It’s On Sale: Footwear at Urban Outfitters

I have a long-standing teenage grudge against Urban Outfitters, but why let integrity and principle get in the way of a 25% discount? All footwear at UO is on sale right now, making a lot of classic casual shoes like Clark’s Wallabees or Red Wing boots one-fourth more affordable, and  unimpeachable summer sneakers like Vans Authentics downright cheap. If you download their app, you also get free shipping.

-Pete

What I Take Long Walks In
With the exception of running shoes, the most comfortable shoes I’ve worn have always been built on Plantation crepe. Crepe refers to a sort of soft rubber - usually slightly yellow-ish in color - that comes in large sheets. Shoe manufacturers take these sheets, cut them down to the size and shape necessary, and then layer them to form a sole. The result is something that’s very, very comfortable. They make you feel like you’re walking on soft clouds, or more realistically, like those big rubber pads that toddlers play on. 
The upside to crepe is that they’re comfortable, particularly on hard concrete, and look suitably stylish for spring through fall wear. The downside is that they might not last as long as a pair of hard-bottom leather soles. Still, they can still be replaced by an experienced cobbler when the time comes. I’ve also read that crepe can get rigid and crack. I don’t know if this is because of harsh weather conditions or just plain age, but for what it’s worth, that’s never happened to any of my crepe soled shoes. 
There are a number of shoe styles that are commonly made with Plantation crepe - boots, plain toe derbys, moccasins, etc. My favorites are perhaps brown suede chukkas, which I think look particularly nice with cotton trousers, casual shirts, and even the occasional soft-shouldered odd jacket. The pairing of suede and crepe makes for a particularly stylish casual combination, and you can find suede, crepe soled chukkas at a pretty wide range of price points. On the high end, A Suitable Wardrobe has my favorites - a really handsome model that looks sleek enough to be worn with grey wool trousers. For something more casual and affordable, consider Church’s Sahara, Loake’s Gobi, or Clarks’ desert boots. The third retails for about $120, but it’s not hard to find them for under $100. Just Google around or check eBay. 

What I Take Long Walks In

With the exception of running shoes, the most comfortable shoes I’ve worn have always been built on Plantation crepe. Crepe refers to a sort of soft rubber - usually slightly yellow-ish in color - that comes in large sheets. Shoe manufacturers take these sheets, cut them down to the size and shape necessary, and then layer them to form a sole. The result is something that’s very, very comfortable. They make you feel like you’re walking on soft clouds, or more realistically, like those big rubber pads that toddlers play on. 

The upside to crepe is that they’re comfortable, particularly on hard concrete, and look suitably stylish for spring through fall wear. The downside is that they might not last as long as a pair of hard-bottom leather soles. Still, they can still be replaced by an experienced cobbler when the time comes. I’ve also read that crepe can get rigid and crack. I don’t know if this is because of harsh weather conditions or just plain age, but for what it’s worth, that’s never happened to any of my crepe soled shoes. 

There are a number of shoe styles that are commonly made with Plantation crepe - boots, plain toe derbys, moccasins, etc. My favorites are perhaps brown suede chukkas, which I think look particularly nice with cotton trousers, casual shirts, and even the occasional soft-shouldered odd jacket. The pairing of suede and crepe makes for a particularly stylish casual combination, and you can find suede, crepe soled chukkas at a pretty wide range of price points. On the high end, A Suitable Wardrobe has my favorites - a really handsome model that looks sleek enough to be worn with grey wool trousers. For something more casual and affordable, consider Church’s Sahara, Loake’s Gobi, or Clarks’ desert boots. The third retails for about $120, but it’s not hard to find them for under $100. Just Google around or check eBay. 

Style for College Students
There’s no kind way to put this: college students are some of the worst dressed people in America. I say that as man who has spent the last eleven years on college campuses – four as an undergraduate, two as a researcher, and five as a graduate student. This has been at three universities, but with many visits to other schools throughout the years.
To be sure, students are in a uniquely hard bind. They’re broke, very busy, and have little time for gainful employment. Not having a lot of time or money doesn’t lend itself well to picking up nice things. Plus, as a graduate student instructor, I’d rather see students spend more time on their studies than worry about what they should wear.
Still, dressing well in college isn’t that hard. Especially when the bar is set so low. So, in an effort to help students smarten up, I’ve come up with some tips.
Focus on Smart, Mid-quality Basics
The downside to being a student is that you’re broke, but the upside is that you can have a complete wardrobe with very few pieces. No need to worry about having separate weekend and weekday wardrobes; it’s just off to class and libraries for you. So, focus on buying mid-quality, versatile basics. Don’t go for anything too nice. Whether you’re getting straight-As or barely passing class, your lifestyle in college will be mostly rough on clothes and probably not very hygienic. Get things like decent jeans that can take a beating, or thicker merino sweaters, not thin cashmere-blends. Build your wardrobe off grays, blues, and browns, so things can easily coordinate without you needing to have to put in too much thought.
Upgrade 
The best way to not look like a college slob is to not dress like a college slob. Instead of graphic t-shirts, pick solid colors tees. Better still, try to wear shirts with collars, as they’ll help frame your face. Plaid flannels for fall, colorful madras for summer, and stripes year-round will help make those button-up shirts look less like office-attire. Long sleeve polos can also work, so long as they don’t look too fratty (I like Kent Wang’s). 
Instead of ratty or pre-distressed jeans, pick up a solid pair of dark, raw denim jeans that fit well. Levis is relatively cheap and easy. Maybe add a pair of chinos and corduroys too, so you have other things to wear.
Instead of college-branded sweatshirts, get merino sweaters. Club Monaco’s are pretty good on sale (they also offer a student discount year-round, which you can stack on top of sale prices). Cardigans can also work in theory, but they’re much harder to fit well than a simple crew- or v-neck sweater.
Instead of flip-flops and running shoes, get camp mocs, boat shoes, plimsolls, or desert boots. Clarks desert boots are a particularly good option if you’re on a student budget. You don’t have to put too much care into them besides applying some Obenauf’s LP for the beeswaxed versions or waterproof spray for suede, and the crepe soles will be comfortable for long-walks. Jesse has some other suggestions here as well.
Finally, there’s no alternative to cargo shorts, sweatpants, or basketball shorts. You just have to stop wearing those (unless, you know, you’re exercising or playing basketball).
Don’t Overdress
I know this site is often about sport coats and ties, but unless you’re a member of the Model United Nations or College Republicans, I encourage you to not wear ties as a college student. There are some campuses where this is normal, and you’ll know when you’re at one, but for everywhere else, you’ll just look out of place and over-dressed. For many campuses, sport coats may also make you stick out in a bad way.
If you really want to wear a sport coat, tweeds and corduroys can look a bit more natural on a college campus. For everyone else, I encourage reaching for more causal options. A vintage peacoat can be had for $50-75 through eBay, Vintage Trends, or a local thrift store. You can use this guide to help date your peacoat finds. For something new, check Fidelity.
There are also some go-to brands for decent, cheap(ish) outerwear. LL Bean Signature, Land’s End Canvas, and J Crew can be workable once they have their end-of-the-season sales (when things will be discounted 50-75%). J Crew also has a student discount, but only for in-store purchases. Additionally, Land’s End mainline is probably be less well-suited for a younger person, but this oilcloth jacket might be a good Barbour alternative. It can be had for under $100 if you wait for the right coupon codes. You can read Broke & Bespoke for a review. Lastly, Ben Sherman’s Harringtons can also be had through eBay for about $80.
And the Standard Advice
Add to this the standard advice.
Learn how clothes should fit. We have a few guides you can read through here. You have more wiggle room as a young, college student, but avoid things that are skin-tight or overly baggy.
Find a good alterations tailor and bring as much as you can to them. There are very few things a good alterations tailor can’t improve.
Make a wish list and tightly edit it. Make sure you’re building a wardrobe, and not just a collection of outfits. If something doesn’t mesh well with the other things you plan on buying, strike it off your list.
Set a budget and shop slowly. Especially at this age, your tastes can change rapidly, and if you buy everything now, you may find yourself regretting it next semester.
(Photo by John Morgan)

Style for College Students

There’s no kind way to put this: college students are some of the worst dressed people in America. I say that as man who has spent the last eleven years on college campuses – four as an undergraduate, two as a researcher, and five as a graduate student. This has been at three universities, but with many visits to other schools throughout the years.

To be sure, students are in a uniquely hard bind. They’re broke, very busy, and have little time for gainful employment. Not having a lot of time or money doesn’t lend itself well to picking up nice things. Plus, as a graduate student instructor, I’d rather see students spend more time on their studies than worry about what they should wear.

Still, dressing well in college isn’t that hard. Especially when the bar is set so low. So, in an effort to help students smarten up, I’ve come up with some tips.

Focus on Smart, Mid-quality Basics

The downside to being a student is that you’re broke, but the upside is that you can have a complete wardrobe with very few pieces. No need to worry about having separate weekend and weekday wardrobes; it’s just off to class and libraries for you. So, focus on buying mid-quality, versatile basics. Don’t go for anything too nice. Whether you’re getting straight-As or barely passing class, your lifestyle in college will be mostly rough on clothes and probably not very hygienic. Get things like decent jeans that can take a beating, or thicker merino sweaters, not thin cashmere-blends. Build your wardrobe off grays, blues, and browns, so things can easily coordinate without you needing to have to put in too much thought.

Upgrade

The best way to not look like a college slob is to not dress like a college slob. Instead of graphic t-shirts, pick solid colors tees. Better still, try to wear shirts with collars, as they’ll help frame your face. Plaid flannels for fall, colorful madras for summer, and stripes year-round will help make those button-up shirts look less like office-attire. Long sleeve polos can also work, so long as they don’t look too fratty (I like Kent Wang’s). 

Instead of ratty or pre-distressed jeans, pick up a solid pair of dark, raw denim jeans that fit well. Levis is relatively cheap and easy. Maybe add a pair of chinos and corduroys too, so you have other things to wear.

Instead of college-branded sweatshirts, get merino sweaters. Club Monaco’s are pretty good on sale (they also offer a student discount year-round, which you can stack on top of sale prices). Cardigans can also work in theory, but they’re much harder to fit well than a simple crew- or v-neck sweater.

Instead of flip-flops and running shoes, get camp mocs, boat shoes, plimsolls, or desert boots. Clarks desert boots are a particularly good option if you’re on a student budget. You don’t have to put too much care into them besides applying some Obenauf’s LP for the beeswaxed versions or waterproof spray for suede, and the crepe soles will be comfortable for long-walks. Jesse has some other suggestions here as well.

Finally, there’s no alternative to cargo shorts, sweatpants, or basketball shorts. You just have to stop wearing those (unless, you know, you’re exercising or playing basketball).

Don’t Overdress

I know this site is often about sport coats and ties, but unless you’re a member of the Model United Nations or College Republicans, I encourage you to not wear ties as a college student. There are some campuses where this is normal, and you’ll know when you’re at one, but for everywhere else, you’ll just look out of place and over-dressed. For many campuses, sport coats may also make you stick out in a bad way.

If you really want to wear a sport coat, tweeds and corduroys can look a bit more natural on a college campus. For everyone else, I encourage reaching for more causal options. A vintage peacoat can be had for $50-75 through eBay, Vintage Trends, or a local thrift store. You can use this guide to help date your peacoat finds. For something new, check Fidelity.

There are also some go-to brands for decent, cheap(ish) outerwear. LL Bean Signature, Land’s End Canvas, and J Crew can be workable once they have their end-of-the-season sales (when things will be discounted 50-75%). J Crew also has a student discount, but only for in-store purchases. Additionally, Land’s End mainline is probably be less well-suited for a younger person, but this oilcloth jacket might be a good Barbour alternative. It can be had for under $100 if you wait for the right coupon codes. You can read Broke & Bespoke for a review. Lastly, Ben Sherman’s Harringtons can also be had through eBay for about $80.

And the Standard Advice

Add to this the standard advice.

  • Learn how clothes should fit. We have a few guides you can read through here. You have more wiggle room as a young, college student, but avoid things that are skin-tight or overly baggy.
  • Find a good alterations tailor and bring as much as you can to them. There are very few things a good alterations tailor can’t improve.
  • Make a wish list and tightly edit it. Make sure you’re building a wardrobe, and not just a collection of outfits. If something doesn’t mesh well with the other things you plan on buying, strike it off your list.
  • Set a budget and shop slowly. Especially at this age, your tastes can change rapidly, and if you buy everything now, you may find yourself regretting it next semester.

(Photo by John Morgan)

Casual Summer Footwear

Like most men of my generation, I rarely wear more “formal” clothes such as dark wool suits and black oxford shoes. Much of my wardrobe consists of more casual items, though I admit it leans towards the dressier side of things. That means lots of odd trousers and sport coats, casual button-up shirts, and shoes such as derbys, boots, and slip-ons. With the passing of Memorial Day and the unofficial arrival of summer, I thought I’d review some casual footwear options for the new season. Basically things that will work with what I think most men already have in their closet.

Generally speaking, I think men tend to look smarter in a pair of leather shoes than trainers. The one exception is white sneakers during the summer. For some ensembles, such as a pair of navy chinos and a colorful madras shirt, there may be nothing better. My favorites in this category include Superga, Chuck Taylors’ All Stars, and Vans’ Authentics, but there are many others. I covered a bunch of them last year in a post about plimsolls. In addition to those, you can consider the Common Projects and German Army Trainers that Jesse has talked about, as well as Svensson’s Classic Low Whites, Superga’s 1705s, and Superga’s decks. Svensson is a bit more refined looking, like Common Projects, but comes at a lower price point and even less branding. Men of Ilk is offering a 20% off discount code right now (GLCCW49), which puts the Svenssons at $180 for American customers. As for the Supergas, I bought a pair of the 1705s a few months ago and have been really enjoying them. The branding is less obvious and the design is basic enough to pair with most things.

For something slightly dressier, you can consider chukka boots. I know boots are a bit of an odd suggestion for summer footwear, but depending on your regional climate, I think they can work quite well. Alden’s unlined suede chukka, for example, is so soft and buttery that it wears very much like a slipper. The lack of leather lining inside makes the upper more malleable and breathable, much like a canvas shoe. My friend Stephen at The Simply Refined has said everything I could say about them. For something similar, you can consider Church’s Sahara and Allen Edmonds’ Amok. The brown version of the Amok is on clearance right now for $125.

If you prefer a bit more structure in your leather chukkas, you should check out Loake’s Kempton, Sahara, and Camden. Brooks Brothers also has a suede boot that gets discounted to $130 or so at the end of every season, and there’s of course Clark’s desert boots that everyone already knows about. If you have a bit more money to spend, I would also recommend A Suitable Wardrobe’s crepe sole chukka. I really like the shape of the toe box and think the crepe sole/ suede upper combination helps underscore the casualness of the shoes.

Finally, I’ll also suggest you get a pair of loafers this summer. Like with chukkas, these can be worn mostly year round, but feel especially nice for the warmer seasons. There are a good number of styles to consider, but for the purposes of this post, I’ll stick with the classic American penny loafer. Inspired by the Norwegian moccasin, the penny loafer was the sine non-qua for the post-war “Ivy Look,” and still looks quite sharp today. I recommend getting them from American manufacturers such as Alden, Allen Edmonds, Ralph Lauren, Brooks Brothers, Rancourt, and Oak Street Bootmakers. Bass also has some, though their quality is much lower these days. Outside of American companies, you may also want to look into Markowski, Herring, and Loake, as well as some of the models that Crockett & Jones offers.

Of course, there are dozens of good causal footwear styles, and some may be better suited for warm weather conditions than the ones above (e.g. espadrilles, white bucks, and spectators). However, for good, versatile basics that can work well for summer and transition into fall, I think you’d do well with white sneakers, suede chukkas, and leather penny loafers. 

It’s On Sale: 6PM.com Boot Sale
6PM.com is having a sale on boots. Among the offerings are Sorel Caribous, a classic snow boot offered here at an exceptionally reasonable price: $65. I know warm temperatures are here, but for those of you in snowy places, I can promise: it will get cold again eventually. Winter is coming.
There are also a pile more Sorels available, including some other classic models, like their 1964 line. They’ve got the Allen Edmonds Bayfield for $261.99 (from $350), some nice boots on deep discount from Timberland Boot Company like these Tackheads, Polo Ranger boots at 40% off, and a couple pairs of decent Clarks, like these Desert Mali Boots.
I’ve clicked a few brands we think might interest you in this sale link.

It’s On Sale: 6PM.com Boot Sale

6PM.com is having a sale on boots. Among the offerings are Sorel Caribous, a classic snow boot offered here at an exceptionally reasonable price: $65. I know warm temperatures are here, but for those of you in snowy places, I can promise: it will get cold again eventually. Winter is coming.

There are also a pile more Sorels available, including some other classic models, like their 1964 line. They’ve got the Allen Edmonds Bayfield for $261.99 (from $350), some nice boots on deep discount from Timberland Boot Company like these Tackheads, Polo Ranger boots at 40% off, and a couple pairs of decent Clarks, like these Desert Mali Boots.

I’ve clicked a few brands we think might interest you in this sale link.

Q and Answer: Ten In-Between Shoes

Matt asks: I need a new pair of shoes!  What I have right now is either too casual (a sneaker) or too formal (a fancy dress shoe), but I’m trying to figure out something in between. Any suggestions?

This is a question we get a lot. For men who want to wear something a little more put-together than their beat-up Nikes, but aren’t yet ready for a full-on sportcoat-trousers-dress-shoes ensemble, is there anything in between?

The simple answer is: yes. Here are ten choices for casual footwear that will keep you a head above the dirty sneaker crowd. (It’s a little tougher in the summer, so I’ll start there - the pictures run left to right and top to bottom.)

  1. Refined sneakers. When choosing sneakers, look for simplicity. White’s a great color for spring and summer, black and brown will do you well in the cooler months. You want as few details as possible here, and if you’re going to try and dress them up, they should be clean and sharp. I’ve got some Common Projects, the gold standard for this kind of thing, pictured above, but if you can find similarly simple leather sneakers from a brand that doesn’t cost a bajillion dollars, go for it.
  2. Boat shoes. While their ubiquity the past few years or their inherent preppiness might be a turn-off, boat shoes remain the default casual summer shoe (non-sneaker category). Wear them without socks in pretty much any casual situation during the hot-weather months. Then put them away.
  3. Espadrilles. These are the classic European vacation shoe - what Cary Grant might wear to the French Riviera. They’re cheap, comfortable and refined. Just don’t try to wear them outside of summer vacation, and for goodness’ sake don’t wear those awful Toms.
  4. Crepe-soled Chukkas. Desert boots are a comfortable, good-looking mostly-casual shoe for nine months of the year. Like boat shoes, they’re starting to overwhelm with their ubiquity, but if you try an alternative style like the calf version above, you can get a little more refinement and a little less “been there, done that.” (I can’t believe I just typed “been there, done that.”)
  5. Leather-soled Chukkas. Chukkas with leather or dainite soles like the brown suede pair above are one of the most versatile shoes you can own. They’re great with jeans, and in a pinch they could even be worn with a suit (though maybe not in suede). 
  6. Camp Mocs. Camp mocs are the cool-weather equivalent of the boat shoe. Inexpensive, casual, preppy and a little more refined than sneakers. The LL Bean Blucher Moc is the standard here, though the quality isn’t as high on them as it once was. Works great with jeans or chinos, but not so much with a more formal look.
  7. Plain-Toe Bluchers. This is the classic casual shoe. My own pair is an old double-soled pair of Florsheims in shell cordovan. I wear them with everything short of a suit. Black looks like security guard shoes, so avoid it. Brown is a touch more casual than burgundy, and crepe soles a touch more casual than leather.
  8. Country Brogues. Grenson is the classic maker of real country brogues, so that’s what you see above. The leather in shoes was originally perforated by folks who lived in marshy, wet conditions and wanted shoes that shed water. It’s purely decorative now, but still casual relative to other oxfords. If you want to wear brogues casually, look for prominent broguing, a stout shape and heavy soles. These are too casual for most suits (save country suits like corduroy or tweed), but if they’re clunky enough, they can stand up to blue jeans well. The boot equivalent of these shoes is even more casual. Note, also, that crepe soles or (especially) suede can turn down the formality of most dress shoes.
  9. Work and Outdoor Boots. There are a broad range of work-style boots. I’ve pictured something in the middle, the Red Wing Gentleman Traveler. On the casual end are hunting and hiking boots (like Danners) and real work boots (like traditional Red Wings, with lug soles and moc toes). I love my Alden Indy Boots, which are moc-toed, but otherwise quite refined - I wear them with chinos or jeans and a casual blazer all the time. Also in this category are military-inspired boots, like Polo Rangers.
  10. The Chelsea Boot. I’ve pictured a pair by the Australian maker R.M. Williams. A hefty, chunky Chelsea like these is more casual. A more refined model can even be worn with a suit. In fact, the Chelsea is probably the shoe that most comfortably goes from casual to formal.

Remember: city is more formal than country. Leather soles more formal than rubber (and lug soles the least formal of all). Smooth leather is more formal than textured, which is more formal than suede, which in turn is more formal than unpolished. Shoes are more formal than boots. Shapely is more formal than clunky.

And always, always stay away from hybrids. Nothing good can come of two shoes mating.

Finding a level of formality that’s between slovenliness and traditional business dress is vital for anyone who isn’t a slob or a traditional businessman. Hopefully this will set you on your way.

thisfits:

The laces on one of my DBs snapped last week, so I rode down to the shoe shop yesterday to buy new ones. Just for kicks, I opted for brown laces.
Picture doesn’t do them justice. I should have done this as soon as I got them. They look fantastic.

Sand-colored desert boots, fall-ified.

thisfits:

The laces on one of my DBs snapped last week, so I rode down to the shoe shop yesterday to buy new ones. Just for kicks, I opted for brown laces.

Picture doesn’t do them justice. I should have done this as soon as I got them. They look fantastic.

Sand-colored desert boots, fall-ified.

(Source: thisfits)

thisfits:

Just got a sales alert that Clarks Desert Boots are $66.50 on endless.com. That’s 30% off, folks, plus free shipping and returns. Get ‘em while you can.
Clarks Originals Men’s Desert Boot: Endless.com

Free shipping and returns on Endless, too.

thisfits:

Just got a sales alert that Clarks Desert Boots are $66.50 on endless.com. That’s 30% off, folks, plus free shipping and returns. Get ‘em while you can.

Clarks Originals Men’s Desert Boot: Endless.com

Free shipping and returns on Endless, too.

Q and Answer: Suede and Water
Avi writes:  I recently picked up a pair of Clarks Dessert Boots, of the Oakwood  Suede variety. Continuing your recent shoe care theme, how do I go  about keeping suede shoes clean and unmarked? Can I waterproof shoes of  this type? I’ve noticed a few minor watermarks already—am I stuck with  these discolorations?
Suede is extremely difficult to keep clean and unmarked, particularly if it’s a lighter color.  Even water can leave a spot and ruin the nap of the leather. 
There are a couple of paths you can follow.
When your shoes are new, you can spray them with a silicone-based water sealant.  These are available in the shoe section of your local drugstore, or from your shoe repair shop.  A few coats (let them dry thoroughly in between) won’t turn them into galoshes, but it will help if you get caught out there. 
You can also buy a suede kit.  Most are two tools and a stain remover.  The tools are essentially a gum eraser, for rubbing the soil off, and a brush, for bringing up the nap.  If you get a spot, this can really help.
The third course of action is probably the best, though.  Just accept that they’ll get dinged up.  It’s pretty much the nature of the beast.

Q and Answer: Suede and Water

Avi writes:  I recently picked up a pair of Clarks Dessert Boots, of the Oakwood Suede variety. Continuing your recent shoe care theme, how do I go about keeping suede shoes clean and unmarked? Can I waterproof shoes of this type? I’ve noticed a few minor watermarks already—am I stuck with these discolorations?

Suede is extremely difficult to keep clean and unmarked, particularly if it’s a lighter color.  Even water can leave a spot and ruin the nap of the leather. 

There are a couple of paths you can follow.

When your shoes are new, you can spray them with a silicone-based water sealant.  These are available in the shoe section of your local drugstore, or from your shoe repair shop.  A few coats (let them dry thoroughly in between) won’t turn them into galoshes, but it will help if you get caught out there. 

You can also buy a suede kit.  Most are two tools and a stain remover.  The tools are essentially a gum eraser, for rubbing the soil off, and a brush, for bringing up the nap.  If you get a spot, this can really help.

The third course of action is probably the best, though.  Just accept that they’ll get dinged up.  It’s pretty much the nature of the beast.

Q and Answer: Dr. Martens
J.C. askes: I love my Doc Martens (classic black 8 holes)—they’re solid shoes, have lived through several moves, jobs, era’s of my life, and numerous repairs. I have been told, however, that they are not exactly a fashionable boot. Is this true? I’ve always assumed that they were at least not embarrassing shoes/boots, but I’m worried that such may not be the case.  If they are an embarrassment, do you have suggestions for something as durable and comfortable that is also a bit more fashionable?
Dr. Martens are indeed a classic.  We learned from Quadrophenia that they’re the only thing that the Mods and the Rockers have in common… they’ve always been a symbol of youthful rebellion.
But let’s get semiotic for a moment.  Like many sub-culturally specific clothes, they’ve developed very specific associations.  Their roots are in mods, punks and skins, but for most people, they recall something else entirely: grunge.  They are, essentially, the uniform of the man who has a crush on Janeane Garofalo.  Also, Janeane Garofalo.
If you’re old enough to have worn Docs in the early 90s, and you’re not a mod, a punk or a skin - that’s how you’ll be received.  As a guy who’s watched “Slacker” too many times.  Or, worse, like a guy who’s watched “Reality Bites” too many times.  Or even, possibly, like someone who’s watched “Empire Records” too many times.  And that’s not really going to fly in 2010.
That said, there has recently been a bit of a revival in skinhead and mod fashion.  In the last five years or so, brands like Fred Perry and Ben Sherman have gone from British niche products to worldwide, mass-market fashion.  And Dr. Martens have, to some extent, ridden that wave.  They even did a collaborative collection with Raf Simons, which yielded some crazy stuff, but also some really nice stuff.  So if you are a mod or a skin or a punk rocker - or even if you’re just cool or young enough not to send the message that you’re stuck in 1992 - then Docs can be a great way to go.  Just don’t ever, ever, ever wear those God-awful sandals.
One further word of warning.  When Docs last had a great revival, they were being made in England.  In the early aughts, all production of Dr. Martens shoes and boots was moved overseas to China.  If you’re the kind of guy who cares about that kind of thing, they brought back some UK production in 2007, with a line called “vintage.”
As for alternatives, if you’re looking for a Dr. Marten-style boot, Solovair or Gripfast are solid options.  Still made in England, and preferred by many of those in the know for that reason.
If you’re willing to consider other styles of boots, we’ve recommended the Red Wing Gentleman Traveler before, and will gladly do so again.  A much heavier boot, but it will take anything you can throw at it.  Other classic choices include the Alden “Indy” boot, which even looks good with a tweedy sportcoat, or a moc-toe work boot, like the Red Wing 875.  You might also consider these, from LL Bean.  In a completely different vein, I believe I’ve mentioned how ape-shit I am for my Arrow Moccasin Lace Boots, which can be ordered with a double leather or crepe soul.  And don’t forget Clark’s desert boots.

Q and Answer: Dr. Martens

J.C. askes: I love my Doc Martens (classic black 8 holes)—they’re solid shoes, have lived through several moves, jobs, era’s of my life, and numerous repairs. I have been told, however, that they are not exactly a fashionable boot. Is this true? I’ve always assumed that they were at least not embarrassing shoes/boots, but I’m worried that such may not be the case.  If they are an embarrassment, do you have suggestions for something as durable and comfortable that is also a bit more fashionable?

Dr. Martens are indeed a classic.  We learned from Quadrophenia that they’re the only thing that the Mods and the Rockers have in common… they’ve always been a symbol of youthful rebellion.

But let’s get semiotic for a moment.  Like many sub-culturally specific clothes, they’ve developed very specific associations.  Their roots are in mods, punks and skins, but for most people, they recall something else entirely: grunge.  They are, essentially, the uniform of the man who has a crush on Janeane Garofalo.  Also, Janeane Garofalo.

If you’re old enough to have worn Docs in the early 90s, and you’re not a mod, a punk or a skin - that’s how you’ll be received.  As a guy who’s watched “Slacker” too many times.  Or, worse, like a guy who’s watched “Reality Bites” too many times.  Or even, possibly, like someone who’s watched “Empire Records” too many times.  And that’s not really going to fly in 2010.

That said, there has recently been a bit of a revival in skinhead and mod fashion.  In the last five years or so, brands like Fred Perry and Ben Sherman have gone from British niche products to worldwide, mass-market fashion.  And Dr. Martens have, to some extent, ridden that wave.  They even did a collaborative collection with Raf Simons, which yielded some crazy stuff, but also some really nice stuff.  So if you are a mod or a skin or a punk rocker - or even if you’re just cool or young enough not to send the message that you’re stuck in 1992 - then Docs can be a great way to go.  Just don’t ever, ever, ever wear those God-awful sandals.

One further word of warning.  When Docs last had a great revival, they were being made in England.  In the early aughts, all production of Dr. Martens shoes and boots was moved overseas to China.  If you’re the kind of guy who cares about that kind of thing, they brought back some UK production in 2007, with a line called “vintage.”

As for alternatives, if you’re looking for a Dr. Marten-style boot, Solovair or Gripfast are solid options.  Still made in England, and preferred by many of those in the know for that reason.

If you’re willing to consider other styles of boots, we’ve recommended the Red Wing Gentleman Traveler before, and will gladly do so again.  A much heavier boot, but it will take anything you can throw at it.  Other classic choices include the Alden “Indy” boot, which even looks good with a tweedy sportcoat, or a moc-toe work boot, like the Red Wing 875.  You might also consider these, from LL Bean.  In a completely different vein, I believe I’ve mentioned how ape-shit I am for my Arrow Moccasin Lace Boots, which can be ordered with a double leather or crepe soul.  And don’t forget Clark’s desert boots.