The Three Types of Shoes to Add to Your Wardrobe

A continuation of the How to Dress Well series

Welcome friend.

I hope this finds you and your loved ones well and safe. We’ve just begun another lockdown in California, which has a lot of people frustrated and overwhelmed. Even while we’re stuck inside, for the time being, I pray this newsletter will help provide some relief and spark a little joy in your day.

This week, I wanted to talk about my three favorite types of shoes—all made here in the USA—that will match almost every outfit in your wardrobe. 

Volume is a newsletter where you’ll learn about my favorite brands, opinions on dressing well, and great pieces to add to your wardrobe. Subscribe here.

What types of shoes do you need?


For this week’s series on How to Dress Well, I’ll be answering the question of:

What types of shoes do you need in your wardrobe?

There are many types of shoes in the world. Luckily, you don’t need to own them all to look stylish and have a complete, matching wardrobe.

Let’s take a look at my three favorite types of shoes.

The Penny Loafer

I’d say amongst men in their early 20’s, about 90% have a pair of Sperry Top-sider’s. And, almost all end up keeping them until their late 30’s. Thanks, Urban Outfitters. 

While it’s understandable that we all need a starting point, another option for a classic shoe that still shows a little skin is the Penny Loafer.

Penny Loafers are having quite a comeback moment right now. Not only are they stylish, but they also make excellent shoes to wear around the house—where most of us tend to be in our daily routines. The slip-on, slip-off factor also makes them a great option when you need to hop outside, run a quick errand, or walk the dog.

There are numerous options available in this style of shoe. I particularly like these from G.H. Bass—who claim they are the original creators of the loafer—in the black colorway with a lug sole. I’ve also recently discovered a smaller, lesser-known brand via Aaron Levine, senior vice president of Men and Women’s Design at Abercrombie & Fitch, called Blackstock and Weber. These loafers from last season caught my eye. I’m hoping they decide to do another run of these soon. 

Continue reading in the Shopping Wishlist section below to find out about the pair of loafers I’m wishing for Christmas.

The Chukka Boot

I was heavily debating between recommending a Chelsea boot in place of the Chukka. Ultimately, it came down to what ended up being more versatile. Also, I’m very particular as to which types of Chelsea boots I prefer. I’ll be sure to follow up in a future post.

Back to the Chukka.

Given its slightly funky name—originating from Polo just like the OCBD, it represents a period of time in play called the “chukker”—you may be stumbling to recall what this shoe looks like. Essentially, it’s a two-eyelet, ankle-high boot with a leather sole. 

Another silhouette that you might be more familiar with is the classic Desert Boot by Clarks. I’d say the primary difference between the Chukka and the Desert Boot is the sole. Traditionally, crepe soles—the squishy, gummy rubber piece—are reserved Desert Boots only; however, I’ve seen some Chukka’s with them as well. 

I think this boot is excellent for both casual and dressier occasions, especially in a dark brown suede with a flex sole. They particularly look great with a suit, tailored pants, and for a more casual look, any colored chinos. Indeed a versatile option to have.

The Plain Toe Blucher

The Plain Toe Blucher, also referred to as the “PTB,” rounds out this list, coming in as one of the slightly dressier options. This silhouette is simple, yet I find it quite elegant.

Another strange name for a shoe, right? Here’s what Wikipedia says about the one:

“The blucher is named after the 18th-century Prussian field marshal Gebhard Leberecht von Blücher. General von Blücher commissioned a boot with side pieces lapped over the front in an effort to provide his troops with improved footwear. This design was adopted by armies across Europe.” — Wikipedia

At one point in my fashion journey, I under-appreciated this option and stuck to my long wing-tipped brogues for years. Looking back, while those wingtips came to define my style, and I loved them, I wish I also gave the PTB a chance. With their design consisting of a single cut of leather and lack of any brogue patterns, these shoes go well with almost every outfit. They especially look great after they’re beaten up a bit.

When I think about where I’m heading now with my wardrobe, including these shoes makes the most sense. They lean more towards the formal side, especially if you buy them in a material such as Shell Cordovan, but you can wear them casually as well.

Alden of New England


The Alden Shoe Company has been making shoes in the United States since 1884—that’s a long time—and its focus on providing quality, well-made shoes has never waned.

Having been around for so long, Alden has nailed many features on their shoes. The primary features being comfort and durability.

These shoes are made to last. That’s why they’ve decided to continue offering the Goodyear welt. This feature allows the shoes to be resoled as often as needed during the owner’s lifespan, and potentially for anyone else who wears them after. Also, the materials they use are top-notch and undergo lengthy tanning processes to produce high-quality leather.

Something that is common knowledge amongst Alden fans; they not only create some of the best dress shoes in the world but in the past, they’ve also specialized in orthopedic and medical footwear.

With the need to have all-day comfort for people in the workplace, they introduced a tempered steel shank in all of their dress shoes, which provides the support and shape needed for comfortability. FYI, you’ll need to take these bad boys off when you find yourself back in the security line at the airport.

“Alden is now the only original New England shoe and bootmaker remaining of the hundreds who began so long ago. Still a family owned business, still carrying forward a tradition of quality genuine-welted shoemaking that is exceptional in every way.” — Alden Shoe Company

I love this shoemaker. I’ve now owned close to six pairs of Alden’s in the past six years or so and can say they are one of my only vices. I’m always on the lookout for new collaborations and try to get notified whenever there are sales. Even though they are costly—starting at around $500—the price point represents the type of quality shoe you’ll be receiving.

Instagram: @aldenshoeco

The Leisure Loafer in Dark Brown Kudu by Alden


My favorite details

The material used on these is exceptional. They are constructed of Alden’s signature Oiled Kudu Leather, a soft Chromexcel leather that is rarely used in their lineup of shoes. While the oil gives this leather a unique look, appearing almost chalky upon opening the shoe box, its purpose is to protect the leather from weather conditions like rain or snow. I have a pair of the 404 Indy Boots in the same material, and they held up great on a skiing trip to Tahoe.

And of course, as soon as I saw the lug sole on these, I fell in love. Usually, I’d opt for the Commando sole from Alden, but this lug sole gives the loafer a bit of heft, which I very much like. I think sometimes loafers can appear slightly feminine with a traditional leather sole, and these feel much beefier and look like they’ll remain comfortable for an entire day’s walk around the city.

What to wear it with

I’d say during the warmer months that no-show socks are almost a must with these loafers. I admit, I used to wear my loafers without any socks, but that felt unsanitary, and the odor wasn’t great. Also, it wasn’t as comfortable to wear them all day with no socks.

One of my favorite looks came as a recent discovery after browsing Colhay’s latest collection. You can take a look here as they showcase a pair of crisp, unwashed selvedge denim, olive fisherman cable sweater, white chore coat, and loafers. 

Where to buy

You can purchase these at my preferred online shop, The Shoe Mart. Unfortunately, Alden does not offer an online shop on their site. If you’d like to browse their other styles, they do have most showcased on their catalog.

Price: $517 USD

The Unlined Chukka Boot in Snuff Suede by Alden


My favorite details

This colorway is one of my favorites. Snuff was a term used in past years to describe tobacco’s color and ended up sticking with this particular shade of brown. This color adds an extra but much-needed color to your shoe collection rather than going for the traditional chocolate brown.

These shoes are comfortable, but I’d say the least comfortable out of the three options I’ve shared with you today. The flex sole looks the best on this pair; however, it’s not always the most sturdy. I found myself feeling slight hints of the rocks and bumps beneath my feet as I was walking on the sidewalk around San Francisco. It was noticeable enough for me, and I wish Alden would fix this. They do offer a double leather sole as well, but it’s heavier and much more slippery, at least for the first couple of wears.

What to wear it with

As I mentioned in the Style Advice section above, you can dress these shoes up nicely by pairing them with a suit, like this olive one from Drake’s. To complete the suit and tie look, you could also add a crisp white Oxford Collar Button Down shirt, a khaki grenadine tie, and this 1998 Rolex Explorer II with a white dial.

Where to buy

You can also purchase these at The Shoe Mart. If you’re able, I’d invest in a pair of the Dark Brown Suede as well.

Price: $571

The Plain Toe Blucher in Black Shell Cordovan by Alden


My favorite details

I’d say this is the most comfortable dress shoe you’ll ever wear.

The amazing thing is, they get even more comfortable over time and they will last you generations—if you want them to.

One detail that’s different about these pair of shoes compared to any others is the material: Shell Cordovan. Here’s what the process looks like to just make the material used on these shoes:

“Using the centuries-old method of pure vegetable tanning and hand finishing, the single tannery still producing genuine shell cordovan today is indeed practicing a rare art. The tanning process takes a full six months to complete and produces leather that is soft and supple, yet very durable.”The Shoe Mart

After receiving the finished leather, an Alden master craftsman provides the finishing touches to make these shoes into the beautiful pieces of art they are. If I ever meet one of these people, I’d want to hug them and thank them for their work.

The last piece of information you should know about these shoes is that the leather will show creases instantly once you take that first step. At that point, you begin the journey towards creating your shoes’ patina—a term used to describe the look of something that has been worn for a long time.

What to wear it with

Again, these shoes are traditionally made for formal attire, but I’ve seen them worn with dark blue selvedge denim, and they look fantastic. I think dressing these down provides more opportunities for daily usage and creates more chances for increased patina. You could also pair these with a pair of dark gray chinos, a long overcoat, and a light grey sweater

Where to buy

Again, you can purchase these at The Shoe Mart via the link below.

Price: $770


Watch: Stylish with Jenna Lyons

A new series on HBO Max follows the former Creative Director and President of J.Crew as she embarks on a new journey starting her own company. I’ve found the show delightful and uplifting. Highly recommend.

Read: Konfekt Magazine

The folks behind Monocle recently launched a sister publication focused on fashion, food, travel, and design. I’ve been admiring their superb design and branding, and it’s served as inspiration while I’m determining the look and feel of Volume. 

Listen: Stuck @Om Podcast feat. Steve Tidball of Vollebak

For years, I’ve had my eye on Vollebak—makers of unique fabrics used for clothing purposes—and this podcast episode with Om Malik was extraordinary. I enjoyed hearing about the thinking that goes into creating their garments and how they aim to make them last for over 100 years.

Thank you for reading

These past few weeks have gone by fast, and as we approach the end of the year, I want you to know how much I appreciate you. I’ve grown this newsletter to 40 subscribers in the past month, and it makes me so happy to have you here along this journey.

See you next time. Stay safe.