As a menswear guy who loves tailoring and got his start wearing period accurate vintage, I had no place for sneakers in my wardrobe. Now they’re a welcome alternative to loafers for me, being worn with jeans and shorts to even full trousers.
It helps if you understand the different types of sneakers out there and how they fit into different vibes of classic menswear. Hopefully this proves useful to me; if not, you can just look at the great pictures!
I used to have an aversion to sneakers. I’m sure many of you guys did too, considering my readers (or people who find this blog) have an affinity for classic menswear. When you first start out, you most of the rhetoric around sneakers are “why wear them when you can just wear loafers”, as loafers are the go-to casual shoe for classic menswear. Or hell, “why wear sneakers at all, since a gentleman should always be formal and well dressed“. I might be exaggerating, but you get the point. I just struggled to see how it would work in my wardrobe. Especially during my vintage-accurate period.
So for a long time, I never really wore sneakers (outside of the gym). I had a pair of vans I wore in high school (that carried over a bit into college) but they didn’t feel right. It just never occurred for me to wear them, as I took every opportunity to wear some form of tailoring (and I wasn’t exactly going to just be that #menswear influencer who wore sneakers with a suit). I only started to make a change when I realized that I also didn’t want to be the guy who only wore suits and ties all the time; I needed a way to dress down.
I’ve talked about this on the podcast/twitch, but before I started to develop a real casual style (which includes rugged ivy, vintage casual, and that slouchy tailoring-adjacent vibe) I really wanted my casual style to contrast against my regular tailored looks. If that action could talk it would probably say “hey look, see, I can be normal!”. I wanted to quell the jeers of my friends and potential Tinder dates.
So then I bought Nike Killshots (because MFA told me to), Onitsuka Tigers (because I thought they looked cool) and Stan Smiths (r/MFA). And I wore them…kinda. I had pieces just for wearing sneakers since the footwear didn’t really fit in with my “regular” clothing. I mean jeans and sneakers are a classic look (see the basic bastard), but it wasn’t me or at least I didn’t yet understand how to do my own spin on it. I kept thinking that the outfits I made would be more interesting (and subversive) if I wore loafers instead! The sneakers were then pushed down in the shoe rack, only coming out for extremely lazy days.
Of course, that mentality didn’t stay for long. Like my long (dress) shoe journey, what I really needed was a deep dive into finding inspiration in both modern and vintage menswear in order to find a natural way to make it work with the look I wanted to go for.
Sneakers in Vintage Menswear
Obviously, the “hate” against sneakers really is only present in hardcore vintage communities or delirious menswear enthusiasts. Like white socks, sneakers in vintage and classic menswear have been a thing for years. You can just look at old tennis photographs and illustrations, where guys are wearing canvas shoes for “sporting”. Sneakers for workwear and basketball have their precedent in the early 1900s while the USN has been using deck shoes since the 1930s. My point is that sneakers have their place in menswear. Denying their history and the fact that they do look good with classic clothing is just idiotic.
Now obviously in the past, sneakers weren’t as wide spread for mainstream wear as they are now. In those days, you had separate footwear (and even clothing) for certain activities. Deck shoes were worn on the boat, rubber hightops were worn for workwear, loafers were for casual days, and lace ups were for when you wore full tailoring. Even then, sneakers were mainly worn by youth, since they were something you could get dirty and replace more easily than leather shoes.
Keds, PF Flyers, and Converse are the ones that come to mind most prominently, as they are tied to the famous vintage look of straight leg denim and tucked-in sportshirts in the postwar period, though there were certainly copycat brands even back then. It really is an iconic look that exemplifies that mid-century Americana look that the basic bastard has it’s roots in. Hell, a lot of vintage enthusiasts who actually dress down do this look quite well; it’s also a springboard for a lot of the non-boot outfits frequently found at Inspiration LA.
Sneakers fully exploded in the late 60s-1970s. While still utilizing smart-casual, canvas “play” sneakers of the decades prior, the decade also focused on athletically-inclined leather-suede designs. Sure they were made prominent by actual athletes (especially tennis), but you didn’t have to be an sporto to wear them. People wore sneakers with jeans, cords, and even suits. Like we stated in that 70s essay, people were now free to make their own context with clothing and not be beholden for the original intended purpose of the garment. A lot of our ideas for how to wear sneakers came from that era!
It’s hard not to look at the old pictures and advertisements of sneakers and wonder how we could just capture that same easy vibe in the modern world.
Sneakers in Classic Menswear
It’s no secret that sneakers are the king of footwear, considering the fact that the world is increasingly casual (and of course the rise of streetwear). Because of that, sneakers have definitely found their way into the classic menswear world. In some cases with tailoring, sneakers can be a bit bad or try-hard, especially in the #menswear/influencer style, but when you take a broader look, you find a few places to gather some inspiration.
One particular source of good sneaker inspo was Chase Winfrey, who funnily enough wrote a small list of sneaker recommendations over at The Grange. He’s always been a fan of different types of sneakers and even wore them quite interestingly, both casually and with tailoring. Seeing him do a variety of different things like Sambas, Tretorns, and Novestas in a way that seemed a bit retro, a bit ivy-prep, and just subversive in general made me rethink about the sneakers I had pushed away in my closet.
It had this NYC/practical vibe, as I’m sure that it’s much better to trek the blocks and subways in sneakers and not dress shoes all the time.
I finally had evidence that sneakers looked just fine with traditional trousers and leg lines. They could literally become an acceptable alternative to a loafer than requiring a completely casual outfit to “make it work”!
With that mental barrier broken, I finally saw how sneakers could work in my view of menswear, but I still decided to make some mental notes when looking at the wider menswear world. And after a while, I noted that there are a few schools of thought that I’ve seen when menswear guys wear sneakers. These aren’t hard rules or even guidelines, as many of the most stylish menswear guys mix and match vibes at will. YMMV.
The most popular is the use of sleek white sneakers, as a way of bringing a luxury mindset to casual shoes. Common Projects are a prominent example of this, as well as the Stan Smith. You can see this minimal style worn by newbies who want an “elevated sneaker” to established guys like Mark Cho. I can certainly see the appeal, as can be compared to the clean vibes of a nice oxford or loafer, as well as not leaning too far into rugged ones like Converse. This is as far as I’ll get into fashion sneakers, as I also definitely don’t like minimal suede or brown/navy ones.
As you could see in my earlier pictures, I used to be into this style, but I don’t think it works for me. It doesn’t feel slouchy, since minimal white sneakers works best for clean looks that I definitely don’t really do. Instead, I rather enjoy it when people wear the white canvas sneaker, since this still lends itself to being worn instead of being clean.
Converse (and similarly Chuck-style designs like Jack Purcells) are a no brainer, providing a vintage 50s vibe as well as a modern skate/punk vibe to an outfit, both casual/workwear and “formal”. I say that since chucks with a worsted super 150s suit seems a bit try hard, but a heavy cotton twill “suit” is an absolute banger of a look. Of course doing it with denims and chinos is great too. Low tops are probably the most versatile, but a hightop presents an interesting challenge that I rather enjoy. Black also works too, though it may not be as versatile as the classic off-white (though reds or other colors can make a 60s-70s vibe). Getting the white ones dirty is definitely the way to go, since having a completely pristine wardrobe doesn’t feel authentic, at least to me.
Now obviously, Converse isn’t the only sneaker brand to go for that classic hightop/Chuck Taylor/”many lace” design. Moonstar is one that I aspire to try, as this Japanese brand makes a great model that seems more like a boxing shoe rather than a skate shoe. The tops have an oxford-esque appearance due to their closed-lace design, which makes the shoe look cleaner and has through-line through tailored aesthetics (rather than it simply being white leather). Whether it’s the lowtops or high tops (or even their other models which have a heavy “sole” for a workwear vibe), they’ve become something I lust for, though Moonstar is hard to get here in the states.
Drake’s carried the white ones a while back and it really made an impression on me: closed-lace sneakers are the GOAT.
Another avenue is to go back to leather sneakers, but to go retro, which typically favors 70s-80s style sneakers rather than 90s, since bulky high tops (more specifically basketball shoes) don’t really fair well with clean tailored lines. There’s just something special about this type of sneaker since they bring a slightly subversive (since they’re for athletes) vibe since its not always fully white (some utilize retro color ways) and the logos are abstract/minimal. The Nike Killshots come to mind, though there are plenty of other examples out there.
When worn with classic menswear, or more specifically, rugged casual stuff like workwear or milsurp, they have a “cool hipster dad” approach, which I rather like. It’s a bit self-aware and goofy, which is great to make classic menswear more approachable and easy going. When 70s-80s sneakers are worn with vintage casual/milsurp, it has a post-modern vibe as contrasted against Converse, which technically would be the period correct thing to wear with them.
You could also just straight up lean into milsurp with the German Army Trainer, which the guys at Broadway & Sons stock and wear to great effect. It’s a true vintage design, but it’s not as widely worn as a Converse, so they still provide a subversive vibe. In fact, I think it blends the best of a retro 70’s leather sneaker with the clean minimal vibe of a Common Project. They seem to be a favorite of Andreas Larsson of Berg & Berg.
Now the last part of this analysis is ivy, which has historically loved the deck shoe. To me, the deck shoe is the most tailored of the bunch, since like the Moonstars, it also utilizes the closed-lace aesthetic, making them look like a derby just made out of canvas and a rubber sole. It’s no wonder that deck shoes look amazing with OCBDs and trousers/jeans, since they can literally replace a casual loafer or lace up.
As Wooden Sleepers will tell you, the Sperry Cloud CVO is the ultimate and traditional deck shoe, though Keds are also noteworthy (though I’ve heard their quality has declined). I love seeing him, Dick Carrol, and a plethora of other true-ivy enthusiasts wear the CVO, as they provide me with a lot of inspiration. Doek is the elevated version of the deck shoe, though like Moonstar, they are a Japanese brand and are hard to obtain in LA. You would think that LA’s fascination with sneaker culture would make it easy, but it’s probably because a deck shoe aren’t exactly hype.
To me, deck shoes still aren’t as wide spread as Converse or the sleek Common Projects, so I personally think they’re underrated in terms of their use. If you can’t already tell, subversive choices within classic menswear (as subtle as it may be) is totally my jam.
The other preference for ivy enthusiasts are the chunky (but not basketball chunky) athletic sneaker, like New Balance or Novesta, that utilize leather, suede, and fun colorways. Despite their larger silhouette, they still look great with ivy-trad l looks, whether done “normally” like on Jerrod or done a but more “weirdly” (like with wide legs and cropped pants) a la Japanese-Americana. It’s a tougher aesthetic to pull off, and the connotations to certain r/MFA or J. Crew lookbooks can’t be avoided, but I still like it more than just wearing a minimal white sneaker.
The chunky profile also lends itself to be used in streetwear context, when you want to go for a slightly Americana/tailored spin (in my eyes) and not exactly hype.
After years of taking in all this inspo, I finally decided that sneakers do have a place in my wardrobe. Not only is it pertinent to my own developing journey of ensuring that everything in my wardrobe should be cohesive and be worn together, but that I literally can’t live my life wearing penny loafers (though my trusty pennys are extremely comfortable). Some days just require a sneaker!
Like I mentioned early on in the introduction, I was lucky to have already purchased on a few sneakers that actually work with my desired aesthetics, though that didn’t mean a few things were passed on. This is mainly in reference to my Stan Smiths, which I got as a Common Project alternative before realizing that they are just too “clean” for my wardrobe and have a bit of an odd, bulky shape (and not in the good way).
The ones I did keep finally had some ideas on how to wear them effectively without defaulting to something basic or “not me”. I even took the opportunity to get some new ones, just to fill out the collection. And I’ve actually enjoyed wearing them!
Before we move on, you’ll notice that many of these outfits are done with some form of headwear, namely a beanie or bucket hat. It’s just something I do to lean into the casual vibe of the outfit, especially if it leans more so tailoring. Without a slouchy piece of headwear, sneakers seem too intentional, akin to a modern influencer, at least to me. You don’t have to follow this mindset, but I think it at least makes the use of sneakers in casual menswear much easier to get into.
As stated in the big AMA episode, my absolute favorite sneaker are my Vans Authentics. Compared to my Nike Killshots and Onitsuka tigers, they are a more recent acquisition, purchased during a deep J. Crew sale, which allowed me to get the shoes for around $30. They originally had some weird rope-esque lacing (since they were a J. Crew exclusive) but I just replaced them with regular white laces.
I bought these canvas Vans Authentics because like the Moonstars and CVOs, these Vans have closed laces. I wasn’t sure if the deck shoe look was right for me, hence why I went with Vans as an alternative; plus they have a youthful skate/punk vibe to them (at least for the brand in general), which is what I’ve been going for lately, at least in my absolute casual outfits.
Quite obviously, they are a great deck shoe/Keds alternative with my only gripe being the slightly “stubby”, rounded toe which honestly actually sets them apart from the typical deck shoe. In fact, I don’t think many menswear guys wear Vans anymore, in favor of more high quality/menswear-focused footwear brands.
The Authentics have really served me well (I wore them during my Japan trip and my feet didn’t die) and I’ve worn them across a variety of different fits, with both slouchy minimal casual “suiting” and ivy casual fits. Initially, I was concerned with how they interacted with slim and wide legs, but the Vans are extremely versatile. The Authentics’ success really just means that I’m going to wear them until they die, which opens them up to be replaced by proper deck shoes. That may happen soon, because these really are my absolute favorite shoe and I wear them as much as I can.
The success of the Vans eventually lead me to purchase the Sperry Cloud CVOs; I just really wanted to get that deck shoe vibe. It’s actually the newest shoe I own! For reference, I took the same size in my Vans: an 8D (which is a size larger than my Aldens).
Obviously the CVOs have a different vibe to them when compared to the Vans. provides a bit of an older, mature vibe, presumably because they remind me of the Keds worn by Mister Rogers. The blue color also plays with trousers instead of contrast (as white sneakers do), which can make it a bit tricky to wear. The last is sharper than the Vans authentics and the vamp is higher, which also ads to the “grown up” look of the CVOs.
I still prefer my Vans, but I do like the challenge of breaking out the CVOs (especially since I bought them during quarantine). Leaning into the old man look is definitely how I approach it, with more on the ivy side than the workwear. They’re still vibrant and new, but I’m sure I’ll find more ways to combine them as I wear them in and get them dirty and faded.
My other main sneaker are my vintage 80s Converse chucks that I got for $35 at the Rose Bowl Flea Market. These were actually the first sneakers I bought after the Killshot and Tigers, but I still struggled to wear them since they’re envisioned as a punk/skate look, at least as the mainstream world is concerned. They’re beat up and old, but they were really just a great way for me to officially experiment with the Converse look.
Like I stated before, these give a true vintage-youth look It was the latter that made me a bit hesitant over them, since they were a far cry from my “loafer vibe”; in essence, I was scared that Converse were “too cool” for me. As a result, I struggled to wear them openly.
It wasn’t until I decided to wear them while painting that these Converse began to take on a new light. With the paint spatters and fun arrow and smiley, they became my “painting shoes”, subverting the straight forward skate/edgy vibe (as well as the vintage-youth aesthetic) I felt with them and turned it into something a bit more personal and fun for me. Fits my personality, don’t you think?
Now when I wear them, they provide a different allure. Sure, they’re still the more straight forward vintage-casual sneaker, but with the paint, they can contrast strongly against other pieces, much like the paint splattered chinos. If I could compare them to a shoe, I’d make them similar to a PTB or any chunky shoe.
They’re a great alternative to the Vans Authentics, particularly when I want to lean into a more rugged or overt casual vibe. Wearing them with tailoring is kinda cool and subversive, but I really just prefer them with jeans, wide chinos, and shorts (or lazy Sunday burger runs). I find that they work when I want to double down or exude a workwear vibe, while the Vans are done for a clean, preppier look.
Obviously I am not immune to menswear’s love of retro 70s-80s sneakers. But that’s not why I initially bought the infamous Nike Killshots at J. Crew. I did it because r/MFA was obsessed with them as a sneaker that was clean, but not too clean; of course the 80s allure was a bonus. In terms of the overall narrative, they were the first sneaker I bought during my entire menswear journey. However, despite loads of general inspiration from many users on Reddit, I found that nothing in my wardrobe really worked with it (other than plain tees and jeans) until I started bridging the gap between dressed-up and dressed-down Ethan.
While I haven’t really worn them as much as my beloved Vans or the fun Chucks, they still occupy a nice spot in my shoe wardrobe. Since have more noticeable vintage tones to them (Chucks are vintage, but they’re more general), they can be a bit tricky. I actually like wearing them as an alternate those other two shoes. Am I wearing something ivy-prep that Authentics/deck shoes would be great for? Killshots make it more interesting and less straight forward. How about workwear? Killshots change it up.
The Killshots really are like a loafer in that their use (with white socks) with certain outfits create a different (or subversive) vibe when it isn’t the traditional choice. I also like emphasizing the colors on the shoe by wearing them with minimal outfits; Killshots and Converse help tone down “active” outfits.
Lastly, we have my Onitsuka Tigers, also bought at J. Crew about a year after the killshots. At that point in my style journey, I could already tell that chunky, New Balance-esque sneakers were a cool style move, especially if you felt pigeonholed by just white sneakers. But, as you can probably surmise, these were even tougher for me to wear. Dedicated readers may remember this cringe worthy article, where I tried my best to make them work!
I love the silhouette of these Tigers since they are much more subversive than the other choices, and as you saw earlier in the post, there are plenty of great classic menswear inspo (some with an edge) that prove it can be done well. I’ve only had the chance to do it a few times, mainly because some of my pieces aren’t exactly in the same cut as the inspo. Cropped trousers (both slim and wide) seem to help play with the chunky, round last, and I don’t really go too far in that regard.
When I do fight the urge to simply wear my other sneakers and actually wear them out, I don’t hate it. It’s a challenge and a much different vibe than the others, but I like it. Due to the shape, it leans further into the current “big” sneaker trend but not overly so, since it still looks like a dad shoe. If anything, it brings in a modern Japanese-Americana vibe to give an even bigger edge to ivy-prep. For a while, it was the only blue shoe I had, so I just had to lean into all of these details whenever I didn’t feel like just wearing another white sneaker, because despite all of them having different details, shapes, or styles of lacing, they were still just a white sneaker.
As much as we love tailoring and shell cordovan tassel loafers, we can’t survive without sneakers. Whether it’s the guys in the Golden Era of Menswear or our current heroes like Mark Cho and Michael Hill, you can’t escape sneakers. Not only are they just necessary for everyday life (I’d get bored of dressing up so much), but they can still be cool, and the whole world of classic/vintage menswear provides ample inspiration for you to draw from and choose your desired style.
In fact, I think that sneakers are the one thing I’ve come around full circle on. I bought some when I started, but then found it hard to wear naturally and effectively. Thank God I didn’t throw them away, because now, they are just as loved as my Alden loafers. Sure they’re not as elegant and may not go with my full cut suits, but I still wear them very often. After years of expanding my style, experimenting, and analyzing so many other well dressed guys, I finally know how to wear them in a way that embraces my wardrobe, rather than sneakers just being a default I go to.
Now I’m not going to be a full on sneaker head nor do I think my sneaker collection will ever outpace my loafers and lace ups, but I’ve found that I pay more attention to casual shoes much more than I ever did before. It’s all about seeing the sneaker as a welcome alternative to all your other footwear, which honestly, is a great way to approach your closet in general. Seeing the nuances between Vans Authentics and a Sperry Cloud CVO are just as noticeable to me as a low vamp shoe or the almond shape of a toe- these all contribute to the overall vibe of the outfit it’s worn with. And of course, the choice between a Converse or the Onitsuka tiger puts a spin on an outfit as well! You’ll soon find that combinations are endless because everything should work together, at least if we share the same taste (which I hope we do).
What writing this article has taught me is that tracing my aversion and now heavy use of sneakers really just shows a full embrace of dressing down. No one has ever lived in an idealized world where all we do is wear loafers and and ties everyday. But we shouldn’t think of being casual with sneakers as a bad thing. In fact, I think that they’re just a fun as dress shoes and even if you like classic menswear, vintage, and ivy, they fit in quite well. It just takes the right shoe and the right cut.
Though I think we can all agree that the skinny suit and knock off Common Projects is a a look to avoid. But WWII chinos and killshots, blending 50s and 70s in one? That I can get behind.
Always a pleasure,