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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.

  • Rad And Retro Under The Knee Boots

    Totally rad and retro, you'll be one edgy chick in these fab under-the-knee boots featuring an almond toe, chunky platform sole and block heel, and side zipper closure, and are composed of faux leather material. Complete the look in a printed mini-dress for a party!

    Fit & Features

    • Almond toe
    • Chunky platform sole and block heel
    • Side zipper closure
    • Under-the-knee length
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07402-0865

    Category Name: Women’s Shoes

    Price: $28.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Trendy Moves Lace-Up Combat Boots

    Make major trendy moves in these cool combat boots. They feature a round toe, a lace-up front, a ribbed knit sock design at the ankle, and a chunky platform. Style with a cropped sweater and your fave pair of denim.

    Fit & Features

    • Round toe
    • Lace-up front, tie closure
    • Ribbed knit sock design
    • Lug sole platform
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07403-1443

    Category Name: Women’s Shoes

    Price: $12.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Winged Whispers Butterfly Rhinestone Mules

    These gorgeous stiletto mules showcase a sophisticated rhinestone-embellished strappy design accented with delicate butterfly details that'll make your formal or dressy look soar!

    Fit & Features

    • Stiletto heel
    • Square toe
    • Rhinestone-embellished strappy design with butterfly accents
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07401-000365

    Category Name: Women’s Shoes

    Price: $28.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: 5.5, 6, 6.5, 7, 7.5, 10

  • Line Dance Fringe Cowgirl Boots

    You'll scoot and boogie to the beat in these cowgirl boots for a night of line dancing! They feature a pointed toe, block heel, side zipper closure, and an under-the-knee shaft length with fringe on faux leather material. Complete the look in a western style hat.

    Fit & Features

    • Pointed toe
    • Block heel
    • Side zipper closure
    • Under-the-knee shaft length
    • Fringe 
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07402-0820

    Category Name: Women’s Shoes

    Price: $40.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Effortlessly Chic Over-The-Knee Boots

    These fitted over-the-knee boots are so effortlessly chic. They feature an almond-shaped toe, a block heel, and an inner zipper closure. The boots are composed of a half faux suede and half stretchy knit composition. Style with a sweater dress and a trendy boater hat.

    Fit & Features

    • Over-the-knee fitted design
    • Almond-shaped toe
    • Block heel
    • Partial inner zipper closure
    • Half faux suede and half stretchy knit composition
    • Runs true to size

    Style Number/Barcode: 07402-0812

    Category Name: Women’s Shoes

    Price: $12.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Make It Slay 50/50 Stiletto Boots

    Make every outfit slay with these stiletto boots featuring a sleek pointed toe, side zipper closure, a knee-high shaft length, and a 50/50 faux leather and scuba knit material. Style with a longline coat for a dinner in the city!

    Fit & Features

    • Pointed toe
    • Stiletto heel
    • Side zipper closure
    • Knee-high shaft length
    • 50/50 faux leather, scuba knit material
    • Runs true to size

    Style Number/Barcode: 07402-0802

    Category Name: Women’s Shoes

    Price: $4.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • First Sight Lug Block Heel Booties

    It's love at first sight when you set your eyes on these faux leather booties featuring an almond toe, block heel, lug sole, side zipper closure, and an ankle-length fit. Complete the look in a cool moto jacket.

    Fit & Features

    • Almond toe
    • Block heel
    • Side zipper closure
    • Lug sole
    • Ankle-length fit
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07403-1609

    Category Name: Women’s Shoes

    Price: $8.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Strut In Style Over-The-Knee Boots

    Strut in style in these sleek faux leather over-the-knee boots. They feature an almond-shaped toe, a tall block heel, an inner zipper closure, and a tie-back detail at the top. Pair with a bodycon dress and a moto jacket.

    Fit & Features

    • Over-the-knee design
    • Almond-shaped toe
    • Block heel
    • Partial inner zipper closure
    • Tie-back detail
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07402-0811

    Category Name: Women’s Shoes

    Price: $4.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Walking Tall Over The Knee Boots

    These over-the-knee boots were made for your daily stylish walks to and from the coffee shop! They feature a round toe, side zipper closure, PU front panel, a back knit panel, a flat sole, and low heel. Complete the look in a trendy crop jacket. 

    Fit & Features

    • Round toe
    • Side zipper closure
    • PU front panel, back knit panel
    • Flat sole
    • Low heel
    • Runs true to size

    Style Number/Barcode: 07402-0839

    Category Name: Women’s Shoes

    Price: $4.97 $40.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Howdy Partner Metallic Cowgirl Boots

    Say howdy to your new partner in crime! These metallic cowgirl boots will take you from the rodeo to line dancing at the bar. They feature a pointed toe, stacked block heel, side zipper closure, and a below-the-knee shaft length. Complete the look in a trendy denim jacket.

    Fit & Features

    • Pointed toe
    • Stacked block heel
    • Side zipper closure
    • Below-the-knee shaft length
    • Metallic faux leather material
    • Runs true to size

    Style Number/Barcode: 07402-0823

    Category Name: Women’s Shoes

    Price: $19.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Retro Gal Rhinestone Heel Booties

    Embark on a retro style quest with the help of these rhinestone booties featuring an almond toe, side zipper closure, an ultra-tall chunky platform sole, and a block heel. Complete the look in a flare jumpsuit.

    Fit & Features

    • Almond toe
    • Side zipper closure
    • Tall chunky platform sole
    • Block heel
    • All-over rhinestone embellishments
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07403-1607

    Category Name: Women’s Shoes

    Price: $4.97 $90.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Peek-A-Boo Faux Suede Booties

    Peek-a-boo do you see these chic shoes? Strut the catwalk in these faux suede booties featuring a peep toe almond toe, block heel, and a front lace-up placket and side zipper closure. Complete the look in a wide-leg jumpsuit.

    Fit & Features

    • Peep almond toe
    • Block heel
    • Front lace-up placket
    • Side zipper closure
    • Faux suede material
    • Runs true to size

    Style Number/Barcode: 07403-1483

    Category Name: Women’s Shoes

    Price: $38.90

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Catch My Drift Lace-Up Booties

    Everyone will catch your drift and step aside cause you'll be looking so stylish in these lace-up booties featuring an almond toe, block heel, platform sole, and ankle-length fit. Complete the look in a crop denim jacket.

    Fit & Features

    • Almond toe
    • Platform sole
    • Lace-up front closure
    • Block heel
    • Ankle-length fit
    • Faux suede material
    • Runs true to size

    Style Number/Barcode: 07403-1579

    Category Name: Women’s Shoes

    Price: $4.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • In Control Over The Knee Lug Boots

    Take charge of your edgy style in these over-the-knee boots featuring an almond toe, block heel, lug sole, and a 50/50 faux suede and knit material panel. Style with an oversized blazer to complete the look!

    Fit & Features

    • Almond toe
    • Block heel
    • Lug sole
    • Side zipper closure
    • Over the knee shaft length
    • 50/50 faux suede and knit material
    • Runs true to size

    Style Number/Barcode: 07402-0809

    Category Name: Women’s Shoes

    Price: $4.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Close Up Square Toe Block Heels

    You'll be ready for your close-up in these faux leather block heels featuring a trendy square toe, platform sole, and an adjustable buckle ankle strap. Complete your gorgeous look in a chic ring set.

    Fit & Features

    • Square toe
    • Platform sole
    • Block heel
    • Adjustable buckle ankle strap
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07401-3973

    Category Name: Women’s Shoes

    Price: $4.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Shimmer Down Rhinestone Block Heels

    Shimmer down to your toes in these rhinestone block heels featuring an open square toe, wide toe strap, and closed ankle with an adjustable buckle strap. Complete the look with an embellished clutch.

    Fit & Features

    • Open square toe
    • Wide toe strap
    • Block heel
    • Closed ankle with adjustable buckle strap
    • Rhinestone embellsihed
    • Runs true to size

    Style Number/Barcode: 07401-3968

    Category Name: Women’s Shoes

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Retro Babe Over-The-Knee Boots

    Show off total retro vibes in these sleek faux leather boots! They feature an over-the-knee height with an inner zipper closure, a pointed toe, and a stacked block heel. Style with your fave mini dress.

    Fit & Features

    • Over-the-knee height
    • Inner zipper closure
    • Pointed toe
    • Stacked block heel
    • Faux leather material, elastic detail at the back
    • Runs true to size

    Style Number/Barcode: 07402-0815

    Category Name: Women’s Shoes

    Price: $34.97 $43.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • City Streets Slouch Stiletto Boots

    Walk down the city streets like it's your runway in these chic slouch stiletto boots! They feature an above-the-ankle height with a trendy slouched design, a pointed toe, and a sleek stiletto heel. Style with a crossbody bag.

    Fit & Features

    • Above-the-ankle height
    • Slouchy silhouette
    • Partial inner zipper closure
    • Pointed toe
    • Stiletto heel
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07403-1592

    Category Name: Women’s Shoes

    Price: $8.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Smooth Like Me Over The Knee Boots

    Smooth and sultry, these over-the-knee boots are the ticket to an elevated style! They feature an almond toe, block heel, and side zipper closure, an adjustable drawcord at the top, and are composed of faux suede material. Complete the look in high-rise skinny jeans.

    Fit & Features

    • Almond toe
    • Side zipper closure
    • Block heel
    • Over-the-knee shaft length
    • Adjustable drawcord at the top
    • Faux suede material
    • Runs true to size

    Style Number/Barcode: 07402-0851

    Category Name: Women’s Shoes

    Price: $12.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sleek Moves Over-The-Knee Stiletto Boots

    Make sleek moves in these chic over-the-knee stiletto boots! They feature a pointed toe, a thin stiletto heel, dual buckle accents at the ankle and knee, and an inner zipper closure. Style with a sweater dress and hoop earrings.

    Fit & Features

    • Over-the-knee fit
    • Pointed toe
    • Stiletto heel
    • Dual buckle accents
    • Partial inner zipper closure
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07402-0850

    Category Name: Women’s Shoes

    Price: $6.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Peep This Chic Cutout Booties

    Check out these chic nubuck booties and imagine all the ways you'd style them! They feature an almond peep toe, platform sole, stacked thin block heel, cutout sides, and an adjustable buckle strap and back zipper closure. Complete the look in a wide-leg jumpsuit for cocktail hour.

    Fit & Features

    • Almond peep toe
    • Platform sole
    • Stacked thin block heel
    • Cutout sides
    • Adjustable buckle strap and back zipper closure
    • Nubuck material
    • Runs true to size

    Style Number/Barcode: 07403-1567

    Category Name: Women’s Shoes

    Price: $4.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • In The Details Faux Leather Platform Booties

    You may want to get a close look to admire the details on these faux leather platform booties! They feature an almond toe, block heel, side knit panels, and zipper closure with an above-the-ankle shaft. Complete your edgy-girl look with a moto jacket!

    Fit & Features

    • Almond toe
    • Block heel
    • Platform sole
    • Side knit panels and zipper closure
    • Above-the-ankle shaft
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07403-1568

    Category Name: Women’s Shoes

    Price: $10.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Love Story Era Heart Rhinestone Thong Heels

    These stilettos add a touch of romance to any outfit, featuring a chic square toe and a delicate thong strap adorned with a sparkling rhinestone heart.

    Fit & Features

    • 3" Stiletto heel
    • Square toe
    • Thong strap with rhinestone heart
    • Cushioned insole
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07401-000047

    Category Name: Women’s Shoes

    Price: $28.90

    Availability: In Stock

    Available Color: BLACK, WHITE, GOLD

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

  • Miss Stylish Lace Up Stiletto Booties

    Live up to your name in these showstopping stiletto booties featuring an almond peep toe, a cutout design with lace-up straps, and a back zipper closure on faux suede material. Complete the look in a sultry sweater dress.

    Fit & Features

    • Almond peep toe
    • Stiletto heel
    • Cutout design
    • Lace-up straps
    • Back zipper closure
    • Faux suede material
    • Runs true to size

    Style Number/Barcode: 07403-1564

    Category Name: Women’s Shoes

    Price: $4.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale