It's Hard To Dress Comfortably & Still Look Chic, But These 45 Things Make It Easy

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by Sabrina Crews
Originally Published: 

These days, when it comes to getting dressed, it seems like there’s this constant push-and-pull between looking your best and feeling your comfiest. If you’ve tried to negotiate between the two with mixed results, you’re not alone. After all, it’s hard to dress comfortably and still look chic, but these 45 things make it easy.

If you’re someone who prioritizes comfort just as much as fashion, finding ways to elevate your style that feel true to who you are — and make you feel good — can be tricky. Conversely, if you’re that person who’s always overdressed for any given situation, it can be hard to know where you stand in a world where athleisure and streetwear reign supreme.

Don’t worry. With these 45 things, you can achieve looks that are understated enough to pass for casual, but elegant enough to catch notice and garner compliments (as well as stunned expressions if you choose to reveal you found them on Amazon). Plus, they can be yours in just two-days’ time with Prime shipping, so you can start incorporating your secrets to comfy-chic style as soon as possible. And trust us: When you see what’s in store for you below, you won’t want to wait.


This Flowy Maxi Dress That’s Sold In 25 Eye-Catching Prints

It’s no wonder this floral print maxi is dubbed the “sunset dress.” Ideal for a stroll along the beach at dusk, the unlined rayon dress exudes instant, laidback glamor — it’s that ready-in-an-instant piece you’ll keep reaching for all summer or vacation long. Ringing up at less than $30, the dress features a ruffled hem, belted waist, and low V-neckline to better showcase your favorite statement necklaces. Choose from 25 chic colors and patterns, like the tangerine paisley print pictured.

  • Available sizes: Small — XX-Large
  • 25


A Popular Set Of 4 Skinny Belts — For Less Than $20

“Fits amazing, super versatile — these are all you need,” one fan — there are over 6,000 and counting — who gave this skinny belt set five stars on Amazon raved. “A quick and easy way to add some visual interest to an outfit,” raved another. Made of quality, synthetic leather and featuring an eye-catching metal buckle, the skinny, retro-inspired belts come in a variety of easy-to-match color combinations and provide ample stretch. Comfy and versatile, they can make even a standard shirt-dress look like a completely different (and super-chic) outfit.

  • Available sizes: 22”-29” — 30”-42”
  • Available Colors: 8


This Best-Selling Bodysuit You’ll Wear Several Times Per Week

The best thing about this best-selling racerback bodysuit is its sheer versatility. Pair it with some polished trousers for a formal dinner, a cute mini skirt for date night, your comfiest sweats when you’re working from home... the styling possibilities are truly endless; and thanks to its silky-soft material (it’s made of nylon and spandex), you’ll feel like you’re wearing nothing at all. And of course, the beauty of the bodysuit is that it’ll create a smooth, seamless line underneath any bottoms you wear with it. Considering how often you’ll wear this per week, you’ll want to pick it up in multiple colors.

  • Available sizes: Small — XX-Large
  • Available colors: 18


The Wrap-Style Jumpsuit Comfy, Stylish, & Versatile

A simple one-piece that fits just right never goes out of style — case in point? This sleeveless, wrap-style jumpsuit. Not too loose and not too tight, the effortless V-neck jumpsuit is made of a soft and stretchy interlock fabric; features a removable belt at the waist; and comes in three goes-with-anything colors: black, navy, and olive. Throw it on in mere seconds to look fabulous all day long, but you’ll feel as comfy as if you were in your favorite PJ set.

  • Available sizes: XX-Small — 5X
  • Available Colors: 3


These Pretty, Platform Espadrilles You Can Wear With Practically Everything

The beauty of espadrilles is the way they’re able to combine both natural and upscale elements for a distinctive overall look — and these flatform espadrilles are no exception. Available in 18 colors, like the natural ‘Tan’ shade pictured, the shoes feature a stylish, faux-leather ankle strap and braided, synthetic soles. Wear them with your prettiest sun dress or a pair of beat-up denim shorts — and nail the look either way.

  • Available sizes: 5.5 — 11
  • Available colors: 18


A Tiered Tent Dress That’s Perfect For Warm Weather

If you love a loose, flowy, effortless look, this tiered maxi dress is for you. Available in four unique colors — navy, black, and two shades of beige — the sustainable, gently sloped dress is made of ultra-soft Tencel Lyocell fibers and features practical, roomy side pockets. Plus, you can wear the adjustable straps either straight or crossed to achieve different looks.

  • Available sizes: XX-Small — 5X
  • 4


This Smooth & Cozy Sweater Tank That Works In Every Season

From light pink to sage green, this fitted racer tank comes in five stunning colors and a range of sizes for the perfect fit. It’s made of a soft viscose fabric, which the brand promises will feel super luxurious against your skin, and features a chic crew neckline and narrow upper cut to accentuate your shoulders. The tank’s longer length makes it ideal to pair with leggings and bike shorts, but you can also tuck it into high-waisted trousers or jeans for a sleek, tucked-in look. Since it’s made of a substantial, sweater-like material, this’ll work well under jackets and blazers in the fall and winter, too.

  • Available sizes: XX-Small — 5X-Large
  • Available Colors: 5


A High-Waisted Maxi Skirt That Comes In Fun, Seasonal Patterns

Tuck your favorite spaghetti-strap bodysuit into this high-waisted maxi skirt, throw on a pair of chic, strappy sandals or slides, and get ready to take on the summer. The breezy skirt comes in over 15 unique patterns and features a soft and slightly stretchy texture that’s sure to keep you comfy and cool in the heat. Plus, it’s so affordable ($30), you’d be wise to stock up on more than one.

  • Available sizes: Small — XX-Large
  • Available Colors: 16


The Classic Oxford Shirt That Everyone Should Own

Made of 100% cotton, this long-sleeve button down from Amazon Essentials will keep you cool and comfy all day long and earn you serious style points at work (or wherever else you choose to wear it). With over 5,000 perfect five-star ratings on Amazon, the shirt is a hit among shoppers for its relaxed, but just tailored enough, fit (size up if you like an oversized look). Plus, it comes in 13 unique colors and patterns that give its understated construction and polished vibe a pop of preppy personality.

  • Available sizes: X-Small — XX-Large
  • Available Colors: 13


The Perfect Pair Of Comfy-But-Polished Travel Pants

It’s so hard to look polished when traveling when comfort is the first priority. But you don’t have to sacrifice your coziest go-to joggers — just buy an upgraded pair, like this one. Made of nylon and spandex, they feel like a super-comfy pair of athletic pants, but they look 10 times chicer. They’re designed so as not to pill, they have four-way stretch for easy movement, and they come in eight neutral, goes-with-everything colors. They’re lightweight, too, so you won’t have to worry about overheating on long, crowded flights.

  • Available sizes: X-Small Petite — XX-Large
  • Available Colors: 8


A Long, Cozy Cardigan That Comes In 6 Bold Shades Of Leopard

Now here’s a versatile staple you can use as a cardigan, robe, or house coat. Soft and stretchy, this fun cardigan comes in six bold shades of leopard print — including army green, brown, red, and this easy-to-match khaki pictured — and features an open front, maxi length, and two deep side pockets. Keep it within reach all year long for whenever you need a warm-up.

  • Available sizes: Small — Large
  • Available Colors: 6


This Fit-&-Flare Dress That’s Good For The Planet

This fit-and-flare dress from Amazon Aware won’t just look good on you — it’s good for the environment, too. Made of 100% certified-organic cotton, the tiered dress features an empire waist, ruffled hem, and elegant flared sleeves that hit right at the elbow. While it’s easy to spend way more than you bargained for on carbon-neutral clothing, this dress rings up at a mere $40 — so, both you and the planet win.

  • Available sizes: XX-Small — 7X-Large
  • Available Colors: 6


These Slightly Stretchy Drawstring Shorts With A Comfy Elastic Waist

It’s hard to find a pair of shorts that feel and look just the way you want them to — not to mention a pair that won’t even cost you $25. But look no further: these elastic waist drawstring shorts are it. Made of a slightly distressed fabric blended with spandex, the high-rise shorts boast roomy front and back pockets, a flowy fit that screams summer, and a turned-over hem. Choose from over 40 colors, or just admit that you’re going to need a few.

  • Available sizes: Small — 3X-Large
  • Available Colors: 6


A Fan-Favorite Mini Dress With All The Cutest Details

It’s pretty obvious why this vintage-inspired A-line mini dress has garnered thousands of glowing ratings. Just look at it: Featuring an open, tie back; ruched, square neck; ruffled hem; and elegant lantern sleeves, the lightly lined mini dress combines a variety of subtle, stylish details to make one bold fashion statement. Best of all, it won’t even cost you $40.

  • Available sizes: X-Small — XX-Large
  • Available Colors: 14


These Cropped, Knit Pants That Are *So* Cuddly Soft

Think of these cropped, knit pants as a lightweight sweater for your legs. The brand even defines them as “cuddle chic.” Not too tight and not too loose, these just-right pants feature a high, elastic-ribbed waist and turned-over cuffs that hit at the shins. Choose from six neutral colors including pink, brown, and a pretty gray-white.

  • Available sizes: XX-Small — 3X
  • Available Colors: 6


A Super-Soft Jumpsuit That’s Like A Chic Version Of Pajamas

The main selling point of this casual, wide-leg jumpsuit? Looks dressy, but feels like pajamas, the brand promises. You can keep the look casual at home by going barefoot, or by pairing it with flat sandals to run errands; but it’s easy to dress up with some gleaming gold jewelry and heels. And with over 30 styles to choose from at less than $35, why wouldn’t you add this versatile piece to your closet?

  • Available sizes: Small — XX-Large
  • Available Colors: 31


This Preppy V-Neck Sweater Vest That Doubles As A Dress

You can wear this V-neck sweater vest in limitless ways — as a dress with your favorite pair of Docs or thigh-high boots, over leggings, and with (or without) a button-down shirt or dress layered underneath. The versatile vest comes in over 20 styles and patterns — khaki, beige, gray, and black are particularly popular. And it won’t even cost you $40.

  • Available sizes: Small — XX-Large
  • Available Colors: 23


A Pair Of Chic Backless Loafers For Just $25

According to The Zoe Report’s Caroline Goldstein, loafers are “the most relevant shoe in streetwear right now,” and you can score a backless pair for just $25 thanks to Amazon Essentials. Available in five easy-to-match colors (you can also score a beige or black pair in imitation crocodile leather), the popular mules come with comfy, memory foam padding and a half-inch heel for a little extra height.

  • Available sizes: Small — 3X-Large
  • Available Colors: 5 — 9.5


This Oversized Shirt Jacket That Makes Any Outfit Cooler

If you love an oversized statement piece, this long plaid shirt jacket is it. Available in seven varieties of plaid — like coffee, khaki, and brown (pictured) — this shirt jacket epitomizes versatility and lends everything from your favorite jumpsuit to your turtleneck dresses a super cool and laidback aesthetic. Featuring a turned-down collar, shirt-tail hem, and matching flap pockets at the chest, this amazing jacket is bound to become your new go-to for the chilly weather months.

  • Available sizes: X-Small — XX-Large
  • Available Colors: 7


A Cozy, Cropped Turtleneck With Cute Button Details

When it comes to shopping for fall and winter clothes, it can be hard to find pieces that simultaneously flatter your shape and keep you cozy, but this slightly-cropped turtleneck nails it. Made of what the brand dubs “soft cuddle yarn,” the comfy turtleneck features long, ribbed sleeves with thumb holes; a matching, ribbed turtleneck collar; and cute buttons going up each side. It also comes in five goes-with-everything colors including olive green and black.

  • Available sizes: XX-Small — 3X
  • Available Colors: 5


This Hand-Knit Shoulder Bag With A ‘70s-Chic Vibe

As the crochet craze continues to rage, it’s clear that right now, everyone loves the homespun look. You can incorporate the throwback aesthetic into your own wardrobe with this exquisite woven handbag. Due to the amount of time and craftsmanship that goes into handmade pieces, prices on handcrafted items can sometimes be more than you’d hope to pay. Yet somehow, this hand-knit, cotton wonder — available in brown, dark brown, khaki, and white — is a mere $25. And who would ever guess that you scored it on Amazon?


A Pair Of High-Waisted Biker Shorts With Nearly 50,000 Perfect Five-Star Ratings

With 60,000-plus fans on Amazon (and counting), these high-waisted bike shorts from Baleaf are an absolute crowd-pleaser. Made of a super-smooth, polyester and spandex blend, the moisture-wicking shorts are more than equipped to weather your high-intensity workouts — just don’t be surprised if you find yourself wearing them out to coffee, happy hour, or other social outings (with your favorite crop top or oversized Oxford shirt) where exercise is totally not on the agenda. They’re that comfy. And how convenient is that smart phone-sized side pocket?

  • Available sizes: X-Small — 3X-Large
  • Available Colors: 40


This Soft, Cotton Shift Dress That’s Perfect For Spring

Greet the warmer weather in this delightful babydoll dress. Available in a range of bold colors and pastels, like the pretty lavender pictured, the fully lined, cotton dress boasts a tiered skirt, lovely V-neckline, flared ruffled sleeves, and a matching ruffled hem. You can be sure to start turning heads the second you step out in it, it’s just that charming. But it’s super comfy and breathable, too (and looks great with everything from white sneakers to strappy heels).

  • Available sizes: X-Small — X-Large
  • Available Colors: 40


The Matching Knit Sweater Set You’ll Want To Live In

You can never have enough matching lounge suits, and ringing up at less than $30, this knit duo is well worth adding to your collection. The two-piece set comprises a crewneck crop top with a curved hem and ribbed, bubble sleeves, and cozy, high-waisted shorts with an elastic waist and adjustable drawstring. Available in nearly 20 striking solid colors, this two-piece set is one you’ll want to stock up on, because you’ll be living in it in no time.

  • Available sizes: Large — XX-Large
  • Available Colors: 18


A Pair Of Lace-Up Combat Boots That Typify ‘90s Cool

The ‘90s fashion resurgence has gifted us with so much: acid-wash jeans, plaid flannel, baggy everything, and of course, combat boots. You can expect to pay a hefty price to score a pair for yourself, and that’s what makes these lace-up mock Docs from Amazon Essentials such a find. Made of a smooth leather-like material with quality rubber soles, these chic, lace-up boots can be yours for less than $30. Choose from four different colors and styles, like this stylish, imitation croc pair.

  • Available sizes: 5 Medium US — 13 Medium US


This Strapless Jumpsuit That’s Both Comfy & Chic

This polyester and rayon jumpsuit is so soft, the brand promises it’ll feel like a second skin. Featuring a strapless top, wide legs, and an elastic waist with a removable tie belt, this is the kind of versatile one-piece that’s as equally at home at a cocktail party as it is on the beach. So you’ll certainly get way more use out of it than its reasonable price tag suggests.

  • Available sizes: Small — XX-Large
  • Available Colors: 18


A Silky-Soft Tank Top That’s Worth Buying In Multiples

This soft scoop-neck tank top from Daily Ritual is so endlessly wearable, and so affordable, you’re definitely going to need to stock up — good thing it’s available in a two-pack. The long length and racerback give the tank a relaxed look that makes it an ideal warm-weather essential, but it’s great for layering in the fall, too. Plus, it comes in over 10 solid colors and patterns that go with practically everything.

  • Available sizes: X-Small — XX-Large
  • Available Colors: 11


These Office-Friendly Trousers That Feel As Comfy As Sweats

There’s a reason why these paper bag waist pants are so popular (thus far, they’ve been awarded over 10,000 five-star ratings on Amazon). Mainly, it’s because they’re chic and office-appropriate — yet they feel as comfy as your favorite lounge pants. Designed with spandex for stretch and two roomy pockets, these stylish trousers are available in a wide array of gorgeous colors.

  • Available sizes: X-Small — 3X-Large
  • Available colors: 20


A Sunny, Off-The-Shoulder Dress With A Dainty Scallop Trim

This scallop-trim dress epitomizes sunny weather. Available in over 20 cheerful colors like the royal blue pictured, the dress is made of a comfy, slightly stretchy fabric and features a Bardot-style top, cinched waist, and gorgeous scallop detailing at the hem. Just think of all the warm-weather adventures you can have in it.

  • Available sizes: 0x — 4X
  • Available Colors: 21


This Classic Crewneck Sweater That Amazon Shoppers Adore

This stylish crewneck sweater comes in a variety of whimsical patterns, including several variations of animal print (some in neon colors, some in neutrals). Gently ribbed at the neckline, cuffs, and hem, the sweater is made of super-smooth fabric and makes the perfect statement piece for when you want to look fashionable, but can’t be bothered to do more than throw on a pair of jeans. It’s comfy and warm — but not too warm — too.

  • Available sizes: X-Small — XX-Large
  • Available Colors: 9


A High-Waisted Maxi Skirt That Comes In Tons Of Unique Prints

This tiered, A-line maxi skirt comes in so many distinctive patterns, it’s impossible to choose just one. And with its super-reasonable $35 price point, you won’t have to, either. Go ahead and add all of your favorites to your cart. Made of a soft, comfy, rayon fabric, the eye-catching skirt features a high, elastic waist, relaxed fit, and breezy, ruffled hem. Plus, it’s got pockets.

  • Available sizes: Small — X-Large
  • Available Colors: 23


This Comfy Seamless Bra For A Smooth, Polished Look Up Top

A good bra is hard to find, but this one — which doubles as a comfy undershirt — won’t ever let you down. Its moisture-wicking fabric will keep you dry in the heat or during workouts, and its flexible side panels contain a bit of extra stretch that makes it a cinch to pull on and off. Plus, due to its seamless construction, the bra looks completely invisible under your clothes, so it’ll make any top look smoother and more polished, unlike all your wired bras.

  • Available sizes: X-Small — 3X-Large
  • Available Colors: 21


This Square-Neck Mini Dress With Subtle Cottagecore Vibes

If you’ve been wanting to incorporate more Regency-inspired pieces into your wardrobe, this square neck dress provides a sultry and modern way to do it. Featuring long, puffed sleeves; a low-cut, square neckline; an A-line skirt; smocked back; and an empire waist; the dress is both comfortable and gorgeous. Pair it with your favorite necklace and any shoes you like, from combat boots to block-heeled sandals to platform clogs. Honestly, how is such a versatile frock going for less than $40?

  • Available sizes: X-Small — XX-large
  • Available Colors: 13


A Pair Of ‘90s-Chic Yoga Pants That Can Be Dressed Up, Too

Even if you’re a diehard lover of leggings — they’re everywhere, after all, and they’re not going away — it’s only natural to want to switch up your workout apparel from time to time. These bootcut yoga pants present the perfect opportunity to do just that, and for less than $25. The high-waisted pants are made of a flexible, four-way stretch fabric that can take on your most high-intensity exercises, and were designed to accentuate your shape and height. But at the same time, they double as the kind of black bootcut pants that were so popular in the ‘90s — and that are, once again, experiencing a resurgence — so you can dress them up for nights out, too.

  • Available sizes: X-Small — XX-Large
  • Available Colors: 41


This Comfy Blanket Scarf That Comes In Over 20 Unique Plaid Prints

Available in over 20 varieties of Scottish-inspired tartan, this oversized scarf adds a warm, cozy touch to any outfit. But it also doubles as a blanket — it’s that big and warm — making it a must-have for travel. Even if you’re just in jeans and a simple sweater, this cozy-chic accessory will make you look 10 times more stylish. You can’t beat the price, either.

  • Available Colors: 23


This Short-Sleeve Maxi Dress That’s So Comfy, You’ll Want To Live In It

You can wear this short-sleeve maxi dress from Amazon Essentials with whatever type of footwear you please — be it flip flops or white sneakers — and look put-together regardless. Made of a super-soft jersey fabric and available in nine pretty colors and patterns, the dress effortlessly combines casual and polished elements with its T-shirt top, form-fitting elastic waist, and long, flared skirt. You can wear it practically anywhere, and with the assurance that you’re perfectly dressed for the occasion, though it’s comfy enough to lounge in at home, too.

  • Available sizes: X-Small — 6X
  • Available Colors: 9


A Soft, Lightweight Cardigan That’s Perfect For Spring

As its tough-to-top rating on Amazon suggests, this lightweight cardigan from Amazon Essentials is an absolute must-have. Sometimes it’s easy to forget how essential a warm layer can be in the spring or late summer, but all it takes is an abrupt change in the weather or a hyper-air-conditioned space to render one all but necessary. With this flowy, loose-fitting cardigan — made of a soft cotton and modal blend and featuring two convenient pockets — you won’t just feel cozier, you’ll exude laidback elegance, too.

  • Available sizes: 1X — 6X
  • Available Colors: 18


These Western-Inspired Ankle Booties That Go With Just About Anything

Less than $100 is definitely not a price you’d expect to see on a pair of Western-inspired ankle booties — think twice or three times that — so it’s totally understandable if you need to pause right this second and click ‘add to cart.’ Made of a glossy polyurethane material and featuring a 2-inch chunky heel, these boots go with just about anything — midi skirts, babydoll dresses, or your favorite pair of denim cutoffs — and can seamlessly transition through the seasons. They come in multiple colors, too, so be sure to stock up.

  • Available sizes: 5 — 12


A Cute Terry Romper That Nails Casual-Chic Style

This terry romper from Amazon Essentials is exactly the garment you want within reach when you’re still drying off from a shower or a dip in the ocean or pool, but it’s great for lounging at home and running errands in, too. Absorbent as a towel but just as stylish as any of your other going-out pieces, this moisture-wicking one-piece not only saves you time toweling off, but makes you look instantly pulled together for whatever warm-weather adventure follows. Choose from nearly 20 vibrant colors and be amazed at how often you end up in it throughout the summer months — the repeat wear is sure to exceed its (remarkably low) $25 price tag.

  • Available sizes: X-Small — XX-Large
  • Available Colors: 19


The Chunky, Gold Hoops That Are Wildly Popular With Amazon Shoppers

OK, how is a pair of earrings as stunning and on-trend as these chunky gold hoops going for less than $15? The 14-karat gold hoops come in a variety of sizes and boast a top-notch 4.6-star score on Amazon. “I wear them all the time and they never get discolored or hurt my ears,” one of 25,000-plus shoppers who gave the earrings five stars explained. “The gold plating is done really well. I get compliments all the time!” So will you.


The Early Aughts Pants That Are Experiencing A Resurgence

Remember the stretchy, flared-leg yoga pants that were so popular in the early aughts? Well, with everything “Y2K” being trendy again, those same pants are experiencing a resurgence in popularity right now. This particular pair is a best-seller on Amazon, with over 15,000 five-star ratings and 3,000-plus glowing reviews. They’re soft, comfy, affordable, and available in over 15 solid colors and unique prints. What’s not to love?

  • Available sizes: Small — XX-Large
  • Available colors: 16


The Denim Button-Down Shirt That’s Making A Comeback

Don’t sleep on this classic button-down from the master of all things denim. Available in a variety of washes and sizes, the Western-inspired shirt features a pointed collar, pearl snaps, and a sloped hem you can tuck in or out. Plus, the pockets are identical to those typically seen on the back of a typical pair of Levi’s jeans — a detail only some of the world’s the best denim makers would think to include.

  • Available sizes: 1X — 4X
  • Available Colors: 5


A Popular, Quilted Purse You Can Wear 3 Different Ways

Yes, certain bags can be comfier than others — and this one adds instant polish to any casual look. The quilted, crossbody bag currently boasts a hard-to-beat 4.6-star rating on Amazon, with reviewers especially loving its size (it’s super lightweight), value, and versatility. For less than $25, you essentially get three bags in one — a crossbody, shoulder bag, and clutch — thanks to its adjustable, and detachable, chain strap. The gorgeous, faux-leather bag also features a convenient front pocket and an adorable tassel, and comes in over 20 brilliant colors. What a steal.

  • Available Colors: 24


These Timeless Skinny Jeans With Over 30,000 Perfect Amazon Ratings

Yes, bootcut, baggy, and Mom jeans are certainly having a moment, but that doesn’t diminish the enduring power of a well-fitting pair of skinny jeans — especially from a brand that’s as celebrated as Levi’s. These vintage-inspired skinny jeans from Levi Strauss & Co.'s Gold Label are super stretchy and snug, feature a mid-rise waist, and boast upwards of 30,000 perfect ratings on Amazon. Available in a variety of washes and sizes, this is one pair of skinnies that’ll always be in style.

  • Available sizes: 16 — 28
  • Available Colors: 13


An Outfit-Transforming Accessory That’s Also Cozy & Warm

Despite its intermittent bursts of popularity, the beret is here to stay. So, if it’s a staple that’s missing among your winter accessories — and even if you’ve got plenty, how could you not want one more? — at less than $15, this one couldn’t come at a better price. Choose from over 20 colors — one style even boasts a lovely, embroidered heart — and wear it one of two ways: tilted back over your ears like a true winter cap or to the side (as pictured) for a little Parisian flare. Magnifique.

  • Available Colors: 38

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