jewelry.

      Fit & Features

      • Above-the-ankle height
      • Square-shaped toe
      • Tall platform, block heel
      • Inner zipper closure
      • Faux leather material
      • Runs true to size

      Style Number/Barcode: 07403-1576

      Category Name: Women’s Shoes

      Price: $28.97 $40.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Sultry Lace-Up Thigh-High Boots

      These sultry lace-up thigh-high boots deserve all the attention! They feature a pointed toe, a sleek stiletto heel, an inner zipper closure, a stunning lace-up back design, and a form-hugging fit. Style with a mini dress and a faux leather clutch.

      Fit & Features

      • Thigh-high design
      • Pointed toe
      • Stiletto heel
      • Partial inner zipper closure
      • Lace-up back design, stud accents, tie closure
      • Form-hugging fit
      • Runs true to size

      Style Number/Barcode: 07402-0824

      Category Name: Women’s Shoes

      Price: $5.97 $42.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Such A Doll Patent Mary Jane Heels

      Doll it up, girl! These patent leather mary jane heels feature an almond toe, platform sole, block heel, and dual ankle buckle strap closures. Complete the look in a flirty skater dress for a party!

      Fit & Features

      • Almond toe
      • Block heel
      • Platform sole
      • Dual buckle strap closures
      • Patent leather material
      • Runs true to size

      Style Number/Barcode: 07401-4103

      Category Name: Women’s Shoes

      Price: $12.97 $32.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Contemporary Moves Stiletto Heels

      Shift towards a chic contemporary style in these nubuck heels featuring an almond toe, stiletto heel, wide toe strap, and criss-cross ankle straps with buckle closure. Complete the look in a statement crossbody purse.

      Fit & Features

      • Almond toe
      • Stiletto heel
      • Wide toe strap
      • Criss-cross ankle straps, buckle closure
      • Nubuck material
      • Runs true to size

      Style Number/Barcode: 07401-3975

      Category Name: Women’s Shoes

      Price: $4.97 $30.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Take A Peek Nubuck Lace-Up Booties

      One peek at these nubuck booties and you'll have to add them to your cart! They feature an almond peep toe, stacked block heel, lace-up front placket, side zipper closure, and fit above the ankle. Complete the look in a sweater dress for your weekend plans!

      Fit & Features

      • Almond peep toe
      • Stacked block heel
      • Lace-up front placket
      • Side zipper closure
      • Above-the-ankle
      • Nubuck material
      • Runs true to size

      Style Number/Barcode: 07403-1612

      Category Name: Women’s Shoes

      Price: $4.97 $38.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Glam Up Rhinestone Strappy Low Block Heels

      Amp up the glamour while still keeping it comfortable in these low block heels featuring an open square-shaped toe, a thin asymmetric strappy design accented with mini rhinestone embellishments for a pretty sparkle, and an adjustable ankle strap. Pair with your fave clutch!

      Fit & Features

      • 2.5" Low block heel
      • Open square toe
      • Asymmetric strappy design, mini rhinestones
      • Adjustable ankle strap with buckle detail
      • Closed back, faux leather padded insole
      • Black heels are faux nubuck
      • Gold and silver heels are faux leather
      • Runs true to size

      Style Number/Barcode: 07401-5113

      Category Name: Women’s Shoes

      Price: $9.97 $32.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • I Need Chunky Nubuck Block Heels

      A cool girl like you is in need of these Y2K-inspired nubuck heels! They feature an almond toe, chunky platform sole, block heel, wide cross-toe straps, and an adjustable ankle buckle strap closure. Complete the look in a sundress for a daytime soiree!

      Fit & Features

      • Almond toe
      • Chunky platform sole
      • Block heel
      • Wide cross-toe straps
      • Adjustable ankle buckle closure
      • Nubuck material
      • Runs true to size

      Style Number/Barcode: 07401-4014

      Category Name: Women’s Shoes

      Price: $25.97 $34.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Extra Spicy Nubuck Platform Heels

      Extra spicy with eye-catching allure! These nubuck platform heels elevate your look featuring an almond toe, chunky sole and block heel, wide cross-toe straps, and an adjustable ankle buckle strap closure. Complete the look in a casual mini dress for a birthday brunch!

      Fit & Features

      • Almond toe
      • Block heel
      • Chunky platform sole
      • Wide cross-toe straps
      • Adjustable ankle buckle strap closure
      • Nubuck material
      • Runs true to size

      Style Number/Barcode: 07401-4013

      Category Name: Women’s Shoes

      Price: $25.97 $34.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Retro Moments Metallic Platform Heels

      Slip on these metallic platform heels for a retro vibe! They feature an on-trend square toe, dual thin toe straps, an adjustable ankle strap, a platform, and a tall block heel. The heels show off a gorgeous iridescent metallic sheen. Style with a club dress and rhinestone fringe earrings.

      Fit & Features

      • Square-shaped toe
      • Dual toe straps
      • Adjustable ankle strap, buckle detail
      • Heel strap
      • Platform, block heel
      • Metallic sheen
      • Runs true to size

      Style Number/Barcode: 07401-4079

      Category Name: Women’s Shoes

      Price: $12.97 $32.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Fashion Strut Faux Leather Platform Booties

      The world is your runway fashionista in these strut-worthy faux leather booties featuring an almond toe, block heel, side zipper closure, and platform sole. Complete the look in skinny denim jeans.

      Fit & Features

      • Almond toe
      • Block heel
      • Side zipper closure
      • Platform sole
      • Faux leather material
      • Runs true to size

      Style Number/Barcode: 07403-1562

      Category Name: Women’s Shoes

      Price: $4.97 $34.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Glossin' Platform Block Heels

      Serve up major style in these patent block heels featuring an almond toe, platform sole, block heel, ankle strap with buckle closure, and a shiny faux leather material. Complete the look in a club dress for a night on the town. 

      Fit & Features

      • Almond toe
      • Block heel
      • Platform sole
      • Ankle strap with buckle closure
      • Patent faux leather material
      • Runs true to size

      Style Number/Barcode: 07401-3971

      Category Name: Women’s Shoes

      Price: $9.97 $30.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale