Comfort and style intersect through all types of sneakers, albeit in varying degrees. We’ve come along way from the canvas athletic shoes of the mid-20th century. The present, by contrast, spans smart-casual, office-ready kicks to athletic-inspired to classic and beyond.
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Especially if you’re a casual-first dresser and avoid reaching for a pair of oxfords or derbies as frequently as possible, understand the different types of sneaker constructions available:
Dress and Smart Sneakers
No matter the name, this sneaker type conjures up a specific silhouette: one of smooth, polished leather, a round toe, and a form, down to the midsole, inspired by skate shoes but far more elevated.
These are built to be paired with a casual or party suit and preferably chinos but also won’t look out of place next to a pair of faded jeans.
Allen Edmonds Porter Derby Sneaker
A full-grain leather upper paired with a responsive insole and skate shoe-style cupsole represents the confluence between a performance sneaker and a classic derby.
Cole Haan Men’s 2.ZERØGRAND Lined Laser Wingtip Oxford
The presentation of wingtips elevates a perforated, ultra-responsive design built for comfort.
Koio Capri Triple White Sneaker
Toio has quickly turned into the go-to dress sneaker brand, thanks to monochromatic styles like the Capri, characterized by clean lines and quality Italian construction.
Plimsoll
This is a fancier term for what’s basically a pair of low-top sneakers. Spanning classic, lighter-weight Chuck Taylors to something with more body, this describes a shoe that curves around the ankle and typically has a lace-up vamp. As these aren’t performance shoes, the midsole will be minimal.
Vans Old Skool Core Sneakers
As one of Vans’ low-top styles, the Old Skool incorporates classic skate features through its two-toned paneled upper paired with a more responsive, grippy outsole.
Dockers Frisco Sneakers
Keep it simple with this low-height, low-profile canvas sneaker from Dockers giving you an even stride with a textured outsole and EVA foam.
Sperry Men’s Striper II CVO Sneaker
While Sperry is primarily known for its boat shoes, this canvas plimsoll given an aged treatment holds up all the same with its signature Wave Siping outsole texture.
High-Tops
The opposite of a plimsoll, high-tops extend above the ankle to provide a greater degree of support. Encompassing Chuck Taylors to old-school skate shoes to chunkier, heavier basketball shoes like the Air Jordan, they cast a boot-like profile – and have become fodder for sneaker-boots in recent years – yet include the same features as the plimsoll.
Chuck Taylor All Star Classic High Tops
They’ve held their own for over a century, thanks to their mix of a sturdy canvas upper, well-placed eyelets for ventilation, and an outsole with just the right amount of texture.
Awearness Kenneth Cole Barker High Top Sneakers
Make it old school but sleek. These capture the high-top silhouette in ‘80s-esque glory, with details like a box-weave outsole transporting it to the present.
Champion Men’s Arena Power High-Top Sneaker
A tri-colored chunky, padded design nods to the basketball shoes of the ‘80s and ‘90s.
Slip-On Sneakers
You’re likely thinking Vans, like the checkerboard pair Sean Penn sported in Fast Times at Ridgemont High, and that’s a solid starting point.
Transcending skate, dress, and more casual types, slip-ons have one definitive feature: no lace-up vamp. This attribute is then accompanied by a rounded toe and often a more sizeable midsole.
Vans Classic Slip-On
Comfort doesn’t get any more effortless or practical than this slip-on skate shoe Vans launched in the 1970s.
Perry Ellis Slip-On Sneaker
Find a dress shoe that’s more elevated yet more comfortable. This Perry Ellis sneaker fits the bill with a faux suede slip-on design.
Lacoste Jump Serve Canvas Slip-Ons
Skate construction informs this textured canvas slip-on featuring a responsive vulcanized outsole.
Retro Sport Shoes
Although you can argue that these overlap with other sneakers already listed here, there’s another, more significant factor to consider: athletic shoes have undergone a metamorphosis over the past three decades.
From all-leather with thicker outsoles, construction now centers around lighter-weight, breathable mesh accompanied by selectively placed overlays for support, plus features for impact absorption and cushioning.
Older basketball and running shoes started in this direction, promising improved performance, be it a more even stride, higher jump, or better responsiveness. Yet, compared to the present, a color-blocked, thicker, more substantial build feels like a look back to a different time.
Puma Super Liga OG Retro Men’s Sneakers
A slimmer, more streamlined silhouette keeps all the color-blocking and paneling of the original in place.
Nike Air Jordan 1 Mid SE High-Top Sneakers
While the Air Jordan isn’t really court-ready anymore, its classic, recognizable form remains ripe for plenty of color and pattern combinations.
Reebok Royal High-Top Sneaker
The ultimate ‘80s throwback proves its relevance through its retro vibes and adaptable, supportive silhouette.
Dad Shoes
While Gucci parodied the chunkier outsoles common among ‘80s and ‘90s cross-trainers, this old school athletic offshoot often goes back to the normcore vibes of a pair of New Balances, preferably paired with tapered, mid-wash jeans and a button-front shirt.
New Balance Men’s 608 V5 Casual Comfort Cross Trainer
A thicker, paneled leather upper takes us back to ‘90s athletic shoes.
Nike Air Monarch IV Sneakers
While foam trims down the weight, the exterior gives us old-school workout looks.
Fila Oakmont TR Mid Athletic Shoe
Inspired by hiking boots, this chunky, multicolored sneaker draws the eye with its vibrant appearance.
Skate Shoes
From the casual-yet-functional construction of Vans to the streamlined performance of Lakai, skate shoes toe the line between performance and style.
The former is often due to the textured, gummy outsoles that improve grip with a skateboard’s surface, plus impact-absorbing midsoles. The latter comes through old-school-always construction, be it suede, leather, or canvas with a color-blocked, paneled appearance.
Nike SB Zoom Blazer Mid Skate Shoe
Nike’s ‘80s-era Dunks formed the template for its first SB shoes, launched in the 2000s. You can still see the semblance here while still getting the grip and responsiveness to try out kickflips.
Lakai Brighton Skate Shoe
Although Lakai’s clearly inspired the breathability of modern athletic construction, you still get all the elements of a classic, functional skate shoe.
D.C. Men’s Stag Shoes
Thicker overlays and D.C.’s retro “puff” design deliver the performance you seek while harking back to the 2000s.
Sock Sneakers
With the Yeezy Boost as the template here, knit sneakers – also frequently called “sock sneakers” – feature a stretchy, pull-on high-top design attached to a sturdier outsole.
Adidas Yeezy Boost 350 Sneakers
A slouchy knit upper with stretch laces and Adidas’ Boost outsole gets an upgrade through UV-sensitive color-changing technology.
Balenciaga Speed 2.0 LT Sock Sneaker
An articulated, segmented chunky outsole delivers the looks with more flexibility for improved movement.
Nautica High-Top Sock Sneaker with Extra Ankle Support
This price-accessible sock sneaker stays on-brand for Nautica with a white and blue colorway.
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Ivan Yaskey is a Philly-born menswear fashion blogger and copywriter. When not writing about men's style he's also an EDM and synthpop enthusiast.
