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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.

  • Minimal Moment Thin Block Heels

    Keep it minimal in heels that simply go with everything. Dress up your casual outfits with these fab heels. The heels feature an adjustable ankle strap, an open almond toe with a single strap over the toe, and a sleek thin block heel. Complete your look with a ribbed midi dress and blazer.

    Fit & Features

    • Adjustable ankle strap
    • Open almond toe
    • Single strap over the toe
    • Thin block heel

    Style Number/Barcode: 07401-2407

    Category Name: Women’s Shoes

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Get On My Level Chunky Sneakers

    Step up in chunky sneakers that elevate your streetwear looks! The sneakers feature a round toe, bungee lace-up straps, a velcro strap detail at the ankle and a chunky sole. Complete your look with boyfriend jeans and layer with a denim jacket. 

    Fit & Features

    • Round toe
    • Bungee lace-up straps
    • Velcro strap detail at the ankle
    • Chunky textured sole

    Style Number/Barcode: 07407-0163

    Category Name: Women’s Shoes

    Price: $12.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • All White Chunky Lace Up Sneakers

    These all-white chunky dad sneaks will make you the trendy member of your squad! They feature a chunky sole and a lace-up design. Pair them with some distressed mom jeans and a graphic tee for a fun shopping day with your girls.

    Fit & Features

    • Round toe
    • Chunky sole
    • Lace-up front
    • Pull tab
    • All-white hue

    Style Number/Barcode: 07407-0165

    Category Name: Women’s Shoes

    Price: $18.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Boot Scootin’ & Vibin’ Cowboy Boots

    Giddy up, but make it fashion. These cowboy boots bring rodeo realness with a side of city-girl sass—perfect for concerts, content days, or just stomping through life like it’s your personal runway.

    Fit & Features

    • Stacked block heel
    • Almond toe
    • Western-inspired pattern
    • Inner zipper closure
    • Knee-length shaft height
    • Faux suede material
    • Runs true to size

    Style Number/Barcode: 07402-000046

    Category Name: Women’s Shoes

    Price: $52.90

    Availability: In Stock

    Available Color: CAMEL

    Available Size: 6, 7, 7.5, 8, 8.5, 9

  • Clearly On Trend Chunky Sneakers

    Clear stay on trend in sneakers that give your streetwear outfits major style! The sneakers feature a lace-up front, a round toe and a clear insert at the sole. Complete your look with a cute crop top and high waist jeans.

    Fit & Features

    • Lace-up front
    • Round toe
    • Pull tabs at the back of the ankle
    • Clear insert at the sole
    • Chunky sole

    Style Number/Barcode: 07407-0173

    Category Name: Women’s Shoes

    Price: $23.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sultry Snake Faux Leather Block Heels

    Keep it sassy in heels that bring some serious sultry appeal. The block heels feature a trendy snake print, a closed-back, an open square toe with a single strap over the toe, and a block heel. Complete your night out look with a black dress and silver accessories. 

    Fit & Features

    • Closed-back 
    • Snake pattern 
    • Open square toe
    • Single strap over the toe
    • Block heel
    • Faux leather material 

    Style Number/Barcode: 07401-2434

    Category Name: Women’s Shoes

    Price: $16.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chrome Cutie Block Heels

    Keep it chic in chrome heels that will create head-turning looks! The heels feature a chrome finish, an open almond toe with a single strap over the toe and a sturdy block heel. Complete your outfit with a stunning formal dress. 

    Fit & Features

    • Narrow adjustable ankle strap
    • Open almond toe with a single strap over the toe
    • Closed-back 
    • Block heel
    • Chrome finish 

    Style Number/Barcode: 07401-2433

    Category Name: Women’s Shoes

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Moment Faux Leather Stiletto Heels

    Create a chic moment in heels that slay! Perfect for styling with your brunch outfit, these heels are a must. The heels feature an adjustable ankle strap, a strap over the back of the ankle, a trendy square toe, and wide stiletto heel. Complete look with a midi dress and hoops. 

    Fit & Features

    • Adjustable ankle strap
    • Strap over the back of the ankle
    • Double-row of narrow straps over the toe
    • Square toe
    • Wide stiletto heel
    • Faux leather material 

    Style Number/Barcode: 07401-2424

    Category Name: Women’s Shoes

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Chic and Charming Criss Cross Platform Block Heels

    Charm them all in heels that bring the chic factor to your looks! 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 leather material 

    Style Number/Barcode: 07401-2396

    Category Name: Women’s Shoes

    Price: $16.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wild and Fierce Chunky Sneakers

    Keep it wild in sneakers that show off your fierce side! The sneakers feature a high arch, a leopard print detail, a lace-up front, and a chunky sole. Complete your look with a sleek midi dress and layer with a denim jacket. 

    Fit & Features

    • High arch with pull tabs at the ankles
    • Round toe
    • Lace-up front
    • Leopard print trim 
    • Chunky sole

    Style Number/Barcode: 07407-0161

    Category Name: Women’s Shoes

    Price: $18.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Glam and Chic Chunky Sneakers

    Keep it glam and sporty in sneakers that bring the chicness to your look! The sneakers feature a high arch, lace-up front, a multi-tone design, and a chunky sole. Complete your look with a sleeveless mini dress and a cropped denim jacket. 

    Fit & Features

    • High arch with pull tabs at ankle
    • Round toe
    • Multi-tone design 
    • Lace-up front
    • Chunky sole

    Style Number/Barcode: 07407-0160

    Category Name: Women’s Shoes

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Pop of Pink Chunky Sneakers

    Keep it pretty in pink with sneakers that bring a pop of glam to your trendy streetwear look! The sneakers feature a round toe, a lace-up front, a two-tone design, and a chunky sole. Complete your look with skinny jeans and a crop top.

    Fit & Features

    • Round toe
    • Lace-up front
    • Two-tone design
    • Pull tabs at the ankle
    • Chunky sole

    Style Number/Barcode: 07407-0164

    Category Name: Women’s Shoes

    Price: $21.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wild Instincts Leopard Lug Booties

    Channel your fashion instinct in booties that reflect your fierce side! These ankle booties feature a trendy leopard print, a round toe, goring at each side to easily put on, and a textured lug sole. Complete your look with biker shorts and a statement top. 

    Fit & Features

    • Leopard print
    • Ankle-length
    • Inner zipper closure, pull tabs at back
    • Goring at each side
    • Round toe
    • Stacked block heel
    • Textured lug sole

    Style Number/Barcode: 07403-0314

    Category Name: Women’s Shoes

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Totally Grounded Two-Strap Sandal

    Equal parts versatile and vibrant, these summer sandals make a statement, and the statement is chill, down to earth, boho babe.

    • Round toe
    • Double buckle design
    • Slide on 
    • Cork + lug sole
    • Silver hardware

    Style Number/Barcode: 07404-0530

    Category Name: Women’s Shoes

    Price: $6.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

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

    Everyone needs that basic pair of faux leather booties for the fall season! These feature a trendy pointy toe and a sturdy heel with a zip-up closure at the back. Transition your summer dresses into fall by pairing them with these booties and layering on a cozy cardigan. Wear to a coffee date with bae!

    Fit & Features

    • Pointy toe
    • Zip-up closure at back
    • Sturdy heel
    • PU material

    Style Number/Barcode: 07403-0363

    Category Name: Women’s Shoes

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sassy Straps Faux Suede Stiletto Heels

    Lace-up in stunning heels that elevate your outfits. The heels feature lace-up straps, a zippered back, a square toe, and composed of faux suede material. Complete your look with a bodycon dress and duster earrings. 

    Fit & Features

    • Lace-up straps 
    • Zippered back 
    • Open square toe
    • Strap over the toe
    • Faux suede material 

    Style Number/Barcode: 07401-2427

    Category Name: Women’s Shoes

    Price: $17.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sassy Leopard Print Square Toe Stiletto Heels

    Make a sassy statement in these of the moment stiletto heels! With their trendy leopard print and wrap-around design, you can take these from brunch to date night. Pair with some distressed mom jeans and a chic blouse for an elevated look.

    Fit & Features

    • Open square toe
    • Strappy wrap-around design that ties at the ankle
    • Back zipper closure
    • Stiletto heel
    • Faux suede material

    Style Number/Barcode: 07401-2428

    Category Name: Women’s Shoes

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • The Everyday Faux Suede Booties

    Keep it chic every day in booties that go with every outfit! The booties feature an around the ankle fit, a trendy pointed toe, and a sturdy block heel to take you from day to night. Complete your look with high waist mom jeans and an off the shoulder top.

    Fit & Features

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

    Style Number/Barcode: 07403-0308

    Category Name: Women’s Shoes

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Bold Edge Platform Zipper Booties

    Bold and edgy, these faux leather booties step up your everyday vibe with a platform sole and zipper detailing.

    Fit & Features

    • Block heel
    • Square toe
    • Dual zipper closure sides
    • Platform sole
    • Ankle-length shaft height
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07403-000011

    Category Name: Women’s Shoes

    Price: $15.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bringing It Back To Basics Faux Nubuck Block Heel

    Bring it back to basics in heels that go with everything! Perfect for your next date night and workwear outfit, these heels are a must. The heels feature a wide velcro ankle strap for a secure fit, an open almond toe, and a sturdy block heel. Complete your outfit with a ribbed sweater dress and fringe earrings. 

    Fit & Features

    • Wide velcro ankle strap
    • Open almond toe
    • Single strap over the toe
    • Block heel
    • Faux nubuck material 

    Style Number/Barcode: 07401-2397

    Category Name: Women’s Shoes

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Major Metallic Moment PU Booties

    Have a major metallic moment in these stunning PU booties! They feature a trendy lace-up front with a lug sole and a thick block heel. Pair with a simple little black dress to let your booties make a statement at your next party.

    Fit & Features

    • Lace-up front
    • Inner zipper closure
    • Dual ankle straps
    • Lug sole
    • Thick block heel
    • Foiled PU material

    Style Number/Barcode: 07403-0348

    Category Name: Women’s Shoes

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Square Toe Strappy Stiletto Heels

    Get ready to strut it out in these sassy stiletto heels! They feature a trendy square toe shape and a strappy design. A must-have for date night, pair with a chic mini dress and layer on a faux leather jacket.

    Fit & Features

    • Square toe
    • Dual thin toe straps
    • Wrap around strappy design
    • Thin adjustable ankle strap
    • Open back
    • Stiletto heel
    • PU material

    Style Number/Barcode: 07401-2423

    Category Name: Women’s Shoes

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Glow Goals Rhinestone Block Heels

    These heels are giving us major glow vibes! Dazzle up your night out outfits or add a glam touch to your formal outfits in these stunning block heels. The heels feature an around the ankle strap, an open almond toe, and a rhinestone embellished strap over the toe. Complete your look with dazzling rhinestone earrings. 

    Fit & Features

    • Around the ankle strap
    • Zippered back 
    • Open almond toe 
    • Rhinestone embellished strap over the toe
    • Block heel 
    • Faux suede material 

    Style Number/Barcode: 07401-2409

    Category Name: Women’s Shoes

    Price: $18.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So Sleek Block Heel Booties

    Take these perfectly polished booties from work to the weekend without a hitch! Booties feature a faux leather outer, a gently pointed toe, a low shaft with back zip, and a stabilizing, medium-height block heel. Complete your look with high waist jeans and an oversized sweater for the perfect fall outfit. 

    Fit & Features

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

    Style Number/Barcode: 07403-0313

    Category Name: Women’s Shoes

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free