Fall Boot Guide For Shorter Men

Fall Boot Guide For Shorter Men

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Wow, just wow! Temperatures finally hit the sixty-degree mark for a few consecutive days here in the concrete jungle known as the City Of New York for the first time in months, and I’m seeing some brave heroines adorn some sleek knee-high boots along with longer shirts and ripped jeans, click-clacking their way across crowded crosswalks in both midtown Manhattan and Downtown Brooklyn. All of these things combined with the sun positioned almost directly over the equator must mean one thing—Fall is near! In fact, it really is!

See Also: Fall Outerwear Guide For Shorter Men

In just a few days, Summer will be officially gone! For us shorter men, this means those low-tops, flip-flops and no-show socks are about to be shelved for the next six months or so (along with those white sneakers – you know the supposed “no white footwear after Labor Day” rule). Boots must make their way to the front! Otherwise, we’ll be cleaning leaf slime from our sneaker soles. To prepare for the coming gorgeous peak foliage, we’ve decided to compile a boot guide just in time for the pumpkin spice and apple-picking. Without further delay (come on and take in some of those images we just spoke about, don’t be a boring Bob!), gentleman, welcome to the Fall Boot Guide for Shorter Men.

A FALL BACK INTO HISTORY

Fall boots, like our brief overview of Winter Boots in our Winter Boot Guide, evolved across centuries from rugged necessity into the polished fashion staples we know of today. Originally designed for foot protection during hunting, horseback riding (try doing that in Sandals!) and military service, boots were built for battle-tough utility. By the 1800s, however, they became refined for both formal and semi-formal wear, especially in Europe and North America.

Gentlemen in Victorian Britain popularized Balmoral boots—sleek lace-ups named after Balmoral Castle, while the Chelsea boot, with its elastic sides, rose to popularity. In the 1900s, work boots like moc-toe wedge styles transitioned from factory floors to casual and dress casual fashion, while harness boots pointed toward a rebellious spirit via a growing motorcycle culture. Yeah, “Bad-To-The-Bone” (think of every guy you’ve ever seen annoyingly revving their motorcycle engine on the highway next to your car, or worse yet, at three-o-clock in the morning up a hill in your neighborhood).

These days, boots strike a balance: practical enough for the fall weather, yet stylish enough to pair with jeans, chinos, or even suits if done right.

FALL BOOT TYPES EVERY MAN SHOULD KNOW

CHELSEA BOOT

The Chelsea boot is minimalism at its best. Defined by its elastic side panels and pull-on tabs, it’s sleek, versatile, and ankle-skimming. Black or brown leather or suede Chelseas pair effortlessly with slim trousers or dark denim, making them a go-to for those who want clean lines without visual bulk. Dressy in appearance, they add just enough formality to make you look like you’re going somewhere special.

Examples: Red Wing, Thursday Boot Company, Blundstone, Call It Spring, Morjas

BALMORAL BOOT

The Balmoral (from my point of view) is the embodiment of formality. It features closed lacing, often in polished leather, with a seamless look that complements tailored suits and well-fitted chinos. Because of its slim profile, it commands attention without widening the foot. For those aiming for a pairing with denim, add a simple cuff for businessman-on-the-weekend or entrepreneur vibes. Add a cardigan and scarf, and you’re ready to take over the world, or at least a trip on Fifth Avenue.

Examples: Allen Edmonds, Beckett Simonon, Carmina, Cobbler Union, Aldo

CHUKKA BOOT

This funny-sounding boot (at least to me—I laugh just saying it) gets its name from the sport of polo, where chukka refers to a period of play. Casual but refined, chukkas typically feature two or three eyelets and hit just above the ankle. Suede chukkas in earth tones are perfect for fall weekends, while leather versions can transition into business casual settings. They’re high enough to qualify as a boot, but low enough to retain a shoe-like appearance. If they’re good enough for Lenny Kravitz (we published an article on his style choices some time ago), then they’re good enough for the everyday guy who wants to exude a bit of humble hipness on a cool breezy day walking around downtown.

Examples: Clarks, Padmore & Barnes, John Lobb, Astor Flex, DSW

CAPTOE DRESS BOOT

My absolute favorite boot because they can be paired with just about anything and can even make a casual outfit look more than casual. I am being a bit biased because I love captoe shoes, so then what better way than to get the best of both worlds (boots and shoes) and make any ensemble look spectacular? With a horizontal stitching line across the toe, captoe boots strike the balance between formal and everyday wear. Black versions work well with suits, while brown versions transition easily into smart-casual outfits. Rather wear denim? With a nice solid or plaid button down, cardigan or v-neck sweater and leather jacket, add shoe polish and you’ll look like you own something or are about to own something. From the Upper West Side to the Upper East Side, you’ll look like you belong when you slip into some captoes.

OXFORD & WINGTIP BOOTS

As the name implies, these resemble oxford shoes, making them easy to pair with formal or dress-casual ensembles. Oxfords got their start from students in 1800s England, who wore half-boots with side slits called “Oxonians” rather than the stiff knee-high boots of the day. Plain Oxford boots do not have stitched cap toes, so have a plainer appearance. Wingtip boots, on the other hand, feature a W-shaped toe cap along with perforations around the tip and sides of the boot like their Wingtip shoe counterparts. Those perforations add nice accents and style to what would otherwise be a plain affair, and as a bonus, may provide a bit of ventilation. Just for clarity, Wingtip and Oxford boots can also be cap toes, which means these classifications can overlap. While I personally would rather wear wingtip shoes than wingtip boots, their existence provides more options for those who want formal aesthetics with cooler weather functionality. In my book, they are perfect to pair with darker jeans, button-downs and double-breasted cardigans—a dress-casual gentleman’s delight.

HARNESS BOOTS

Get ready for the ride, because that’s where these boots originated. Gaining popularity in motorcycle culture, their straps and rings lend a rugged and rebellious feel, making them a great statement piece for casual outfits—think “Uncle Jesse” from Full House (or you can always watch “Fuller House” if you’re not interested in time traveling to the past). These are not boots that you’d want to wear to the eight o’clock meeting in the office, but they would look great on a night out to the bar or brewery, for a stroll on your typical fall Saturday afternoon or to your favorite classic rock concert. Think jeans, think a leather or suede jacket and your favorite flannel or button-down shirt. If you’re into studs on your outerwear, you can lean into your inner “Uncle Jesse”—I think John Stamos might approve.

MOC-TOE WEDGE BOOTS

In my opinion, these are your “fall classics”. If you’re an older millennial or younger gen-xer, the mid-‘90s “Eastlands” craze will bring back some fond memories (or if you couldn’t afford them like me, then those Payless knockoffs might invoke the same feeling lol). Moc-toe wedge boots are generally built for durability and comfort, with a moccasin-style and thick rubber sole. Traditionally a work boot, they have crossed into streetwear and casual fashion, pairing best with raw denim or flannel layers. Opting for higher quality leather exteriors with a nice thick sole can have you feeling like you’re walking on air, especially on the tough and sometimes unforgiving city concrete in the urban streetscape of your choice. Here in New York City, I can’t go one year without seeing them being worn by many once the crisp weather kicks in.

MATERIALS

Boot Material goes further than appearance – it’s about function, durability, occasion and what’s allowable depending on the forecast. Here we will cover the most common fall boot materials:

LEATHER

We recently published a leather jacket guide, and while we’re talking about boots, the same considerations about materials apply here. Leather is classic, durable and versatile. Polished calfskin works for formal boots, while full-grain or tumbled leather suits casual designs. Expect the same best practices for keeping leather jackets in great condition to apply here. Wear them proudly, but protect them from punctures and rips — you’ll feel the pain more than the leather. Shoe trees are my best friend to keep those creases at bay—creases will have everyone looking at them instead of admiring your fashion sense, especially here in the five boroughs.

SUEDE

There’s something regal about suede. Its soft texture creates a more relaxed, but refined look. Working best with chukkas and Chelseas, especially in fall hues like taupe, brown and navy, they’re perfect for both sunny and overcast fall days, but are not the go-to the moment the sky gives and H20 begins its descent. Protect them from the elements and you’ll wow onlookers every time you put them on your feet (as long as your ensemble looks great of course—we all can’t be Times Square’s naked cowboy).

RUBBER

Typically used for soles, rubber provides traction and weather resistance. Full-rubber boots are more functional than stylish, but useful when weather becomes a challenge. Rainy days? Snow days? The proverbial nor’easter? Rubber boots will be your go-to. Stylish options do exist. Knee-high wellington-style will always get the nod from me as they provide the best protection for your feet and pants and look great with formal outfits. For those looking for a lower profile, ankle and calf-high options exist. Rain boots in the Chelsea style are also fairly easy to come across. Unlike your grandpa’s department store, there are plenty of choices in this category here in the present.

NYLON

Lightweight and durable, nylon appears in tactical or hiking boots. It’s functional, but generally less stylish for dressy settings. You’ll find plenty of hybrids though—plenty of weather boots feature nylon tops with insulated lining along with rubber or polyurethane bottoms. Ugg Stapd Classic Laceup boots come to mind (these feature nylon uppers). When you’re nearing the end of the season, these may end up in the front of your closet. You can check out our Winter Boot guide and upcoming Hiker’s Guide for more examples of nylon or nylon-hybrid offerings.

See Also: Leather Jacket Guide For Shorter Men

FALL COLORS

We have an upcoming article about the Fall Color Palette where we’ll do a deep dive, but we’ll keep it simple here. You already know that autumn is about rich, earthy tones. Boots are no exception.
 

BROWN

The most versatile for casual and business casual wear. You can’t go wrong with brown. From Chelseas to Oxfords, brown just works.

BURGUNDY/OXBLOOD

How dramatic of a color name is “oxblood”? Lol. Striking in name or not, this color adds depth and pairs well with navy or gray. Remember those Eastlands I spoke about earlier? Their most popular hue was this color.

TAN

Another fall staple, though I’m cautious about what I pair this with. Best for casual fall outfits with denim or chinos, but I personally pair tan with lighter denim. If you have to wear dark colors (i.e. black pants and a black shirt), I’d be sure my outerwear or accessories (i.e. hat or scarf) match, or is a lighter color to add some overall contrast.

BLACK

Come on… Do we even need to discuss this? Black almost always works. It adds formality, sharpness and pairs well with suits, monochrome getups, casual outfits and anything in between. If not suede, then it’ll hide dirt and hold up the elements a bit better as a bonus. Add a bit of gloss (just a little bit) and you’re ready to add a bit of class to any dress casual outfit. With black, you can’t—or rarely can’t—go wrong.

NAVY AND FOREST GREEN

For those looking for a bolder edge or to make a statement, these are worth looking into. For navy, tan chinos or corduroys will complement well. Black pants and a navy Henley or sweater would also work well. Forest green will require a bit more discernment with your ensemble choices. The proverbial green bomber or green trench with a brown scarf will complete the look.

OUTFIT IDEAS

THE CENTRAL PARK STROLL

Starting off with something casual enough for long walks on winding asphalt paths and Belgian-block Manhattan streets, but presentable enough to receive a wink and a nod just in case you run into your manager, grab a gray overcoat (preferably a three-quarter-length overcoat), and pop on a multicolored scarf featuring red, black, and gray (nothing wrong with hinting that the holidays aren’t that far away).

Underneath, have that medium-gray crew-neck or V-neck sweater you’ve had at the back of your drawer since the last day the thermometer had a five or less as its first digit. Add a pair of black medium-weight chinos and round everything out with some fine dark brown leather Chelsea boots with black gussets. For the icing on the cake, slip on some matching dark brown leather gloves.

The average passerby may note that this guy wearing this outfit has just enough time to take a stroll around the southern confines of Central Park and window-shop the regal Fifth Avenue storefronts with the lady he fancies, but has somewhere to be. That guy, my friend—is you!

A DAY IN LONG ISLAND CITY

When it comes to autumn, there are those days when you can feel the sun make its last hurrah as it warms your face while competing against crisp wind gusts that make their way through the wind tunnels created by those newly-built luxury apartment skyscrapers (I’m staring at you 7-train riders who get off at Queensboro Plaza!). On the other hand, there are those overcast days where you’re reminded there are only a few pages left on this year’s calendar. For the latter, consider the following dress casual ensemble—a navy blue trench coat and matching navy blazer, navy scarf to keep out the drafts.

Underneath, add a button-down shirt with thin black and white vertical stripes, some khaki chinos, and dark brown leather cap-toe boots. Add a subtle rugged touch with a wide dark brown leather belt with gold anchor buckles and matching backpack for your laptop and mirrorless camera (I’m a Canon guy, but you may be one of those Panasonic or Sony guys—no shade!). Now you can traverse outer-borough Urbania while channeling your inner entrepreneurial spirit. The crunch of autumn leaves and the occasional discarded newspaper beneath your boot soles won’t faze you one bit.

THE UPPER WEST SIDE PREP

Whether you’re a college student trying to get through his final semester or a solopreneur looking for his next lead, this particular outfit will scream “success is imminent, but it’s Saturday and the middle of fall”, and with it, you’ll fit right in with those who look like they just bolted out of the northbound exit of the 72^nd Street 1/2/3 station to dash across any Broadway crosswalk (Seinfeld anyone?).

Start with a navy-blue V-neck sweater (cable-knits are okay for this one). Layer a medium-weight blue chambray long-sleeved shirt underneath. Now you’re ready to handle those random fall breezes. Round the outfit with a pair of olive-green chinos (yes, you’ve finally found a way to pair navy and olive!) and some brown leather cap-toe boots, ideally with the toe portion being a slightly richer hue than the rest of the boot. Now for the best (read: weird, but gnarly) part—grab a pair of beige suspenders with black leather fasteners (hit up your nearest department store or your father’s dresser drawer now) to wear over the sweater. You can even add a bit of extra cool by wearing sunglasses with beige frames and brown lenses. Yeah buddy! You’re ready to create the next Apple, Samsung, or ahem—The Lower View! Just make sure you look both ways before entering that crosswalk I mentioned earlier.

THE URBANITE DAPPER DON

Channel your inner “Michael Corleone” without the arrest warrants and combine that with a cosmopolitan edge that would fit right in among Soho’s boutique-laden narrow streets with this chic, but masculine smart-casual autumn ensemble.

Pick up a charcoal wool blazer (I always see some iteration of this at Express every fall season) and navy waistcoat. Underneath, have a Henley with a waffle-like texture to keep that epidermis at room temperature (I’m no Neil deGrasse Tyson, but tried to do something there lol). Add your favorite matte-black chinos and a plain beige alpaca scarf (texture matters). Slip on some dark brown leather Oxford boots and you’re ready for an impromptu visit to family in that walk-up apartment or to shop for garments in your favorite hole-in-the-wall mom-and-pop clothier below Houston Street.

THE SOUTH STREET SEAPORT FOMO

Plaid can find its way right into any relaxed, dress-casual fall ensemble, bringing rustic vibes reminiscent of windblown leaves on city streets when paired with the right denim and footwear. For our last outfit idea—here’s how you can make that happen.

Pick up a predominantly red and blue plaid shirt with intermittent white stripes and pair it with some athletic-slim charcoal jeans—darker than dark gray, but not full-on black. Faded is our goal. Pull out that denim jacket that you swore you purchased just for the spring, jump into some mahogany wingtip boots, and boom! You’ll look ready to explore South Street Seaport or any other city waterfront destination before the fun is gone when fall comes to a close. Ever see those mature but not quite over-the-hill guys enjoying a daycation in places like the Intrepid Museum or Mystic Seaport, strolling around, taking in the views (or Shelter Island if your money is old—mine certainly isn’t!)? This is the image we’re going for here. For the younger shorter guy, you’ll have “potential” written all over you as you pick up bric-a-brac for your humble abode.

BUT WAIT!

We’ve spent time discussing everything from different styles and materials to outfit combinations, but what about where to buy fall boots? I’ll cover that a bit here with a few suggestions:

For absolute bargains, my go-tos are Call It Spring followed by Nordstrom Rack. At the time of writing, Call It Spring is running a 40% BOGO sale and has Chelsea, Moc-Toe, Captoe and Balmoral options with sizes down to 7. Their Dempsey model, a cap-toe boot, has a particular elegance to it and looks as if it costs twice as much as what they’re asking for. Most of their offerings are described as vegan leather, with the company stating that “no animals were harmed in the fabrication of materials”. Many vegan options are obvious, but I’ll admit that these were harder to differentiate from their “real” cousins. As someone with quite the Call It Spring collection, comfort has always been their strong point for me with their boots. The only bummer is that half sizes (i.e. 10.5, 11.5, and so on) don’t seem to be available in their online inventory (which for me blows, as I personally wear a 10 ½, but can sometimes pull off a 10 or 11 depending on the boot). Nordstrom Rack runs the gamut in terms of price. Shopping in person can be a shot in the dark because selection varies, but bargains can be found if you look hard enough. Unlike Call It Spring, Nordstrom Rack is more of a department store, so offers a wide range of brands. Their current online offerings show a wide selection of just about every boot type we discussed here. Standouts at this time are the Fyre & Co Dunn Moc-Toe Leather Boot, All Saints Chelsea Boot, Allen Edmonds Leather Lug Boot and Madden Taskorn Combat Boot (these in particular are comfortable). Shiny leather finishes regardless of color are my personal preference, so keep that in mind when considering my recommendations. That, and comfort is a must. I highly recommend visiting (especially with Nordstrom Rack) and trying boots on before tapping that debit card. Your feet will thank you. Don’t trust the “just break them in” rhetoric.

And what about items in the “stretch your wallet” category? For more luxurious options, the Thursday Boot Company has caught my attention in recent months. The aesthetics of their products match their eye-candy-esque advertisements on social media. For the most part, you’d be spending over $150, but many of their leather offerings come in mouth-watering shades of brown, such as Whiskey, Anejo, and Mocha. In my experience, their boots fit great! My next purchase will be a pair of “Presidents” (Oxford Boots) in Brandy. As mentioned above in our paragraph about bargains, Allen Edmonds has a nice offering of Oxfords and Wingtip Boots, but you’ll be looking in the $350 and up price range to play! At the top of our comfortable-to-discuss price range, there’s White’s Boots. Most of their offerings feature handsewn stitchdown construction and can be resoled. Their prices reflect this. Be prepared to spend upwards of $800 for a pair of White’s. Custom sizing and durable materials can make these boots a worthwhile long-term investment.

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CONCLUSION

While you can technically wear boots any time of the year, there’s just something really special and almost ceremonial about the fall. In other words, autumn is showtime!  Get out there, window shop, treat yourself and add some more items to your fall footwear arsenal. You don’t have to buy a whole bunch at once! For our budget-minded readers (and that includes me), one or two pairs a season is enough to build up your fashion war chest over time. Whether you’re shopping at Burlington or an expensive Soho boutique, there’s something for just about every taste, budget and level of formality, from leather to suede and brown to gray, you will find a pair that makes your day! Hopefully, you’ve gotten that message from this guide.

What are your thoughts? Maybe you have some criticism. I’m ready! Bring it on! As I always say, I’m a native New Yorker, built for dangerous verbal activity—with my head on a swivel, of course, lol! Remember, here at The Lower View, we want all shorter men to look and feel their best. Step into some new boots and chukka your way on to your next destination—in style (okay, I tried 🙂 !). See you in the next article!

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