19 Trending SHOES Everyone Should Own – The Timeless Classics

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Trending Shoes 2023: Timeless Classic Shoes

Fashion trends are constantly evolving, making it challenging to stay up-to-date with the latest styles. But it seems like we keep coming back to classic, timeless looks—the same applies to footwear. So to make it easy for you, the King Kat fashion enthusiast editors have curated a list of shoes we consider to be timeless and somewhat versatile. With a price range of $80 to less than $300, everyone now has the opportunity to own pairs that can be styled in so many ways.

It’s safe to say that we wear these pairs on a regular basis. Whether it be for casual outings or formal, elegant occasions—everything can be mixed and matched, really. These pairs never fail to create that classy, yet never boring look. From the allure of dad shoes paired with blazers to the timeless classic sambas matched with leather ensembles, and even zip-up unitards paired with the right kind of boots—you can go crazy with any style and still get that head-turner look, as long as you got that eye for fashion.

This one might be no shocker, but when we talk of “classic,” Samba is the first one we think of. A timeless classic that has effortlessly bridged the gap between sport and style for decades and is now widely embraced in street style and minimalist fashion. Renowned for its distinctive design that blends athletic functionality with a versatile aesthetic, the Adidas Samba features a sleek leather upper, complemented by the signature three stripes on the side.

Fashion icons such as Bella Hadid, Kendall Jenner, Kaia Gerber, Hailey Bieber, and even Rihanna have been spotted wearing these pairs on multiple occasions. This pair comes in three main variations: Samba Classic, Samba OG, and Samba Vegan.

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New Balance has made a name for itself with its vintage dad shoes, and this particular model stands out as one of the best dad shoes to date. Loved by all generations—from dads to millennials to Gen Z—it’s becoming more mainstream (in a good way) as time goes by. You’d be surprised how widely you can style these classic running shoes. You can pair them with casual blazers, neutral-colored long coats, or pair ’em with iconic pieces with a touch of avant-garde style; it all works. Now go get your pair of 530s and make your dad proud.

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Still one of the most trending shoes in 2023, Low Dunks have excelled at staying in the game. While some people might have grown weary of them, it’s undeniable that they possess that classy street-style look. Pair it with relaxed baggy jeans or leather bottoms and call it a day. Works even when styled with cozy sweats.

Any color of Nike Dunk Lows is totally acceptable, but if you’re looking to get your first pair, we highly recommend getting the Black and White Panda, as black and white pairs are the most versatile colors—making it easier to match with any palette of your choice. The Varsity Green variation comes in a close second in the editors’ picks.

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If you’ve been eyeing Converse Chuck Taylor All Stars, the Chuck 70s are undoubtedly the best pair to own. Not only loved by bedroom pop and punk-rock-indie artists, the iconic Chuck 70 can also be styled with minimalist or complimentary-colored co-ords and chic dresses. Perfect to wear for any season or occasion, these retro sneakers are a must-have staple. Chuck 70s can keep up with any fashion style or trend. Wearing this classic vintage pair sometimes invites a nostalgic teenage vibe.

Fun fact: Converse All Stars began as a basketball shoe in 1917.

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We’ve finally come to the one pair that our fashion editors can’t shut up about. They’ve coined these running shoes the ‘daddiest-looking dad shoes’ ever created. Just like the other certified favorites of dads, the Asics Gel-Kayano 14 has that classic, timeless look you can style with elegant or bold colors. These running shoes effortlessly bridge the gap between functional active wear and a fashion-forward statement, embodying a versatile essence that suits both active lifestyles and stylish ensembles.

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The Reebok Club C 85 Vintage is a timeless classic that seamlessly blends vintage charm with contemporary style. These tennis-inspired shoes encapsulate the essence of retro cool, featuring a clean and minimalistic design that effortlessly complements any outfit. The ‘chalk’ color is the obvious winner here, by the way. You could never go wrong with these retro sneakers.

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Chelsea Boots

Boots are one of those things that you never knew you needed in your wardrobe, and Chelsea boots are a classic addition for sure. But when we talk of Chelsea boots, the first thing we usually recommend is our shopping team’s favorite—Prada’s Monolith brushed leather Chelsea boots for women and their brushed calf leather Chelsea boots for men. But considering the fact that they are Prada and cost somewhere around $1500, we’ve come to terms with offering more affordable alternative classic boots.

The Ash Genesis Stud Boots are a bold and fashion-forward statement for those looking to make a striking impression. With edgy stud detailing and a sleek leather construction, these boots exude confidence and attitude. But if you’re looking for something that’s a little bit longer than the Ash Genesis Stud Boots, you definitely should check out their Ash Elite Tall Chelsea Boots.

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Made from high-quality leather, these 2976 Dr. Martens Chelsea Boots effortlessly combine rugged style with sophistication. They’re versatile enough to elevate any outfit, whether you’re going for a casual look with distressed denim or dressing up for a special occasion. These boots are more than just fashion; they represent a timeless sense of confidence and individuality, making them a standout choice in the ever-evolving world of style. Dr. Martens certainly has that reputation.

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The Asics Gel-Quantum 360 Chelsea Boot, designed for men, offers a fusion of athletic performance and sophisticated style. With the renowned Gel-Quantum cushioning technology for exceptional comfort, these boots seamlessly bridge the gap between sportswear and fashion. These bad boys deliver a unique blend of comfort, versatility, and contemporary flair, making them a standout choice for the modern man.

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You might wonder, why recommend so many ‘dad’ shoes? Well, it’s because ‘dad’ shoes bring a remarkable versatility that can elevate the aesthetic of various outfits, whether it’s halter tops, trousers, bodycon and ribbed dresses, sweats, leggings, cargos, or even leather materials. This isn’t as trendy as some other items on this list, but our fashion team suggests otherwise. They say it’s like the Gel-Kayano 14 from Asics—a dad-inspired look for a street and sporty style. Sold.

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Let’s change things up for a while. If you’re a fan of bold and vibrant colors, the Onitsuka Tiger Mexico 66 Yellow sneakers are a must-have for your collection. Even Kaia Gerber wears this old-school babe. These sneakers feature a classic silhouette with a twist—a vibrant yellow colorway that adds a pop of color to any outfit. The Mexico 66 Yellow is a versatile shoe that can be paired with jeans, skirts, or dresses. We’ve seen fashionistas confidently pair these retro sneakers with their avant-garde wardrobe pieces. You can go crazy with styling these classic sneakers.

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People often confuse Jordan 1s with Nike Dunk Lows because of how similar they look. These basketball shoes remain a classic for sneakerheads—some are obsessed with constantly adding different variations of these OG classic sneakers to their shoe collections. Nike Jordan 1s are prominent within the skateboarding community too. But personally I like to dress my Jordan 1 with elegant upper pieces, mixing them with the streetwear-y, playful look of the Jordan 1.

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Another banger from New Balance. These modern-retro sneakers have swiftly become a staple in streetwear fashion, thanks to their ability to effortlessly merge style and comfort. The fashion crowd of late is starting to appreciate these vintage shoes. With a nod to retro aesthetics and an oversized N logo that’s iconic in its own right, it’s regained its well-deserved place in the ‘trending shoes’ spotlight. Even folks that I know in real life who are actively involved in the fashion industry own these pairs.

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Yep, the famous Boston Clog from Birkenstock is still a thing. Worn by all genders, especially in the summer. It’s what one of our fashion editors loves to wear because of its coziness and ease of wear; it’s a classic even when you’re planning on going grocery shopping or running any errand. Though personally I usually like how it looks when worn with socks.

With their austere colorways and comfortable fabrications, these clogs, part slipper and part chunky loafer, symbolize both style and relief. Originally launched in 1979, they found a resurgence in luxury fashion circles, bridging the gap between orthopedic comfort and fashion-forward sensibility and earning admirers among celebrities like Sienna Miller, Kendall Jenner, and Kristen Stewart. In a year marked by uncertainty, these clogs, much like shearling-lined Ugg slippers, have become a homely counterpart, offering solace and style when everything else seems in flux.

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The Nike P-6000 isn’t really trending as much as the others on this list, but this Nike classic deserves to be on the list of trending shoes. Some fashion enthusiasts love to style them with a Y2K flair, considering them a source of Y2K-inspired fashion. The color ‘silver’ is a style in itself, but when dad shoes meet silver? That’s what I’m here for.

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Once again, the signature three-strap detail joins the list. Just like Samba and Superstar, the Forum Low also got that retro sneaker aesthetic, which gives it a timeless vibe. It can be worn with any style by people of any generation. The cream white soles and royal blue stripes just make it look way better—these colors are the first ones you should consider.

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This list wouldn’t be complete without a pair of sandals, and the best one we recommend is the famous cork-style sandals by Birkenstock. These aren’t just your everyday errand shoes; they’re a versatile classic that effortlessly elevates your style, whether you’re strolling through charming cafes or going on a leisurely walk date. Even fashion icons such as Gigi Hadid and Kendall Jenner were spotted effortlessly donning these Birkenstock ensembles.

What we noticed is that women love to style these Arizona slides with that off-duty or ‘lazy day’ look. For men, styling Birks sandals with an ‘old money’ aesthetic works best, creating that head-turning luxury look. On an unrelated note, I can’t remember a beach vacation without spotting these sandals.

Birkenstock sandals might not be everyone’s cup of tea though. It all comes down to one’s fashion preferences.

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Converse x CDG basically is like the classic Converse Chuck Taylor, except this one has a heart—quite literally. The heart design, the signature logo of the Comme des Garçons Play line, transforms these sneakers into a statement of love for both fashion and street culture.

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Converse Run Star Collection

The Converse Run Star Collection has swiftly risen to become a trendsetting choice in the world of footwear, thanks in large part to its distinctive high soles. The high soles not only offer an edgy and modern aesthetic but also provide an easy way to add height for wearers. Whatever color you choose works, but the classic colors are bussin’.

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With their minimalist design and effortless slip-on functionality, they redefine the concept of luxury loungewear. Styling these slides comes naturally, but for the ladies, our fashion editors love to pair them with upper pieces like unitards, biker shorts, or leggings.

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I’d say it’s been a great year for New Balance. The New Balance 550 is very much in right now. You might want to check out their 650 version if you’re a fan of high-top shoes. Embracing the resurgence of vintage aesthetics, particularly harking back to the stylish era of ’80s basketball footwear, the 550 effortlessly aligns itself with contemporary fashion trends. Its retro charm and timeless design gracefully merge with the current fashion landscape, emphasizing the enduring appeal of these basketball-inspired sneakers.

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