$20 Dress Shoes

$20 dress shoes are the answer to your “I need to look put-together, but my bank account says otherwise” dilemma. Whether you’re RSVPing yes to something fancy or just want to upgrade your everyday, these picks prove that style and savings actually can go hand in hand. No more sacrificing your vibe for your budget—step into something polished without overthinking the price tag. Your outfit (and wallet) will thank you.

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Windsor Chic Trend Thong Strap Kitten Heel Mules in Beige

$9.97 $24.90 60% off

A beige faux leather mule with a thong strap, buckle detail, kitten heel, and cushioned insole.

Windsor Sweet Attraction Toe Ring Strappy Block Heels in White

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Windsor Sweet Attraction Toe Ring Strappy Block Heels in White

$9.97 $26.90 63% off

A pair of white faux leather block heels featuring a trendy toe ring trim and strappy design.

Windsor Walking Pretty Toe Ring Heels in White

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Windsor Walking Pretty Toe Ring Heels in White

$9.97 $28.90 66% off

A sleek white leather block heel mule featuring a metallic toe ring and strappy design for standout style.

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Windsor Princess Calling Satin Slingback Heels in Blue

$9.97 $44.90 78% off

A modern blue satin slingback heel featuring a pointed toe, kitten heel, and adjustable ankle strap.

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Windsor Studded Edge Pointed Kitten Pumps in Black

$12.97 $32.90 61% off

A black faux leather pump featuring a pointed toe, studded grommet trim, and a 2.5" kitten heel.

Windsor Strut Bold Pointed Slingback Pumps

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Windsor Strut Bold Pointed Slingback Pumps

$12.97 $42.90 70% off

A multi-colored satin slingback pump featuring a pointed toe, kitten heel, and adjustable ankle strap.

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Windsor City Lights Bow Grommet Block Heels in Black

$12.97 $34.90 63% off

A black faux leather block heel featuring grommet-studded crisscross straps, bow detail, and cushioned insole.

Windsor Playing It Cute Strappy Buckle Wedge Heels in White

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Windsor Playing It Cute Strappy Buckle Wedge Heels in White

$9.97 $26.90 63% off

A chic pair of white faux leather wedge heels featuring strappy design and an eye-catching buckle accent.

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Windsor Smooth And Sleek Block Heels in Black

$26.90

(74)

Step out in style in these chic low block heels! Create the perfect stylish graduation outfit or gorgeous prom look in these comfortable heels. This open-toe design features a stylish ankle strap detail with a zipper-closed back on a trendy block heel. The lower heel silhouette creates a supportive and comfy fit, perfect to wear with a semi-formal gown or dressy pant outfit. Fit & FeaturesZippered closed back , Ankle strap strap, Open almond toe , Single strap over the toe, Low block heel , Faux leather and nubuck material , Luxe fit cushioned insole, Runs true to size, Stylish looks perfect for video calls, virtual meetings, happy hours, e-dates, and remote work from home. Free Shipping on All Orders Over $75. | Windsor Smooth And Sleek Block Heels in Black | Size: 6 | Leather/Nubuck

Windsor Endless Glam Rhinestone Bow Block Heels in Silver

$36.90

(7)

Every step will look so glam in these rhinestone block heels featuring a statement bow and a luxe fit insole for comfort. Pair with a clutch. Fit & Features3" Block heel, Almond toe, Adjustable ankle strap, buckle closure, Luxe fit breathable cushioned insole, Rhinestones, Bow accent, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Endless Glam Rhinestone Bow Block Heels in Silver | Size: 8

Flirt Mode Activated Strappy Block Heels in White

$30.90

(6)

These heels understood the assignment—flirty, chic, and ready to turn heads. With strappy detailing and a comfy block heel, they’re made for rooftop hangs, brunch dates, and everything in between. Fit & FeaturesBlock heel, Open square-shaped toe, Asymmetric strappy design, Adjustable ankle strap with buckle detail, Faux leather material, padded insole, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Flirt Mode Activated Strappy Block Heels in White | Size: 10 | Leather

So Much Personality Strappy Block Heels in Black

$28.90

(4)

Give your outfits some cuteness in these strappy block heels, perfect for pairing with your favorite bottoms or dresses! Fit & Features3" Round block heel, Square toe, Strappy design, Cushioned insole, Faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor So Much Personality Strappy Block Heels in Black | Size: 5.5 | Leather

Windsor Chic And Polished Pearl Satin Block Heels in White

$35.90

(4)

The kind of heels that take you from “just cute” to “can’t look away” in one step. With faux pearl embellished straps and a sleek block heel, they’re a dream for bridal celebrations and birthday soirees! Fit & Features3" Block heel, Square toe, Faux pearl embellished straps, Adjustable ankle strap with buckle closure, Satin material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Chic And Polished Pearl Satin Block Heels in White | Size: 8

Feeling Chic Thong Square Toe Heels in Wine

$26.90

(4)

From daytime outings to nights out, these thong heels are perfect for dressing up any look for every occasion! Fit & Features2" short kitten heel, Square toe, Thin thong toe strap, Cushioned insole, Faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Feeling Chic Thong Square Toe Heels in Wine | Size: 7 | Leather

Starlight Steps Strappy Block Heels in Gold

$34.90

(4)

Shine with every step—these strappy block heels bring the glam with glittery straps and a sturdy heel that’s perfect for dancing all night. Chic, comfy, and totally party-approved. Fit & FeaturesBlock heel, Almond toe, Rhinestone-embellished straps, Closed ankle, back zipper closure, Luxe fit cushioned insole, Glitter material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Starlight Steps Strappy Block Heels in Gold | Size: 6.5 | Rhinestone

Chic Crush Strappy Block Heels in Wine

$36.90

(3)

Bold, sleek, and made to steal the spotlight—these strappy heels bring the drama with a deep red shine and chic block heel. Perfect for everything from cocktail nights to holiday parties. Fit & FeaturesBlock heel, Square toe, Asymmetrical strappy design, Luxe fit cushioned insole, Adjustable ankle strap with buckle closure, Patent faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Chic Crush Strappy Block Heels in Wine | Size: 8 | Leather

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Windsor Sweet Attraction Toe Ring Strappy Block Heels in White

$9.97 $26.90
63% off

(3)

A pair of strappy block heels with a trendy toe ring trim that gives every outfit a sweet look! Fit & Features2.5" Block heel, Square toe, Strappy design, Toe ring trim, Luxe fit cushioned insole, Faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sweet Attraction Toe Ring Strappy Block Heels in White | Size: 10 | Leather

Ultra Luxe Rhinestone Short Block Heels in Pearl

$32.90

(3)

Ultra-luxe rhinestones embellish the asymmetrical toe straps on these chic short block heels perfect for brides, birthday babes, or dressy events! Pair with a clutch. Fit & Features2" short block heel, Square toe, Rhinestone embellished asymmetrical toe straps, Closed ankle with adjustable strap, buckle closure, Faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Ultra Luxe Rhinestone Short Block Heels in Pearl | Size: 8 | Leather/Rhinestone

$20 Dress Shoes

Let’s be honest: finding the perfect pair of dress shoes for under $20 feels a bit like catching lightning in a bottle. But when you do, it’s a total game-changer—suddenly, the “I have nothing to wear” panic before a dinner date, office party, or last-minute invite basically vanishes. $20 dress shoes are the unsung heroes of your closet, quietly boosting your confidence without draining your wallet. Whether you’re prepping for a winter formal, piecing together a polished look for Friendsgiving, or just looking to refresh your workwear rotation, affordable dress shoes make it possible to experiment with trends, play with textures, and try out those bold styles you’ve been eyeing—without the commitment of a major splurge. And let’s not forget the satisfaction of snagging something chic that looks way more expensive than it actually is. There’s a little thrill in knowing you can step out looking like you spent hours curating your look, when really, you just found a deal that works as hard as you do.

Dress shoes in this price range are all about versatility and accessibility. Think of them as the ultimate style chameleons—ready to elevate your look for a holiday party one weekend and then seamlessly transition into your everyday wardrobe for the rest of the season. They’re perfect for anyone who loves to switch up their vibe depending on the occasion, and they’re an especially thoughtful gift for friends, siblings, or roommates who are always on the go (or always borrowing your shoes). Imagine gifting a pair to your bestie who’s got a packed calendar of winter events, or to your cousin who just landed her first job and wants to look sharp without overspending. Even if you’re shopping for yourself, $20 dress shoes let you take a few more style risks—maybe a pop of metallic for New Year’s Eve, a classic pump for office hours, or a strappy heel for that one night out you’ve been planning since September. The best part? You never have to stress about saving them “for special occasions”—these are shoes meant to be worn, loved, and lived in, season after season.

When it comes to choosing the right pair, comfort and fit are everything—especially as the temperatures drop and you’re spending more time on your feet at holiday gatherings or braving chilly sidewalks between parties. Look for cushioned insoles, supportive straps, and walkable heel heights that let you move with confidence (and maybe even dance a little longer). Don’t be afraid to step outside your comfort zone with textures like faux suede, patent finishes, or bold colors that add a little extra energy to your look. And if you’re in the market for something that can pull double duty—from daytime errands to after-dark plans—consider styles that are easy to dress up or down with a quick change of accessories. For even more inspiration, check out our curated collection of $20 Going Out Shoes—because sometimes, the right pair is all you need to turn a regular night into one you’ll actually remember. With so many options at this price point, you can finally give your closet the refresh it deserves, without sacrificing your budget or your style.

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