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Chukkas are one of those rare shoes that bridge the casual-dapper divide. They dress up your weekend jeans and tee and add a sporty vibe to your suit. I love to have a few pairs on hand so that I know I’ll be ready for any occasion. I’m showing off three different chukkas to test them out on my day out in the city. With three very different looks, the chukka takes me from rugged to refined and everything in between. Here’s how to style them.

823_look1 (Photo 1)

Laidback On-The-Go

I do all of my work on the move. As a style blogger, my day can take me all over the city and I’m usually working in a coffee shop or sending emails from the subway (Yep, someone’s using that WiFi for things other than Snapchat and Instagram. Like, me. Hey, fashion isn’t going to blog about itself).

I carry a backpack everywhere I go because I’m pretty much a digital nomad. My daily uniform is made up of casual, laidback pieces, updated with a unique touch. This blue pair of Preston Hills Chukkas is a perfect example – a classic shoe made modern in a bold hue.  It sets you apart without having to try too hard.

Style tips:

  • Wear chukkas with denim or chinos for a casual look. I went with camo chinos for an extra twist, but made sure it was the only pattern I was wearing.
  • Stick to a neutral color palette. Avoid reds, yellows and oranges. They will clash with the blue leather. Neutrals or shades of blue and green (and yes, denim is considered a neutral) work best with these shoes. Tip: Muted shades are better since the blue is a saturated hue.
  • Bring it all together with the details in your accessories. The chukkas have a thin brown leather detail around the bottom, so I went with a brown bag and belt. Your shoes almost always dictate accessory choices. Complement the shoe color without getting too matchy matchy. A blue belt with blue shoes would be overkill.

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Weekend Style

I love a pair of shoes that are aged to perfection and look like they have a story behind them. These brown leather Revenia Chukkas have a lot of history . The top leather is slightly worn, and the corners at the top are folded over to expose the suede inner. It’s a really cool look. You don’t want to go overly polished with a heritage shoe. Keep it grounded with a mix of rugged and refined pieces.

Style Tips:

  • These would work perfectly with a pair of slim rolled denim. The shoe itself has a slim silhouette, so you should avoid straight or relaxed fits.
  • If you’re wearing them with shorts or cropped pants (I know it’s a little outside the box, but worth trying if you’re feeling adventurous), go with a sockless look. You shouldn’t actually go without socks when wearing chukkas. For comfort of your feet and the comfort of the people around you (sockless + sweat = a certain aroma), do yourself a favor and invest in no-show socks. Cut below the line of the boot, they’re an easy cheat to effortless style.
  • Black and brown DO go together. You can wear all black with brown shoes. Again, pull it all together with a brown belt or bag.

823_look3 (Photo 3)

Dapper Gentleman

As casual as my style is, I have to pull out my dapper side all the time for meetings and events. And let’s face it – we all have those moments when we want to look like a modern day Don Draper. But that doesn’t mean I wear a full suit – you can be refined with just a blazer and trousers. When looking for a refined shoe, polished brown chukkas like these Naples Trail Chukkas are one of those great multipurpose styles. They work great with denim, but look just as dressy as an oxford or brogue. You’ll get a ton of wear out of them.

Style Tips:

  • Keep it classic. Navy and grays are the easiest colors to put together, and always look polished. The navy blazer and pocket square show everyone you mean business, and the texture of the wool trousers is a nice touch.
  • Give it a break. A single, to be exact. Your trousers should not pool at the bottom. Chukkas come up a little higher than a traditional dress shoe, so your trousers should be tailored a little shorter to accommodate. You want a slight break in the front, anything more and it’ll look sloppy.
  • Keep them polished. Shoe care is vital to maintaining a refined look. Polish your leather shoes occasionally and be sure to spray them with a protector such as Timberland’s Balm Proofer™ All Purpose Protector right when you get them (I do this with all of my shoes. The city will stain and scuff a great pair of shoes without regard.).

The ever-versatile chukka packs in a lot of history and style in one punch.