how to style chukkas for guys

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!

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?

Editor’s note: To learn more about great gear to buy for spring, click here.

Suede chukkas work in plenty more seasons than one. Read on for more details on the pair at left. Image courtesy of Huckberry.

As soon as the calendar really gets rolling into spring, there are certain items I’m anxious to shelve — and certain items that I’m ready to keep on wearing (or at least, wear more). One of those such items is the versatile suede chukka — it’s arguably a three-season shoe, well-suited to the colder temperatures of fall but providing some nice textural difference from shiny leather shoes during the sunnier days of spring and summer. When it gets snowy is when it’s tough to put ’em away — but now that those days are (hopefully) long gone, it’s time to break ’em out more. So that’s what we’re getting into here. The texture isn’t the only great thing about a suede chukka — the ankle cut of a classic chukka boot makes it the perfect go-between from, say, a lightweight, low-cut sneaker and a thicker winter boot — that means they’re ideal to style with everything from slim stone chinos to some rolled lightwash denim. They come in both casual and slightly more formal iterations, too. And that’s just the tip of the iceberg! Peep the full set of picks below, and let me know on Facebook if you think I missed any key brands.

Stay stylish!

#1. Thursday Boots Honey Suede Scout Chukka Boot — $149

Eye-catching honey suede from Thursday Boots makes this pair of chukkas a stunner.

Finding a well-made, reliable chukka (especially in a rich shade of honey suede) is a somewhat tricky endeavor, but Thursday Boots delivers again with its durable Scout Chukka. This writer has a pair of the Scout Chukkas in Chocolate Suede, and if the quality is anything like those, the Honey Suede version should hold up handsomely. The slightly higher-than-normal ankle cut is a continental touch, the studded rubber sole is tough on the ground yet comfortable on your feet, and in this instance, the honey suede is a colorful hue that’ll look great with slim white denim now and even better under dark raw denim come fall.

#2. J. Crew Classic MacAlister Boots in Stone — $148

J. Crew’s take on the classic style.

For Thursday Boots taking the cake with its $149 chukka, J. Crew’s MacAlister Boot in Stone comes in a close second — at a very slightly cheaper price (ha!). This is certainly the more casual of the two boots, as this number has all the makings of a traditional desert boot (different from a versatile leather chukka). That goes for the traditional crepe rubber sole and continues on through the raised contrast stitching between the sole and the upper. This boot is still made in Italy, and it should certainly pack in all the quality one would expect from a pair of J. Crew footwear. For weekend brunches and coffee runs (or a casual Friday), this is your go-to boot.

#3. Clarks Desert Boot in Wolf Suede — $130

An iconic silhouette rendered in a unique suede.

One would be remiss to talk about desert boots or chukkas and not give a look toward Clarks, the originator of the style (for the general public, at least). The Wolf Suede Desert Boot takes the iconic Clarks silhouette and does it up in a beige suede that should make these another reliable, casual footwear option for a ton of situations — be it a fall coffee date (paired perhaps with a shawl-collar cardigan and denim?) or a spring weekday with a slim polo and chinos. Plus, the price and quality are both very hard to top among like-minded brands.

#4. Oak Street Bootmakers Chocolate Suede Campus Chukka — $426

Perhaps the most premium pair of suede chukkas on the market, totally ready for anything.

Think a darker suede can’t be worn in the warmer months? Think again, my friend. If you’re on the hunt for a pair of chukkas that are worth the investment and the styling potential, the Chocolate Suede Campus Chukka from Oak Street Bootmakers is the chukka for you. It’s crafted in America with beastly construction, from the Goodyear welt to the waterproof suede (really), and the oiled leather soles. The color is rich and beautiful, equally fit for pairing with slim tan chinos now and your toughest pair of dark denim later this year.

#5. Astorflex Greenflex Chukka in Stone — $145

One seriously stylish and sustainable pair of desert boots.

For the last entry on this list, we turn to a boot that combines all the inspiration of the classic desert boot with some seriously eco-friendly construction (be warned that it’s only available in sizes 9-12 right now, though). Yes, Astorflex certainly knows what it’s doing when it comes to combining quality, style and sustainability. This pair is made in Italy, yet rings up (or rather, charges your card) for an incredibly low price. The memory foam footbed should be comfortable, and the organically treated leather is processed slowly for more than a month, resulting in a pair of footwear that you can also feel good about buying.

So, picking up a new pair of footwear to add to your rotation doesn’t have to be an expensive or time-consuming process. Starting by looking for quality materials and versatile style potential is going to take you much further than settling for something less expensive — in that case, Florsheim’s Constable Chukka was also close to making the cut. If you’re uncertain about how to style a suede chukka, rest assured that it does just as well as a sharp leather chukka when paired with like-minded outfits — whether that’s a slim T-shirt and denim or a polo and lightwash jeans. If you play your cards right (and the weather holds out), it’s a style that could be in your rotation ’til fall.

Do you have a pair of suede chukkas in your closet? Which of the above pairs would you pick up for this spring?

The Style Guide

All the best men's style essentials you need, every day.

Tag / how to style chukkas for guys

#OOTD: How to Style Leather Chukka Boots

Online Shopping Picks: Best Suede Chukkas to Buy For Spring