#OOTD: How to Style Leather Chukka Boots

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 series will take one great item and put together a versatile, stylish outfit around it. Look for past features here.

As I’ve so often written about on The Style Guide, style doesn’t have to be too taxing or complicated. It’s not about chasing too many trends (things like athleisure and ridiculously distressed clothing come to mind), but I find that it’s about taking basic pieces and making them work for you by nailing the fit, texture and color. And if you stock a wardrobe full of versatile, casual pieces, that’s a job that can be taken care of quite easily. Take the below #OOTD. It’s perhaps endlessly versatile, from a first (or second, or heck, third) date to a day at the office to weekend brunch or shopping. That’s what you get when you focus on pieces that are relatively classic and dial in the fit and proportions to make them work for you. So in the case of the chambray shirt you’ll see below (spoiler!), that means looking for a piece that fits trim and flatters your frame. The same goes for the chinos on display. When you check those boxes off, it then gets easier to focus on other crucial areas – like pattern and color (or, grabbing a great pair of essential chukka boots). With all that being said, let’s not waste another moment! Onto the #OOTD below.  Hit me up on Twitter or Facebook if you like what you see!

Taking a classic pair of brown leather chukka boots and pairing them with style staples -- simple, effective and sharp!
Taking a classic pair of brown leather chukka boots and pairing them with style staples — simple, effective and sharp!

The Boots: Thursday Boots Brown Scout Boot, $149 — While plenty of brands make a solid leather chukka boot (see here for one option), it’s tough to find a brand that’s nailing a solid price point for even higher quality.

The Shirt: Old Navy Slim-Fit Chambray Shirt, $25 — Because we’re starting with the boots and building from there, a solid, reliable and remarkably affordable chambray shirt is for sure the way to go.

The Chinos: Bonobos Jet Blue Washed Chinos, $88 — Again, navy chinos are classic, reliable (saying that a lot, aren’t we?) and well-fitting — particularly with your pick of three fits. The navy blue plays nicely off the chambray, too.

The Socks: Pair of Thieves Splelurking Socks, $10 — You might recognize this brand from a past Style Guide #OOTD, and this pair is a nice way to break up the shades of blue between the chinos and chambray shirt.

The Belt: J. Crew Factory Braided Leather Belt, $27.50 — Playing off the adage that simple is better, this relatively affordable and durable belt breaks up the outfit with solid texture and keeps things casual yet crisp.

The Watch: Timex Weekender Fairfield Watch, $75 — A new introduction from a brand that’s really upped their design as of late — the casual nature of this outfit means you needn’t worry about matching the leather to the chukkas all that much.

The Money Clip: Owen & Fred Brass Money Clip, $19 — If you live by the principle that style is in the details, this money clip streamlines your everyday carry and looks great in the process.

The Bag: Owen & Fred Flight Brief, $245 — If you prefer a larger bag, this might be a bit small for you. However, if you prefer to keep things simple, sharp and stylish, picking up this flight brief is a great investment.

And with all of that, we’re set. This outfit isn’t tremendously groundbreaking, and it’s not build to turn all that many heads in terms of street style. But it’s sharp, effective and versatile — be it going from the office to a weekend trip, or out and about on the weekends. Pairing shades of blue is a personal favorite of this menswear writer (although I’m trying to mix up those colors!), so it’s a tried-and-true combination. And crucially, starting with a remarkably handsome pair of shoes — chukka boots in this case — is always a solid bet no matter what occasion you might be dressing for. Be sure to take care of them with brown leather shoe cream or polish, and they’ll stand up to everything from tailored wear to a casual weekend outing.

Are you a fan of this week’s #OOTD? How would you style brown leather chukka boots?

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Florsheim

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14 thoughts on “#OOTD: How to Style Leather Chukka Boots

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