#OOTD: How to Wear Classic High-Top Sneakers this Fall

It could be easy to dismiss something as simple as the classic high-top sneaker, but we here at The Style Guide think that would be … well, a mistake. Classic high-top sneakers — like the Chuck Taylor high-tops featured today — can work with just about anything in your wardrobe, especially for fall. A navy blazer, tan chinos and a white Oxford? Yes, that’s a winner. Something as laidback as tailored sweatpants and a stylish white T-shirt? Go for it. What about other men’s style essentials, fall-ready pieces like a rugged henley and classic dark denim? Rest assured, a pair like the Converse Chuck Taylor All-Star can work with ease. These shoes have history and style to burn, and they’re the perfect pair of kicks to reach for when you want to shake up an outfit filled with mostly easygoing pieces (such as the classic crewneck sweatshirt & Oxford shirt combo as featured below). Throw in a stylish casual watch and you’re ready for casual style scenarios aplenty. Heck, the sneakers on their own have enough style and street cred to carry most outfits, and they’ll put you over the top in most instances (no one else at your tailgate has these, right). Now, without further ado, let’s get you acquainted with this full ensemble — fall fashion can’t wait, after all.

RELATED STORY: The Best High-Top Sneakers to Wear Now

A clean, classic and easy way to wear high-top sneakers this fall.

  • The Sneakers: Converse Chuck Taylor All-Star High-Tops, $55–Don’t mess with a stone-cold classic — the Converse Chuck Taylor All-Star looks great in any season, especially early fall.
  • The Crewneck Sweatshirt: Myles Apparel Elements Crew, $64.98  — For a casual fall weekend, you can’t top the rugged appeal and comfort of a classic crewneck sweatshirt like the Myles Apparel Elements Crew.
  • The Oxford Shirt: Outerknown Nomadic Oxford in Army, $54 — Heading to Sunday brunch? Or a coffee date? Or a casual weekend round of beers? This sustainably made, stylish Oxford goes a long way.
  • The Classic Dark DenimFlint and Tinder Stretch Selvage Jeans, $118 — You know what never fails? A pair of slim dark blue jeans — particularly the Flint and Tinder Stretch Selvage Jeans. Comfort and style rolled into one.
  • The Belt: Beltology Radius Woven Belt, $50 — There’s no sense in skimping on your accessories. This textured belt adds some visual interest and keeps in line with the casual vibe of this #OOTD.
  • The Watch: Timex Navi Ocean Watch, $131.98 — How best to offset classic high-top sneakers, rugged dark denim and a classic crewneck sweatshirt? A stylish casual watch from Timex.
  • The Weekend Essential: Huckberry Blue Hour Growler, $75 — From the neat artwork to the fact that the Blue Hour Growler just looks plain cool, you’re gonna need this for a fall weekend camping trip.
  • The Wallet: Taylor Stitch Minimalist Billfold Wallet in Brown, $98 — Yep, Taylor Stitch makes wallets, too. The Minimalist Billfold is handsome, rugged and surely essential.
  • The Backpack: Fjallraven Greenland Top, $120 — Like we said earlier, this outfit can go anywhere from a day hike to a brewery visit, and the durable, affordable Fjallraven Greenland Top can go with you.
  • The Grooming Essential: Maapilim Hair Cream, $32 –Go for a slightly more laidback ‘do with Maapilim’s Hair Cream, geared toward a light hold and subtle shine. Fall weekend-ready, anyone?

That’ll wrap up this #OOTD quite nicely, don’t you think? Like other fall style essentials, if you start with something as classic and recognizable as stylish high-top sneakers, you’re in good shape — heck, you can do almost anything. The Myles Apparel Elements Crew is a prime casual layer, fit for throwing on over a unique Oxford shirt or a thermal long-sleeve tee in equal measure.  The Flint and Tinder Stretch Selvage Jeans are the perfect antidote to overly stiff stretch selvage, and they’ll look sharp when rolled up atop your Converse. On to your accessories: Never underestimate the versatility of a stylish casual watch, especially one that’s made for a bit of adventure (or tailgating). From there, we really get rolling — you’re going to want to bring the Blue Hour Growler to your next fall weekend get-together, along with the tough (and beer-friendly!) Fjallraven Greenland Top. Of course, a stylish leather wallet is always something you should have handy, and keeping that ‘do fresh with Maapilim Hair Cream is a wise, wise bet. Alright, my friends. What do you have to say about this #OOTD? How are you accessorizing your high-top sneakers? 

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