Dress Boots – Complete Your Date Night Outfit With These Picks

If there’s one thing we believe in wholeheartedly at Jacob Graye, it’s the importance of getting the details right from the ground up. No menswear essential is too small to be overlooked, whether it’s boot socks or the watch on your wrist. This, you see, is where dress boots enter the fray, here to claim their rightful place in your footwear rotation as a badass, go-to pair of footwear, especially when the occasion calls for style that’s sharp as nails.

Make no mistake: Dress boots aren’t quite combat boots. Dress boots have a slimmer profile and feature a design that’s less bulky by nature.

Dress boots are the ultimate date night outfit addition, just as they’re the right way to add a bit of devil-may-care appeal to even your most finely tailored suit. For inspiration, just look at Peaky Blinders and how the lads of Birmingham stomp their way through the city suited and booted, as it were. And if you need any more inspiration beyond that, take a look at how even James Bond has been wearing chukka boots with a suit in recent years.

If you’re not yet convinced, we’d implore you to, well, get with the program and find yourself some of the best dress boots to add a sleek finish to your tailoring. These types of boots are especially useful when you’ve got to tread a bit more carefully across slick city streets or rain-soaked pavement, and yet, you’ll stay on your feet in style all the while. Besides, you shouldn’t have to worry about falling down yourself — you’ve got your date to keep an eye on, after all.

Make no mistake: Dress boots aren’t quite combat boots. Dress boots have a slimmer profile and feature a design that’s less bulky by nature. Combat boots are also often built with a heavier lug sole, while dress boots feature a more low-key studded outsole design, all the better to grip slippery pavement without ruining the fine lines of your suit with an overly heavy build. Dress boots also feature, oftentimes, a more sleek finish in terms of leather.

Chukka boots can certainly be dress boots, but in keeping with the spirit of the times, let’s focus today on lace-up dress boots with a sleek, smooth build. Chelsea boots, or “Beatle Boots,” as the style popularized by the legendary band has come to be known over the years, are also a form of dress boots. If you feel like rocking your smooth leather Chelsea boots with a suit, go for it – we’ll explore a few different options of lace-up dress boots in the meantime, though. You can’t go wrong either way when you get suited and booted, as it were.

Those are just the basics: Here’s what else you need to know as you shop for the best dress boots on the market.

How to Choose the Best Dress Boots for Your Look

  • Start with the basics: When we say “basics,” we mean that you’ve got to carefully assess the situation and determine how often you’ll be wearing your dress boots, and with what type of suiting. If you’re opting to wear dress boots with a cotton suit, it’s best to look for a dress boot with a slimmer design and perhaps a more finely finished (I.E. Shinier) leather. If your dress boots are going to offset a heavier wool suit, stick with something with a sturdier design (for example, Tricker’s dress boots have a solid, durable build).
  • Invest in the best: Dress boots are perhaps even more versatile than dress shoes or classic chukka boots, so we’d say it’s more than fine if you drop a few extra dollars on a pair. Dress boots are well-made enough to face harsh elements, they’re easy to wear with rolled denim or chinos (unlike some dress shoes), and the clean finish of a pair of dress boots makes them even better to wear with a suit than chukka boots (although James Bond got it right when he teamed black chukka boots with a grey sharkskin suit).
  • Know how to style them: Picking up a pair of finely crafted dress boots is far from the end of the story. We think it’s just the beginning, in fact. Like we said when we urged you to start with the basics, buying dress boots requires proper care and thought as you put together a date night outfit. Dress boots can work with slim black or blue denim and a chambray shirt, but they can also offset a classic navy suit, a crisp white dress shirt and a navy knit tie. If you find the right pair for the style mood board you’ve got in mind, there’s no telling how many combinations you can dream up.

So, you’re well on your way to shopping for dress boots just like the pros do. Now, let’s talk about our favorite pairs, shall we?

The Best Dress Boots for Men to Buy Now

Tricker’s Buford Lightweight Country Derby Boots

Tricker’s Buford Lightweight Country Derby Boots

Here they are: Perhaps the boots most likely to be worn by the members of the well-tailored, suited-and-booted Peaky Blinders. They feature a watertight seal, a durable build, sleek black leather and the kind of expert blend of refinement and functionality that the best dress boots bring to the table. Tricker’s is a classic and much-loved British brand, with all kinds of heritage and history built into every pair of boots. These would wear especially well with a grey flannel suit come fall, but we could also see them working for country summer weddings when you don’t want to worry about dress shoes as you traipse through an idyllic meadow setting (to name but one example). Any way you want to wear these dress boots, rest assured that they’ll pass muster.

FRYE Chris Lace-Up Zip Boots

FRYE Chris Lace-Up Zip Boots

FRYE is to fashionable Americans what Tricker’s happens to be for our neighbors across the pond: A long-running, ever-reliable fan favorite that excels at making the best boots for men across the board, be it chukka boots, Chelsea boots or lace-up dress boots. They’ve got more than 100 years of fine boots under the belt to prove it, too. And the admirable thing about FRYE is that they’ve stood the test of time and evolved along the way to produce styles that are both dressy and yet highly wearable with denim or chinos as well as business casual and tailored looks. The Chris Lace Up Zip Boots blend a bit of rock n’roll edge with the finely tuned style you need to impress on date night, especially in the rich burnished Bronze colorway shown here. They’re a bit pricier than your average pair of boots produced by a fast-fashion brand, but that’s no matter: You’ll have them for years and years to come.

Thursday Boots Limited-Edition Captain Boots

Thursday Boots Limited-Edition Captain Boots

Across the past handful of years, Thursday Boots has only gotten bigger and better, and this growth (combined with a commitment to quality and style) makes them one of the best dress boot brands on the market today. The Limited-Edition Captain Boots in particular really are a sight to behold, featuring handsome brogue captoe detailing and a rich color that’ll stand out handsomely beneath the cuff of your suit trousers. The brogue detailing is a throwback touch to a time when boots were worn purely for work, out in the country (the characteristic decorative perforations provided improved airflow). Nowadays, boots can be worn as a dress shoe alternative, as you no doubt know very well in reading this post. And the Captain Boots are a fine example of how boots can rise above their humble beginnings and turn into a durable, well-regarded and seriously cool dress shoe option for the modern man.

Allen Edmonds Hamilton Weatherproof Oxford Dress Boots

Allen Edmonds Hamilton Weatherproof Oxford Dress Boots

Remember the brogue detailing we mentioned above? Well, it’s squarely at the forefront of these refined and elegant dress boots, which just so happen to be the perfect pair to wear with burly fall fabrics like wool, not to mention lightweight cotton chinos and denim. That’s the thing with Allen Edmonds dress boots: The construction and design is impeccable, the styling potential is top-notch and you can feel great about the fact that you’re investing in a quality pair, to say the very least. The brogue styling is a standout touch, and you can’t help but love the fact that these feature weatherproof technology for maximum wearability in multiple seasons. Plus, the sleek, clean lacing system and Chili leather are nice touches you won’t find on too many other pairs of dress boots.

Adelante Shoe Co. Havana Boots

Adelante Shoe Co. Havana Boots

Going back to what we said earlier about boots that might be favored by Peaky Blinders, well, this pair might do the trick, especially in rich Mahogany leather. These are a pair of surprisingly tough and yet well-crafted boots, the kind that sit nicely underneath cuffed selvedge denim with an Oxford shirt and a navy cotton blazer. They also stand out quietly beneath the cuff of sturdy wool suit trousers, all the better to add some functional appeal to a winter date night ensemble. The rest of the time, the handcrafted Adelante Shoe Co. Havana Boots are just a damn fine pair of boots for all occasions, even in the summer months (although the boots themselves are sturdy, the leather is lighter in weight than you might think). Dress boots you can count on is the name of the game, and Adelante Shoe Co. delivers.

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Beau is Brooklyn-based style and lifestyle writer. He covers menswear, gear, spirits, craft beer and music. When not writing, Beau can be found shopping for vinyl or sipping on a Brooklyn beer.

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