5 Pairs of Shoes You Should Buy for a Classic Casual Wardrobe

It’s a lot of work to explore different brands, silhouettes, aesthetics, and stores, narrowing down what you like most. I’m reminded of Greg from No Man Walks Alone replying to a compliment on his store’s well-curated selection of goods, saying that finding the gems at a show like Pitti is incredibly difficult, requiring lots of patience wading through a nearly unlimited number of booths. Sometimes it’s nice for someone—like Greg—to simply say, “here are the best options. Choose from these.”

In the same spirit, I thought I’d share the five pairs of shoes I think you would be best-served buying—either as a capsule shoe wardrobe or simply as your starting point as you build a larger wardrobe. It goes without saying this advice comes from a point of view that favors versatility with tailoring, denim and chinos as my “what I wore” posts will attest. As a complement to this advice, read my “Versatile shoe” piece from last year. Thankfully there are lots of brands who make each one, so I’ll recommend a maker for each type at different price points for you to consider. In no particular order:

1- Chukka Boots

I wear these most of the time October through April. My chukkas are snuff suede with a Dainite sole so that I never think twice about wearing them if it’s wet out. I hiked Quiraing at the Isle of Skye wearing them, so they’re rugged enough in a pinch. Versatility wise, suede is the best, and with a more pointed toe, you’ll be able to wear them with a sport coat just as easily as with a full workwear fit. A rounder toe would help them match more closely with denim or moleskin pants.

Low price: Meermin (same as mine). Mid: Kent Wang. Mid-High: Sid Mashburn.


2- Penny loafers

I wear these most of the time May through September. Mine are—surprise—snuff suede. I walked throughout the cobblestone plazas and streets of Florence, seeing David, visiting the Uffizi Gallery and enjoying Florentine steak in mine. I prefer an elongated toe on these to the rounder ones you might see on a classic Alden, but that’s a personal preference.

Low price: Meermin. Mid-high: Sid Mashburn.


3- Longwings or Wingtips

I’ve always loved the brogue, at time shifting my preferred model back and forth between the wingtip silhouette or the long wing silhouette. I’m currently in the long wing camp, but I only own wing tips. Perhaps the grass is always greener. Mine are a pebble grain with Dainite sole, which came with me this past winter during our travels in Scotland. The Dainite sole came in handy for the rugged outdoors. I wore them on our road trip through the highlands, from Glasgow to Glencoe and Fort William, during which we stopped many times to jump out and photograph the scenery. Versatility wise, they can indeed be worn with denim, but really only dark denim. They look great with flannel or tweed trousers.

Low price: Meermin. Mid: Brooks Brothers. Super High Grail: Polo Cordovan.


4- Cap-toe Oxfords

You need something to wear dressed up more than just a sportcoat and jeans. For many years I went through that phase where you hate black shoes, and even today I think probably most of us could get away with only dark brown calf cap-toes in this category. But I think around the time Skyfall came out I realized black shoes in a tapered, chiseled toe last can make you look like James Bond – or, more realistically, they can make you feel like you look like James Bond. In any case, dark brown will help you through almost all the time, and it looks great with navy suits, gray suits, the navy blazer with gray trousers look, and almost every other tailored outfit.

Low: Meermin. Mid: Kent Wang. High: Carmina.


5- The Wild card

I know I said up front I’d tell you exactly what to buy, but this last one is going to come down to you making a decision for yourself based on your personal taste. It’s the dressed-down-but-contemporary-and-stylish slot, and which one you pick will depend solely on your preferences. For me, it’s a canoe moccasin, which I wear constantly. I walked from the Colosseum, the Roman Forum, and all the way to the Spanish Steps in mine. For others, it might be a pair of sleek white sneakers: they look great with jeans, khakis and some brave souls even wear them with tailoring. Other options are Wallabees and desert boots. Instead of prescribing exactly what to get, take stock of your aesthetic preferences and make a choice to help fill out your own individual wardrobe.

My favorite canoe mocs: Oak Street. My favorite white sneaker: Tretorn. My favorite desert boot: J.Crew.

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5 Shopping Mistakes and Lessons Learned

When I was young, I used to conscientiously try to live by the motto “Live with no regrets.” At that time in my life, this generally meant working up the courage to ask a girl out on a date or trying something I had never done before. Of course, the longer I’ve lived, the more complicated life has become and I have–inevitably–made poor choices that I regret. Over the roughly ten years during which I’ve been interested in menswear, I’ve had much the same goal as in my personal life: Try to make intentional choices in purchasing clothing so as to avoid buying items I come to regret.

I’m here to tell you that, sadly, as in normal life, my best intentions haven’t stopped me from making some mistakes. Here are five bad menswear mistakes I’ve made over the years, and the lessons I had to learn the hard (and sometimes pricey) way.

1. Full-price J.Crew flannel plaid shirt.

jcrew flannel shopping mistakes

This was an impulse buy I made one day when my wife and I were shopping for her back in 2010. She had picked out a cute women’s flannel shirt and with the Americana workwear movement in full swing, I was enamored by the idea of getting one, too. I bought one. I wore it to work one day, which at the time I worked part-time in a small print shop as a salesman. My boss asked why I was so dressed down, and told me I wasn’t dressed well enough to see clients that day; instead I’d work in the back of the shop. That confused me—didn’t they know about the heritage movement and Americana and all that? How was this less dressy than a Walmart polo shirt, which would’ve been perfectly acceptable?

Lessons: Never buy anything full-retail at J.Crew. Also, have a pulse on what normal people actually think about clothing.


2. Ultra-slim low-rise J.Crew wool trousers.

jcream slim pants shopping mistakes menswearOff the rack trousers almost never flatter or fit me well. In my quest for affordable wool trousers that were decent, I went slimmer and slimmer. After all, slim jeans and chinos fit me okay so maybe slim wool trousers would fix my normal fit problems. This pair of trousers was so slim that when I stood up from being seated, I had to pull the hems down off my calves, where they’d be stuck because they were so tight.

Lessons: Good wool trousers need some room to drape. Unlike slim denim or even chinos, they can never look right in a skinny fit. And if your body type allows a high rise without going bespoke, it looks more elegant worn with a jacket, covering up more of your waist below the jacket’s buttoning point.



3. Too-small vintage tweed Brooks Brothers sport coat.

shopping mistakes menswear brooks brother tweed jacket

This thing never fit and never had any chance of fitting. But I bought it because the tweed was fantastic. Around this time, I was also itching to try a different tailor in town, and I used this garment as a test for them. It was a disaster. They did awful, amateur work. My normal tailor, bless his heart, didn’t just fix it for me, but made some highly technical adjustments I didn’t think possible that actually made it fit halfway decently. And he didn’t charge me a dime for the work, which he did out of principle. Nonetheless, the cut and style of the jacket just weren’t my taste, and the fit was still not quite right. I sold it off several months later.

Lessons: Don’t try to take an ill-fitting garment and force it to work. If a jacket is tight in the shoulders or chest, let it go. Also, if you’re going to try a new tailor, do it on something with low stakes rather than something requiring a major sartorial surgical intervention.

4. Beautiful Peal & Co. wingtip boots.

shopping mistakes menswear peal co boots

I got an absolute killer deal on these at Brooks Brothers a few years ago. They fit fine in the store, so I immediately began wearing them. But within a day I noticed they were tight on my right foot. I tried every trick on YouTube to stretch them out, while still wearing them regularly for a few months. But of course, nothing worked and I reluctantly sold them off because they simply hurt my feet to wear.

Lesson: With shoes and boots, do your due diligence by trying them on at different times of day indoors on carpet for a week or so to assess whether they truly fit.



5. Brown Eidos topcoat that I thought was gray.

shopping mistakes menswear eidos grey brown coat

I was communicating with one sales guy who sent me pics of the coat, then switched to another guy at the store to complete the purchase. Due to bad photo quality and bad communication, I got a brown coat instead of a gray one. I found out it was brown while I was on the phone about to complete the purchase. I bought it anyway, and wore it for a while. I loved everything about it except the color—I had had my heart set on the gray, and the brown version just didn’t fit my aesthetic. So I reluctantly sold it off. I found out later they did have the gray one after all. And it was actually even still available in my size, but at that point I wasn’t in a position to afford it. It sold out later that season. I am still on the lookout for one in my size, so if you have one, please let me know (see my Styleforum signature for details).

Lessons: Be communicative and ask questions to an irritating and meticulous fault. Also, stick with one sales person through the entire process as much as is within your control to prevent easily avoidable miscommunication.


What about you? What are some of the worst mistakes you’ve made in building your wardrobe and discovering your style? Leave a comment in the Menswear N00b Mistakes and Pitfalls thread!

Man on the Move, Paris: A Menswear Outfit

One thing that I love about the way Parisian men dress is the use of simple, often iconic pieces, to create very simple, but sharp, outfits. And in quite a few cases, I’ve seen French men take the best from an international mix of makers, and make them their own by combining all the pieces expertly.

Here is an outfit based on one I saw in the Air France Lounge at CDG on the way back from our trip to Paris Mens Fashion Week last winter. There was a taxi strike starting the day we were slated to leave, so we got the last shift of cabs to avoid and a good scarf and gloves elevates itany issues. Five hours in an airport is too long for anyone, but luckily, we got a good breakfast and some decent people watching. Thanks, www.mytravalet.com for boosting us up to Business Class so that the boredom of our wait was mitigated by good croissants in the lounge and good surreptitious snapshots of the other lucky people.

A sharp coat is the basis of this outfit and a good scarf and gloves elevates it.  Here, the classic blue Crombie coat evokes the modish looks of the 60s. Paraboot, from France, makes some of the best shoes for business travel – they are sensible shoes for the stylish man.


1. Classic “retro” Crombie Coat with contrasting lining, 895 GBP from Crombie.

2. Loro Piana Scarf – just enough color to stand out, $635 ftom www.mrporter.com

3. Peccary gloves by Merola in cork (no need to hide your hands), 185 GBP from www.exquistetrimmings.com

4. Reeves Navy Blue Flannel suit, custom made.  Available by special order from www.reeves-nyc.com

5. White shirt by Brooks Brothers, $185 from www.brooksbrothers.com – An oxford cloth shirt is the perfect shirt for business travel – always have an extra change in your carryon. I really don’t think that anyone does a traditional, minimal, oxford cloth shirt with no embellishments, like the American classic

6. Chocolate Grenadine Tie by Chipp Neckwear, $55 from www.chippneckwear.com – a NYC stalwart throwback.

7. Briefcase by Pierpoint Leather, by commission, at www.pierpontleather.com

8. Paraboot shoes Oscar Patine scotch, approximately 420 Euros.  At Paraboot locations throughout the world, or inquire at www.paraboot.com

9. Brunello Cucinelli medallion pocket square, $185 at www.mrporter.com

Styleforum’s Favorite Brands

Styleforum has a lot of “favorite” brands. They wax and wane in popularity over the course of months or years, and because of the diversity of our members these brands range from the rigidly conservative to the breathtakingly avant garde. Although this isn’t a complete list, it does capture a snapshot of some up-and-comers alongside a number of old standbys. Let’s take a look at Styleforum’s favorite brands, and what they say about us – the people who love to wear them.


Styleforum's Favorite Brands

Photo: Epaulet

The Dream: You’re a globe-trotting gentleman-explorer, and your footwear reflects that. No matter the occasion, you’re always well put-together – but you never stick out. Several people have referred to you as “dashing.”

The Reality: You spend more time applying leather-care product to your massive collection of Alden shoes than you do wearing them.

Brooks Brothers

Styleforum's Favorite Brands

Photo: Brooks Brothers

The Dream: Your life is a perfect blend of work and play. You roll up your chinos and play tag football on the lawn. You are happy and content, your collar roll is always immaculate, and you spend your summers vacationing on the Vineyard.  You know it’s gotten crowded but you just can’t imagine going anywhere else – you’ve made such meaningful connections.

The Reality: You have recently discovered that penny loafers don’t go with everything. You constantly talk about how “real men wear pink,” but you’re uncomfortable and fidgety every time you do. Recently, you have begun to fear that people find you boring.


Carol Christian Poell

Styleforum's Favorite Brands

The Dream: You curate a minimalist gallery in a European city. Or if not a gallery, you curate a hugely popular photo-slash-contemporary philosophy website with descriptions of each photo posted in all caps. You curate something. People admire your taste.

The Reality: Upwards of five people owned your “collection” before you. You rarely wear any of it, and when you do, you remember why you don’t. You think about selling all of it constantly, but worry that you won’t be able to make back what you paid. You wonder why you don’t just start curating sweatpants instead. You have begun to suspect that no one cares about your moody photography.


Christian Kimber

Styleforum's Favorite Brands

Photo: Christian Kimber

The Dream: You’re a free spirit, the kind of guy who spends weekends at destination flea markets looking for antiques to furnish the quirky studio apartment you keep in a neat, artsy neighborhood. You ride your skateboard to the coffee shop every morning; not to work, but to read several Very Interesting Books every week. Your signature touch is a giant scarf. You eat a lot of noodles.

The Reality: You’re an internet hobbyist who spends his days browsing web-stores.


Eidos Napoli

Styleforum's Favorite Brands

Photo: Eidos

The Dream: You are an Italian bon vivant who has excellent hair and rides a scooter through the hills of Tuscany.

The Reality: You got the suit 40% off  at Bloomingdales. Sometimes, guys at work ask if you have an interview.  Now you mostly wear it for your Instagram. You have 200 followers.


Engineered Garments

Styleforum's Favorite Brands

Photo: Stitched and Stitched

The Dream: You make a living as a travel correspondent, and spend your days fishing, surfing, and hiking with your group of friends and photogenic dogs. All of you carry vintage film cameras – even the dogs. You routinely get your fancy clothing very dirty, but you don’t care. Sometimes candid photos of you appear in Japanese style magazines, with captions like “How to live a care-free life.”

The Reality: Your apartment doesn’t allow dogs, and people wonder why you’re always wearing the same jacket and carrying a camera around.




Styleforum's Favorite Brands

Photo: Kapital

The Dream: You are a carefree artistic type, a creative director at an independent magazine. You are well-read and your friends are regularly featured in iD magazine.

The Reality: On the street, people wonder if you are homeless.  You tell your friends you got it all on sale so that they won’t ridicule you for the prices you paid. You secretly wish you lived in Japan and owned an Indigo dye-house.


Robert Geller

Styleforum's Favorite Brands

Photo: Barney’s

The Dream: You spend your time drinking ironic beer on urban rooftops around the world with your friends, all of whom are models, photographers, and graphic designers. You just launched a fashion magazine that has disrupted the industry and brought you several publisher’s accolades.

The Reality: You have three bomber jackets in your closet. You never know what to wear with any of them.



Suit Supply

Styleforum's Favorite Brands

Photo: Suit Supply

The Dream: You are a successful young entrepreneur. You are stylish and always up-to-date on the latest New Yorker. You have respected opinions on everything from art to the economy to the state of the Great Barrier Reef.

The Reality: People wonder why your pants are so tight, and most women you meet find you just creepy enough to avoid. Your boss thinks you spend too much time looking in the mirror.





Styleforum's Favorite Brands

Photo: Antik Boutik

The Dream: You drive a vintage Defender, and all of your most precious belongings can fit into a single well-worn duffle bag. You live authentically. You eat interesting street food all over the world. You laugh constantly. Visvim is the only brand in your closet.

The Reality: You talk about hating John Mayer because he’s not authentic but deep down you burn with unbearable jealousy.