What am I wearing? – Alden to White’s, How to Style a Footwear Collection
The one question I often get asked that I don’t answer in reviews is how I pick which shoes to wear. How I style them, when I pick one over the other, etc. With 100wears hitting the one-year mark, I thought it might be worth providing a mini update on the current collection from a personal viewpoint.
Importantly, while I try to be as objective in possible in reviews elsewhere on the site, the reviews below are entirely subjective. In other words, these are shoes and boots and how they work in my personal end-ish-of-a-pandemic lifestyle, and my current look. It’s worth mentioning, prior to March 2020, my day job was suits 4 days a week, and a formal interpretation of business casual on Fridays.
This is a little bit different, and I don’t expect it to get much traffic from Google so it will be hard to figure out how much regular readers enjoy this. Knowing that, please reach out in email (firstname.lastname@example.org) or in the comments below let me know if you like this sort of content.
Alden 975 “Longwing”
Total Wears: 1
As one of the newest pairs in the collection, a series of rainy days has kept these shoes from getting much wear. The double leather sole is the classic design, but the shell upper and leather outsole make these better fitted for dry days. The time I did wear it, I paired this old-school classic with an old-school look: tan colored wool pants and a dark olive sport coat.
With such little wear, there isn’t too much to add here, but being upset I don’t get to wear these is probably a sign they have a long life left in the collection.
Alden 405 “Indy”
Total Wears: 37
When I picked these up, I was looking for a pair of boots that could be worn in outfits up to smart casual. Something to wear when meeting up with work colleagues as a bar for a drink. Personally, I think these nail it. Unlike the other boots on this list, these have a bit of New England charm that turns the formality up slightly. Typically, I’ll wear these with heavier tan or khaki chinos and an oxford cloth button down.
This particular pair of Indys has also gotten more comfortable with wear. The longer I have them, the more convinced that people should not be sizing down for the Trubalance last. The extra space in the toe is a feature, not a bug.
Alden x Brooks Brothers Unlined “Leisure Hand Sewn”
Total Wears: Approximately 250
These are the first pair of shoes on this list to win a pandemic all-star award. My job has gone almost 100 percent remote in the last 18 months, but I do have to go in on occasion. These office visits are a bit of a minefield on what to wear. Some people will be in full suits, others in jeans and a t-shirt. The Alden LHS in Color 8 shell is versatile enough that I can put on a medium blue suit and either put on a tie and jacket or not based on what the person I am meeting with is wearing.
This pair is almost ready for a resole, which is a bit less milage than I would have hoped. Other, more affordable, brands have had leather soles see a much greater beating before wearing down.
Allen Edmonds Park Avenue
Unreviewed [a different Park Avenue Review is Here]
Total Wears: 10
This is actually a replacement for the pair reviewed last year. The resole from Allen Edmonds started to come apart and it was actually more affordable to sell the older pair (with full disclosure) and buy a new pair on sale. I regret it.
These have really shown how far down hill Allen Edmonds has gone. My last pair was from right around the time they were bought out by Brentwood Associates, and since then the quality has gone severely downhill. The leather (both upper and outsole) is thinner, cheaper, and these firsts have many more problems than my last pair of seconds.
Brentwood themselves brag on their website that they have “commenced a lean manufacturing initiative,” and are using “psychographic data overlays” to better target customers. In non-marketing speak that means they’ve cut production quality and instead are using marketing to move product.
As for how I wear them, even before the pandemic the need for a black cap toe decreased every year. This particular pair is really only for the most formal occasions: funerals, interviews, and big presentations. They are exclusively paired with navy or charcoal suits.
J. Crew Ludlow Penny Loafer
Total Wears: 1
These are a shoes that I have a monumental respect for. The quality to price ratio (at least when on sale) is simply off the charts. The materials, construction, and design are 80% as good as anything else on this list, but the transaction price is the lowest.
That being said, I’ve had a real problem figuring out how to wear these during the pandemic. In my opinion, these are a casual Friday shoe. The cut and shape are too formal for anything but the office, but the material and contrast welt stitching are too casual to wear when you’re in a suit. In a pandemic world where you don’t go into the office on days without meetings, I found the Jay Butler Cromwell has done a much better job for strictly casual environments.
Jay Butler Cromwell Penny Loafer
Total Wears: 175
This is the second pandemic all-star on this list. The Jay Butler Cromwell, especially in this color and material, are perfect for a casual-but-put-together vibe. They are great with a pair of light colored chinos and a polo, and are super easy to slip in and out of.
The color has been surprisingly versatile as well. I originally went with it because I had so many other brown/red loafers, and thought the green would pop better on camera, but I would strongly recommend this color if you’re looking to pick up your own pair. It nails the aesthetic that these shoes put out.
I do wish the sole was a bit longer lasting, or easier to replace. I know that would kill the look and break-in ease of the shoe, but they probably won’t last into next summer.
L. L. Bean
L. L. Bean Maine Hunting Shoe
Total Wears: 119
There are very few shoes on this list that I view as irreplaceable. I don’t mean that you couldn’t buy another pair, but that when they wear out I wouldn’t even cross shop other brands to fill that hole in the collection. These are one of those pairs.
The Maine Hunting Shoe isn’t just fairly unique in it’s design, it is far tougher than it’s given credit for. This pair really has seen it all. I’ve worn them to push out a car from a flooded street with 10 inches of standing water; took them out on muddy hiking trails; and even cleared a section of forest. They really can do almost anything.
Style on these is obviously subjective, but I find they work great in a preppy-leaning wardrobe. Styling aside, when faced with muck, grime, or water, there is nothing I own – White’s included – that I trust more than these.
Oak Street Bootmakers
Oak Street Bootmakers Camp Moc
Total Wears: Approximately 200
These are the oldest pair of shoes in my collection, and they are still here for a reason. While not the easiest color in the world to style, I find the red sets these apart from the typical see of brownish-leather handsewns. It also makes them a lot easier to wear into fall – one of my favorite things to do on a warm fall day is to take an outfit I’d normally wear in the summer with brown boat shoes but swap these in instead. It works perfectly.
While I’m not exactly in a nursing home yet, the older I get the more I appreciate the extra leather footbed and arch support these give. While I still think that for most people OSB’s cost over their competitors is hard to justify, if you’re looking for more support these could be it.
Total Wears: Approximately 200
The Quoddy Blucher an incredibly casual shoe. The leather is a patina monster, which, combined with the light color, red sole, and heavy pinking, means these are hard to style with anything more formal than a polo and chinos.
If getting older has made me appreciate the Oak Street Bootmaker’s build more, it’s done the opposite with the Quoddy Blucher. The thin outsole on these is brutal for walking around all day.
Unfortunately, for me, the extreme casual nature means that this shoe is often competing with sneakers for wear time. The lack of comfort means these are often the odd man out. However, for people who are not big sneakerheads, these can still be a great pair of shoes.
Quoddy True Penny Loafer
Total Wears: Approximately 500
More than any other pair, the Quoddy True Penny lost out due to the pandemic. I wore this shoe basically every Friday for years. It is just formal enough to wear at an office meeting, but casual enough that you can wear it on a night out. However, in a blow to this pair, casual Fridays and late nights in downtown restaurants have not been a regular occurrence for some time.
In fact, despite being my most worn shoe previously, I’ve probably only worn these twice in 2021.
When I do get back to wearing them, styling these is easy. They are just as at home with a pair of wool trousers and a broadcloth shirt as they are in chinos and a polo, or even a pair of shorts and a t shirt.
Rancourt “Blake” Wingtip
Total Wears: Approximately 400
The third, and final, pandemic star of this list. These shoes have been an absolute work horse. When going to off-site meetings where I know I’ll be walking on gravel, concrete, or grated metal floors, these are my go-to. The chunky rubber half-sole can take anything a normal office-worker day can throw at it, and the short-wing style can go with anything but the most formal suits suits, and excels at odd-jacket combinations.
The addition off the Alden long wing was because of how much wear this pair was getting. I wanted to find something similar in design that could give these a bit of a rest.
Rancourt Horse Bit Loafers
Total Wears: Approximately 75
The Rancourt Horse Bit Loafers are probably the most controversial shoes on this list. To many, horse bit loafers are an absolute no-go. However, I live in a city where loafers with suits or odd-jackets is accepted and often the norm. A horse bit loafer gives me a different style to play with. More often than not, I’ll wear these with grey wool trousers and navy odd-jacket.
These are not my normal go-tos, but if you’re in a city where loafers and more formal outfits are accepted, it’s worth giving it a try.
Rancourt “Read” Boat Shoes
Total Wears: 104
As long as you’re OK with the frat-boy vibes, brown boat shoes are one of those things you can throw on without really thinking about it – and these Rancourt Read Boat Shoes are no different. From shorts to light weight chinos, these are easy to style. They are also the perfect compliment to the red Oak Street Bootmakers camp mocs – just change the shoes and the belt and it goes from a summer outfit to a fall one.
I’m not sure there is such a thing as a formal boat shoe, but if there is these are not it. The thick chromexcel leather gets heavy creases and the stark white outsole shows every stain.
Sperry x Band of Outsiders Tassel Boat Shoe
Total Wears: Approximately 100
I think everyone has heard of go-to-hell pants, but these are my go-to-hell shoes. The type of shoes you can only wear when the rest of your outfit shows you know what you should be wearing, but specifically decided on green-tassel-loafer-boat-shoes instead. As with all go-to-hell outfits, that means the rest is toned down. White shirts, tan pants, brown belt, no socks.
Unfortunately, these are not getting much wear anymore. The lining on the inside is literally crumbling, and every time I check the outsole gets noticeably closer to a hockey puck. These are probably the next pair on this list to move onto the great shoe store in the sky.
T.B. Phelps Weekender
Total Wears: 63
For casual wear, I’m a big fan of the handsewn moc toe. When picking these up, I was hoping to find a way to keep that style into the colder months. While I have not had them quite long enough to try out if they are comfortable in the cold, I’ve been pleasantly surprised how easy these are to style. Think of them like slightly puffy brown boat shoes, and you’re good to go with any outfit that the boat shoes work with except for shorts.
These have been in pretty heavy rotation, and I hope to get a long-term update out before December of this year.
Viberg Service Boot “Tochigi Natural Cowhide”
Total Wears: 6
Another recent pick up that hasn’t gotten much wear, this is definitely a pair that takes some thought. The one look that I’ve really started to like is navy chinos with a white shirt – t, polo, or oxford cloth. This is the colors that Withered Fig used in the promo shots for their version of the shoe, and it’s a great (if loud) option. Raw denim doesn’t seem to work quite as well to me, and tan pants are pretty questionable.
While I adore the leather – it’s so buttery soft and will patina in an amazing way – if I was going to do it again, I probably would have gone with something a shade or two darker. The boots bring up memories of the Walnut Allen Edmonds Strands with Dark Suit phase that everyone went through in 2012. Others have seen their pairs darken with age, so I’m still hopeful mine will as well.
Total Wears: 15
I’m really looking forward to getting to wear these more once the weather cools off. These boots manage to just push the limit of what I can get away with living in the city, but in a way that I love. The natural pairing for these is jeans, and what I’m normally in with these, but there is an irreverence to wearing these with a pair of tan chinos and a broadcloth shirt that I really enjoy.
That just-barely-not-crossing-the-line look is the main reason why I prefer White’s over Nick’s. For whatever reason, Nick’s style just leans slightly too hard into the workboot look. I’m not sure a normal guy could pull them off in a place with a population density over 50 per square mile.