Off the beaten path male wardrobe
December 26, 2007 11:48 PM   Subscribe

Changing my wardrobe.

I'm a tired of wearing bowling shirts and Hawaiian shirts, which are the easiest to acquire but laziest and most clichéd examples of a male hipster's wardrobe. Looking for suggestions for something more outrageous. Just this side of kitsch, but dressy. Already thought of: Nehru jackets, leisure suits, mod suits. What are your suggestions?
posted by Astro Zombie to Shopping (36 answers total) 8 users marked this as a favorite
Well, I will give an example of how my friend was dressed the other day and I thought he looked pretty snazzy. He was wearing a pair of black skinny jeans, black chucks, a nice button-up deep purple dress shirt layered under a semi-casual black pinstripe sport coat.
posted by MaryDellamorte at 11:54 PM on December 26, 2007

Response by poster: Nice, but I'm thinking more along the lines of what you might wear for a night out with, say, Zsa Zsa Gabor, or Liberace, or Mamie Van Doren, or Tiny Tim.
posted by Astro Zombie at 11:58 PM on December 26, 2007

Are Hawaiian shirts hip? If you like bowling shirts, maybe some snazzier western shirts? Somethin' with lots of piping and stitch work. Daddy-o's has a nice selection, and I see from google that there are a lot of western outfitters in your area.
posted by Roman Graves at 12:02 AM on December 27, 2007

Buy a sweater? I have a red cashmere sweater, crew neck, that I thought I would never wear. But it has become my favorite thing to just throw on. It takes no time to get well-dressed. I never looked good in bowling shirts, however. I also recommend trying out button-downs with zip hoodies (is that bad??) Also, one tweed jacket that's one size too small always got me a lot of compliments. I am losing weight to fit back into it.
posted by parmanparman at 12:22 AM on December 27, 2007

Dude! Leisure suits? Just say no. I've met Zsa Zsa and she is one crazy potato but if you're determined here are my suggestions: Outfit #1: white boxy tuxedo jacket with black lapels, white-based western shirt with black bolero tie, or white t-shirt if you're really skinny, colored slim but not skinny pants (I suggest shiny deep jewel tones if you can carry it off), white socks and white shoes (or black patent if that's too much for ya). Outfit #2: gray tuxedo pants with shiny contrasting stripes on the seam paired with a brown or purple (dark, basically) shiny-satin military inspired short sleeved shirt (epaluettes, cuffed sleeves etc). This outfit requires some kind of cuff jewelry, the man-lier the better. For fun throw on a fedora and either a brightly colored vest or blazer. And wear your dancing shoes.
posted by fshgrl at 12:33 AM on December 27, 2007

That you posit this wardrobe to be apropos to a night out with Zsa Zsa, Libarace and Tiny Tim while remaining "just this side of kitsch" is straining credulity a bit. Other than Nehru jackets, leisure and mod? Velvet frock coats and admiralty uniforms with loads of braid?

Is this for daily wear, or special occasions? Because the more outré, the more difficult a time you're going to have putting together a 7-day-a-week wardrobe to reflect your new sartorial perversion.
posted by mumkin at 12:36 AM on December 27, 2007

Response by poster: Everyday wear. Because it just doesn't do to be occasionally ridiculous.
posted by Astro Zombie at 2:22 AM on December 27, 2007 [4 favorites]

What about a shirt like this ?
posted by selton at 2:55 AM on December 27, 2007

nothing is outrageous anymore, short of a bunny suit. you have to be careful about that sort of thing, or else you look like you're wearing a uniform/costume.

slim jeans with button-down shirts and blazers or sweaters in unusual color combinations would be cool.
posted by thinkingwoman at 4:34 AM on December 27, 2007

How about one outrageous accessory, like a huge, black, silk lined cape?
posted by shothotbot at 4:50 AM on December 27, 2007

I'm no Zsa Zsa Gabor, but I've always found embroidered western shirts to be quite fetching.
posted by suki at 5:32 AM on December 27, 2007

Have you looked through some of the "street fashion" photo sites, like The Sartorialist and all the others like that? Most of the photos tend to be of pretty conservative dressers, but there are plenty like this guy who are much less restrained.

But you have to have a lot of confidence and personal style to carry off the kind of look you are talking about; it's pretty easy for that kind of get up to instead wear you, with you looking like a trick-or-treater rather than a hip guy.
posted by Forktine at 5:58 AM on December 27, 2007

No capes. No Hawaiian shirts (which always look bad, no matter what, they are always, always tacky). No bowling shirts. No "cute" sayings t-shirts (i.e. "The voices like me better" or whatever idiocy can be found at Target). No fedoras. No hats for comedy's sake. No clothing for comedy's sake, for that matter. And, once again, no capes.

Your former wardrobe sounds more nerd-chic than "hipster" - if you're really looking for hipster, go with a bold graphic-t (think threadless or enclothe), slim-fitting or slightly bootcut dark denim pants, perhaps a cowboy shirt over top, and a zip-up plain hoodie (think american apparel). Simple trainers are a nice finish, but can be dressed up with a simple loafer.

IMO, go with more of a laid-back J.Crew style. Nice sweaters, classic colors, clean lines and jesuschristdeargod no name/logo print. Not even necessary to be had at J.Crew, as Gap offers nice khakis, solid color t-shirts, and basic sweaters. This style is timeless and classy, easily transitions in different situations/settings.

Once again, no capes.
posted by banannafish at 6:03 AM on December 27, 2007 [4 favorites]

I love a man in a guayabera. They can be formal or casual depending on the condition and make of the shirt. Not outrageous, but good everyday wear.
posted by dog food sugar at 6:16 AM on December 27, 2007

Once again, no capes.

I must second this. Although you did say you want outrageous and "just this side of kitsch", and capes are definitely both of those things. Me, I would point and giggle if I saw any man that wasn't either a superhero or a vampire / dashing count wearing a cape, but that may be part of what you're after.

Other things that spring to mind that may be either outrageous or kitschy - a 70s prom-ish tuxedo in a pastel color, a 17th century poet shirt (with extravagant cufflinks if possible), brocade slacks, velvet bellbottoms (think that gorgeous blue suit that Austin Powers wore) a smoking jacket a la Hef.
posted by iconomy at 6:21 AM on December 27, 2007

You need some of the older style tuxedo shirts that have the frill down the front.
posted by hermitosis at 6:40 AM on December 27, 2007

It sounds like you're looking for the kind of style that would annoy me if I saw you on the street. In that case, I think vests and pointy dress shoes in colors other than black and brown are the ticket.
posted by mullacc at 6:59 AM on December 27, 2007

Response by poster: Don't worry, capes won't be happening.
posted by Astro Zombie at 8:58 AM on December 27, 2007

A kilt. It's unexpected AND air conditioned all in one.
posted by contessa at 9:19 AM on December 27, 2007 [2 favorites]

I'd accessorize the J Crew look with some dashing goodies like this:

- CyberOptix "Ties that Don't suck"

- Excellent belt buckles, like the ones here

- Items that are silk-screened and tailored - like this , or this blazer

- Etsy has a HUGE selection of goodies like this

- Finally, good shoes offer a nice piece of flair - try this search or this

A little bit more grown up, but doesn't lose its sense of fun. Now, just don't wear all those things at once!
posted by beezy at 9:36 AM on December 27, 2007

That "hipster" look always screams "trying to hard".

Stick with the classics, like the above-mentioned J. Crew or Ralph Lauren. Check out a Lucky Brand shop if you want to look "hippie" or western - without looking like you are desperate for attention.

The trick is to look like you don't care but still look good. The stuff you seem to be gravitating to will always make you look like you are trying to hard.

Like someone mentioned above: "timeless" - not time capsule.
posted by wfc123 at 10:00 AM on December 27, 2007

Response by poster: I want to look like I'm trying too hard. Class is overrated.
posted by Astro Zombie at 10:08 AM on December 27, 2007 [6 favorites]

Puffy Shirt?
Or maybe traditional golfer garb, complete with men's knickers?
posted by Stewriffic at 10:12 AM on December 27, 2007

A velvet blazer in some jewel town with lapels as wide or narrow as you desire can work the kitsch/dressy angle.
posted by mandymanwasregistered at 10:14 AM on December 27, 2007

AZ, you need to get down to a vintage store. Shirts with character leftover from the 70s sound right on target.
posted by Ambrosia Voyeur at 10:14 AM on December 27, 2007

er jewel tone
posted by mandymanwasregistered at 10:21 AM on December 27, 2007

Nice, but I'm thinking more along the lines of what you might wear for a night out with, say, Zsa Zsa Gabor, or Liberace, or Mamie Van Doren, or Tiny Tim.

Well, half of those people are dead. So wardrobe wouldn't be as important.

Here's what I've found... it's good to have a classic wardrobe base (kind of a blank canvas) and then to have certain little pieces you add to it that shows you have some sense of individuality. But you can't just walk around bathed in kitsch as you age, it's more impressive to dress in a really flattering way for your particular body and then add some fun to it. You must wear the kitsch, do not allow the kitsch to wear you. When you're 19 you can pull off pretty much anything and people will dig it, but when you're over 25 it makes you look like someone people might be afraid to be stuck in an elevator with. For example, the other day I worked in an office with someone who decided to get decked out in green and red tartan for the holidays, and not only was it too much, he then put on a hat that made him look so ridiculous I half expected him to start singing Thank You Very Much... except he was too overdressed even for that.

So I'd say first look for classic, really nice clothes in solid colors that really fit you well and you like. Nothing too baggy. Neutrals are good. But then keep your eye out for pieces that catch your eye, and look everywhere. Thrift stores, online, ebay, wherever. Don't wear more than two funky pieces at a time... they'll compete against eachother and lose points. You want people to notice those cool items without thinking, "Wow, this guy's wardrobe is hurting my eyes. He doesn't know when to stop, does he?" For example, maybe you find a pair of funky shoes and you have a cool jacket on. Or a hat and some funky pants. Sometimes just wearing one funky thing makes even more of an impact. If you're wearing a black shirt and black pants but have on funky shoes, people really notice. And if you don't pay attention to shoes, that should be top on your list because your shoes REALLY matter.

One other thing people forget about... you should consider your haircut as part of your wardrobe. If you dress cool but your hair looks like you aren't paying any attention to how it's cut, the rest of your outfit loses points for how it's put together. You have to pay attention to the whole package to impress.
posted by miss lynnster at 10:55 AM on December 27, 2007 [2 favorites]

Say no to girl jeans and elf shoes.

Say yes to guayaberas (what my brother calls a "Mexican daddy shirt") and kilts. Though maybe not at the same time.
posted by oats at 11:45 AM on December 27, 2007 [1 favorite]

Everything very Brooks Brothers, with a kilt and some Red Wings. Swoony.
posted by thinkpiece at 12:06 PM on December 27, 2007

There has got to be a way to dress creatively without going over the top or sticking too closely to the rules of modern fashion. I don't know what that way is, but I'm just sayin'.
posted by mazatec at 12:21 PM on December 27, 2007

BTW, my apologies for offending any grammar police in the audience. It's ≠ its. Yeah, I know.
posted by miss lynnster at 12:23 PM on December 27, 2007

Best answer: I can really relate to the just not caring if you're completely over the top and in dubious taste in your sartorial preferences.

My particular bad taste is quite a different flavor from yours, though, so I apologize if my recommendations are off.

My aquaintance Blake is quite the role model in regards to smart Mod wardrobe, including some fabulous secondhand suits. Upscale British clothier Paul Smith also has the dapper, natty look down pat, along with a touch of humor.

Cufflinks, collar stays, argyle socks. Monocramatic black, but with interesting cuts and textures and bright white shoes(NOT 80s tennis shoes).

Retro to Go has a very wide scope, but they occasionally feature clothing items you would enjoy.

Vintage Designer Clothing has the sort of unique, distinctive pieces that can put your personal touch on everyday outfits. Extensive mens section including, yes, Hawaiian shirts.

You don't sound like you are bound to any one decade or style. If you are willing to go to the effort of typing this up, you don't mind putting some effort into looking good.

I'd hit up the usual thrift stores and vintage shops, and look for anything well made and in good condition, that fits you well. Don't buy anything stained. Don't buy it if it doesn't fit you; you know you're never going to get around to altering it. Don't pay attention to color or any traditional decorum.
posted by Juliet Banana at 4:44 PM on December 27, 2007 [1 favorite]

Zoot suit!
posted by freshwater_pr0n at 6:18 PM on December 27, 2007

Best answer: The secret to pulling off arcane and loud fashion statements is taking good care of what you wear, making sure it both fits you and is flattering, and not mixing and matching styles and eras unless you absolutely are certain the fusion works.

I wager that what you actually need is some much better Hawaiian shirts. The real McCoy: silk or rayon, WW2-through-1959 era, selected because the pattern is truly gorgeous. It'll cost you. Pair them up with appropriate retro-cut khaki trousers and non-descript, classic casual footwear. Are you slim? If so, the western look suggested above is a good one--but again, you must pair the piped shirt with mother-of-pearl buttons with a nice slimline gabardine slack and understated, well-kept boots. A bolo tie is fine, but please, no lucite embedded scorpions.

Or hell, just have a tailor whip you up some jumpsuits with your name and stars embroidered all across the shoulders.
posted by Scram at 8:03 PM on December 27, 2007

Best answer: I'm saying this as a former habitual Guayabera and occasional bowling shirt wearer. Don't be that guy.

These shirts look like crap on 90% of the male population. Bowling shirts especially have a contrived faux rockabilly aesthetic that just make you seem lame. It's like that drama kid in high school who started wearing a bowler everyday as an affectation. Yeah, he went to my high school too. I'm sympathetic to the rationale behind wearing such clothes. I understand the look that you're going for, but you're probably not pulling it off. Even if you're going for the cool uncle look, it doesn't come off as casual as you might like.

In the summer time a good fitting guayabera can look pretty snazzy, but don't overdo them and don't wear them if they're too loose. That's the biggest problem with guayaberas and bowling shirts, they have a very unflattering boxy shape. Loose clothes my people look schlubby. At best they make you look like a little kid.

When I stopped wearing my clothes so loosely, many many people complemented me on how much weight I had lost, when actually I just started wearing clothes that fit me. A good fit beats any specific cut or style of clothing.

I agree with the above posters who recommend wearing classic, well-made brands with a bit of flair. I know it sounds boring, but buying clothes from J Crew, Banana Republic and similar stores ensures that you'll have a foundation of classy clothes that go well with each other. From this foundation you can add your own style. I really like expressing myself through my shoes and maybe a unique watch. Zappos and Endless both have a great collection of retro or fashion sneakers. Retro trainers are a good way to be comfy and look good. Avoid lame ass predominantly white plasticy Nike basketball shoes like the clap. Again, they make people look like lazy 12 year olds.

Similarly pick a few central colors for your wardrobe. Having a lot of naturally matching clothes makes it easier to dress well. Pick a good color or tone and make it your home base color. It's a lot easier to look sharp when you have multiple tops, bottoms and shoes that all look good with each other. Again you can pick one article of clothing to stand out.

Unfortunately, a lot of kitschy clothes just look bad at a very basic level. There are better ways to show your individuality. It's really hard for guys to make that transition from dressing like a kid to dressing like an adult. At first you might feel pretentious, but you'll look better and feel better.

Sorry if this came off as condescending. This post is personal to me as it reminds me of how I used to dress. I look at old pictures of myself and shudder.
posted by Telf at 8:59 PM on December 28, 2007 [2 favorites]

Are you familiar with Lord Whimsy? He may provide you with some inspiration.
posted by fidelity at 11:49 AM on December 31, 2007

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