One of the many #menswear sins that people like to spout out is to never wear brown shoes with a black suit. It causes repulsion in some, conniptions in others, and a shunning glance to all. Even so, there is one sin that is far worse than even that: wearing white socks with dress shoes. In fact, I haven’t seen too much of it since the 1990s thanks to multiple #menswear bloggers and vloggers who aim to stamp out this inglorious affectation. However there’s something intriguing about pairing white socks with formal clothing that has been calling out to me. This practice started in the 1950s and 1960s, and while I take a lot of my cues from the 30s, its time we look somewhere else for inspiration.
The Ivy Roots?
White has typically been associated with luxury and status, akin to how a bride wears a white dress to appear pure and “unsoiled”. This color has even been co-opted to military and athletic wear since it is probably the easiest color to clean. A colored garment must have extra care taken during cleaning as to prevent bleeding or fading. In contrast (quite literally) a white garment will show dirt or other stains very prominently, making it a simple job to apply bleach or detergent and get rid of the offenders. Additionally, using hot water works best on white garments, which as fantastic cleaning and health benefits (since bacteria will be eliminated).
I always assumed that this was why ivy students wore white socks. Something about rich students wearing white socks resonated reason in my head. The truth is that it probably just came from trends. I can’t find too much on the subject, but one of my vintage menswear expert friends said that it probably had to do with surplus military clothes. This lead to tons of white socks (and khakis!) flooding the market. Maybe these ivy league kids had the same mentality as many of us today: buy whenever there are good deals. Either way, this trend permeated through colleges of the 1950s and 1960s, marking white socks a staple of ivy style.
The Ivy Style website has two brief articles on the subject, with one directly referencing white socks and the other talking about the use of light colored socks. What intrigues me the most is seeing white socks seem to have no real rules. Usually you have to match socks with certain colors; brown shoes usually have patterns and colors while black shoes tend to need black or navy blue to work. However, these ivy guys didn’t give two shits about it. They wore these white socks with everything whether it was black loafers, brown loafers, jeans, khakis, or shorts. Such a huge contrast to typical suiting and formal wear which typically requires rules and more thought. Ivy (and trad) style has been known to be easy and relaxed on the #menswear sepctrum. As a result, these white socks (along with the use of loafers and separates) tend to characterize what it means to dress “ivy”.
White Sock Inspiration
What I love about these looks are that they aren’t too different than what guys wear today. You can see that most of the white sock images from the 1960’s have the gentlemen wearing them with more “casual” outfits. You can see them in conjunction with button ups sans neckties and khakis or chinos. Note that these guys had the tailored casual look down, with a tucked in short sleeve shirt. However, some guys did push the boundaries and wear them with sportcoats.
While white socks tend to have super “old school” connotations (especially with niche streetwear or the 1980-90s), I love them. They provide great contrast between your shoes and pants without having any need to consider patterns or other colors. It’s like a dark navy sock; chances are it’ll go with everything. It might be a bit rakish for some, but that’s why I like it. It has both vintage and streetwear inspirations if you wear it out today. Very different than the peacock method of wearing the craziest socks imaginable, which (in my opinion) is a mark of a beginner since crazy socks are the current trend of #menswear.
Here are a few of my favorite modern looks with white socks! These are courtesy of Benjamin Levy, another ivy-inspired Armourer. Note that he wears them with both light and dark colored pants! I believe they look extremely natural on him, as they aren’t calling too much attention. Perhaps that’s the key to wearing white socks!
For my take, I decided to follow Mr. Levy’s lead and wear my white socks with jackets and ties instead of going “casually tailored” as men did back in the 1960s. I normally wear slightly patterned socks when I want to stand out, but the white socks provides a contrast on a whole new level. They aren’t athletic tube socks but simple white dress socks from Uniqlo. They don’t have a “fuzzy” texture and are actually ribbed and soft like a dress sock should be! I wear mine with both white and black loafers so you can see that they aren’t all that different than other socks. Additionally, both of these outfits have a slight ivy inspiration!
Brown Tassel Loafers
Here’s my first outfit with trying out the white socks. I went with a pretty neutral outfit (which is pretty ivy/trad), consisting of earth tones and a slight color pop within the shirt and tie. The jacket is 3-roll-2, an ivy staple, in a lovely beige color that contrasts with the deep brown of my high waisted trousers. It may seem like this outfit is suited for fall, thanks to the light fabrics of the pants (rayon) and the jacket (half lined wool), it works comfortably in the warm California weather. It’s hard to see the white socks in the outfit at first glance, but they’re in it!
The true measure of an ivy look lies within the shirt and jacket. The jacket has been desrcibed already, but just look at that button down collar! Having a great collar roll makes the ivy look. However, I still decided to let my 1930’s styling shine so I used this print tie to complement the vertical stripes of the shirt. Remember that pattern mixing (along with stripes + prints) is a great 1930’s styling point!
Here’s a great look at the entire outfit together; you can also see how the socks really pop in the outfit as they contrast greatly with the dark brown pants. Normal guys would definitely have worn a light brown or even a blue sock, but you can’t deny the appeal of the white sock. It calls a bit of attention to itself, but remember never to wear it with the typical, terrible dress shoes. With brown loafers, the choice of white socks seems more intentional as a throwback to “old school style” instead of pure lazyness or indifference.
Southwick Jacket, Custom Shirt from Natty Shirts, 1930’s tie,
1960’s Rayon Pants, White Socks from Uniqlo, AE tassel loafers
Black Penny Loafers
This next outfit is a retread of the outfit I wore on my trip to San Francisco; brown jacket, grey pleated pants, and black penny loafers. The outfit is more rooted with my typical “Italian does 1930’s style” due to the striped shirt, wide lapels, and geometric print tie. Not exactly true ivy, but the simple ideas can be seen there! I definitely had to dress up the top half to prevent myself from looking like this. Having a tailored jacket, expert pattern matching, and slim (but still pleated) trousers definitely help too!
The combination of brown flannel and grey trousers definitely make this a great fall piece. Normally black shoes are reserved for more formal outfits but having black loafers bridges the gap between formal and casual. I have a trad friend who abhors black loafers due to this reason, but I think they’re a great way to anchor down an outfit without being too stuffy with a lace up!
I really wanted to include black loafers in this article due to the huge amount of contrast between the sock and the shoe. It does have a bit of a Michael Jackson vibe but you could still argue that he had great style. The contrast that it creates is just something unexpected and a big style move that most guys out there won’t do. Overall, it just depends on how you pull it off. With light wash jeans they look 1980s; with tailored garments its a rakish 1960’s affectation! If nothing fits well, then it looks terrible.
Flannel Suit Jacket from Suit Supply, Shirt from Massimo Dutti, thrifted tie,
Thrifted pleated pants, AE Penny Loafers
White socks are a definite oddity to see in menswear. While they have roots in one of the greatest movements in menswear, they are currently ruined by men who wear them with baggy suits, thick/wide ties, and square toed black shoes. It’s that reason that wearing them intrigued me so much, the balance between breaking the rules and going vintage. It’s also a stark rejection of the #menswear/dapper bro movement where every instagram famous brand-whore is advocating “crazy/fun/patterned socks”.
Wearing white socks (and everything else tailored) will give you a throw back ivy look, which most people won’t get. They won’t know that you aren’t wearing white athletic socks from Walmart. The most you can do is keep your look tailored and well put together and make sure you wear thin, dress socks. Tailoring in general is the key to pulling most of the stuff I show on this blog.
The glances and second-looks I got to my feet while wearing these outfits is one of the reasons I started this blog. My style doesn’t adhere to a single set of rules; it goes from true vintage, to modern #menswear, to semi-streetwear, to taking cues from all of the previous styles. White socks are a vintage affectation that no one really does well anymore, like the fedora, the tie bar, or even double breasted suits. It’s too weird for many guys who appreciate tailoring and the guys who don’t dress up at all. Wearing white socks with tailored clothes isn’t quite streetwear or sprezzatura. It’s both and neither at the same time!
If you want to get ones of your own, make sure they are ribbed and aren’t too white since the contrast will be even more apparent . The ones featured in this article are from Uniqlo; they are off-white but they still look pretty bright in the pictures! It’s not a look for everyone, but I hope you get some inspiration to try something new and stand out when suiting up or dressing up. Taking cues from the past and putting your own spin on it is a great part of personal style; I’m not here to tell you how exactly to dress up but to show you an example where you can still break the rules in suiting and stand out in a classic way. I’m not hating colors and patterned socks, but you can still have personality with going ivy and wearing white socks instead!
Always a pleasure,