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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 summer 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 Summer Flex

Scroll less and slay more with Windsor’s must-have summer 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.

  • 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
  • Full Bloom Floral Cowboy Booties

    You'll be the cutest around in these cowboy booties at bachelorettes, festivals, or concerts! Featuring intricate floral embroidery, these pointed-toe Western booties offer a Western charm to any look.

    Fit & Features

    • Stacked block heel
    • Pointed-toe
    • Ankle-length shaft height
    • Floral embroidery
    • Runs true to size

    Style Number/Barcode: 07403-000010

    Category Name: Women’s Shoes

    Price: $55.90

    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
  • 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
  • Moving On Faux Leather Lucite Booties

    Move on from basic to chic in booties that elevate your looks! The booties feature an around the ankle fit, an inner zipper closure, a pointed toe, and a narrow lucite block heel. Complete your look with high waist jeans and an oversized sweater. 

    Fit & Features

    • Around the ankle fit
    • Inner zipper closure
    • Pointed toe
    • Narrow lucite block heel
    • Faux leather material

    Style Number/Barcode: 07403-0311

    Category Name: Women’s Shoes

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Clearly Chic Lucite Block Heels

    Clearly stay on trend in heels that keep your looks stylish and chic. The heels feature an adjustable ankle strap, an open almond toe with clear strap, and a lucite block heel. Complete your look with a chic sweater dress and duster earrings. 

    Fit & Features 

    • Adjustable clear ankle strap
    • Clear strap at the heel
    • Open almond toe with clear strap
    • Lucite block heel
    • Faux patent leather sole

    Style Number/Barcode: 07401-2388

    Category Name: Women’s Shoes

    Price: $12.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Keep It Classic Block Heels

    Sometimes you just have to keep it classic with a good pair of block heels! These feature an open almond toe and a shorter block heel. Pair with your fave paper bag pants and a chic blouse for a look you can totally wear to the office.

    Fit & Features

    • Open almond toe
    • Toe strap
    • Adjustable around the ankle strap
    • Open back
    • Short block heel
    • Faux nubuck

    Style Number/Barcode: 07401-2383

    Category Name: Women’s Shoes

    Price: $12.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Spin Me Around Spiral Rhinestone Stiletto Heels

    Give it a twirl in rhinestones! These heels make a true shining statement and we are obsessed. They feature a rhinestone adorned spiral wrap around ankle strap. Style with a mini dress and let those legs shine!

    Fit & Features

    • Open almond toe
    • Double band detail
    • Spiral wrap around ankle strap
    • Rhinestone detailing
    • Shiny faux leather with a metallic finish
    • Skinny stiletto heel

    Style Number/Barcode: 07401-2306

    Category Name: Women’s Shoes

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cute And Chic Rhinestone Bow Heels

    Show off your cute and chic side in these adorable rhinestone bow heels! Glam it up in these shoes that feature a statement rhinestone bow and a sleek stiletto heel. Get ready to grab drinks with your girls in these sweet heels and a stunning little black dress.

    Fit & Features

    • Open toe
    • Rhinestone embellished bow accent
    • Adjustable around the ankle strap
    • Closed-back
    • Stiletto heel
    • Patent PU material

    Style Number/Barcode: 07401-2210

    Category Name: Women’s Shoes

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Just Dance Peep Toe Clear Heels

    These peep toe clear heels are ready for you to dance in and make a statement! These heels have a fun and sexy element with their rhinestone wrap around ankle strap that will really amp up your special event dress. Pair with a sparkly clutch to bring the glamour.

    Fit & Features

    • Peep toe
    • Curved band over the toe
    • Clear heel backing 
    • Chrome lining and on the heel
    • Rhinestone detailing
    • Adjustable pin-buckle closure

    Style Number/Barcode: 07401-2312

    Category Name: Women’s Shoes

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Slay Each Step Block Heels

    You'll slay each step in these adorable faux nubuck block heels! They feature a criss cross ankle strap design and a shorter sturdy block heel. A must-have for wearing from the office to dinner, pair with a chic curve-hugging pencil skirt and a flowy blouse.

    Fit & Features

    • Open almond toe
    • Toe strap
    • Criss cross front design
    • Adjustable ankle strap
    • Closed-back
    • Short block heel
    • Faux nubuck material

    Style Number/Barcode: 07401-2387

    Category Name: Women’s Shoes

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Casual Chic Quilted Faux Leather Sneakers

    Get a casual chic vibe in these adorable faux leather slip-on sneaks! They feature a quilted diamond faux leather design and a thick sole. Pair with a cute mini dress and layer on a denim jacket for a date night with bae.

    Fit & Features

    • Slip-on design
    • Elastic details
    • Quilted diamond design
    • PU material
    • Stud detailing on the back
    • Thick sole

    Style Number/Barcode: 07407-0168

    Category Name: Women’s Shoes

    Price: $12.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Feelin' Wild Leopard Print Sneakers

    Showcase your sassy, wild side in these too cute leopard print sneaks! They feature an easy slip-on design with a thick sole. Pair with some mom jeans and a graphic tee to go shopping with your squad.

    Fit & Features

    • Slip-on design
    • Elastic details
    • Leopard print
    • Thick sole

    Style Number/Barcode: 07407-0167

    Category Name: Women’s Shoes

    Price: $14.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • A Touch Of Glam Block Heels

    Add just a touch of glam to your 'fit with these metallic block heels! These feature an open almond toe and a shorter block heel. Pair with your fave little black dress to make a gorgeous statement.

    Fit & Features

    • Open almond toe
    • Toe strap
    • Adjustable around the ankle strap
    • Open back
    • Short block heel
    • Metallic finish

    Style Number/Barcode: 07401-2385

    Category Name: Women’s Shoes

    Price: $14.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale