Am I dressing dreadfully wrong?
December 4, 2013 9:10 PM   Subscribe

I read this other AskMe that basically turned into a 50+ answer pile-on about wearing sneakers with a blazer, and now I'm worried that I too am doing something dreadfully wrong by mixing solid button-up shirts and dark wool trousers with big clompy Doctor Martens oxfords, a red nylon messenger bag and nylon windbreaker. Also, sometimes (okay, lots of times) I have a red bicycle helmet hanging from my bag. Could the hive mind explain exactly how dorky I look, and why? I'm not sure I care to change, but I would at least like to understand my options and their consequences, and make my self-presentation a deliberate choice instead of a clueless accident.

In more detail:

- Almost always a button-up shirt in a dark solid color (currently, green, blue, red, and several black). Most of my shirts fit; a couple are too baggy because I bought them a few years ago before I stopped growing, but they'll wear out soon.

- Always black or dark grey worsted wool trousers, usually with one or more pleats because they're the only ones that fit my huge 24" thighs.

- Braided brown leather belt (I have been strangely unsuccessful in finding a black leather belt which has a hole small enough to fit a 32" waist---suggestions welcome.)

- When it gets cold enough that a wool base layer under the shirt doesn't cut it, then I add a grey wool pullover with a V-shaped neck or a navy pullover with a standing collar.

- Standard white-face Timex with a blue grosgrain ribbon band

- As mentioned, big clompy black Doctor Martens oxfords

- If it's cold enough, a black nylon windbreaker. I have a heavy double-breasted black wool pea coat and a lovely, sleeker black cashmere coat that hits mid-thigh, but in practice they're just impractical: the pea coat is too warm for New York and God forbid I try to ride a bike in the longer coat.

Again, I've sort of made my peace with not exactly looking fashionable. But I would like to be aware of how dorky I look, and if possible make it a deliberate choice rather than a clueless accident.
posted by d. z. wang to Clothing, Beauty, & Fashion (47 answers total) 4 users marked this as a favorite
Can you post a picture? Kind of hard to decide how dorky you look without a picture.
posted by Ghostride The Whip at 9:13 PM on December 4, 2013 [14 favorites]

You're fine.

I think a guy in my office was wearing this exact outfit today. He's pretty stylish, too.

Also, I think if you're at the level of being concerned about what kind of belt to wear and what your watch is like, you're probably style competent enough to do your own thing without looking like a complete fashion disaster.
posted by Sara C. at 9:14 PM on December 4, 2013 [8 favorites]

If anything, I would upgrade your windbreaker to something that matches the rest of your clothes better. That windbreaker is very sporty, whereas there are a lot of other options out there which would work better.

My first thought is some kind of Barbour thing, but if you can't afford that (and who'd blame you), what about something like this? It's a little more classic/rustic, which likely matches your style better. The windbreaker you linked doesn't seem like it would match the rest of the clothes you've described.

On the other hand, without seeing you in it, it's hard to tell. And you probably look fine.
posted by Sara C. at 9:18 PM on December 4, 2013


Allow me to demonstrate my credentials by saying this: Those Doc Martens that you posted are not oxfords because the upper is actually a distinct separate piece from rest of the shoe. That type of shoe style is actually known as a blucher.

With that out of the way, from your description your outfit sounds fine. Dark colored dress shirts are less flexible than your traditional whites and light blues, but are fine if you're not wearing them with a suit. If you swap out your nylon pieces for something like the Barbour jacket recommended above then you'd have a more classical look but it doesn't sound like you want to change right now.

If you're having trouble finding a belt smaller than 32" then consider ordering one in a custom size at a place like here.
posted by C^3 at 9:30 PM on December 4, 2013 [1 favorite]

This will sound sacrilegious, but I wouldn't let MeFi become some kind of oracle of style. You're an adult, you see people wearing various clothes out in public, you have a reasonable idea of what acceptable wear is. Not wearing some kind of chicken suit or full-body Pikachu costume? I think you're good to go. The clothes you're describing are perfectly decent clothes that lots of people buy and wear. Do you want to look more stylish and fashionable? Then yeah, I guess you'll have to do some work. But worrying if you're "doing something wrong"? I mean, I wear dark-colored tops with light-colored pants, and if someone went out of their way to tell me that I'm doing it wrong, I wouldn't take them or their judgment seriously.
posted by Nomyte at 9:32 PM on December 4, 2013 [23 favorites]

Well I have different, much different, credentials than C^3. I am a 50+ year old who wears button downs with his grey suit from Brooks Brothers and I think what you are wearing is fine. I would not consider it dorky. I would consider it generational.
posted by JohnnyGunn at 9:39 PM on December 4, 2013 [2 favorites]

Honestly, you more than likely look like any given New Yorker on the street. Red bike helmet + red messenger bag is a great idea.

I stole this belt from my old roommate by accident a few years ago. You could get the same thing. Brown belt with black boots ain't such a great look, but compared to a poorly fitting shirt or blazer or pair of pants, nobody's gonna die.

Since you wear a lot of black, maybe you could switch out your watch strap for a different neutral color besides blue? A band that matches your regular gray pants wouldn't provoke jeers, weeping, or gnashing of teeth, I'm pretty sure.

I know that you haven't posted a photo here, but as long as you continue to eschew fedoras and maintain consistently classic well-fitting attire, there isn't much you could improve compared to 90% of the men population.
posted by oceanjesse at 9:40 PM on December 4, 2013 [2 favorites]

I would recommend taking this up with StyelForum or a site that focuses on the minute details of dress and accessories. In the meantime, the biggest changes I'd make are: finding a black belt, finding flat-fronted pants that fit, and considering lighter-coloured dress shirts. Dark-coloured dress shirts scream Dilbert to me (but see above re: other sites knowing better).
posted by Pomo at 9:41 PM on December 4, 2013

Dude, it's all about fit, and anyway-- who cares. It sounds like you look fine, possibly even really nice! You put more effort into your dress than the majority I would say.

If you want fashion advice to up your game though pictures would probably be useful. But seriously, you sound like you look nice, and your functional pieces look functional, so it's up to you if you want to pursue something more functional + organic looking.

You sound like a coworker of mine-- cute.
posted by stoneandstar at 9:41 PM on December 4, 2013

Oh, braided belts though are kind of iffy, though I wouldn't call them dorky-- I wore them for years because I was too bored to shop for a "good" belt. They're not terrible, they're just not great and they kind of remind me of girl/boy scouts (or kids who are still growing, i.e. they read young). So if you're gonna work on one thing I'd choose that.
posted by stoneandstar at 9:42 PM on December 4, 2013 [7 favorites]

Get a "real" jacket instead of the windbreaker, and a bag that is a dark neutral instead of red. Otherwise, assuming that your pants are the right length and everything fits, you're fine.

(Caveat: do your docs actually LOOK big and clompy? That would be not in-style. I'm having trouble visualizing your body - big thighs/small waist- but it'll really depend on the balance between your shoes and how they fit your body's silouette, determined by both your body and the fit of your clothes.)

Post a picture?
posted by Kololo at 9:48 PM on December 4, 2013 [2 favorites]

BECAUSE YOU ASKED, the only thing I can't with is the Doc Martens. To me, they will always read as clown shoes.

Please note that this is merely my preference (I hated the 90's) and not a fashion dictate from above.

Wear what you like and have fun.
posted by Space Kitty at 9:49 PM on December 4, 2013 [3 favorites]

I would ditch the braided belt (you can add holes, and I've never had trouble finding a small-enough belt smaller-waisted than you; my favorite is from Gap of all places) and the Doc Martens. Wool pants are dressy enough to switch the shoes for something like rubber-sole Allen Edmonds (or substitute in your budget) or nice chukkas or other dress boots.

Get a versatile blazer that works with your wool pant colors. If it's something like corduroy, that'll reduce the need for another jacket. Get rid of the pleats. If you're thin, get tailored shirts or get them tailored.

For outerwear, there has been a great rash of cycling-focused jackets for commuters that actually kind of work with business casual. I have the Showers Pass "Portland", which was replaced with the Amsterdam. Mine is waterproof, stretchy and has long sleeves and a long tail that I can button up and hide, but the material almost looks like wool. I love it.
posted by supercres at 9:57 PM on December 4, 2013 [3 favorites]

A black button up shirt seems weird to me but everything else sounds fine. Can't you just poke a hole in a belt with an awl?
posted by fieldtrip at 9:58 PM on December 4, 2013

Dude I am not even a man and I had a complex about my clothing after that thread. Apparently there are actually people out there who look at an otherwise perfectly nicely dressed human and think "MY GOD HIS LAPELS ARE A QUARTER INCH TOO NARROW THE HORRORS".

But the key is, there is no pleasing such people, and one is best served to ignore them. Nothing you're wearing would strike a typical observer as odd. Apart from the baggier shirts possibly looking a little bit frumpy (or more likely, just read kind of older) you're fine.
posted by like_a_friend at 10:07 PM on December 4, 2013 [3 favorites]

The fact is, most men dress awfully. Men are expected to dress awfully because there's no real social expectation for them to dress well like there is for women. In fact, when you start to dress really well other people will start to call you a hipster or gay or tryhard. So even though in the other thread everyone bagged on the guy for wearing a blazer with the t-shirt, honestly, 95% of the human population will not give a shit. I routinely see guys dressed like that and no one except other fashion hobbyists notice or care. Most people don't understand men's fashion and why some outfits look better than other outfits. This is why girlfriends and wives are notoriously bad at dressing their boyfriends/husbands.

So stop worrying about whether or not you look dorky. Looking dorky is the status quo. It's only when you want to start being fashionable that you have to worry about this stuff.
posted by rq at 10:23 PM on December 4, 2013 [3 favorites]

I am truly very judgmental about outfits and even I think you sound fine, although I think you'd probably look better in flat-front pants. Pleats are often awkward if you're not a pro.

It's a shame the cashmere coat doesn't work for your life. A man in a good coat can get away with a lot.
posted by Countess Sandwich at 11:02 PM on December 4, 2013 [2 favorites]

Why do you wear doc martens if you describe them as "clompy"? Clompy isn't usually how people say sexy. Have you considered a more slimming shoe, like a black pair of AE Park Avenues? If it's the wideness you're after, you could pick up some EEEs.
posted by oceanjesse at 11:12 PM on December 4, 2013

I think some of the details in the clothes you describe sound pretty dorky: pleated pants (which always say "mom pants" to me), braided brown belt that doesn't match your shoes (likewise dated style), clompy, dated shoes, and probably too many wool layers which is why you're wearing an overly lightweight coat in what is actually a pretty cold city in the middle of winter. Oh, and shirts that are too big on you. Switch out flat-fronted pants, a flat belt, better shoes, and lighter layers under your coat. And get rid of the clothes that don't fit you. You'll look fine then.
posted by PhoBWanKenobi at 11:43 PM on December 4, 2013 [10 favorites]

To clarify about the other thread, there's nothing wrong with a blazer and "sneakers", the problem is garish cross trainers or basketball shoes. Something like converse or tigers can be fine with a blazer depending on circumstances and the rest of the outfit. Actual modern athletic shoes cannot look good ever with anything.

For your particular case, I would say.... slightly dorky? But totally normal? It's all relative to who's standing near you, isn't it. It certainly doesn't sound like you'd stand out as odd. Like everyone else has said, a flat belt would work better, but the only big change you might want to make is the jacket. Maybe a short duffle coat? Length works well for cycling, and you get a hood.
posted by Pre-Taped Call In Show at 1:00 AM on December 5, 2013 [1 favorite]

First of all, I can't imagine that anyone is talking trash about you because of your clothes. They sound very ordinary, and I have probably seem each and every aspect of your outfit on *somebody* on the metro today. So don't worry about wandering around town looking appalling or anything, you're not a laughingstock.

However, your clothes also sound completely lacking in sex appeal. You're a grown man! It's going to read young and/or dorky if you don't strut your stuff *a little.*

Tailoring, draping, fit -- all that is important. But something that nobody's mentioned that might help, is to try wearing more sensual fabrics. Fabrics that look inviting to the touch and that move with your body will look sexier and more sophisticated. Leather and wool both do the "beaten in and touchable" look very well, if you're looking for winter clothes/accessories. Plastic (or plastic-y looking leather) and nylon aren't very touchable and they tend to be very stiff, so, barring exceptional circumstance, they don't look very sexy or inviting to the touch.

Mixing up fabrics of different textures can also highlight the textures in a very flattering, rich way. For example, think about how leather and silk look together. Layers can help both in terms of fit (you can bulk up areas that would look disproportionately long or thin or exposed otherwise) and in terms of creating some textural depth/touch-ability to what you're wearing. Part of mixing up fabrics is also about mixing up different weights of fabric -- right now, it seems like a lot of what you're wearing is very heavy, stiff, and boxy, and that can look very dull. Mixing in lighter, softer, more fitted clothes/accessories would probably liven up your outfits.

I'm female, so take this for what it's worth. But since you describe your shoes as clunky, I'd get some sleeker, lighter, leather dress shoes instead. Since you talk about having to wear heavier sweaters and jackets, I'd try to balance out that heaviness with a scarf, maybe even a hat (so your head doesn't look like a little bean poking out of your big boxy coat, lol). Since you're saying that you can't find pants that fit, I think you should probably try going to a store that has clerks who can help you or to a tailor, and find/tailor pants that actually drape in a flattering way on you, and that don't need the "cheat" of pleats (same thing with the belt -- you should one that fits, not one that uses the "cheat" of braiding) (both the pants and the belt are also a comfort issue -- you will genuinely feel more comfortable in clothes that fit you better, I've been there and I promise). If you're going to go all out, then honestly, I think JohnnyGunn has the right idea -- you can't go wrong with Brooks Brothers.

Your clothes can be appealing and sensual, they don't have to be just serviceable.
posted by rue72 at 1:58 AM on December 5, 2013

Dude, no one on metafilter can answer this question for you in a meaningful way, much less without actual photos. What you wear is communication, to a specific audience. The exact message and how it's received is entirely dependent on things that no one here knows: who you are, who your audience is, your goals, vocabulary, and syntax.

A lot of engineers specifically fall into the trap of thinking that if they just get enough of a rulebook in place or complete that flowchart/decision tree, they're set. Not just for fashion, but like human relations on the whole. But fashion isn't rules based, at least not in the way they're thinking. It's not like sports where rule changes happen with hand wringing and debate and advanced notice. It's more like calvinball--seemingly arbitrary and capricious to an outside observer, but ultimately borne of a conversation between its participants.

So like when someone says you can't wear a jacket with sneakers, that's like, true, but not true enough to be actually useful in gaining an understanding of the underlying system that makes it true some of the time. Like what kind of jacket? A suit jacket? A sport coat? A blazer? Is it a running shoe? Or a "running shoe"? Are you in soho? Or in sillicon valley? Are you on a boat? Is it summer? Are you trying to fit in? Or stand out? What's your goal? Beware of advice that tells you to just do this, or just do that.

So it really all depends, but I don't think you need to be like into fashion to have some functional ability here. Everyone here is going to have their own assumptions about you, and bias about what "looks good". The thing I would ask you to think about is: when you look at the people around you, what are they saying with what they're wearing? What do YOU want to say? And to who?
posted by danny the boy at 2:29 AM on December 5, 2013 [2 favorites]

I used to wear docs like that, i actually still own them(not the same exact style, but quite similar). They really do look clompy. There's just something about the ratio between the size of the sole, how it extends out from the rest of the shoe, and the stitching exaggerating it that just make them have weird proportions.

I swapped them out for the beeswax ones of these. I wear those quite a lot, in times that i won't just wear tigers and the weather or activity isn't extreme enough for these or my red wings.

I still have the docs, and i use them for projects where i don't want to screw up my other daily-wear shoes. They really do look clompy though, and it's definitely something i can notice where it seems to just throw the entire balance of an outfit off and take it past the margin from "meh, normal" or even "Hey, that looks pretty good" into "goober".

I also can't disagree with the advice to ditch the red messenger bag. If your goal is visibility, get a black one and slap some lights and reflective stuff on it(or get one like the chrome bags that have a BIG reflective stripe on them, but a white one).

I have nothing negative to say about the rest of your outfit though. I live right near Amazon's HQ, and have friends who work at nintendo, microsoft, and various other companies of that ilk. You would blend right in to invisibility on any of those campuses and likely even look more stylish than a lot of them.

I can't even say that much against the windbreaker. A plainer jacket would be better(and god, those barbour jackets are beautiful. but EXPENSIVE), but i see a lot of people wearing even doofier windbreakers every single day in seattle. At least it's black, and not some really ugly "green with silver stripes and inexplicably blue detail" sort of REI jobbie.

There are other jackets out there like the barbour ones. Check out shops like urban outfitters, they LOVE carrying knockoffs of stuff like that, at the higher end but not barbour prices there's stuff like allsaints, banana republic, jcrew, etc. It's not that hard to find something that looks enough like this to instantly look 1000x better than a windbreaker, but also isn't like $400. As long as it fits good and doesn't look blatantly cheap it'll look better. And hey, you're putting in effort! everyone looks better that way.

I will also echo the comments above that you're pretty much doing it right already though, and that you don't need to and maybe even shouldn't listen to us. I'm not really saying you're doing anything wrong here, just making some suggestions and relating some observations i've made over time.
posted by emptythought at 4:00 AM on December 5, 2013

How it works for us people with big, excellent legs is we buy larger sizes of flat front pants and then we have the waist taken in by a tailor. Not as expensive as you think it would be. I've had to do this with almost every pair of work pants I have.

Also just add a hole to your belt.
posted by zdravo at 4:08 AM on December 5, 2013 [2 favorites]

I have been strangely unsuccessful in finding a black leather belt which has a hole small enough to fit a 32" waist---suggestions welcome.

Macy's. I'm not going to claim it's a high quality belt, but there were choices and it was inexpensive.
posted by hoyland at 4:30 AM on December 5, 2013 [1 favorite]

Both of my kids have 32" waists. I have never had trouble finding belts that size. Even Target/Kohls have basic black/brown reversible men's belts in that size. Try zappos online or any department store site.
posted by headnsouth at 4:51 AM on December 5, 2013

Are you comfortable? Are your clothes clean and without stains? If you answered "Yes" to these two questions, you are fine. Who cares if people think you are dorky? I am sure there are plenty of people who think you look great. So get your bad self dressed and go out with a smile on your face. You look fine.
posted by Yellow at 4:52 AM on December 5, 2013

Agreeing that this is difficult to answer without photos. Based on your description and the items you've mentioned, it sounds like you've got a mishmash of stuff going on. Nothing unusually dorky, but nothing particularly stylish. But depending on the cut of the garments, how they fit you, and what sort of condition they're in, you may end up looking reasonably put together or not.

Here is an often-unspoken, awful rule about style: it often depends on attractiveness, more than is fair. If you have a traditionally attractive face and a body that off-the-rack clothes fit easily, you can get away with more. Someone with good posture will look more pulled together than someone slouchy or sway-backed. Well-groomed hair looks nicer than hair that hasn't been cut in months. Et cetera. Take these things into account when you're evaluating yourself. Good grooming and posture can make you look classier instantly, whatever you wear.

If you want to upgrade your stuff, start with finding a black belt and less clunky shoes, since you'll be wearing those all the time. (I like clunky shoes, but they're not currently in fashion. It's still possible to look good in them, but for clothes that are "out" you need to be more deliberate when planning outfits around them.) Then work with the shirt and pants. I think the advice to find flat-front pants and get them tailored to fit is very good. I'd save the new jacket and bag for last; neither are exactly stylish, but you aren't wearing/carrying them around all the time in the office. People often forgive unhip outerwear, especially in the winter.

Everyone has their own spot on the continuum between fashion plate and "fuck it," and it's perfectly fine to park yourself towards the fuck it end. If you're just starting to wonder whether you look okay, I would guess that either dressing well is unimportant in your job and social circle, or it is important and you're passing okay.
posted by Metroid Baby at 5:02 AM on December 5, 2013

Let's start with the nerdy, hardline ideal of a business casual uniform:

Fitted white or light blue shirts. Depending on formality, could be an Oxford cloth (less formal) or a broadcloth or poplin shirt (more formal). Avoid dark colours, like deep blues and black - they're very hard to pull off, and are definitely not traditional.

Well fitted, simple chinos. Black or grey wool trousers. Potentially slim (not skinny) black jeans, but that depends on your workplace.

DMs could be okay, but they're a bit "fussy" with the contrast stitching and massive, unsightly sole. The toe box is also a bit chunky for my liking. They're far from the worst black shoes I've ever seen though. I would actually think about wearing brown shoes - black's quite a formal colour. How about some chukkas. Clarks' Desert Boots are the classic example, and the beeswax colour is very versatile.

There's nothing wrong with that jacket, but it does scream techwear. If you don't need much warmth, this Levi jacket is quite a good-looking, more neutral option.

Honestly, what you say doesn't sound eye-gougingly dreadful. Just be mindful of fit and fuss.

If you want some good advice, post some outfit pictures over at r/malefashionadvice, and have a look through their wiki. Styleforum is also good, though a bit more daunting in volume.
posted by Magnakai at 5:25 AM on December 5, 2013 [1 favorite]

You look like the men I just saw in the coffee line at work (a university campus) -- so not dorky and probably just fine. The only three things to consider are: flat front pants, a better belt and less clunky shoes.
posted by Lescha at 6:00 AM on December 5, 2013

Echoing that we can't do much without a picture. Your clothes selection has as much to do with your build as it does the actual clothes.
posted by FAMOUS MONSTER at 6:08 AM on December 5, 2013

You're fine.

Except for the pleated pants.

Never, ever.
posted by MisantropicPainforest at 6:16 AM on December 5, 2013 [8 favorites]

I was thinking about this on the way home the other day, because so many things contour our perception of fashion and all kinds of rather ugly or at least unwanted sentiments can creep in.

Clothing access, for one thing - dressing "well" is expensive even if you thrift, particularly if you're a nonstandard size or live somewhere without a rich population to donate to the thrift stores. If you're a fairly standard size and live on the NY/Boston axis, you have a lot more choices than if you live in, like, Sioux Falls. Thrift store prices have been creeping up where I live for even the junkiest used Target sweaters, and the internet means that thrift stores tend to cut deals with pickers, price according to eBay or just sell directly online. Also, the more people are all "I will dress well by buying fancy things secondhand", the more prices on the secondhand market go up - I have seen this since the nineties.)

Culture - honestly, dressing "well" (ie, employably-yet-fashionably) is pretty much dressing according to either arty white people or WASPy norms, even though there's a lot of variety, regional styles and influences from other places like Japan and Hong Kong. What does that mean if all your peers dress really differently? What does that mean if your culture tends to dress differently? (And that's a real thing, even though it can mean just "people of my cultural background tend to wear looser clothes") How do you square that circle?

Bias - why, for instance, am I dressed "well" if I am wearing chinos and a button-front and a structured cardigan and leather boots, but the kid on the corner who is wearing new and interesting sneakers and a really beautiful hoodie that looks like a fifties brocade opera coat redone in terry (I coveted it instantly) is not dressed "well"? We both made some significant choices about our clothes, we both spent money on it, we're both clean and well-turned-out...

Bourgeois display of taste and political disempowerment - first, in making a big fuss about "correct" taste, I'm behaving just like a middle class person, very anxious about discerning and enforcing "timeless" rules since I am neither a working class person nor an aristocrat, either of whom would have different reasons for not caring or else for being strategic. (No, seriously, this is pretty standard "how does the middle class form itself during early modernity" stuff.) Second, I feel like matters of "taste" come to the fore in times when political power is locked away from ordinary people. I've noticed that in the past few years, taste/lifestyle/"correctness" have become much more powerful discourses for ordinary people than they used to be, and while some of this is due to the internet, I think part of it is due to the fact that we don't have unions, churches, political clubs, intellectual projects, etc to take up some of the self-formation burden.

Strategy - clothes are for things. If your clothes do what you need them to do, you don't need to care. For instance, one reason I dress so fussily is that I'm a secretary, and dressing in a particular middle-class-men's-style-blog way helps me assert status in that role. Also, I'm queer, and dressing in a butch/gendernon-conforming way helps me feel better about myself and also be visible as a queer person.

On another note: I have a lot of opinions about clothes, but they're all sort of "strongly held but really very weak". If you ask me which shoes to buy, I can rattle off a list as long as your arm; if you tell me that you don't really want any of them, I'll be all "eh, sure, get the sneakers". It's much more like having music preferences than really strong social preferences - I will talk your ear off about Janelle Monae and Henry Cow, but if your thing is Nicki Minaj or Scriabin, I'm just as happy to talk about them.

Personally, actually, I find it most appealing when people have their own style preferences - they need not be the same as my style preferences, but I would find it pretty cute that someone has a consistent style and red accessories. Also, as a child of the grunge era, I never really dislike Docs.

Vis-a-vis the pleated pants: pants orthodoxies change over time while retaining certain classics. Dramatic pleats will eventually come back and even now there's plenty of space for your basic men's dress pants with a small, simple pleat - probably half the people who say "never wear pleats" are thinking of giant puffy eighties/early nineties pleated pants and don't even notice that there are men all around them wearing the classic simple pleat.) There's no reason not to wear pleated pants if they fit you well and are not super-outre with fifty tiny pleats on each side (and actually, if you have a source for super-outre pleated pants, please tell me, as I like to incorporate the occasional dramatic "menswear but very weird" item into my wardrobe.)

Basically, you don't sound as if you're dressing badly, assuming that you're not, like, a stockbroker's clerk or a funeral director. Your clothes sound low-authority and high-individualism, so as long as you're cool with that, carry on.
posted by Frowner at 6:41 AM on December 5, 2013 [11 favorites]

You sound OK to me, as far as I can tell from a description on the Internet.

I would keep looking for a black, non-braided belt. Braided belts can look a bit little-boy, especially if they don't go with your shoes. Adding an extra hole is no big deal, and shopping around online may help you get the size you need.

What helps me to remember is that the situation plays a huge part in determining what clothes are right. I wear more trousers to work that I did at my last job, because almost none of the other women here wear skirts. And what works well on one person might not on another. If it's something that interests and concerns you, you'd benefit from taking a closer look at the clothes of the people around you in different situations.
posted by The Underpants Monster at 6:47 AM on December 5, 2013

dump the braided belt. reads young. if you can't find one that has a hole small enough, you can punch one in. not hard.

i'd also try to find pants that aren't pleated. i'm trying to envision a 32" waist with 24" thighs...athlete of some kind? pleats pouf out and make you look either fat or erect.
posted by misanthropicsarah at 7:46 AM on December 5, 2013

Echoing several others above - ditch the braided belt, baggy shirts and the Doc Martens for sleeker options. Oversized reads as very adolescent, like you're not done growing yet.

It also sounds like your shirts & pants combos are very dark, if you're wearing grey pants and dark green, red, or black shirts regularly. That, to me, looks late 90's and pretty dated. Think about a lighter colored shirt, maybe a light plaid if you don't want to go to the full-on white oxford or button-down shirt. Something like these shirts could look very nice: one, two (also works without the blazer and tie), three.
posted by foodmapper at 7:48 AM on December 5, 2013

Frowner: you might be interested in the high-fashion trend of goth ninja/darkwear as popularised by Rick Owen and Yohji Yamamoto. Tounge-in-cheek Reddit guides: 1 2
posted by Magnakai at 8:19 AM on December 5, 2013 [1 favorite]

For me, anyone wearing Doc Martens gets an automatic approving pass, and I assume their outfit is intentionally chosen, regardless of what they are otherwise wearing. And as someone said above: don't use Metafilter as an arbiter of fashion sense. Anyone saying that Doc Martens are currently 'dated' couldn't be more wrong (from a fashion-y perspective at least. They are currently perfectly on point. And not just because I want them to be, although I will always love them!) Also: your outfit sounds a little 'absent-minded professor' to me, which has elements of dorkiness, but also classic-ness. In conclusion: wear whatever the heck you want, and whatever seems good enough for your needs.
posted by thegreatfleecircus at 9:21 AM on December 5, 2013 [1 favorite]

Hey, don't worry about your clothes too much! You are probably fine as long as people are not shielding their faces and turning away in disgust as you walk down the street.

I wondered about the brown braided belt, too, because you don't mention wearing anything else brown, and my son has a size 28 waist (skinny cyclist), and we can find him belts just fine. Plus you can always added a hole (with just an ice pick even, if you don't have fancy tool skills).

BUT! As long as you are happy and comfortable, and your look works for you, go with it! This is not high school and the cool kids do not get to decide how you live your life.

You know, I often think these sartorial threads would be better AND shorter if anyone commenting with fashion advice were required to include links with photos of them wearing the kinds of clothes they consider acceptable. So, say you have a comment from Greg Nog, on what to wear to a Metafilter Maine Coon meetup. You just look at his photo and you're all, 'Okay, yeah, that guy looks good. I will listen to your advice, well-dressed guy!'

Oh, hey, Greg Nog made a Thing where you can actually play with his wardrobe?! How did I not know this? Neat!
posted by misha at 10:27 AM on December 5, 2013 [2 favorites]

Seconding that the Gap has really shockingly nice belts, and most of them are unisex enough that if the men's are too big, you could get a women's belt, which will certainly fit. I am wearing a unisex-looking leather belt from the Gap right now, and it's at least eight years old; the one it replaced lasted over 15 years. The belt is an easy enough thing to change, and it sounds like you don't like the current one that much anyway.
posted by dizziest at 11:11 AM on December 5, 2013

This probably goes without saying, but I'm going to say it anyway because I think it's really important. If you're wearing your shirts buttoned all the way up (top button buttoned) and you're not wearing a tie, then you are dressing dreadfully wrong. I've known several men who seem to think this is an acceptable way to wear a shirt, but unless you're extremely hipstery or otherwise very very fashionable, buttoning the top button is always wrong.
posted by gueneverey at 12:18 PM on December 5, 2013

Don't wear green with red. Exceptions for this time of year if you really, really can't resist showing your Christmas spirit.

Docs aren't going to look clompy on you with thighs that size. Avoid those pants that taper in at the ankle.

Could the hive mind explain exactly how dorky I look, and why?

Not without pictures.

Also, depends where you are wearing this and what your role is there.
posted by yohko at 12:24 PM on December 5, 2013

(I did want to add a clarification to my comment upthread: historically speaking, there have been lots of modifications and important contributions by people of color to "WASP" men's style - for instance, jazz styles hugely influenced preppy/WASPy suit-wearing and a lot of norms we have today derive from jazz musicians of the forties and fifties. We also see a lot of zoot-suit influence periodically - I think a lot of the pleats and soft volume from the eighties/early nineties (which was perfectly conventional then) is zoot-suit derived. And I'm sure there's a million things I'm not thinking of. I do not want to imply that wearing, like, a suit and a tie is a "white thing" - just that there is some stuff in the history of those fashions that is racially and class marked in ways that are very white and privilege-y and that this may affect how people use, access and feel about clothes.)
posted by Frowner at 1:37 PM on December 5, 2013

You sound fine- I'm in favor of more casual workplace environments anyway.

The one piece of advice is to keep a good shine on your Docs. Docs take polishing really well, and it will make your entire outfit seem more professional, without people really noticing why.

I often wear a pair of vintage 1490s to work (I work in advertising, so I can get away with slightly more idiosyncratic footwear choices), but I always keep a good shine on them.

Is there a shine stand near your office? If not, get some Kiwi polish, a shine brush and buffing cloth, and give them a good shine every couple of weeks, or when they start to look scuffed.
posted by TheWhiteSkull at 1:49 PM on December 5, 2013

This probably doesn't apply to your braided belt, but here is an instructable showing how to remove certain types of buckles to remove material from the back end of a belt. You might have to buy the very small screwdriver, but at least you'll be able to use it on future belts.

On the back of the buckle, there are two screws holding the belt, which has been inserted into a recessed area of the buckle. You remove the screws and separate the belt from the buckle, and then cut the desired amount from this back end of the belt. Then place the belt end into the recess and replace the screws. Depending on how firm the belt material is, it might be a good idea to punch indentations into the belt so the screws can get better purchase.
posted by wryly at 2:25 PM on December 5, 2013

Nobody really should care too much about what you are wearing. You're you.

Unless you are dressing for work in a job which values a certain style of presentation. Then you should just wear the exact same wardrobe that your peers are wearing.
posted by ovvl at 2:46 PM on December 5, 2013

You can find a nice, classic leather belt (32") at Century 21 for $10-15.
posted by valeries at 5:56 PM on December 5, 2013

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