$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 Sweet Step Bow Detail Slingback Pumps in Blush

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Windsor Sweet Step Bow Detail Slingback Pumps in Blush

$9.97 $36.90 73% off

A blush patent faux leather slingback pump featuring a satin bow, rhinestone accents, and stiletto heel.

Windsor Glam Line Rhinestone Slingback Pumps in Silver

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Windsor Glam Line Rhinestone Slingback Pumps in Silver

$9.97 $40.90 76% off

A dazzling silver slingback pump featuring allover rhinestones, a pointed toe, and a sleek stiletto heel.

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Windsor Strut And Stun Thong Mules Shoes in Clear

$11.97 $28.90 59% off

A pair of clear faux leather thong mules featuring sleek straps, a square toe, and stiletto kitten heels.

So Much Personality Strappy Block Heels in Red

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So Much Personality Strappy Block Heels in Red

$11.97 $28.90 59% off

A chic pair of red faux leather strappy block heels with a cushioned insole and square toe.

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Sun Chaser Stiletto Buckle Mules Shoes in Beige

$9.97 $34.90 71% off

A chic pair of beige rafia stiletto mules featuring wide dual straps and a stylish buckle accent.

Glam Steps Rhinestone Buckle Strap Mules Shoes in Black

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Glam Steps Rhinestone Buckle Strap Mules Shoes in Black

$9.97 $38.90 74% off

A black satin mule featuring an oversized rhinestone buckle and cushioned insole for glamorous evenings.

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Windsor Own the Moment Patent Heeled Mules in Burgundy

$30.90

(5)

Strut like the sidewalk is your runway in these patent heeled mules! Perfect for dressing up your everyday slay or for a night out plans. Fit & FeaturesShort stiletto heel, Pointed toe, Luxe fit cushioned insole, Patent faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Own the Moment Patent Heeled Mules in Burgundy | Size: 9 | Leather

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Strut And Stun Thong Mules Shoes in Clear

$11.97 $28.90
59% off

(5)

From day to night plans, these thong heels are the ultimate stylish shoe to have this season. Sleek straps and a chic square toe make them the perfect pair with your casual or dressy looks. Fit & Features3" Stiletto kitten heel, Open square toe, Thong straps, Faux leather material, Luxe fit cushioned insole, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Strut And Stun Thong Mules Shoes in Clear | Size: 10 | Leather

Classy Luxe Rhinestone Strappy Stiletto Mules Shoes in Gold

$32.90

(4)

Step out in these classy luxe stiletto mules with glitzy rhinestone embellished straps perfect for bringing glam to every party or event. Pair with a clutch. Fit & Features3.5" Stiletto heel, Square toe, Rhinestone-embellished straps, Luxe fit cushioned insole, Glitter material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Classy Luxe Rhinestone Strappy Stiletto Mules Shoes in Gold | Size: 6.5

Sips And Sunshine Strappy Thong Mules Shoes in Blue

$28.90

(4)

Made for selfies at brunch and champagne toasts. These strappy mule heels are your instant plus-one for every outfit that deserves a little flirty flair. Fit & Features3" Kittel heel, Square toe, Strappy thong design, Cushioned insole, Faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sips And Sunshine Strappy Thong Mules Shoes in Blue | Size: 6 | Leather

Romance Hour Velvet Bow Mules Shoes in Burgundy

$34.90

(4)

All charm, no effort. These velvet bow heels bring that perfect mix of luxe and flirt—with a soft, sculpted bow and sleek kitten heel made for dancing (or just looking fabulous). A little vintage, a little modern, and totally irresistible. Fit & FeaturesKitten heel, Velvet closed-pointed toe, Statement bow, Cushioned insole, Velvet material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Romance Hour Velvet Bow Mules Shoes in Burgundy | Size: 8

Windsor Strap In Thong Buckle Mules Shoes in White

$28.90

(3)

The heel that knows how to keep it classy but still turn heads. With a sleek square toe, thong strap, and ankle buckle, these mules are ready for everything from hotel brunches to date night. Fit & Features3" Thin block heel, Square toe, Thong strap, Adjustable ankle buckle strap, Cushioned insole, Faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Strap In Thong Buckle Mules Shoes in White | Size: 7 | Leather

Windsor The Night Is Yours Bow Mules Shoes in Black

$40.90

(3)

Dress to dazzle in these rhinestone-studded mule heels featuring an oversized bow accent that steals the spotlight with every step. The sleek stiletto heel and slip-on design bring instant glam to your night-out rotation. Fit & FeaturesStiletto heel, Square toe, Statement bow detail and rhinestone embellishments, Luxe fit cushioned insole, Faux suede material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor The Night Is Yours Bow Mules Shoes in Black | Size: 7 | Faux Suede/Rhinestone

All That Glitters Rhinestone Mules Shoes in Gold

$32.90

(2)

The heels that never miss. These stiletto mules bring effortless glam with rhinestone straps that catch every bit of light—and attention. Designed with a sculpted heel and sleek silhouette, they’re your not-so-secret weapon for any night worth dressing up for. Fit & FeaturesStiletto heel, Square toe, Rhinestone-embellished strappy design, Luxe fit cushioned insole, Metallic material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor All That Glitters Rhinestone Mules Shoes in Gold | Size: 9

Windsor Chic Strut Strappy Block Heel Mules in Red

$28.90

(1)

Show off a chic strut in these block heel mules featuring an open almond toe and a dual strappy banded design. The open back offers effortless on-and-off styling. Fit & FeaturesAsymmetric block heel, Open almond-shaped toe, Dual strappy banded design, Patent faux leather material, Open back, on-and-off styling, Cushioned insole, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Chic Strut Strappy Block Heel Mules in Red | Size: 8 | Leather

Windsor Sleek Luxe Strappy Stiletto Mules Shoes in Camel

$30.90

(1)

These strappy square toe stilettos feature a sleek mule silhouette topped with a chic gold ball accent that turns every step into a statement. Fit & Features3" Stiletto heel, Square toe, Strappy design with gold ball accent, Cushioned insole, Faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sleek Luxe Strappy Stiletto Mules Shoes in Camel | Size: 8 | Leather

$20 Dress Shoes

Finding the perfect pair of dress shoes for $20 isn’t just a budget win—it’s a style power move, especially when your calendar is filling up with everything from winter formals to spontaneous dinner plans. January’s chill might call for cozy layers, but your shoe game doesn’t have to hibernate. Affordable dress shoes are the unsung heroes of a well-rounded wardrobe, stepping in when you want to look pulled together without feeling overdone (or overdrafted). Whether you’re heading to a last-minute job interview, RSVPing to a friend’s engagement party, or just want to elevate your everyday jeans-and-sweater combo, these shoes deliver polish without pressure. They’re the secret weapon for anyone who wants to look like they planned their outfit days in advance—even if they only had ten minutes between Zoom calls and Uber rides.

Let’s be real: not every occasion calls for a splurge. Sometimes, you need a pair of dress shoes that can handle a night out, a family dinner, or a quick coffee date, and still leave enough in your wallet for brunch the next morning. That’s where $20 dress shoes shine—versatile, reliable, and ready for whatever winter throws your way (including surprise slush puddles and impromptu dance floors). They’re a smart pick for students building their first “grown-up” wardrobe, anyone experimenting with new trends before committing, or the friend who’s always the designated gift-giver—because yes, these shoes make a thoughtful, practical present for birthdays, graduations, or just-because moments. Picture gifting a pair to your roommate before her big presentation or your sister who’s finally agreed to try something other than sneakers. There’s something satisfying about seeing someone’s confidence click into place with the right pair of shoes—especially when you know they didn’t break the bank to get there.

When you’re shopping for affordable dress shoes, it’s all about balancing style with practicality. Look for details that feel intentional—sleek silhouettes, subtle hardware, or a pop of texture that sets them apart from basic flats or pumps. Comfort matters, too; nobody wants to spend the night counting down the minutes until they can kick off their shoes. Think cushioned insoles, flexible materials, and just enough support to carry you from dinner to drinks without missing a beat. And if you’re eyeing shoes for a specific event—say, a winter wedding or a first date—consider classic colors that go with everything, or a bold hue that turns your outfit into a statement. The beauty of a $20 price tag? You can try something new (like that metallic finish or pointed toe) without second-guessing your choice. If you’re planning to build out your shoe closet or just want more options for your next night out, don’t miss our curated selection of $20 Going Out Shoes—because you deserve options that work as hard as you do.

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