Oh boy I can’t wait for the shitstorm that’s about to erupt from this one.
I live in LA and it’s fucking hot. And when it’s hot-as-balls, you gotta take steps to be comfortable! Now I’m all for keeping things dressy, to a certain extent. I take care to keep some full cut linens and knit polos for days when it’s unbearable; there are even times when I actually like to break out shorts and a tee. But what about footwear?
A lot of guys like to shun sandals for a lot of reasons, mainly because it’s so inherently casual. Tons of Youtube “menswear” guys shout plenty of reasons: they expose your foot, provide no real shape, and aren’t “dapper” enough. like a lot of the controversial stuff on this blog (knit caps, berets, bucket hats), I was initially against them. But that was during when I was over correcting (which I briefly talked about it in the sock article) and felt that formal = stylish. Now I’m much more open to different styles and certain odd pieces, like the Birkenstock Arizona, that are a bit more subversive (if you can even call it that) to traditional fashion choices. Plainly said, we like weird things on this blog.
Whether or not you like the look of sandals and their open-toed glory, the fact remains that they are incredibly comfortable and appropriate for warm weather. I mean I love my espadrilles, but a canvas skin and rope sole isn’t all too utilitarian or ready for hard wearing. Now my Birks have been worn a lot since I first got them, but it’s mainly in a lazy-man context, for doing chores/errands near the house. I mean why would I put on a lace up (or even a leather loafer) if I’m just going to be lazy?
Honestly, I don’t mind sandals. I don’t think they’re ugly or terrible, though keep in mind I’m not talking about flip flops, athletic slides, and whatever the fuck these are. I’m mainly talking about ones that are elegant, made of leather or suede, as they are easily worn with classic, non-dad clothing. Some menswear guys agree: Articles of Style was my first exposure to the Jesus Sandal; Male Fashion Advice even recently put a post about recommending Birks for summer wear; and Put This On kept it going by providing a list of other acceptable sandal types.
Jesse Thorn (of PTO) recommends that they be worn with loose pants and fun, printed shirts in keeping with the fun/casual nature of sandals. I definitely second this, as I think that the exposed “foot” that lacks structure (compared to a closed-toe shoe) is best served with a wider leg with a bit of a crop or no break. You can’t really wear overly long pants with sandals, with excess fabric breaking all over your foot! In general, keep the summer vibes at the forefront of the outfit in order to really pull it off.
Inspiration
Occasionally I would see a couple of people rock Birkenstocks on MFA with some more minimal/casual attire. Obviously it’s best done with shorts, but if you read their post, they also recommend it with loose pants and denim, with either a breezy button-up or a tee. What I like about the following pictures is that they are still semi-dressy but incredibly casual at the same time. It also seems vaguely Asian-esque to me, maybe because I’ve seen my grandparents wear sandals with rolled up trousers around the house. It’s got some casual 1970’s vibes as well.

A little out there, but I like it.

Super good.
You can really see how easy going it is. Like I said earlier, these outfits really lean into the casual nature without doing and offset the slightly clunky footwear with full cut trousers (or slim) that are rolled high. Sure they would work great with a tee shirt and shorts, but I tend to gravitate toward more interesting ideas.
Now there have been a few times when sandals have been worn with menswear that isn’t as simple as a shirt and pants. I think that it takes cues from old vacation wear; I remember seeing pictures of guys wearing sandals and espadrilles with pleated trousers back in the 1930s-1940s. It also gives me a sort of hippie or a louch 1970’s aesthetic that I can definitely get behind. While Birkenstocks are my preferred choice, these gentlemen go with Jesus sandals for an elegant approach or huaraches, which are shaped more like a regular shoe, but are “ventilated” (the Birkenstock clogs would be a similar option). The latter opts for an “old man” aesthetic (they were common in the 1940s-1960s for sandals), but you should know that we like that.
Again, you can pay attention to the tailoring; the trousers are slightly higher and fabrics are all summer appropriate and have a bit of texture to make it more casual. You’d be foolish to wear sandals with a dressy worsted suit or a tweed trouser. And while slides are more streetwear choice, it’s really hard to make them work well unless you are damn confident and have an aesthetic that fits in with them (like athleisure). It’s better to pick a sandal that has more “structure” that covers more of the foot if you want to stick in the classic menswear camp. And obviously flip flops are right out.

Just imagine the espadrilles are sandals.

1940’s ad.
While I was no stranger to some of these pictures before, it was actually the picture of Tony Sylvester that inspired me to make this post. The photo was taken by Styleforum at the most recent Pitti Uomo, where Mr. Sylvester is seen rocking huaraches with a green seersucker suit and a 1960’s tiki-esque aloha shirt. It’s so badass. I was intrigued by his pairing that I decided to do some looks on my own. Not copying, but just to see how I would interpret sandals and classic menswear.
Unfortunately, the only sandals I own are a single pair of Birkenstock Arizonas, but that’s okay! Sandals aren’t really something you need multiple versions of (though I wouldn’t mind a pair of disposable flip flops for the pool). I’ve come to embrace their chunky silhouette and it made for fun challenge on how to create some warm weather looks that fulfill my love of classic menswear.
I’ve made some looks that I think are way better and more congruent with classic style, instead of the monstrosities I came up with when I first got the sandals.
My Looks

This first look is probably the quintessential summer look for me and a perfect one to wear sandals with. It’s fairly simple, consisting of a vintage sportshirt and my high rise Stoffa trousers. Yes, espadrilles or sockless loafers would have been the “correct” piece but we’re not always about making the correct choice all the time; I also don’t think that a rope sole fairs better than a thick, sturdy cork.
Even though I’m wearing sandals, the entire outfit is still a pretty smart combination, almost a modern interpretation of a 1940s-1950s vacation outfit. The main idea could be translated to different things; you could wear a fun aloha shirt or even trade the chinos for linens or even wide legged, cuffed denim. And like I stated before, the bucket hat only adds to the slouch relaxed vibes. It makes it more of an intentional casual look instead of simply wearing sandals with traditional items.
This next one is more of an experiment and not something I’d consider wearing as a full outfit. My first thing was to try and see how sandals would work with a full suit. As I don’t have many casual suits other than this brown cotton one, it’s what I went with. Instead of an aloha shirt like Tony or attempting to try a tie like Nicola Radano, I just leaned into the casualness and wore an indigo striped tee. It’s sort of inspired by an outfit worn by Camoshita-san at last year’s Pitti, but I’m sure I’ve seen a similar look in a Japanese magazine.
I’m not a huge fan of tee shirts and suits, especially when dress shoes are worn with it, but that’s why I think the sandals are a better choice; again the bucket hat helps tie it in. It’s a pretty minimal look (all blues and browns) that has enough casual nature (cotton suits are GOAT) that it’s not too out of place. Honestly, it would probably be best without the jacket!
Can you tell that striped tees are great? If you don’t have any, they’re really useful allowing for some visual interest even when you’re dressing down.
These next two outfits are inspired by the rugged vintage style of Tony Sylvester. The top one has some slight safari esque vibes due to the linen chore-blazer and the gurkha shorts. The use of a tan top and bottom layer give it a pseudo-suit vibe, but the hues are different enough to make it work. I think that the faded leather of the birkenstocks helps tie in the brown theme of the outfit. I honestly can’t think of any other footwear that would be better than the sandals here other than a white sneaker, and even then the vibes would be different. Plus, why wouldn’t you want your feet to breathe?
This is one of my favorite summer looks (shorts are a no-brainer) and I’m probably going to do this theme again.
Speaking of being breezy, this is another favorite of mine. Worn to the Rose Bowl Flea market, this again has a safari/military vibe due to the browns and the fact that I’m literally wearing an vintage army-inspired cap. A lot of that Sylvester/Newton casual style incorporates a lot of loose fitting vintage military-esque clothing, and subverting it slightly with things like a high cuff, a silverbelly fedora, or dressy footwear.
I’m not as bold as they are, but I do like the ideas they have! So for this Birk outfit, I wear a 1930’s rayon polo (which is super light) and some wide legged Uniqlo trousers that are rolled pretty high to let my feet breathe. The chunkiness of the Birks help ground the hovering hem. I think this outfit is perfect for a casual day, just add a jungle jacket for the evening to really lean into that americana vibe.

With a chambray shirt and gurkhas.
I actually wore this when shooting an editorial for the Wellema Hat Co at the Huntington Gardens. Because it was a hot day, I wanted to make sure that I was comfortable but not dressed sloppily, as I knew I’d get some pictures of my own in such a beautiful location.
I used the opportunity to revisit the ideas from the first two outfits. I kept the striped tee (since I didn’t want to wear a button up) but swapped the suit for an odd pairing consisting with my navy hopsack jacket and brown 1950’s rayon trousers. Again, this gives me some Japanese-esque vibes that I’ve been really digging for casual attire, if you haven’t noticed. While the navy blazer is such a traditional piece, the fact that it’s unstructured and softly tailored allows it to be worn seamlessly with both chambray shirts and breton stripe tees. I don’t think any of the pieces look particularly out of place here; the brown trousers help make it a confident choice, more so than if I went with boring khaki or with try-hard white. And again, the Birks help anchor in the entire thing. If I went with Jesus sandals, it would’ve been too “dressy”.
The outfit is like something a stylish grandpa would wear on a walk in the park, and I love that! It’s dark and minimal, yet perfectly suitable for the warm weather
Conclusion
Even though we all like classic tailoring and prefer it over “sloppy clothing”, I don’t think that means that we should take an elitist stance toward sandals. The fact remains that they are a wardrobe essential for the spring/summer season and offer more air and comfort than a leather loafer or a rope-soled espadrille. And there are plenty of ways to make them stylish instead of delegating them to lazy outfits that end up using cheap slides and flip flops; it just takes some inspiration.
Obviously the easiest way to wear sandals are with inherently casual clothing, but that doesn’t mean that you always have to wear shorts and tees! It looks smart with slim-straight or wide legged trousers/jeans that are rolled up quite high in order to provide visual contrast and interest. And then when you want to try and use them in a classic menswear context, you can always just lean into that vintage vacation vibe. Wear those fun cuban collars and put them outside your lapels and be sure to wear earth tone tailoring in summer appropriate fabric. A lot of great dressers wear them today and pull off the look so well. You can not wear them with “normal fabrics”; that’s where sandals and classic menswear don’t work.
While there are different styles that call out to to me (Jesus sandals and huaraches), I’m glad that this post allowed me a chance to revisit my Birkenstocks. Like I said early in the article, they were simply regulated to lazy, at home attire. Elevating them with legitimate outfits really helped me see how cool/interesting they are and let me stretchy my creative juices by creating some different-than-usual outfits! The dark brown leather straps helps them work seamlessly with trousers, providing a chunky/structured silhouette that makes me think of a sizable blucher but just opened. Plus, I like that they are fairly minimal in nature and not as busy as the multitudes of straps or perforations on Jesus and huaraches respectively.
So don’t knock out sandals just because you like tailoring! Lean into those summer vacation vibes and wear them with casual trousers and shorts. I think you’ll like letting your feet breathe.
Always a pleasure,
Ethan W.
Love love love sandals with traditional menswear. Recently picked up the monk sandals from Sid Mashburn – sick. I rock em with casual wear as well as dressier chinos and a sport coat.
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Monk sandals! That sounds awesome!
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