What I Would Wear (If I Were A Guy)

For a long time I've toyed with a kind of "Dress A Day Guide To Style For Guys" but I've never done it, mostly because I hate any kind of fashion writing that says YOU SHOULD WEAR THIS, NO, REALLY, BECAUSE I SAID SO, C'MON NOW, ARE YOU TRYING TO MAKE ME MAD? People should wear what they want to wear (as long we all agree that "want to wear" = "made a conscious, thoughtful decision to wear").

So yesterday I realized, hey, I could do a post about what *I* would wear if I were a guy. And yes, I know, unisex styles, androgyny, blah blah blah, but let's face it: nobody who calls her blog "A Dress A Day" spends a lot of time Dietriching around in a suit.

First off: if I were a guy I would totally do the kilt thing:

David Tennant IN A KILT.

Because, despite being named "Erin", I'm Scots (if you go back a couple hundred years or so) and secondly, girls love 'em. (I'm just assuming here that if I were a guy I'd be a straight guy.) Believe me, walk down the street in a kilt (even if you don't look like David Tennant) and you'll be beating them off with a stick. You might actually need a caber, come to think of it.

I also like the suit and sneakers look:


David Tennant as Doctor Who.

(What, did you think I was going to use someone other than Ten to illustrate this point?)

I think this works best when the sneakers are not of the highly-athletic sort. Saturday sneakers rather than performance sneakers, if you know what I mean. (Although this also mostly works.)

I also like the ironic and somewhat ratty t-shirt look:

Hugh Laurie as Dr House.

In fact, if I were a guy, I would INVENT pretend bands, photoshop up the tour t-shirts, and have one-offs printed up for me. Then, when asked if I liked the band whose shirt I was wearing, I would say "These guys? They sold out. They suck now."

If I were a guy, I would only wear Levi's jeans. Period. No fancy jeans. This would be non-negotiable. In a pinch, or if I were invited to a rodeo (AS A PARTICIPANT) I would consider Wranglers.

If I were a guy, I would wear these shoes with everything.

If I were a guy, I would always have a brushed-aluminum mechanical pencil on my person. (I usually do now, anyway.)

If I were a guy, I would totally copy Francis and wear the funky tie/shirt combo.

If I were a guy, I'd wear seersucker suits, only I'd wear them with a t-shirt & sneakers, not a dress shirt and tie:

Seersucker suit

If I were a guy, I'd wear paisley shirts.

Of course, lots of things would still be the same in my closet. I'd still wear heavy-framed glasses, bright colors, plastic watches, and Jack Purcells.

I even like the sport-coat-and-shorts combo. But never, under any circumstances (unless maybe I lost a serious bet) would I show up in this:

Really, really, really bad shorts.

I promise.

0 thoughts on “What I Would Wear (If I Were A Guy)

  1. (‘m with you on the kilt look. Did you see Tom Selleck on the Tonight Show in his kilt a few years back? Memorable [drool}!

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  2. You know what does NOT work with a kilt – a short sleeved man’s dress shirt and tie. I went to a Scottish country dance thing and one of the guys was all dressed up except that he wore a short sleeved shite shirt and tartan tie. All that was missing was a pocket protector – the whole thing looked like high school chem teacher meets Braveheart. Too weird for words(and yes, the guy looked geeky anyway, with glasses and red hair). The other thing is – everyone is attracted to men in kilts. Case in point: My DH and I once worked for a post-modern(not naming them but they are West Coast)kilt co at a gay rodeo in Maryland(do NOT ask why/how we ended up working for this company in their booth at a gay rodeo..the story is too long). In any case, to promote product, we had to both wear these kilts. I looked like exactly what I am: slightly pudgy short middle aged housewife. My husband – well, he was being hit on by everyone, of every gender persuasion, all…day…long. After the first three, I told him that he was embarassing himself and that he had to come up with some sort of clever answer because there were some very persistent guys who thought this kilt-wearing, white-bearded guy in the teeshirt was catnip. Funniest day I’ve had in years.

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  3. Yes! Who else to model suit and sneaks but Doctor 10! 9 worked the jumper and leather look really hard (and the simple sweaters were perfect on Mr. Eccleston, they really softened his intense, athletic Doctor) but I think that 10 has redefined the Doctor AND the suit/sneaks look for me. LOVE!Where’s my sonic screwdriver? I know the mechanical pencil will not cut it…..

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  4. I have made pretend band t-shirts. That is to say…I have a Weird Sisters Tour t-shirt that I made. Concert locations include Transylvania, Salem, Giza, Stonehenge, and of course…Hogwarts Castle.

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  5. So DT (Scottish, from Paisley), and Hugh Laurie (English) – if you are going to come back as a guy, you want to be a British guy!?You know kilts aren’t that big a magnet in Glasgow – usually only worn to football matches and weddings. Unless you are actually from the Highlands. And in Partick. In the case of the Tartan Army look it is accessorised with a football (soccer) shirt, in the team strip, a flag (wrapped round the shoulders), a “hey you, jimmy” hat (fake red hair under a tartan bunnit)and several identically attired mates. This should be worn especially on trains, the underground and at airports and requires loud shouting of the “we are going to win” variety (it doesn’t bear repeating in the vernacular!)on the way there and by drunken ‘singing’ on the way back.In the case of the weddings, its the full velvet jacket and bowtie get up, flags not usually worn and the drunken ‘singing’ doesn’t happen until after the photies are took and the reception gets under way.You can take my word for it Scottish men don’t all look like David Tennant!Cheers,AJ

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  6. Like Julia C, I have made fake band shirts. My BFF in high school and I reveled in coming up with band names. But we couldn’t get our hands on screenprinting back then, so it was pre-indie/pre-emo & done with Sharpies.Also: LOVE that tie & wacky shirt site. Wow!And: My fella has saddle shoes, plus will be wearing a seersucker suit for our wedding. I seriously dig the Tom Wolfe look. And brown. And pinstripes.

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  7. My husband actually has invented a fake band. And, since he’s into screen printing, he prints up fake concert T-shirts for the fake band. Often with tour dates on the back. People ALWAYS ask about his shirts—it’s hilarious. ~Sarah

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  8. Honestly, I don’t know how theybesides Francis, of coursestand it. Men’s clothes are so boring.I think that if I were a man, I would concentrate on having cool shoes, and I would seek always to wear a crisp shirt (preferably striped or patterned) and (unpleated!!!) trousers. Because so many guys dress so rattily every day that wearing even slightly formal clothes stands out.I’m with you on the suit-and-sneakers look, though. One of the cutest weddings I’ve ever been to was the one where all the groomsmen (the groom’s fellow rock band members) wore brown suits with cream-colored Jack Purcells. It helped, of course, that they were also all wearing athletic-style medals, hanging from fat red-white-and-blue ribbons, commending them for “Excellence in the Field of Excellence.” Needless to say, this wedding also had the most excellent music.And I share your distaste for the shiny shorts-wearer’s outfit, but I’d like to make it clear that it’s because of the shine, not the shorts. Just this weekend, my mother was going OFF on men’s shorts and how she’s so, so sick of this baggy, knee-length thing. “I wanna see some leg!” she said. I must concur.

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  9. I wholeheartedly agree — all of your choices are contained in the list of ‘things I love on guys’, with the exception of the funky shirt/tie look — although I do like it. I feel like I was the first girl to wear my black pumps with my levis and my WLUP tee (too small)– back in ’78 (in Chicago) — was I? So, I sure do love the ratty t/levis and unexpected shoes choices! Thanks Erin,b

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  10. If I were a guy, one thing I would NEVER wear is the ubiquitous polo shirt. No style at all! I make my hubby’s shirts: he likes the 4 pocket style of the guayabera. I put 4 pockets on a hawaiian shirt, match the print, and they are almost invisible. He loves them!

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  11. I love this post! I like so many of your choices. My husband is amazing at combining very classy dress pants with shirts and sweaters that his dad or my stepdad wore in the ’70s, along with his tweed Macbeth sneakers. He also wears a handlebar mustache with aplomb and sports flesh tunnels in both ears. I love his quirky style and that he enjoys shopping as much as I do. Right now, for him, we’re on the hunt for a summer suit (possibly seersucker), some linen shirts, and an old-man sweater (deep v-neck, three buttons – I can see it perfectly buy can’t find it anywhere).And agreed about the kilts! We’re going to a German-Scottish wedding next month and I’m sure the groom will be wearing his kilt – he wore it to the last wedding we both attended and it was great.

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  12. Ooh, thanks for those pics of David Tennant – that totally is what I need to get my day goin’. I’m a big fan of his Doctor Who close-cut striped suit and Converse combo, too.

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  13. My husband has been wearing the ratty t-shirt and levis for years with cowboy boots and I told him to grow up (he’s 40). He still wears them, but has grown-up for going out to wranglers, ropers and nicer shirts. Going out is wrangler khakis, nice dress shirt, ropers and blazer. (We live in a rural So. TX town)

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  14. Who cares WHAT they are wearing, just give me Tennant and Laurie and all would be good :)Although men in kilts are almost always hot, of course. Unless they are wearing it with the wrong shirt (see above poster’s comment about the short sleeved dress shirt).

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  15. As an aside, I’m finding the Hugh-Lawrie-as-sex-symbol thing (nearly wrote “sex-thimble” there – nice freudian slip) deeply amusing. He’ll always be feckless old Bertie Wooster to me, reluctantly accepting sartorial advice from Stephen Fry’s Jeeves. Or the stupid Prince Regent in Blackadder. Not sexy at all!But I’m with y’all on the Tennant-appeal. The brown suit/trenchcoat/white sneaker thing works mighty finely. My cool-dude 8-year-old emulates it well too – too cute for words.

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  16. I think I’m in love with Francis. Just don’t tell my husband–he’d never wear those combinations. But maybe I’ll just hijack one of his white button-ups and try my hand at tie-dye.

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  17. Ooh! Erin, thank you so much!First of all, I will forward this to my husband, because he is likes to dress well and this post will give him some new ideas.Secondly, I just read about a new BBC drama, and I had no one to tell about it; but it stars David Tennant (in a nice fifties suit and some granny specs), so now I can tell you!It’s called “Einstein and Eddington”. Tennant is going to be Eddington and Andy Serkis will be Einstein. It’s a drama about the theory of relativity, and the lives of the men behind it. Geeky Joy!BBC Press release here:http://www.bbc.co.uk/pressoffice/pressreleases/stories/2007/05_may/21/einstein.shtml

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  18. Yep, kilts are hot. I have a couple of friends who wear them. I have unsucessfully tried to convince my husband to try one. I have pondered if it is the actual appearance, or the sort of naughty potential for flip-up that makes them appealing. Why wouldn’t men want to wear a garment that lets their stuff breathe? I don’t know, but I will say this: when Smithsonian & History Channel did that coverage of the building of the two trebuchets at Loch Ness and all of the traditional carpenters donned kilts—whew!—hot flash!Hey, what is up with the guy in the suit, tie, saddle shoes and no socks? Yep, I bet it’s hot, but the sockless thing blew it for me. I think the discomfort of not wearing socks offsets the discomfort of the heat. How about a very thin pair of silk socks? That would make the whole thing.

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  19. I bought my husband a seersucker suite for our anniversary. After looking everywhere for white dress shoes he finally settled on white-on-white shell toe Pumas. He also wears an Italian straw boater with this getup. It works.

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  20. @San Antonio Sue: Absolutely on the polo shirtsI hateses them! But I know our hostess fancies polos, so I was trying to keep my mouth shut. Oh, well.And I love guayaberashad a boyfriend who rocked thembut why is it so hard to find them in natural fibers? Once I found him a linen one at a thrift store, but every other one I ever saw was polyester blend, at best. Anybody know a good source of cotton or linen ones?

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  21. Oh and I forgot! While the husband can’t be talked int a kilt, he’s been known to don a sarong on particularly hot days. Which makes him a particularly hot husband, imho.

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  22. I 100%, 150% even, agree about the kilt. Seriously love a man in a kilt. Yes, catnip!!!!!And I am warming up to the suit and trainers thing, thanks to ten.I love a man in a suit who looks posh but not stuffy. (I also like a man who can pull off a real hat, like a fedora or panama.) Am I the only one who likes monk strap shoes? I also like mod looking shoes on guys. Also, being trim (or at very least, having a great fit) is a BIG part of pulling off the look. And the jacket and pants need not be the same fabric. Hell, tossing on a nice jacket with your jeans (something I normally say yuck to) classes things up just swell.Some of Dixie Hoyt’s Swoon Inducing Catnippy Examples aside from Mr. Tennant… Richard Patrick (Filter) in a suit…that Three Days Grace vid with the singer is in a deconstructed suit…Alex O’Loughlin in Moonlight…the look just slays me. Oh yeah, not yummy but cool as all get out: OK Go! These lads are the kings of the zany suit.Heavy sigh. Thanks for the happy visuals in the morning. We shall just not speak about that sad, sad, shorts thing…

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  23. Ah yes, good eye candy there with Ten! He makes the best Doctor, and of course those clothes aren’t bad, either.

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  24. india, I had to look up guayaberas cos I had no idea what they were. Then I Googled “100% cotton guayaberas” and got quite a few hits. Maybe someone on here has actually purchased one and can tell you a good store, though.Guayaberas kind of remind me of barongs.

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  25. I’m not sure about the T-shirt idea. There’s a guy in my town, more-than-slightly off center, who silk screens his own shirts with concert info that I’ve never figured out (it’s like, “Grateful Dead, Kingsport TN, 1987” – shows I’m often unsure ever happened). he has a lot of other weird going on for him, but the shirts are integrally related to his persona.

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  26. If I (shudder) were a man, I would rock the accessories: party sox w/clocks, fancy gadgety vintage watches, killer hats, awesome decorative ties. Totally second the seersucker suit w/casual T look, but I think sneakers w/suits only works till age 40….maybe even a little before that.Liz F. from Brooklyn

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  27. I got a crush on Hugh Laurie after seeing clips of him playing guitar and piano and singing. I could almost forget he was Bertie Wooster (loved the show, but the only thing remotely sexy about him in it was the clothes he wore when visiting country estates – houndstooth and fair isle – yum).I want to get my toddler a “sport” kilt. He has cute legs, is named Ian, and my family is mostly Scots (way back when), so he NEEDS a kilt.

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  28. I think my favorite thing about visitng Scotland was seeing the younger guys run around in more modern style kilts with chunky sweaters on. I could have drooled all day. I think the attraction is the flash of thigh you get. Almost all men’s clothes these days cover them to at least below the knees (I don’t know many short short wearers). So that little flash when they walk – *whimper*.Must save money for trip back to Scotland.

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  29. I think my favorite thing about visitng Scotland was seeing the younger guys run around in more modern style kilts with chunky sweaters on. I could have drooled all day. I think the attraction is the flash of thigh you get. Almost all men’s clothes these days cover them to at least below the knees (I don’t know many short short wearers). So that little flash when they walk – *whimper*.Must save money for trip back to Scotland.

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  30. Great post!If you were a guy, and I lived in Chicago, and I wasn’t married, I would TOTALLY have a crush on you.

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  31. My sexy, awesome, and 100% Polish boyfriend has recently discovered the joys of wearing kilts. In about four months, he’s obtained nine of them. He loves the comfort…and the attention. 🙂

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  32. Kilts on men: Functions as Viagra for women. (except when worn as noted above with short sleeve dress shirts and ties.)Ditto great hats.Ditto seersucker suits, slightly rumpled, anytime before sundown. Funny how guys don’t believe this.Even big old fat guys look toothsome in kilts or great hats or seersucker. It is amazing.

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  33. I agree with your choices but you left out the one thing that I really love seeing a man wear and that’s a fedora. When I see a man in a great fedora I just melt. I always tell them how classic they look and they absolutely always give me a great big smile back!

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  34. Paisley shirts make me think of Paul Weller. I swear he’s wearing a Liberty print shirt in the Illumination DVD (and also in the picture on his wikipedia entry.)You forgot the sartorial favorite of thrid world dictators worldwide: the guyabara (and it’s Filipino cousin the Baraong Tagalog!) They’re perfect for those casual summer weddings (much better than sweating in a sportcoat!)

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  35. The guys I work with were told they could not were shorts on Fridays. No more casual. So a couple of them had an idea to wear their dress plaids to work on Fridays, since this was not expressly prohibited by the management. This started quite a fad, and now we have dress plaid kilts from various clans and a less expensive modern concoction called “Utilikilts” with lots of pockets for construction-trade tools and beer. These are brave men, strong men, skirted men. I admire their resolve.-Shaun

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  36. What I really want to know is, what would you wear (as yourself) if you didn’t wear dresses? you know, if you were a pants kind of person.–Anne

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  37. My Husband totally rocks the Southern Gentleman look. We live in New Orleans, so light weight clothing is essential. Guayaberas and linen slacks w/ classic florsheims on the weekends. Seersucker suits, linen suits (3-piece if possible) and bowties during the week. He’s a lawyer and gets lots of comments in the courtroom about his dress. Of course he’s never without his straw fedora. All to match his 1951 Chevy. He also owns his own tux. Is it any wonder I married him? I’ll have to work on him on the kilt though.

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  38. I’m seeing consensus about the kilts. Should we have a DressadayCon in Scotland, perhaps? I’ve always wanted to go there . . .

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  39. My Cuban Store dot com for Linen Guyaberas. (My husband is Puerto Rican – and a very Large man he got his from there. Light blue for our wedding.)

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  40. I was sharing this advice with my 17year old son – who LOVED the fake rock band tour T shirt idea, btw, and he asked,”what is worn under a kilt?”, and I had to answer – “NOTHING! everything is in perfect working order!”I first heard that kilt joke when I was 17 :). He says that’s the worst joke ever.My son is also a sneaks and suit kinda guy. He says BLACK sneaks with formalwear PLEASE.

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  41. I’ve never seen a seersucker suit, except in old b&w movies. I thought they went out in the ’50s. If anyone turned up in Australia in one, they may as well hold up a sign saying “Weird Tourist”.I love the paisley shirt! Has anyone seen any fabric like that? It’s so pretty–I’d love to make a dress from that fabric!And – thanks for the pictures of Dr Who and Dr House 🙂

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  42. Oh Yes!: DressadayCon in Scotland – I’d be there in a flash! Wonderful memories of visiting Scotland, men walking down Princes St. in Edinburgh in kilts, carrying briefcases; men in kilts in Highlands with ratty Aran sweaters & wellies; kilted piper at dusk on walls in Oban, pacing & playing to no one but me, watching the swing/swing/swing of that kilt. My, my…..Although we see kilts fairly frequently in Nova Scotia (“New Scotland”), not frequently enough. Not sure if I could concentrate on work around them, though…Lovely post!

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