There are sneakers and then there are sneakers. The kind of stylish men’s sneakers that make you pause, perhaps do a double-take and then pull out your credit card. That’s what we’re talking about today on The Style Guide. We’re taking it up a notch from past Online Shopping Picks entries and getting a little bit more specific, too. Now, we talked earlier this year about the best men’s sneakers to buy for spring and summer, and today builds off that focus in a whole new way.

Yes indeed, the right pair of leather sneakers offers something a little extra when compared to a pair of standard canvas sneakers, which are decidedly more casual. Equal parts durable and rugged, stylish leather sneakers can team with everything from light wash denim and a pocket tee during the last few weeks of summer to your favorite henley and a classic cardigan come fall. What’s more, I think you’ll find that the below picks hit the sweet spot in terms of style that can transition from August into September, October and heck … November. That’s particularly the case if we’re talking stylish leather high-top sneakers. So, shop on for your new favorite pair of leather sneakers, and feel free to follow me on Twitter for #menswear musings aplenty.

#1. Rancourt Carson Low in Natural Chromexcel — $300

Let’s get this straight right off the bat — the kind of leather sneakers you’re looking for definitely bring a little something extra to the table. That something extra, that “Wow” factor … the handsome, stylish and investment-level Carson Low from Rancourt & Co. certainly has that extra something. Featuring made-in-Maine craftsmanship and beautiful Horween leather, the Carson Low is an absurdly beautiful pair of sneakers, practically begging to be worn right now with a slim white polo shirt and then worn later on this fall with a Todd Snyder crewneck sweater.

#2. GREATS The Royale in Blanco — $169

Before we get too carried away with brown Horween leather sneakers, let’s get back to the basics — and by the basics, I mean perhaps the most affordable pair of premium white leather sneakers on the market.  GREATS continues to make waves in the men’s sneaker market for mixing excellent quality with simple silhouettes — and the Royale in Blanco is certainly a silhouette that’s lifted the brand to new heights. Buy these classic leather sneakers now to wear with slim tan chinos and a navy polo, keep ’em handy to wear with a denim jacket and a rugged henley when you feel an early fall breeze.

#3.  GREATS Royale Vintage in Nero — $179

Let’s go with another pair of stylish GREATS sneakers, this time with some subtle updates to the brand’s tried-and-true Royale silhouette. The Royale Vintage updates that same silhouette with detailing like a back heel tab crafted from nubuck — and the cream Margom sole is a nice deparature from the Royale in Blanco, too. In short, the Royale Vintage is just different enough to justify the slightly higher price tag — and that means you should give it a shot alongside dark denim and a grey Oxford the next time you need to dress to work remotely.

#4. Todd Snyder x P.F. Flyers Rambler Hi Sneaker in Saddle Leather OR White Leather — $160 ($110 When Signing Up for Bespoke Post)

Ahh, yes. The lauded Todd Snyder x P.F. Flyers Rambler Hi — a past entry in our Style Pick of the Week series, and just as worthy of inclusion in today’s list of prime #menswear picks. The essential Rambler Hi might be the perfect leather high-top sneaker. It blends a durable, classic construction with two quality options — either the Saddle Leather Rambler or the White Leather Rambler are solid picks. Plus, you get the sort of style that really can carry over seamlessly into the fall; wear these on a weekend coffee date or a stroll through your favorite park.

#5.  GREATS Royale in Perforated Sand — $179

One more pair of essential GREATS sneakers for your shopping list, ehh? It’s a treat to see how GREATS takes a silhouette like the Royale and continues to update it. In this case, the Royale in Perforated Sand blends a transitional color with perforated leather detailing — a touch that means these are fit to wear into October and November as the leaves start to fall. Pair them up with your favorite pair of dark blue denim and a classic chambray shirt — oh, and sidle up to the bar and get us another round, will ya?

#6.  Nisolo Diego Low — $129

For those of us who like a sneaker that’s got the quality and craftsmanship of a pair of essential leather boots, there’s the Nisolo Diego Low. Made with the same attention to detail as the brand’s handsome leather loafers and Oxfords, the Diego Low has a rugged-yet-sporty vibe that’s tough to come by these days — the Vibram sole and vegetable-tanned leather on the Diego Low are but two quality components of these kicks. They’re perfect for teaming with a rugged field jacket and slim black denim this fall — trust me on that.

Honorable Mention: JAK Royal in Taupe — $102.98

You didn’t think we’d leave out a pair of sneakers that run just over $100, did you? The JAK Royal in Taupe is a recent addition to the Huckberry offering of stylish men’s sneakers. What’s more, it’s an absolutely great set of kicks for a great price. Handcrafted in Portugal, the  JAK Royal in Taupe blends comfortable Vibram construction with flat wax cotton laces — these are certainly sneakers to wear with a blazer or an upgraded T-shirt this summer and into fall.

Well, we’re really just scratching the surface when it comes to stylish leather sneakers that you can wear now and into the fall. Consider this list a good starting point — the right pair of leathr sneakers should blend quality, craftmanship and serious style. I personally think the Todd Snyder x P.F. Flyers Rambler Hi is a heck of a pair of sneakers to wear now with rolled denim, and wear later with a thick cardigan.

If you’re more of a low-top sneakers guy, then the JAK Royal in Taupe could be the right pick for you — or maybe even the Carson Low from Rancourt & Co., a pair that’s as handsome and rugged as anything you’ll find on the market. We’d be remiss not to mention the work being done by GREATS , too. Notably, the Royale in Perforated Sand and the uniquely detailed Royale Vintage are winners in my book for their blend of crisp details and versatile style. What’s your favorite pair from this list? Drop a note in the comments — oh, and get back to shopping!

Thanks so much for reading,

-Beau