Who would’ve thought that with all my free time, I’d regress further and dress like a little boy?

Introduction

Shorts have a weird place in menswear.  If you ask most of us (or at least me a few years ago), we would say that shorts are inferior to full trousers. Perhaps the distaste comes from the fact that shorts are inherently casual and are at odds with what the menswear world stands for.   In their minds, it seemed odd to tuck in a shirt with a pair of shorts and wearing jackets with it just provides an issue with visual proportions.  And like a sandal or going sockless, it exposes the leg, which many conservatively dressed guys are against.  In that side of menswear (and to many new comers to tailoring), a breathable/lightweight trouser or a broken in chino will be fine for hot weather.

Of course, these sentiments aren’t really founded in the roots of classic menswear. The fact that shorts (as well as going sockless) has been around for quite a bit, even in the Golden Era that menswear loves so much.  This is because shorts back in the day had trouser-esque details (like gurkhas), incorporating fun closures and pleats to make them much more interesting and easier to work with a tailored mindset. I mean, they were short-pants after all.  You tucked your shirt into your trousers, right? And you wore socks with your loafers, right?  Shorts simply allowed for more air circulation in the summer; guys just wore them as a summer replacement for pants, nothing more.

This lead to a revival of the tailored short within the menswear world.  Gurkha shorts (or ones that had side adjusters) became the norm for summer wear, becoming just as prominent as the classic off-white linen trouser.  It’s perfectly acceptable to lean into it, going for that 1940’s vacation look meets Italian Riviera, pairing the shorts with sportshirts and alohas.  This is what sold it for me and brought me back to the shorts wearing world, at least for a bit.

Looking back, it was clear that what menswear needed was a tangible look to latch onto that made shorts look cool.  But certainly that meant that there was a shorts-look that was uncool.  Something that the menswear world as a whole was actively trying to avoid, to say that the revamped gurkha-clad, vintage vacation/Italian summer vibe was the way to “correct” the errors of previous generations.  That whatever came before was dorky and just not right.  I believe that was the “school boy look”.

The School Boy Look

Now as much as I love wearing gurkhas and dressing like I’m on a nice vacation, I again felt like I was being pigeon holed into that specific look whenever it came to wearing shorts.  My tailored styles had always a bunch of inspirations, from replicating the 1930’s to doing an updated take on ivy. Even my casual, non-sartorial outfits had some variety, whether they were evoking tailoring or just being edgy in black; all of these theories even go back and influence each other.

Naturally, I felt like there had to be another nuance I could add to my shorts attire. Something that fulfilled my love of vintage and little-appreciated aesthetics that would quite possibly be subversive and yet appropriate for my style.

Then I remember seeing the above picture of Matt Woodruff a few years back when I first followed him during his time at Drake’s.  In theory, this goes against everything menswear stood for in regards to shorts decorum.  Not only is he wearing a jacket with shorts, forcing a play with proportions, but he’s wearing socks.  This was clearly look that menswear avoided by going with the much more tailored and clean vacation/Italian look.   I can just feel you guys shaking your head at it. But the thing was, I didn’t exactly hate it.

All I could think of was that this felt very boyish.  Like a boarding/prep-school kid particularly, due to the combination of plain navy and khaki (classic school colors).  This is a context where socks and loafers are needed, but full chino trousers may be too restricting for recess, so shorts are instead used.  You could say that it was a precursor that my tailoring alternative/replacement theory that swaps out pieces for others to maintain a vibe but add a fun spin.  It was intriguing to say the least.

The image was filed away until this very spring/summer where hot weather  and a desire to dress up as much as I could (for quarantine sanity) lead me to revisit the look with fresh eyes.  And god damn it, I was ready.  Ready to break free from the “uniform” of a camp shirt or Breton tee with gurkhas. I was ready to finally feel like I had options with shorts!

I will say the moniker I’ve given the look isn’t exactly accurate.  However, even though the look was done by men of all ages through out time (golf comes to mind) history has forever attached it to the attire of vintage school boys, even if it doesn’t exactly involve a crest blazer and tie. It does have an inherently preppy nature to it, as it involves wearing “nice” tops/shoes with shorts, instead of leaning into a relaxed aesthetic with a firm look like the Vacation Look or just straight up wearing athletic wear.  Instead, the school boy look seems to be able to be done with a variety of different pieces.

Shorts, socks, and a top (whether a tee, both long and short sleeved, or a jacket), like the Italian-vacation look, has historical precedent. But it’s one that isn’t exactly looked favorably upon by menswear people, almost like a shameful secret. Menswear is entirely about looking classic, elegant and masculine, and this isn’t quite all that. I mean its quite obviously a boyish, youthful look, a temporary one that is meant to be grown out of and cast aside in favor of older, “classic” vibes.  You could also say that it’s quite feminine in that regard (as I’ve seen many women do the look well) But as a guy who likes low cut loafers because they evoke a slipper and women’s flats, this was great for me.

Like I said, shorts back then were meant to just be an alternative to full trousers, and should be worn as such.  Immediately, it puts into a play with proportions and expectations, calling back to my non-sartorial casual style.  Wearing shorts with your regular everyday clothing gives the entire outfit an inherently slouchy-yet-subversive feel.  And perhaps, that why most of classic menswear doesn’t like it.  It’s not clean, streamlined, or traditionally cool. But that’s why I like it; I’m also not clean, streamlined, or traditionally cool.

I mean right here, this is it.  It’s just so good. It just incorporates everything I already like: high rise, soft rumpled OCBDs, white socks, and your choice of loafers or sneakers.

From a purely aesthetic standpoint, I also love how to plays with proportions and subverts classic expectations (yet is firmly classic due to the age).  I love how the high rise yet short length of the shorts are offset by the white socks, providing visual interest that is usually copped out by going sockless.  There’s how a long sleeve interacts with the shorts; it’s not required (as the guy on the left has a short sleeve shirt) but it adds an extra layer of nuance.

Clearly, you can take this further by even wearing the shirt untucked, a term I never thought I’d say.  Normally I like to keep everything inside the waistband (including tee shirts of all kinds), but there’s something gripping about keeping a shirt untucked.  It’s not something I’d do with full trousers, but shorts? Maybe.

To me, its done by thinking of the shirt as the outer layer of the outfit, similar to a sportcoat or a casual jacket. And like how these pieces have front quarters that go beyond the waistband of a trouser and sweep off, so does the front panel of a shirt. Weird thought process I know, but hey, that’s how my mind works.

It’s all in the specific choices behind crafting the outfit. Obviously a tee shirt (or a tank top) makes sense when it’s hot outside, but going with an OCBD (or a sportshirt) is an intentional choice that points toward classic menswear.  It’s just like how going sockless is cleaner, but it’s done because of ivy.  It’s probably not as conventionally attractive as the vacation/Italian look, but thats entirely the point. It’s regular and slouchy without being sloppy.  And like I said on the pod, us young menswear guys tend to be a bit ironic/self-aware in how we lean into our quirky clothing choices.

Now when I was looking up socks with shorts for archival purposes, I did come across a few photographs of guys doing it, but with full blazers. While I don’t whole whole heartedly recommend it, it did exist.  To me, it comes across as different than Thom Brown, which utilizes tight shorts and short jackets.  Everything is done much more relaxed since they’re in a wider silhouette.  Again, it’s about just making regular trousers shorter instead of crafting an entirely new design or going for a themed aesthetic.

Plus, I’m pretty sure the use of a full jacket and tie with shorts was meant to be edgy, even back then.  I can’t say for certain, but I think it was a fad to just fuck with people.

Seeing Japanese brands like Beams (or even just enthusiasts) do an updated spin on it only helped my mind add the ideas to my style lexicon. Not all of theirs pointed directly toward school boy or university-ivy style, but that was a good thing.  Putting in workwear or non traditional pieces only makes the schoolboy aesthetic broader and open to a multitude of interpretations.  In particular, I think the casual outdoor aesthetic is an easy one to combine with it.  And we definitely can’t forget the connotations to skatewear, as shorts and socks have been an essential part of that niche look.

My internet pal Chris from MFA is very adept this very act, blending all of this inspo together in a way that doesn’t rely too much on just lifting things from the past.  He adds in milsurp or takes designers that are themselves inspired (but not just taking) by Americana.  It’s rugged but refined, edgy and classic with a slight retro feel.

Surely there was room for me to do my own thing!

Wearing It

The challenge for me (and probably for you too), is that you don’t want to come across like those old 70’s advertisements of old like this or this.  I could see this as an issue if you’re used to slim shorts and slim shirts, but once you’ve already adopted a wide legged aesthetic, you will naturally not look like you’re trying too hard. It also helps to not wear it with a tie, which you seldom saw in any earlier inspo outside of the college kids just fucking around.

The other concern was that I didn’t want to look like just another frat kid in Vineyard Vines or Ralph Lauren.  That one is harder, since the line between that and what I’m trying to go for is rather thin.  Personally, I think that staying away from pastels and ginghams is a good start.  Of course, opting for subversive things like white socks, classic loafers, adding in milsurp/workwear, and non-slim fits, will take those away.

Again, I can’t emphasize how important white socks are.  Their presence is old school and inherently subversive, since most guys would rather wear no show socks than be caught dead in white socks.  So adding them in will help emphasize the old Americana connotations and provide character to an outfit that can teeter into basic territory.

I also like keeping things untucked. I know that tucking in is a cleaner, more sartorial move, but putting the white socks with a tucked in shirt seems a bit too “dad” to me. It’s just too straight forward.  Having the shirt (whether it’s an OCBD or a sportshirt) untucked gives the outfit a relaxed vibe that is sloppy-but-not, at least to me. It helps if you have some sort of base layer like a striped tee, so you can mentally consider the button up an outer layer.

All of these points have largely has been my strategy for going for the school boy, socks-with-shorts look.  Now let’s dive into some particular favorites.

This was my first ever look that really leaned hard into the school boy aesthetic. It’s directly lifted from that original picture of Matt, but done through my own lens. With it’s use of navy, white, and khaki, it certainly has connotations to school uniforms (it was my Christian academy’s school colors!) which adds to the youthful look.

Upon a second look, I wish I had  tucked in my spearpoint polo in order to go along with how I normally compose an outfit, but it admittedly looks just fine. I think that the long sleeves of the chorecoat was plenty enough to offset the shorts and play with the visual proportions.

The interesting thing here is my flat front, straight fit khaki chino shorts.  They were bought years ago during college and were cast aside in favor of gurkhas, which I believe, wouldn’t have worked so well in this particular case. The slimmer shorts above are understated and normal, being a replacement for the fit of straight fit chinos (considered slim when compared to full tailoring) I wear when doing ivy looks.  The closer fit is closer to what those Take Ivy university students wore in the old photographs, which was important to reference.  It also makes emphasizes the slouchier nature of the other pieces, while echoing how snug a white sock should fit.

This simple, subdued fit that was very close to the vibe I was trying to exude provided the best jumping point for me to explore.

As many of you know, article ideas are written much in advance and are amended as time goes on.  So in the spirit of full disclosure, the previous two outfits were actually done almost a year ago! It wasn’t until this quarantine (and a hot as fuck spring) that allowed me to dive back in.

Now I already knew that the simple combo of a chore coat, button up (plain or not), chino shorts, and white socks/loafers was a winner; I needed to change it up.  So my return to the school boy look was different than the ones before it, incorporating a lot more ideas. The shorts and socks were the same, but it’s the top half that was changed up.

The classic vintage OCBD makes its inaugural appearance here, but it’s done as an outer layer, akin to a chore coat. It’s a wild move for me, since I never do overshirts; typically my outer layers need to have pockets in order for me to justify wearing them. However, seeing that I’m at home and have no need to carry anything in my pockets, it worked out fine! It’s worn over a tee shirt my mom got me when she visited Portland a few years ago, which actually has a bit of a 1970’s retro charm to it.

The combination  of an unbuttoned shirt over a tee is not unlike one worn by many other American college students (like Abed Nadir), which again points toward the vintage inspiration, just done through a different lens. It appears typical but pivots away sharply with all the details, like a large fit in the shirt (with ample collar roll), tucked tee, and the white socks and loafers.

To me, it’s a a bit like the layering of grunge with classic American ivy done in the summer.  Again, a wild connection to make but that’s how I dress.  Pretty college too.

This next one is more straight forward, going with the traditional ivy look of an OCBD, khaki shorts, and white socks/canvas sneakers.  The oxford is long and boxy, as it’s a vintage 70s one I thrifted way back when.  Instead of contrasting the loose fit with slim shorts (as I did in the previous outfit), I actually opted to go with gurkha shorts.

To my surprise, the look was pretty solid, with the shorts and shirts acting cohesively with each other.  I think slim shorts would’ve “sold” the look a bit better (and made it more 60s) but the gurkhas provide a different silhouette  than expected from an ivy-prep outfit. I’m glad to know that wide leg shorts have a place in this weird little style affectation.

I kept the experimentation going with this next one, going back to some original ivy inspo.  A bold blue stripe shirt (a Vintage Ivy from Kamakura) was the star here, pointing to the fact that it’s now spring-summer season. It’s untucked to evoke the feeling of a jacket/chore coat (worn over a tee undershirt), which I think is accomplished well and doesn’t appear sloppy.  Note that the longer length and looser fit are not in the vein of the slim fit, Untuckit shirts that many other guys wear today, a key to make this type of outfit look good and not too “basic”.

This time I went with my navy pleated vintage polo RL shorts to see yet again if a wide fit wouldn’t be overpowering against the loose, untucked shirt. Obviously, it worked out just fine! My idea was reinforced: the shorts really are just trousers hemmed at the knee (at least in my preferred fit). The high rise removes any gap between the unbuttoned part of the shirt and the top of the short, to keep the pieces streamlined.

A bucket hat is used not only practically against the bright sun, but because it adds something extra to the outfit. Since the shirt is closed and therefore not utilizing the effect of the shirt underneath, I felt like the outfit needed something more.  Without the hat, I felt like it was just too much like a typical frat boy look, just over-sized.  With the bucket hat, it becomes something a bit more interesting that elicits the Japanese-Americana influence as well as an overt “old school” vibe. Still school boy/university student-esque though!

I decided to put a little bit of everything in this outfit.  You’ll first notice that there is a workshirt here, but it’s tucked in; I finally had the balls to do shirt tucked in with white socks.  It’s not a bad look on it’s own, maybe just a tad bit on the safari side rather than the school boy side, but in order to do my play with proportions, I wore a a chore coat on top.  Normally, I’d wear my navy one to make a “suit” with the shorts, but I like the red in order to emphasize the separates and makes it a bit more ivy-workwear does school boy.

Other than that, it’s not too far off from my initial take on the outfit, just with bolder colors.  In fact, it’s that reason that I decided to go with black loafers instead of my usual brown.  Just a small detail, but I rather like the black against the blues and reds here.

Honestly though, this is an outfit I would’ve worn even before the whole school boy inspiration. The main difference is the white socks, which give the outfit an edge.  Sockless is expected, white socks and loafers are weird and school boy.

I would be remiss if I didn’t try the jacket + shorts combo at least once and honestly, I don’t hate it. It leans heavily on the grandpa side, but I think the details make it a bit more interesting than what your typical old man would wear.

Firstly, this is in the fit of the shorts.  While gurkhas are more tailored (with interesting details) their wide silhouette wouldn’t do the outfit justice; it would look a bit too costume-y and contrived.  Using my slimmer shorts delves into the school boy aesthetic and actually compliments the high tight socks (note that they aren’t sloppy) and the tassel loafers.  Against the fuller cut navy linen jacket, it exudes those fun 60’s ivy guys rather than simply doing a shrunken school boy a la Thom Browne.

Yes, I did tuck in my shirt (a spearpoint), but I decided to do it sans-tie, so it wouldn’t be exactly like a school boy.  This divergence is further emphasized by the use of a bucket hat. It incorporates the grandpa style but with everything else (especially it’s use with Americana) it puts the whole thing in an intentionally Japanese-inspired mood.

It’s certainly subversive, but I like it. I’m adding it to my arsenal of fun outfits to rock this summer.  I may not get a girl’s number out at a boba shop, but at least I’ll have fun with my attire!

 

Conclusion

I can already tell that this has to be my most divisive article thus far.  I mean, I’m even surprised this particular look latched onto me. The very idea of wearing shorts with socks (not to mention the wide legs and untucked shirts) goes against all previous convention in menswear, at least in the mainstream.  I mean, my actual grandpa does the look quite often, because he literally grew up wearing it and didn’t have the luxury of experimenting with vacation-chic or minimal attire like I do.  But if it’s done right, through a weird post-moderist, anything goes, Japanese-Americana inspired lens, it’s good.  Even if it is school boy-meets-old man type of look.

The thing is, this look totally makes sense to me, the vintage-meets-ivy guy who wears spearpoint collars, sack-jacks, and crazy foulard ties.  To me, adopting the school boy/University look injects the fun details from my regular attire into the days where shorts are absolutely necessary to prevent me from melting. It’s a natural extension of my personal style, at least where it’s currently heading.  Plus, I didn’t have to buy anything new for this; it just took some re-combining of different pieces in my existing wardrobe.

To be fair, it’s not an easy look and one that could go wrong quick. But that’s not the point; it should be easy. A classic fit OCBD (or sportshirt) is something that goes with everything, especially plain shorts, which can be as slim-straight or wide-pleated to your discretion.  Just don’t forget the white socks and loafers/white sneakers. They really make the look old school ivy and are a move that you definitely won’t see from a typical frat boy. Hell, you could say that it points toward skatewear more in that regard, despite being obviously a bit more dressed up. It’s about being edgy in a good way, instead of just literally copying what an old man would wear.

Of course, adding extra pieces help make it an intentionally interesting outfit.  Chore coats or wearing an OCBD as a layering piece over a tee is a great way to add visual complexity. It also helps play with the proportions of a high waist and a proper short length (it should still end slightly above the knee).  And don’t forget headwear; a dad cap or bucket hat is the perfect finishing piece that is not only Americana, but practical in the bright sun. The juxtaposition makes for an intentional look that also brings in the skate vibes.

Feel free to try this weird, school boy-meets-old man style move at your leisure, but it’s certainly the vibe I’ve been going for this season. To me, it’s much more rich and interesting than the monochromatic louche-ness of the typical vacation/Italian summer vibe that most guys default to. That vacation look is still a good look (especially with tailoring) and will always be around for me to go back to, but right now, I’m just intrigued by the options you get when you’re able to do traditional and adjacent ivy looks, just with shorts! If that’s the case, then I’m definitely fine with dressing like a school boy all summer.

Always a pleasure,

Ethan M. Wong