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! 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. For us shorter men, we also get to enjoy a very modest lift since most boots have a slight heel, or at the very least, a pretty thick sole to hold up to the elements while remaining functional.

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

2. Balmoral Boot

The Balmoral 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, 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, its straps and rings lend a rugged and rebellious feel, making it 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 Boot

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 conversation 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. It’s soft texture creates a more relaxed, but refined look. Working best with chukkas and Chelseas, especially in a 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 boots come to mind. 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.

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 outwear or accessory (i.e. hat or scarf) matches, 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 a bit of class to any dress casual outfit. With black, you can’t (or rarely cant) 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

I'm making this thread to talk about (if you haven't figured it out already) boots. I know some of you have a nice dress shoe or sneaker collections, but I love to wear boots. I find with a few exceptions, that boots go with almost any outfit (excluding shorts of course, please don't do that). 

I figured I'd kick of this thread so we can share out what our current flavor of the month is, or to put on display a pair of boots that you own and like, or would like to pick up! We might get some style ideas and inspiration in the process. 

Thought it would be cool to start a thread where we could all get together and share investing, stock ideas and tips on managing money well. At the moment, I tinker with investing on the retail apps (Robinhood, Acorns) with pocket change that I put side when I can. 

At the moment, I own two shares of Apple and a few shares of hotel stocks. I would like to get into investing more and am learning about the market, but am very much a novice.

With this recent crash due to the tariffs, everyone is saying that right now is the time to buy. I figured some of the more knowledgable and seasoned traders, investors and know more about financial management could chime in with tips or trends to watch.

In any case, let's get this conversation going!