#OOTD: How to Dress for the 2016 Olympics

Editor’s note: You’ve surely seen this hashtag lots of different places, including on Instagram. But how does that carry over to real life? The #OOTD will take one great item and put together a versatile, stylish outfit around it. Look for past features here.

OK, so the title of this post isn’t 100 percent accurate — if you’re really competing in the Olympics, you’re probably not wearing the below ensemble. If you’re watching them, however — here we are. They only come up once every four years, so it’s likely that dressing to watch the 2016 Olympics might not have crossed your mind until now. But, like heading out to a warm-weather bar crawl or grabbing Sunday brunch, it’s a scenario that’s an opportunity to look your best when others might not be all that focused on doing so. It’s also a time that can be patriotic and pretty fun — who doesn’t love the Olympics, right? So that’s what this #OOTD is tackling — assuming you’re in a warm-weather area and possibly getting out and trying to recreate some athletic feats of your own in a game of backyard volleyball. With that in mind, this outfit is part sporty, part stylish and filled with a few atypical style upgrades. Those include an upgraded graphic tee and some crisp, classic sneakers — but you can see the full look below. For more daily style inspiration, check out yours truly on Instagram and follow along with my #menswear Twitter.

An ensemble that's sport-inspired yet not packed with athletic gear, finished off with classic footwear and shades.

An ensemble that’s sport-inspired yet not packed with athletic gear, finished off with classic footwear and shades.

The T-Shirt: Todd Snyder Miami Capsule T-shirt, $68 — While you can definitely go with a classic, Olympics-inspired graphic tee, this tee is premium, slim-fitting and still sporty while remaining wearable for other occasions.

The Shorts: Mack Weldon Ace Short, $65 — A pair of shorts that works for both sporty backyard activities and lounging around in style can be tough to find; however, this pair has a more tailored look than one would expect, and still performs well.

The Sneakers: SeaVees Hermosa Plimsoll Standard, $78 — Highly affordable, highly wearable and able to stylishly offset the brighter blue shorts. An American classic.

The Socks: Sock Genius Villa Park Stripe No-show Sock, $10 — If you caught the recent Style Pick of the Week feature on Sock Genius, you know that these no-show socks are durable, breathable and comfortable — that makes ’em  a winner.

The Watch: Stuhrling Aquadiver Manta Ray Watch, $ — You need a durable casual watch in your arsenal for a variety of reasons (particularly if you’re playing some Olympic-inspired backyard games), and the Stuhrling Aquadiver Manta Ray is a personal favorite that’s held up very well over time.

The Briefs: Flint & Tinder Heritage Boxer Briefs, $28 — Although they’re not pictured above, you can’t forget made-in-America boxer briefs that feature a custom woven waistband and comfortable fabric.

The Hat: Huckberry Explorer’s Cap, $39.98 —  Swapping out your athletic logo ballcap for a more subtle, refined hat is a solid style upgrade that makes a difference — this is the perfect cap to wear for the occasion (note the blue-and-white color) and it can even dress down a classic polo and chino shorts.

The Sunglasses: Randolph Engineering Crew Chief Sunglasses in Gunmetal, $158.98 — To root on America, there’s no better pick than sunglasses that are, well, made right in America. These are durable, premium and wearable with your best suit, too.

The Must-Have: Owen & Fred NFL Leather Coasters, $29.98 — Whether you’re enjoying a cold brew or a plain lemonade, some stylish leather coasters are a nice accessory to have, particularly if you’re hosting.

While you can always go full-on patriotic and rock an official USA jersey (soccer jerseys seem to be a popular and relatively refined pick), working with the pieces in this #OOTD provides you with versatility the rest of the summer and beyond. A subtle graphic tee is a more premium pick than a plan tee, and French terry shorts that fit trim and eschew an athletic logo are a great pick, too. Plus, an upgrade ballcap is a solid style move, and a durable rubber-strap watch should have you set for more outdoor activities beyond the Olympics. Have other #OOTD suggestions or style questions? Head over to The Style Guide Facebook page for more #menswear.

How are you planning on dressing for the Olympics? Leave it all in the comments below!
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Style Suggestion: Dark Leather Sneakers

Rocking some leather sneakers -- perfect for the fall & winter. Jacket by Frank & Oak. Long-sleeve T-shirt by J. Crew. Sneakers by Billy Reid for K-Swiss. Watch by Stuhrling. Glasses by Burberry.

Rocking some leather sneakers — perfect for the fall & winter. Jacket by Frank & Oak. Long-sleeve T-shirt by J. Crew. Sneakers by Billy Reid for K-Swiss. Watch by Stuhrling. Glasses by Burberry.  Photo credit: Liz Todd. 

Even though it’s getting closer and closer to December (and thus the start of real winter), there should still be opportunities when the snow clears to put away a pair of thick boots and instead reach for some more casual, laidback footwear. Specifically, a pair of leather sneakers should do the trick. While white sneakers offer lots of wearability in the spring and summer, darker shoes just make more sense for fall & winter. We’ve been seeing a lot of brands launch luxury versions of athletic-inspired sneakers — even Tom Ford offers rich leather kicks now. And brands like Frank & Oak have gotten a lot of publicity for their more affordable takes on the dressed-down silhouette. Given the variety of shades and their versatility, footwear that clean and crisp can easily be worn with chinos and a blazer (my personal favorite from that launch would be the chestnut low-top sneakers below).

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One of Frank & Oak’s takes on the luxe leather sneaker.

However, in the fall and winter, sneakers should definitely also lend a rugged appeal to an outfit. The great thing about the sportswear-inspired takes we’re seeing on so many shoes is that they’re also blending elements of fashion with athletic vibes — take American menswear designer Billy Reid’s collaborations with K-Swiss. The most recent run of sneakers in that collaboration vanished off the site quickly — the pair in the photos here was scooped up in July during a sale, and now they’re nowhere to be found on the K-Swiss site. No need to despair though — other retailers are still stocking them. 

Plenty of excellent, fall-ready alternatives are out there, from J. Crew’s suede Sawa sneakers to the Frank & Oak options mentioned above. Additionally, the Ellington and McQueen models from footwear brand CLAE bring lots of cold weather-centric texture with minimal logos and clean design. Given the nice mix of crisp styling and fall-ready colorways available, matching these sneakers up with an outfit isn’t too hard at all.

More rugged than Frank & Oak's, but just at ease with slim joggers.

More rugged than Frank & Oak’s, but just at ease with slim joggers.

In dark brown or even black leather, sneakers like the ones above can be paired with slim joggers (like J. Crew’s Wool Sideline Pants, as seen here) or dark denim, a henley and a rugged workwear-inspired coat. In particular, the K-Swiss sneakers shown here strike just the right balance between crisp and rugged — the dark brown color allows them to fit right in with auburn chinos, a cardigan and a blue OCBD, while the distressed leather, sporty diagonal stripes and rawhide laces give them a hybrid vibe that pairs perfectly with the equally hybrid wool joggers from J. Crew. Olive chinos or jeans, in a similar shade to the joggers above, would also complement darker brown leather nicely. These have also gotten use with a shawl-collar cardigan and even simple long-sleeve T-shirts. More vitally, these sneakers have held up well being worn two or three times a week — keeping the sole clean is going to be vital with any pair of sneakers, and given the potential for fall or winter rains, treating them with some sort of waterproofer (especially for suede options) will be key.

A fall and winter-ready alternative to the Billy Reid x K. Swiss option pictured.

A fall and winter-ready alternative to the Billy Reid for K. Swiss option pictured.

For the rest of the fall and winter, my Billy Reid for K-Swiss sneakers will continue to get lots of wear — they’re rugged and sporty, yet the rich, distressed leather doesn’t look out of place with less casual get-ups. Grab a clean, crisp pair and they’ll go well with just about any outfit over the coming months.