Poorly Dressed Men and the Women Who Tolerate Them

Whether walking along the streets of hipster neighborhoods or drinking in the random pub/bar/restaurant/lounge it is a common sight: nicely dressed women and their proletariatly attired gentleman date.  Cute and coiffed ladies with men whose attire is more appropriate for a casual picnic than a night on the town are a far too frequent sight.  My general disdain for khakis (garanamals for people who wear adult sizes) shorts (for all men over the age of 14, never appropriate unless athletic activity is involved) and flip-flops (not the political variety but those that may be worn for running errands, beach frolicking, or when sick) is a bit of an aside.  This is a question of balance, and one that I have never understood.


For the longest time I had dismissed this phenomenon as being as relevant to me as Facebook, Late Night Shots, and Abercombie & Fitch – trappings of youth about which I refuse to care.  And then I saw My Favorite Redhead last night.  She walked into our mutual watering hole and was simply stunning in her black and white summer dress and shoes that would have inspired LivLuv’s envy.  She was about to have a birthday dinner with her boyfriend – significant mostly because she is not a woman prone to having boyfriends or other long term romantic entanglements.  Between me and our other friends in the room, she surely received scores of compliments on her hotness in general and the hotness of the dress in specific.


Later in the evening, after her dinner had concluded, she and her beau strolled down the street as I was outside having a cigarette conversation with my crush de jour.  I was gobsmacked by the contrast.  She was dressed in a manner where she could have entered the finest of restaurants, and he looked like an extra in a Gap commercial – cargo shorts and polo shirt but thank the baby Jesus his collar wasn’t popped.


MFR is brilliant, accomplished, funny, an all around terrific woman, and my age – mid 30s.  Yet she, from outward appearances at least, was accepting of her boyfriend having dinner at a nice restaurant in shorts and flip flops while she was dressed to the proverbial nines.


Does it no longer matter to women how their partners and paramours attire themselves?  Has the collective man behaved so badly for so long that treating a woman well excuses poor attire?  Do women simply no longer consider a gentleman’s attire relevant?  Am I so hopelessly old-school, prim, proper, and fashion addicted that I am wrong-headed on this matter?

Feel free to answer those questions in the comments.  I will still follow the only fashion rule I have considered for the better part of two decades – if Cary Grant wouldn’t wear it neither will I.

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39 Responses to Poorly Dressed Men and the Women Who Tolerate Them

  1. freckledk says:

    I’m happy to say that I’ve never dated a man who wore shorts – well, they’ve worn boxer shorts…sometimes.

    Well, that answers the question of your preference.

  2. Lemmonex says:

    You are old school, but it is your charm, friend.

    I think it is just so common that men cannot dress, women have been forced to accept it. At least here in DC. A lot of women cannot dress either, to be fair.

    Thanks, dear. While I agree that so many people dress poorly in our fair city, I think this is a case of effort rather than ability. This was his birthday and a big date night for him and chose to wear shorts? Really? That is a choice.

  3. Shannon says:

    Men just won’t bother, because they don’t think they have to.

    I’ve loved a few fashion doozies myself – my college boyfriend wore sweatpants to meet my parents, and my former husband used to wear baseball caps indoors (even sitting in restaurants!). I’d try to gently suggest changes, they’d get all freaked that I was trying to emasculate them, or that I was too uptight, and resentment would build.

    Finally I just stopped getting involved with men who don’t have enough respect to dress for the occasion. No need to be a fashion plate, but put in at least 1/10th of the effort that I put in.

    Too bad there is no Union for you all. Imagine the resolution: Resovled, any many appearing for a date in any form of asshated attire shall be sumarily dismissed and with prejudice.

  4. i did catch myself a few years back…continuing to date a man…just because he always looked sooo nice…despite not having much in common…. he always looked so sharp… or at least appropriate…that i had a hard time saying no to any invitations that he sent my way…
    xoxo

    Blonde One, I am fairly certain I would have remembered if we had dated.

  5. Dara says:

    To play the devil’s advocate for a minute, men really have no equivalent to the sundress. And a woman can change her sundress look from casual to dressy just by changing the shoes. How can a guy possibly keep up with that?

    Male equivalent to the sundress = linen trousers + a shirt with more than three buttons.

  6. zipcode says:

    I tend to agree with Dara here – I like the khaki cargo shorts look on a guy – if its a casual date I see no problem with that. I am not however not a big fan of flipflops or sandals of any kind on a guy. I also like khaki cargo pants on a guy – as long as the polo shirt isn’t like bright pink then its fine.

  7. freckledk says:

    To be honest, I don’t really appreciate a heightened fashion sense on a guy. A man who knows the names of all the top designers and dresses better than me would not be my cup of tea,romantically speaking.

    That said, I would hope he doesn’t wear Crocs or Wranglers. A button down shirt, a pair of Levi’s and a cool pair of kicks are pretty much all it takes to make me happy.

  8. Alise says:

    Not to be the stranger imposing on a group of friends conversing (don’t you hate that?) but…

    As for the equivalent of a sundress, a gentleman could wear a great fitting pair of jeans, or tailored FLAT FRONT chinos with a casual button down shirt effortlessly rolling up the sleeves during the day, and then, by switching to a pressed shirt of the same type and sliding on a pair of leather driving shoes quickly transition to a nicer look with ease.

    And in my opinion, my dates better not show up in cargo shorts or pants unless there is a present for me in each one of those pockets to merit their existence!

    Everyone is welcome at this table – especially those that agree with me have interesting opinions to share.

  9. Hey Pretty says:

    I’m currently dating a man with good fashion sense but that’s a first. I honestly really don’t care what a guy wears. While I love fashion as art, I feel like people get way too caught up on judging others based on wardrobe choices. On a similar note, I get annoyed when my man takes issue with my wardrobe. If it’s 95 degrees out I really don’t care if he’d prefer that I wear a dress that shows off my ass rather than a loose floppy sundress.

    My only judgement about MFR’s boyfriend, who really is a lovely fellow, is that he is old enough to know better than to wear short pants to a restaurant that has tableclothes.

  10. Oh my GOD, I dated a DC dude for two years and he was obsessed with those gym shorts that make a swishy noise. And then there’s me, a gal who hasn’t owned a pair of sweatpants since sixth grade, thank you very much. It took the better part of that relationship to make that guy over. I got him from tapered Levi’s to Banana Republic dark washed denim, Reebok’s and bunchy socks to Asics and ankle socks. Then he acted like an ass and it ended. But on behalf of the DC people who are now free from seeing one more unsightly male dresser, you’re welcome.

    Dating as community service, I love it.

  11. LivitLuvit says:

    YES, ohmylord YES, it matters. It matters so much, and it’s not about being shallow (okay, maybe a little vain), but how you look is how you present yourself to the world. It reflects how you want to be perceived, and if you’re at my side, what you think of me as well. I’m not saying you have to rock a suit every day, but you can dress appropriately, match your shoes to your belt and show me that you care enough and respect me enough to put in at least half the effort that I do.

    PS- Thanks for the shout out… I think I’m officially the DC Blogger Resident Shoe Whore. And I’m totally okay with that.

  12. Lisa says:

    I like men who can dress, but I don’t know very many straight American men who know how to do so nicely when going out at night. And fortunately it’s not a huge deal to me. Truthfully, Nick and I rarely look like we have the same agenda. During the week, he wears suits to work and I often look like a street urchin who found clean clothes by luck and accident. And then decided to walk next to him and hold his hand. And then we go out at night and I like to get all dolled up, no matter where we’re going, and he likes to wear. . .I cringe as I tell you this. . .khakis and flip flops.

  13. anOCgirl says:

    eh, i don’t know. i’m from cali. i lived in flip flops back home. and every guy i dated there was a shorts and flip flop kinda guy. i didn’t really care much back then. then i met my bf (born and raised in NoVA) and he could not dress himself. first off, every shirt in his closet was some shade of blue. and his khakis didn’t fit or (gasp) had pleats or his jeans weren’t the right length.

    so, i bought him a new wardrobe. i threw out some of the blue shirts (the plaids had to go), got him some green, orange, and red tops, helped him buy some dress slacks for work, etc. and then i introduced him to flip flops.

    i just can’t let the flip flops go, dude.

  14. kris says:

    You are one of a dying breed, friend. Particularly in DC, where the 30-something men I’ve dated can’t wait to get out of even their Friday best into something more . . . unattractive. Amazing the amount of effort we women – in a general sense, of course – put into painting both faces and hair, into wearing something that will make him look more than twice. We’re lucky nowadays if their toenails are clipped short enough not to curl.

  15. Shannon says:

    Kris, ew! There’s nothing nastier than getting impaled by your man’s long, pointy, crusty toenails first thing in the morning!

  16. [...] Men who go out on dates dressed as slobs. RestaurantRefugee, who writes: Does it no longer matter to women how their partners and paramours attire themselves? I don’t miss the earthquakes. Arjewtino, ex-LA, now DC and what he endured to become an official DC resident. Excerpt … And when I complained about the perils of driving through that morning’s fresh snow, another editor shouted across the newsroom, “Hey, everyone! California boy here thinks this is a major snowstorm!” [...]

  17. Ryane says:

    I have dated all of the above described men, from the satorially challenged to the guy who took longer to get ready than me, and was twice as vain about his hair. In the end, I agree; it matters. Not because I expect a guy to dress a certain way, but because I think they should make more of an effort than shorts and flip-flops – especially if it is a special date or evening.

    And for the record, I hate and detest flip-flops on just about everyone unless you are a: heading to the beach or b. in the garden or c. under the age of 5. Flip-flops should never, ever garner date time.

  18. JoJo says:

    Men, listen up…we women LOVE a man who can rock a nice suit and dress smartly (yes, it can be done without a tie) for a dinner date.

  19. Shannon says:

    Congratulations on the DC Blogs Noted listing!

  20. thoughts says:

    OK. A quick thought from a man’s perspective. There’s a time and place for everything.

    If I am taking my wife out to dinner, I want to look my best for her and the others around me. More often than not, people at a nicer restaurant are there for an occasion and don’t want to look at some slob in wrinkled shorts and a t-shirt. So I either wear my best jeans if it’s a lounge-type atmosphere or a suit/no tie if it’s a more classic atmosphere.

    That said, if it’s Saturday and we’re just tooling around the city, I’m in shorts (possibly cargo), a button down (but probably untucked) and…GASP…flip flops (ladies, they’re the most comfortable footwear I can think of…I’m sorry).

    Anyway, we don’t all understand the rules of dress. We look to you for help.

  21. Dara says:

    I think a lot of it is just knowing the agenda and dressing for it. It’s a sign of respect.

    I go to work in dressy clothing and usually wear nice shoes (except when I’m spending the day in the file room, natch). When I go out to a nice place, I usually dress up, do my hair and make-up, and wear nice shoes. When I go to the grocery store or am just hanging out at a friends house, I’m probably wearing jeans and flip-flops. Maybe cowboy boots. But if I showed up in that to a friend’s fancy dinner party, it would be rude and inappropriate. Unless, of course, the friend invited me to hang out, and I didn’t know it was going to be a fancy dinner party — and then I’d be upset that I didn’t get the memo.

  22. Nelle says:

    Some men care about dressing well and some don’t. My boyfriend in college cared and looked good in everything at say, Banana Republic. But I often wondered about his true sexual orientation. There is a bit of an age difference between me and my current boyfriend so we often disagree on what looks good or is appropriate. Also, the “nice” styles don’t really fit his body type. We’ve compromise to the point were he will wear nice jeans and colored tees with no logos, and if I ask he will forgo the baseball cap. Fortunately he feels wearing flip-flops and sweat pant in public is as silly as I do. And he always asks what I’m wearing if we are going out for dinner so we can be somewhat coordinated. But he does wear shorts when the weather permits. I don’t mind, he has nice calves.

  23. KassyK says:

    I am with you here…while I know I am more into fashion than most girls and I accept that most guys have no clue what I am talking about half the time…looking nice is not that hard for men and you show a great example of that.

    And yes, linen trousers and a button are most definately the equivalent of a sundress just like a nice black suit is the equivalent of the little black dress.

    I do like khakis for summer day time–but evening or dress wear? Um…no.

    New York men seem to have a more heightened sense of fashion…not just the hipsters but a lot of them in general.

    I see many men out here with nice button downs and blazers with well cut jeans out at the bars…sharp.

    Good post. :)

    Thank you. Just to clarify – I don’t care about fashion (most of the things featured in GQ do not make my socks roll up and down) for me it is all about style and style is only partly about the clothes.

  24. KassyK says:

    PS–I do think the metrosexual look is just as bad…if not WORSE than the slob look on men.

    Eek.

  25. Gil says:

    RR refugee,

    Thank you for higlighting this. Personally, I believe it is more of a sense of self respect and that of others than fashion here. It seems that society as a whole has relaxed it’s standards of what is acceptable and what is not. At the same time, I have and adhere to my own strict standards of public dress, and sometimes overdress.

    It’s very aggravating to go to a nice restaurant or other public venue and see someone, be it male or female in poor or improper attire. It’s as if the efforts of myself and the other patrons who indeed took the time to look presentable were in vain.

    I will admit If I am going to the store for a gallon of milk, I will throw on a colored T shirt, jeans and flip flops, but will never wear these to do more “formal” errands. I also told my SO if she ever bought me shorts, I would return them :).

    Gil, thank you for reading and for the compliment. I am glad to know that there are more of “us” in the world than the “thems” think.

  26. Andrew says:

    I am impressed by the total lack of explanation for why men dress the way they do (i.e. casually). Most men regard “dressing up” as a method of insincerity, a subtrefuge. Men who dress in what makes them comfortable (jeans and a T-shirt with athletic shoes) regard the guy in the I-know-the-name-of-the-designer suit as: simply using money to impress women. A fancilly dressed man, to men, says one thing: “I have money” and/or “I want to look like I have money” and “looking like I have money is my come on to women”. Men who dress in their shorts and a T shirt and flip flops are desiring to be valued for who they are. They are convinced that women, if they were deep and honest, would look at the shape of the body inside the shorts and the T-shirt, and make a decision based on that. They regard women who will flock to a man with a dorky body but expensive clothing as craven, easily influenced, gold diggers. They regard men who will dress that way as either gay or flagrantly trying to use money to get women. In short, if a relationship is successful based on him wearing suits and fancy clothes, he is depressed or concerned that the relationship is, at core, shallow meaningless and based on wealth, rather than on love. He wants a woman to love him for who he is, not how he dresses, and how he dresses is, to him, absolutely and totally superficial and meaningless. He regards the hours-and-hours women spend on fashiong/outward appearance as superficial and meaningless. That is why you have generations of men unwilling to do it. They think its fluffy garbage.

    • Josh K. says:

      Eh, not really. I’m sure most of these slobs still want a woman that puts a lot more effort into her appearance than them. I doubt many of these men would like a girl who wears cargo shorts and larger than necessary shirts like themselves. And that have plain and short hairstyles. And that is always wearing baseball caps. And that doesn’t shave her armpits and legs. And that won’t add not even a bit of makeup. And that doesn’t pluck her eyebrows. And… so on. it is just that many guys, like you, are so used to having women looking so much better and putting so much more effort into it that you guys don’t even realize this.
      I think it is perfectly fine if guys don’t want to care about their appearance, but at least don’t be a hypocrite choosing the other sex. Because for real, I have seen so many guys complaining women aren’t that “feminine” or “vain” anymore, while they themselves are also far from vain. Of course, the same goes for girls who have double standards as well.

      And once again, this is about style – not fashion or how much your clothes’ worth.

      I agree with the article. Most straight American guys’ (lack of) fashion sense is a big turn off. Good enough for me, when I look around and see poorly dressed men I can already count them as straight. When I see a hottie he is 90% of the time bi/gay, so that is easier. :D
      I’m really sorry for the women, though!

  27. schmooz says:

    wow andrew….and if you took your girlfriend out to a work function and she dressed poorly, would you still feel that angst against dressing appropriately?
    Dressing yourself as if you take pride in your appearance has NOTHING to do with money and EVERYTHING to do with showing respect for your partner. I always work hard to make sure that I present myself in such a fashion that my partner is proud to have me on his arm. I demand the same respect in return – even if he can only afford clothes frm Wal*Mart, I expect the ensemble to be clean, pressed and the colors coordinated appropriately.

    • monacopoloclub says:

      Agreed. Men nowadays are just plain lazy. They’re not deep thinkers that want a woman to look to them inwardly. They’re just slobs. Period!

  28. Ethan says:

    I play guitar for a living and spend a good deal of time on a stage. You can’t play rock n roll looking like a douchebag in linen trousers. I also feel it’s important to play by your own rules, within the broad rules of etiquette. Some people lack the ability to think for themselves in the area of fashion, so they have no choice but to look like everyone else. Personally, I think if your pants ARE tailored, NOT khaki, and DONT have pockets you wouldn’t use when not fishing or building a house, you’re off to a wonderful start.

    Flip flops are wonderful, and in my opinion, can be worn on a casual daytime date (walking around town or hanging in the park) when already in an established relationship. However, wearing them to a dinner date, I’ll agree, is simply disrespectful… unless of course, it’s on the beach.

  29. [...] (No Grace Period), that doesn’t mean your coworker wants to be told that he comes to work in dress that is only appropriate for a picnic.  We really should be saying treat others as they want to be treated since relationships are about [...]

  30. Ken Pollock says:

    I disagree that these men do not care about what they wear and have no interest in clothng. When 80-90% of the men in their 20s and 30s are all dressed in the same slovenly manner at a nice restaurant, even though at least 1/2 of their dates are nicely dressed, to me that means that they are copying each other. Their obnoxious look is “in.” It is just the same old herd instinct.
    It is interesting that their attire is filtering up, however. Almost all of the old geezers have abandoned the necktie in the last few years.

  31. [...] date eventually posted.  He was attired by accident, a subject that I’ve never understood, and there was no apology offered.  He went to get their table and she asked for her check.  I [...]

  32. Allen Shelton says:

    I live in South Texas. San Antonio to be exact. I am a transplant and it’s obvious when one sees my wardrobe. I am always impeccably dressed…even casually. Whenever I take a lady to dinner, I’m always appropriately attired with at LEAST a sport coat and pochette. As you stated in the article, women don’t seem to make much of a big deal about proper attire. While at these restaurants, which are pretty pricey, I see men in cargo shorts, flip flops and, yes, T SHIRTS! How can this be? I remember a time, not too long ago (I’m 41) when a man couldn’t enter a fine dining establishment without at least a sport coat. If they didn’t have one, one was provided whether it fit them or not. Men have lost ALL sense of fashion and self-worth. I’m and old soul, it seems. Grooming as well has all but disappeared from a man’s daily regimen. Most men I see here look like cave men. NO exaggeration. Yet, they always manage to get a pretty girl on their arm. Hell, look at Hollywood. Rachel McAdams, one of the prettiest women out there, is hooked up with Ryan Gosling who, on most all occasions, looks like he crawled out of a dumpster after sleeping in his clothes for a week. Unkempt, wrinkled and unshaven for weeks. Wow. What a tragedy.

  33. irena says:

    You took the words out of my mouth with this post!

    It seems shallow but when something I care so much about is of very little interest to my partner…it seems like such a mismatch. Like I will never understand their attachment to cargo shorts they will never understand my need to own another pair of what may seem like “just black shoes”.

    In the long run I don’t think the relationship would work.

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  36. usanydp says:

    I just let go a relationship–very promising by other important means for a life together.
    My gentleman friend over weight(((no problem I said we will work on it and I will help)))) with a belly of a pregnant woman–5 minutes before delivery–showed up to say Good bye before a trip out of town in shorts, second hand store sweat shirt I believe and to complete the picture he wore knee high white socks…It was our second date.He was pushing me Good Bye kisses with his belly balloon and I was about to vomit–but could say nothing…..It took me about 2 more weeks basically charming me over phone but I got sicker and sicker—he ,killed my on-look on him,his intelligent consideration,his way to embarrassed himself probably even not knowing and his bad taste .He scared me of the future possibilities without questions left to ask him….sad but true…..

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