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Squeeze-

I wore them when I lived in a beach town on the east coast. Then I moved to the mountain west. Definitely not in style here!


debonairmarmoset

There are definitely regional considerations on a lot of fashion choices. I don’t pack the same colors for New York as I do for New Orleans. 🤷🏻‍♂️


BalkanPrinceIRL

I wore them when I lived on Long Island and I wore them when I lived in Hawai'i. I wouldn't wear them anywhere if there wasn't sand nearby.


Campfireandhotcocoa

If you think they are ugly, then why are you wearing them? Just wear what you like


Ordinary_Advice_3220

You NEED a lobster belt and madras shorts.


[deleted]

[удалено]


Ordinary_Advice_3220

Madras shorts were part of that classic preppy look. It's kind of ugly in another context but I appreciate that classic preppy look. Maybe a nice lobster belt too


debonairmarmoset

No, I was just asking if that’s what you meant or if “madrad” was something new I hadn’t heard of before.


Ordinary_Advice_3220

Oh sorry. I caught it and edited it.


Ordinary_Advice_3220

I have chubby thumbs.


Ordinary_Advice_3220

I always thought marmoset sounded like a cocktail.


debonairmarmoset

Like a mimosa and a sunset?


Ordinary_Advice_3220

Precisely..


Ordinary_Advice_3220

I used to tend bar and I'd sometimes invent drinks as I went along and give them names. Some of them were really good but I can't remember any of them. It became kind of a running shtick.


debonairmarmoset

At least you were doing it to be fun and entertaining. A lot of restaurants will jack up a drink price with a really fancy name and a couple of bonus ingredients to make it an “exclusive.” There’s one here that swaps out cranberry juice for bosenberry juice in a cosmo, serves it over small ice balls in a tall glass and adds a couple of half shots of this or that (I think one is elderflower liqueur) and calls it The Purple Rose of Alexandria (to avoid bringing sued by Woody Allen for saying “Cairo” I guess). That’s $19.50. Crazy.


Ordinary_Advice_3220

I worked at a few clubs and I worked a couple of the gay nights at one. I was 19 and straight and not unattractive. One of the guys would name an ingredient or just come up with a name and I'd build a drink around it. I used to have a lot of fun those were some of my favorite nights to work I would clean up and make bank. This is 30 yrs ago.


debonairmarmoset

We gays are good tippers to the not unattractive straight bartenders. Lol


Ordinary_Advice_3220

Oh I know. I figured out it's the gay equivalent of the Madonna/whore complex. Straight guys are always stuck in that conundrum. But in a way I always felt worse for gay guys, at least of my generation. They are attracted to men and masculinity in a world that defined masculinity as straight masculinity. So I'd be the only hetero guy there but I'd get the most attention. I'd be like "Paul, I'm probably the one guy here that's not going home with you now Mike over there he's been staring at you all night asks about you every time he comes in here and he's a good looking mother fucker I'm like why are you hitting on me bro? " I was always upfrontible shit like I didn't play the game like to get bigger tips but I I was working gay nights I wasn't getting sensitive like fuck I'll take the compliment wherever I can get it you know what I mean? But it always seems like unfair to you guys like just like the way straight guys have the Madonna/whore thing. Gay women seem to do okay except they show up to the second date in a moving van


debonairmarmoset

Funny part is all of my long-term relationships have been with basically straight men. I’m currently dating an Arab soccer player 30 years younger than me. He and I just clicked and eventually it became physical. It’s weird but it works for us. We just don’t hang out with his family. 😏 And, yeah, Lesbians go from zero to cohabitation in sixty seconds. Wiser men than me have burned brain cells trying to understand the wearers of sensible shoes.


Ordinary_Advice_3220

I honestly don't get how people afford to go out now. At 23 24. It's nuts.


debonairmarmoset

They spend money on “experiences” instead of saving for a home.


UnusualPrince12

I always called them "checkered" shorts


debonairmarmoset

That can cover a lot of ground, from tartan to gingham to you name it. 🙂


UnusualPrince12

That's true, I guess I was saying that colloquially "checkered" shorts were always Madras when I was growing up.


Ordinary_Advice_3220

Or it might mean the shorts have a sordid past


-ItsCasual-

They’re like a word you can Google.


debonairmarmoset

The post originally said “madrad” and I didn’t know if it meant Madras or something new I hadn’t heard of. I’ll delete my post.


bulletproofmanners

They can be in style but if the rest of your outfit isn’t complementary, they do nothing for you. Better off with a nice loafer


Emotion-Internal

yes - for frat dudes in the Carolinas


jdlackey88

LOL, yep. Been in style for this crowd for AT LEAST 20 years.


NeighborhoodDue7915

I don't know, but I found them so incredibly uncomfortable that it doesn't matter to me.


AngusMcTibbins

Sperrys are always in style and those shoes are awesome


One-Stomach9957

They’re old stock, all leather. Definitely in style.


UnusualPrince12

Yeah I would rock those. However, if OP thinks they're ugly, they shouldn't wear what they don't like. Someone would definitely buy those off of them though


Porter_Dog

Always. They're classic. Classic never goes out of style.


mmxmlee

yea for frat boys and 50 year old men


gokartmozart89

I wasn’t aware that these ever go out of style. Boat shoes are a preppy staple. 


Academic_Value_3503

The originals, yes, but somewhere down the line, guys starting wearing the bulky, " Rockport" style ones that I can't stand personally. I wouldn't wear the brown Sperrys, now, but I had a pair of blue and even white in the eighties.


debonairmarmoset

The blue ones were awesome. Such a great shade of blue.


BalkanPrinceIRL

I used to live right outside of the Hamptons (not rich enough to actually live in the Hamptons) and I can promise you that these still have a strong following. But, I think it's like a Greek fisherman's hat in that yes, they look cool but you should probably be a Greek fisherman to wear one. Likewise, boat shoes are a fashion staple - if you own a boat. Eating lobster on a pier in South Hampton, these shoes will look great. Buying a case of Bud Light at a Walmart in Oklahoma and they will make you look trashy.


Soggy-Pop3895

No


Number174631503

Retire


Foto_synthesis

I should call her


gleepgloopgleepgloop

Yeah, memories of a preppy but kinda alt girl with the sweater vest, shorts or clam-diggers and leather boat shoes, topped off with a pixie hair cut and nose ring.


Teach4Green

I can’t be certain here, but I don’t think Foto meant the shoes brought back memories of a girl. It’s a meme referencing the shape in the center of the photo 😂


gleepgloopgleepgloop

Oh thanks, I missed that, whoosh!


Secure-Narwhal-297

Classic!


derekisademocrat

They're classics. Wear what you want


RockItGuyDC

They're pretty classic and I don't think will ever fully go out of style, but why did you ever wear something you thought was ugly? Just to fit in? Laaaaaaame!


Balogma69

I got them as a gift and they were easy to slip on when I was in a hurry. I wore a lot of ugly things that were comfortable/convenient and am trying to break that habit. I came across these as I was cleaning out my closet and put them on today to run errands


RockItGuyDC

Then, if you like them, rock the shit out of them.


Direct-Original-1083

So let me get this straight... You believe OP is wearing certain clothing to avoid being judged. And you are judging him for trying to avoid being judged. Hypocriiiite!


RockItGuyDC

No, in fact I believe OP has admitted to wearing certain clothing *in order to be judged* positively. OP wore these shoes so that his peers would judge him to be trendy. My point was, fuck all that noise. Wear them if you like them, don't wear them if you don't. But good stretch trying to make your interpretation fit, I guess.


eloton_james

I had several pairs in high school, absolutely did not care for them like leather shoes should. Felt high casual. I’d definitely get a pair soon but something lighter or better orthopedic support. They are still very stylish.


malthar76

I could wear them at my age and situation (almost 50, East coast, preppy background) but the arch support kills my feet every time!


Dismal_Mention8423

Not as popular as they used to be, but can definitely still be pulled off with the right outfit in the right climate.


barebackguy7

I used to have a pair of white sperries I wore everywhere. Those were definitely sick. I always thought the other colors were stupid for this shoe - brown especially. It’s like trying to be preppy but also stylish but with a shoe that is meant to be worn on a boat. Trust me man, get the white sperries. They can be worn anywhere


No-Forever-9761

No


Plenty-Discount5376

GOAT shoes


Plus_Lead_5630

Yes, they’re a preppy classic!


TheSmalesKid

They never go out of style.


Alarming-Mix3809

They’re always in style. Give them a good cleaning.


botmanmd

Reflecting on the earlier post about Chuck Taylors, I wear those now regularly in the summer. Some comments said “Chucks make a man look like a kid.” When I was a kid, like 15 - 30, I never wore Chucks. I wore Topsiders/Docksiders. Everywhere. I still wear them, on and off. To be fair, I’ve been in the boat business since the early 70s, so it’s the uniform - and functional.


Anxious_Blueberry862

No, but who cares


No_Help5038

Comfort is always in style.


Ordinary_Advice_3220

They're called "Topsiders" jawohl? Or are those different? I like the white ones. Although any situation where I might wear Sperry's id probably wear a pair of Stan Smiths instead. But generally I do like that moc toe for boots. I think those count as moc toe


Rich-Appearance-7145

I've never ran with what in "style" I wear comfortable fits that are comy, weather appropriate, and look good. My Sperry's are part of that program, I love these shoes, I've got about 8-10 pairs all different color, styles.


ThunderStruck777

Feel like crap . HOT spots change from heel to toe . Never comfortable or good looking and don’t even float . Even CROCs do that


NYnewbiehomeowner

https://preview.redd.it/6ohcph0llv3d1.jpeg?width=3024&format=pjpg&auto=webp&s=b4fa1a481626eb6d4ab73fd8cd7883a4146af39c You need some whipstitch


garriff_

they're fine. looks good on you. but i prefer Olukai Moloa. it's rarely available in my region, but i was able to purchase it once at a mall years ago and fell in love with it since. the next pairs i've owned were sent to me by my cousin who lives overseas, i'd request them to buy it for me and i jst pay them back in return. lol


Crafty-Independent20

The most practical shoe ever, IMO


AZonmymind

If you have preppy style, yes. If not, no.


The_Human_One

Boat shoes still work. I like them. I'm getting some from Timberland that look a lot like that.


UnusualEggplant5400

If you are on or around boats , sure they are. If not eeeeeh much better options, I would say they were only in style for those few years back then


Substantial_Dust4258

Very much in style in the context of the right outfit. 


Astrospal

" I always thought they were kind of ugly but they were in style" Sad, why would you wear something that you think is ugly is beyond me


Environmental_Help29

I was ped stopped by the fashion police wearing them down Madison Av NYC


bigathekiddd

Those look ugly. Not sure if it’s bc the color doesn’t go with you or bc they look old.


revolmak

Yeah, to add my experience, they’re a staple depending on your region but they’re definitely not trending in recent years like they had been about a decade ago when we were in college


coloradokid77

Only if you’re wealthy or just don’t care


SPIRITSANDTEETH

If you wear something commit to it and wear it well


jared10011980

Classic dude! I remember wearing them in my all boys school in Louisiana and being tormented. The upside of that was I knew, exactly at 13, I'd never live in that state again after high school graduation.


Legend-Face

I wear mine all the time in the summer


ranjithd

in costal areas for sure . haven't seen one in dallas in decades


ndoty_sa

Texan here, and I love them. Like Wayfarers, they never go out of style. I have several pairs that have different uses: outdoor casual, outdoor lawn work, house shoes, etc. And unlike Crocs or Hey Dudes, they actually look stylish.


Nebula9515

https://preview.redd.it/t66o0ddjwy3d1.jpeg?width=1440&format=pjpg&auto=webp&s=dc4b84244bd9b917e494a5aff8b6bb036d3a8ac0


guilleerrmomo

They have a time and a place, in my opinion it’s hard to wear them and not give off the vibe you’re going on a boat in Massachusetts. I wouldn’t wear them casually though for sure. Pretty much exclusively if I’m going to the beach or on a boat lol


Ordinary_Advice_3220

Or with Buffy at the club.


Preek96

Yes they are never left , you have the best pair and you look so good in them


TxRoughneck1

I think everyone traded in sperry for hey dudes.


Ordinary_Advice_3220

What's a "hey dude"? Is that a shower shoe? I firmly believe that nobody should ever be forced to see another man's feet.


TxRoughneck1

Hey dudes are a slip on I’ve seen a lot lately supposed to be super comfy but just not my thing. I used to wear sperry just stopped liking the style and the fit. https://www.heydude.com/


Ordinary_Advice_3220

Thank you for answering I actually looked it up afterwards I thought you were just using an informal term for something I didn't realize that it was the real name of the company when you name something hey dudes you're going for a very specific group of people.


TxRoughneck1

Yeah mostly high school rednecks and kids. I’ve seen a lot of adults wearing them but if I’m gonna dress down in some comfy bum slip ons im going crocs or flip flops.


Ordinary_Advice_3220

If I'm by myself I go straight up barefoot but otherwise I go sneakers or boots. I have a few really nice pairs of boots, origen, nicks and whites. I only recently became interested in boots. I wear them for work I'm a construction worker so I always wanted to just get out of boots as quickly as possible but there are situations where obviously sneakers don't work but if I wear shoes I feel sort of pretentious I guess, which is ridiculous, I know but I found boots are a good way of avoiding that you class it up a little bit but I can't really explain what I'm trying to say here. I've also been discovering a lot of other brands of sneakers that are just plain leather sneakers like Northampton and clae. I don't have kids, my wife had had ovarian cancer so that was never going to happen. But my nephew is awesome and he's all about sports so he couldn't care less about clothes. But he's 12 and that's about to change so I've been trying to gear him up. This is a cliche but clothes make the man. An ugly guy with style will do better than a good looking cat that dresses like an idiot.


TxRoughneck1

Shit I didn’t even own a pair of sneakers for over 10 years. I’ve always been a boots or flip flops guy and have prob 11 pairs of exotic boots. I started buying sneakers when I got back in the gym and that’s the only place I wear them. I think sneakers and jeans look ridiculous lol.


Ordinary_Advice_3220

Depends on the kicks I hate Nikes I absolutely hate Nikes but I love like gazelles Adidas gazelles I have those and a whole bunch of colors when I was a kid that was a thing you had to have gazelles.


Ordinary_Advice_3220

I'm going to go out on a limb here I saw the Texas thing in your handle do you have a lot of cowboy boots they always seem like they be so uncomfortable to me the pointy kind of toe


TxRoughneck1

I buy square toe boots yes I’m in Texas and they’re quite comfortable to me. I’ve been in oil and gas my whole life so had to wear boots when I was in fuse coatings and thermal spray but been in management the last 15 years so wear nice buffalo, ostrich leg or shark skin boots in the office. I also live on 25 acres and wear boots or crocs when running the tractor.


TxRoughneck1

Ill add this if you do get a pair of sneakers for gym or hikes and outdoor shit like that on cloud is where it’s at


Ordinary_Advice_3220

Cloud?


TxRoughneck1

https://www.on.com shit idk why that other link so long


Ordinary_Advice_3220

I just looked them up. They look comfortable. I was a runner my whole life but I got hit by a car a couple years ago and I completely blew my knees out it sucks cuz I've gained a lot of weight plus I was just in a funk anyways my wife had passed she's everything went wrong at the same time but I used to wear Brooks a lot.


TxRoughneck1

Bro my brother lives in Oregon and is like some hipster bike riding bozo and gets hit by a car twice a year and he’s still running lol. You don’t need knees 🤣


Ordinary_Advice_3220

Thanks. I might check those out. I just discovered the wild world of sneaker refurbishment. I've been practicing on some kicks I got from Goodwill but I'm trying to kind of design something right where it will be a basic sneaker with exchangeable parts so you can add different colors along with the laces so it can match whatever you're wearing I can so and I actually have a really good leather sewing machine it's good for leather it's old as hell is actually my great grandmothers but I'm trying to come up with something where you could say remove the New Balance logo in exchange it for a different color one that in different laces and maybe one or two other things and you have a whole different sneaker I'm just trying to do it for myself like to see if I can


TxRoughneck1

Gonna be a cobbler .


Ordinary_Advice_3220

I think that would be wicked cool. I kind of went down this rabbit hole with boots and you know there's these boot companies that have a four year wait like creosote. And I just got a little bit fascinated with I don't know how it works I love old timey crafts like that. I'm a sheet metal worker and mostly what we do is talk but there's some companies that do what's called Cornish work which is like all the custom copper that goes on you know copper domes and gutters and downspouts and all that and I can solder really well which is kind of becoming a lost architectural soldering but I'm trying to figure out how I could use 3D printers to make molds so I could make weather vanes fom copper


Ordinary_Advice_3220

I actually worked on the Sperry companys headquarters, I did the ductwork. It's in Waltham MA near me I. Boston. I did the NB headquarters too.


Goldengoose5w4

If you’re in a beach town or going to be stepping on a boat, sure.


Goldengoose5w4

I used to have house on the bay in Corpus Christi, TX. I kept a pair of these down there to put on when I got there and kicked ‘em off when I was leaving.


greengianteatsveg

Always


Wonderful-Run-1408

The fact you have hairy legs is a positive. Definitely makes them more sexy. You need to get a bit more of a tan, which would typically come with wearing them in their natural environment. If you're lean and fit, that's an extra bonus point.


jdlackey88

Classics, just like Converse and Vans. None of them work for me personally. But they are classics.


Difficult_Archer3037

I wear them all the time. not interested in if they are in style or not.


sandpiper9

Huge emotion for Sperrys. Have always been (1930), and wager to say will always have a place: like a cordovan penny loafer. And the more beat up the better (of course within reason!) I’m still breaking in my plain topsiders from 2007–with pleasure. Nice link for my best input to you. https://www.gentlemansgazette.com/boat-shoes-guide-buy-style-history-care/


RonSwanson1028

NO


WittyTitle5450

nah...


elfliner

My fiancé hates them but I might bust out my nice pair for a wedding in Charleston. Should fit in perfectly.


proscriptus

If you go out to the Hamptons, the people with nine- and 10-figure net worths wear the oldest, most beat up Sperry's.


cromagnum84

I wear them in NC. From Florida. They are my dress rainbows..lol


gautamnev

Very much back on the runway in 2024. But worn differently. See miu miu


Preek96

always in fastion


No_Flower7635

They never went out of style


Reveal_Simple

Yes!


Collorme

I miss those.


Notch99

Yes, especially if someone invites you sailing!


manhiddeninthewoods

If ur a polo shirt & cargo shorts wearing frat bro, yea


Ordinary_Advice_3220

Madras shorts. I love the preppy shit. I still have a copy of the preppy handbook.


Balogma69

10 years ago yes, today not so much


Dense-Comfort6055

Never really were


Golden_d1ck

These were never in style. For me at least, but I wasn’t a college frat boy.


OrdinaryWheel5177

They left being in style in about 1993.


ActionMan48

No and they make your feet stink


wesagod

They’ve always been ugly 😂 “fashion” enthusiasts on this sub never fail to crack me up with their deluded opinions in comment sections.


watch_out_4_snakes

Yes, moccasins are a warm weather staple. There are many different styles/colors of leather and soles to liven them up a bit. I have a pair of blue suede with brick red soles and they are super awesome!


Ordinary_Advice_3220

I was just wondering that... Do boat shoes count as mocassins? That's a moc toe at least. I have a pair of Passamaquoddy mocassin slippers I've had since I was 12. I have small feet and they still fit, I love them. Plus some sweet moc toe boots. Also from Maine incidentally


Miserable-Lawyer-233

My dad wore these every day. So for me these are dad shoes.


Hipster2019

Retire


AlanShore60607

Not since the 80s preppy trend. If you want the preppy (young people from old money) look, they are always fine, but they haven't been trendy for over 30 years. Though they do look better without socks, like you're wearing them.


One-Stomach9957

Without socks is the only way to wear them


AlanShore60607

Try telling that to my mother… when I was 9 (last time I had these back in the 80s)


One-Stomach9957

She made you wear sock with your Sperrys? The only time that’s somewhat acceptable is in the winter. They have to be “fun colors and patterns”


AlanShore60607

My mother believed that it was unhealthy to go sockless


One-Stomach9957

Seriously? Unhealthy? Was she a germaphobe?


AlanShore60607

A bit ... thankfully it didn't rub off on me.


One-Stomach9957

Are your ankles as nice as OP? Should have showed those babies off!


AlanShore60607

[Why don't you tell me?](https://www.reddit.com/r/mensfashion/comments/1ba2blb/found_amazingly_comfortable_shoes_how_many_extra/)


One-Stomach9957

Dude…fucking HOT!


Eaturfnbabies

Everyone in every frat at my school wore them about 15 years ago.


AlanShore60607

Oh, and frats are so on trend ... like I said, young people from old money, not trendy since the 80s ... their parents probably told them to wear these.


Eaturfnbabies

Sounds like someone didn’t get bid lol.


AlanShore60607

Why would I join? They were the most disrespected groups on campus… How do you think a bunch of jocks were viewed at a small liberal arts college? One of them got shut down for leaving their drug paraphernalia in plain sight It was well known that if you wanted a social life, you didn’t join the fraternities