• Go-To-Hell Ankles

    Top Drawer | Style | Prep Essentials  

    As gentlemen, we adhere to a basic uniform. And why shouldn't we? Our adolescence is inundated with uniformed institutions: prep school, team sports, part time jobs, church.  It's only a matter of time before we push against those very foundations erected to mold us into men.  While some act out in the face of authority figures, on fellow classmates, or by skipping class altogether, others opt for a more passive aggressive rebellion—that of the sartorial kind.  They toy with the details of the very uniform itself, such as the frivolous sock—ditching them entirely.

    Function should illuminate form. The longevity of the men's uniform hinges on this very principle.  Losing your socks isn't as much a betrayal of this precept as one might think.  Come the cool of autumn, it's your ankles that actually keep you cool amid the umpteen layers of wool, cotton, and cashmere preppies run around in.  On a commission last fall to photograph Alan Flusser, he mused I was the best dressed photographer he had ever met. "You should wear some socks though," he admonished.  I listened.  After all, the man wrote the book on style...several of them actually.  I ducked into Brooks Brothers that very day and walked out in a pair.  My implicit compliance lasted all of one day.

    With pants, socks come off as deliberately thoughtful.  And while colorful, offbeat socks non-verbally communicate its wearer doesn’t take himself too seriously, they should never be confused for a go-to-hell disposition.  Just as there is no go-to-hell shirt, so too for the sock.  Bare ankles firmly whisper, "I don’t give a damn."  And that statement is all the more punctuated with pants that look like you outgrew them last year.

    "Socks, wear them only to weddings...and then, well only if it’s your own.”

    —Rand, Making the Grade (1984)

    There’s a nonchalance about it—a passive rebellion to the uniform you’ve graduated to for the office, weddings, black tie affairs, Sunday best, et al.  The more formal the occasion the more blatant the indifference.  Ankles are the go-to-hell sock.

    *previously written for of Rogues & Gentlemen.

    Jun 7, 2011 | Permalink (61) Total Comments

    F.E. Castleberry left a comment on 10/23/2013 at 5:59 PM:

    @Alex—If you love the E28s, then owning one will be a labor of love. Because you will labor. Personally, I wouldn’t recommend one as a daily driver because they are now classic cars (at least 25 years old) and might cause more heartbreak than desired. But should you decide to go forward, find one in the best shape with as few miles as possible (given your budget). Allow the previous owner to have incurred as much of the maintenance and repair costs as possible. Secondly, you’re going to want to set aside at least $250/mo in a savings account for repairs and maintenance you will incur once you’re behind the wheel. If you do this, your Bimmer will be reliable…until another original part breaks. If you set aside the $3,000+ a year, it’s fun to keep up with. If you don’t, it’s going to betray you when you need it most. Good luck :)

    Alex left a comment on 10/22/2013 at 9:50 PM:

    I’m not really sure if this is an appropriate place to ask (and an extremely old post), but F.E., could you, or anyone with experience with old BMW’s for that matter, outline to me the advantages and disadvantages of driving a vintage Bimmer? Are they reliable, safe, etc.? I am looking for a first car, and boy do I love the old 5 series.

    Sid IV left a comment on 5/21/2013 at 9:57 AM:

    Dig your site, its a nice refeshing break in my day to browse a little.  With socks for workdays, I am more function over form, although I lean heavy on yellow and light blue.

    Brooks left a comment on 6/4/2012 at 5:47 PM:

    T-shirts, socks and shoelaces are for children and sports.

    Duckboot left a comment on 5/13/2012 at 9:01 AM:

    Cruising old blog posts on a lazy weekend morning ... After I graduated I spent 2 years on the Carolina coast, driving my 86 528e with dogs, bikes, and surfboards. I miss those days.

    Scott left a comment on 4/2/2012 at 2:54 PM:

    Socks?  WTF for?  I live in Boca and dont wear socks to Court - Judges never flinch.

    Phillip left a comment on 3/24/2012 at 12:59 PM:

    I wholeheartedly agree. My sock drawer is full of argyles and stripes but living in Cali, they rarely see the light of day. I love being a preppy rebel!

    Josh left a comment on 10/1/2011 at 5:34 PM:

    Where are your pants from? Im looking for a good green pair.

    chris left a comment on 7/16/2011 at 9:19 PM:

    Loose the socks gain some style, and let the ankles breath.

    Markus DeVall left a comment on 7/9/2011 at 12:51 AM:

    Have you ever considered making “Outfit of the Day” an addition to your blog? I’m sure your readers will enjoy seeing what outfits you wear for occasions. My other question is have you ever visited Austin, TX and what do you think of the style there?

    P.S. Using the letter to submit comments is incredibly innovative.

    Poser left a comment on 7/5/2011 at 12:33 PM:

    First time commenter, long time reader ;)

    I simply hate socks.  I am inspired by your words sir.  Now I have a reason to ditch them :)

    Pat left a comment on 6/16/2011 at 3:54 PM:

    Awesome post Fred, might be my favorite on this blog.  Great car too, I’m also a BMW enthusiast.

    F.E. Castleberry left a comment on 6/11/2011 at 11:20 AM:

    @Miguel Ramalhão—Yes, this is my ‘87 Bimmer. I really enjoy it.

    @Laguna Beach Fogey—Yes, you can quote me.

    @Tito—I don’t typically sweat much throughout the day unless I’m working out.  In the case of stains on my shirts, I pre-treat them before washing them (ie ring around the collar).

    @AEV—In this particular case, Alden over Gucci because I found the Aldens near new for a good price.

    Miguel Ramalhão left a comment on 6/11/2011 at 11:00 AM:

    Is this your bemmer??? Uau!!!!! Beautiful!!!! I love these 80’s BMW’s… I’m thinking about buying a 635csi…

    bprescott left a comment on 6/9/2011 at 8:02 PM:

    RE: uniforms….what prep school did you attend, F.E.?

    MarkJ left a comment on 6/9/2011 at 9:56 AM:

    I like the look.

    Laguna Beach Fogey left a comment on 6/8/2011 at 9:30 PM:

    Awesome! Love everything about this pic.

    I rarely wear socks outside of the office. In fact I’m wearing a pair of Crockett & Jones chisel-toed beechnut penny loafers as I dictate this.

    “Ankles are the go-to-hell sock.” ~ FEC

    Can I quote you?


    PERCY STEINHART left a comment on 6/8/2011 at 6:28 PM:

    WE DONT WEAR SOCKS…NEVER DID…only in the dead of winter….

    Tad Allagash left a comment on 6/8/2011 at 6:18 PM:

    @AEV - completely agree, Gucci loafers have a higher vamp and look much nicer. Easy to spot the Alden or Cole Haan knockoffs from 10 paces. Trads will tell you Italian shoes aren’t as well made but that’s bs in my experience.

    D Kinlaw left a comment on 6/8/2011 at 4:02 PM:

    My thought process is very simple…65 degrees and above the ankles will be out. in South Carolina thats 2/3 of the year.

    C. Wolf left a comment on 6/8/2011 at 1:07 PM:

    Fantastic article.  I agree whole heartedly.  Socks are too often over rated and this is a great look that can make a statement as bold or subtle as desired by the wearer.

    My father, a life-long prep and president of his company, often sported the sockless look in the professional world.  Not only was he was complimented on his style, but because the rest of his attire was always well tailored and pressed, he never looked out of place or too informal at a business meeting or conference.

    This is a look that I have totally embraced and absolutely love.  So save the socks for the ski slope and the stable.  On all other occasions, say hello to ankles!

    RCN left a comment on 6/8/2011 at 11:49 AM:

    Great blog FEC… My father would never win any father of the year awards, but one thing I liked he never work socks and I always loved the look so I’ve always done it. I’m still amazed even living in the south how uncommon it is to go sockless. I think style and certain tastes are all individualistic, sure there are influences which I think we should all embrace, but at the end of the day it’s what makes you feel good and in your eyes look good. One question, can you recommend a loafer sock? I’ve tried several brands and haven’t liked any of them. I’m often on my feet for long periods of time in very warm climates and I’d like to find a good loafer sock to have when needed.

    Christian Bourasseau left a comment on 6/8/2011 at 9:53 AM:

    Lovely look. I like every detail in this picture :)

    Brohammas left a comment on 6/8/2011 at 9:52 AM:

    While I regularly forego socks, its a look I like, I find it interestingthat no socks with pants says I don’t care what you think, quite often socks worn with shorts says , I don’t have a clue.
    Such messages sent by such subtle things.

    Harvey Lindsay left a comment on 6/8/2011 at 5:34 AM:


    Lara left a comment on 6/8/2011 at 4:42 AM:

    Is it just my imagination or are you likening the wearing of socks to the process of conformity within cognitive psychology? I’m impressed.

    Justin left a comment on 6/8/2011 at 12:18 AM:

    This is sort of off topic, but Making the Grade was shot at my college.  It was called Southwestern College back then, but now it’s called Rhodes.  Half my classes are in the building they used for the dorms.

    Ryan S left a comment on 6/7/2011 at 10:57 PM:

    Brilliantly written Mr. FE Castleberry.  Agreed.  Agreed.  Agreed.  I rather enjoy my notoriety among my peers as the sockless man.  The green “show me the money” pants are a fav in my wardrobe as well, especially with some ankle.  I’ll toast to that!

    Tito left a comment on 6/7/2011 at 9:29 PM:

    Hi Fred, I’ve noticed on a comment that you don’t wear undershirts, I’ve tried that technique a few times and doesn’t feel right though.
    Not only that but the perspiration messed up a few of my woven do to deodorant and sweat. so I was wandering how do you take care of it without getting your woven stained?

    Zach left a comment on 6/7/2011 at 9:21 PM:

    I find sockless for me only works for my plimsols, loafers and sometimes, chukkas. I just could never pull it off with my captoes or wingtips. Just too much sweating, and discomfort. Must be my Irish feet.

    Kenneth left a comment on 6/7/2011 at 8:54 PM:

    A few weeks back, a VP at my company noticed I had no socks with a suit and he said to everyone in the room, “Now there is a guy that can do business and party!” An accurate description I thought.

    I’ve gone sockless for years (except for weddings and job interviews) I’ve done it mainly out of laziness, or maybe I grew up as a southern prep and did it subconsciously? Who knows. Coming off of the tennis courts growing up the last thing you wanted on were socks. I think the laziness of it supports the go-to-hell aesthetic.

    @FEC Cheers for a great article I read it a few days Of Rogues & Gentlemen

    SSI left a comment on 6/7/2011 at 8:35 PM:

    Bit loafers are definitely not prep justified anymore in my opinion.  Over saturation will kill take anything out of that classification.  Tassels on the other hand ...

    AEV left a comment on 6/7/2011 at 8:06 PM:

    Great warm weather look Fred. Why Aldens and not Guccis? I always thought the Aldens were oddly low cut (and struck me as copying the Guccis…for essentially the same price).

    KGC left a comment on 6/7/2011 at 7:35 PM:

    Love the look. I personally despise wearing socks with Sperrys, even if it’s 30 degrees in the morning and I’m at rowing practice. My teammates always ask if my feet are cold.

    Pink Socks left a comment on 6/7/2011 at 7:30 PM:

    I go sockless with certain shoes (drivers, decks, sneakers) even in winter. Then again I am in Australia (but it does get cold here in Melbourne). The right shoes always work sockless.


    Richard Ross left a comment on 6/7/2011 at 5:57 PM:

    My only burrial instruction is that I be burried sockless.

    CC left a comment on 6/7/2011 at 4:15 PM:

    Fred, what’s your take on rolling your pants as opposed to having them hemmed above the ankle?  I find that rolling them gives them more versatility, i.e. you can let them down if you so choose.

    Jon left a comment on 6/7/2011 at 4:04 PM:

    Coastal southerners love to rock the no-sock.  Especially with loafers and boat shoes of course.  I’m slowly trying to expand to oxfords.

    G.S.O left a comment on 6/7/2011 at 2:20 PM:

    Chilly spring in London making my ankles cold !

    Niles left a comment on 6/7/2011 at 2:09 PM:

    the nonchalant and “I don’t give a damn” attitude is really about the whole package though…ditching the socks is part of it. driving an old luxury car could be another…..however, it could be said that an obsession with tailoring goes against this attitude a little.

    Thad left a comment on 6/7/2011 at 2:08 PM:

    Do you keep shoe trees in your topsiders (serious question) ?

    Luis Alcaraz left a comment on 6/7/2011 at 1:31 PM:

    Fred, you look very cool I am wearing the same outfit plust the socks for work today. Sock or sockless is a nice look and I think we should give a little resect to certain occasion I dont want that you finish like Mark Zuckerberg wearing sandals everywhere.


    F.E. Castleberry left a comment on 6/7/2011 at 12:52 PM:

    @Alfonso—I personally do not wear undershirts…ever.  They shift, add bulk, come untucked…and they peek out every now and then.  If you choose to wear one, just make sure it’s never seen.  If that means a deep v-neck, A-line, etc, so be it.  My stance, for the record, is to ditch the undershirt, especially with a polo.

    Alfonso left a comment on 6/7/2011 at 12:44 PM:

    Fred, thanks for a great piece, and you look wonderful, as always. The picture brings up an unrelated question—do you ever allow a T-shirt to show from under your polo or button-down shirt? I’ve seen this done and can’t decide what I think about it.

    F.E. Castleberry left a comment on 6/7/2011 at 12:24 PM:

    @Paul—I’m 5’11” and I wear a 29.5” inseam.  You will not be able to get away with a 30” inseam and avoid a break.  Before you buy your next pair of pants, take that money to the tailor.  It’s about $14 a pair to take them up.

    Angel left a comment on 6/7/2011 at 12:24 PM:

    I don’t mind showing my ankles in the warmer months but once winter comes I pull out my socks, mostly solid colors that are bright. Though I wouldn’t consider myself a prep so I guess I don’t mind breaking the bare ankle rule that you promote.

    Angels Point of View - Street Fashion Photography

    Paul left a comment on 6/7/2011 at 12:21 PM:

    ...One other question. I’m a shorter man, 5’-7”, and I typically wear a 30” inseam…and even that produces a break. Any suggestions as to how to get that “just slightly too short” look to work without having all my pants hemmed?

    tlfactor left a comment on 6/7/2011 at 11:29 AM:

    FEC, are these the Rugby chino pants from this year?  I like the color.

    F.E. Castleberry left a comment on 6/7/2011 at 11:22 AM:

    @Cam—I’m not sure where you are from but wherever I go (and I travel quite a bit) I am typically one of the only guys not wearing socks.  You may read about it in men’s fashion magazines or see it on style blogs…but the reality is that most men still don’t do it.

    cam left a comment on 6/7/2011 at 11:11 AM:

    i go sockless a lot myself but i disagree that wearing socks is deliberately thoughtful…in fact going SOCKLESS would be what is deliberately thoughtful…and more and more so over done by all that it actually is no longer a go-to-hell look

    F.E. Castleberry left a comment on 6/7/2011 at 10:47 AM:

    @Stet—These horsebit loafers are Aldens.

    @Tommy V.—The quote from Making the Grade is tongue-in-cheek.  Determine your own level of appropriateness in social situations.  This article isn’t just about going sockless in the summer…but spring and fall.  That’s where it shapes my sense of style.

    @Cameron—I keep shoe trees in my shoes when I’m not wearing them in order to maintain their shape and absorb the moisture from my feet.  In the case that I’ll be doing alot of walking, I’ll utilize a low profile loafer sock.

    Stet left a comment on 6/7/2011 at 10:35 AM:

    What brand of shoes are those?  They accomplish the sockless look quite well…

    christian left a comment on 6/7/2011 at 10:33 AM:

    I’m not wearing any socks to my own wedding this fall :)

    Dennis left a comment on 6/7/2011 at 10:30 AM:

    loved this article, i refuse to wear socks outside of work and the ski slope.

    Kionon left a comment on 6/7/2011 at 10:10 AM:

    Read this on the Brooks Brothers site. And agree completely!

    Glenn Elliott left a comment on 6/7/2011 at 9:43 AM:


    CC left a comment on 6/7/2011 at 9:28 AM:

    Fred - great piece.  I love it.  Thank you.  The only socks I like are the Boston Red Sox.

    bucephalus left a comment on 6/7/2011 at 8:52 AM:

    There’s nothing wrong with the sockless look if that’s what you like and as long as you’re not in a formal situation.

    Tommy V. left a comment on 6/7/2011 at 8:48 AM:

    Just to be clear, Fred: the only occasion you wouldn’t want to be telling those around you, “go to hell” would be your own wedding?

    I’m all for going sockless in summertime while in a casual setting but there are many other situations that call for sobriety in uniform out of respect for others. Rebelling against convention by flashing my hairy ankles is just not appropriate in any and all social/professional settings.

    Cameron left a comment on 6/7/2011 at 8:33 AM:

    What have you found to be the best shoe and foot care regimen since you go sockless?

    Paul left a comment on 6/7/2011 at 8:30 AM:

    I feel like every men’s fashion magazine spread/advertisement/catalogue that I pick up shows bare ankles..with everything from shorts to suits and lace ups.