Dappered

Affordable Men's Style

guilty header

The glory of the style guilty pleasure

By | Heads up: Buying via our links may result in us getting a commission. Here's why.

Style Poll:  What’s your guilty pleasure when it comes to style?

That’s mine.  An old thrift store t-shirt over a long sleeve tee from Target.  Usually both are wrinkled to hell because I either forgot them in the dryer, half folded them and left them in a laundry basket, or shoved them in a drawer that was too full.  There are holes in the t-shirt, and yes, I know it makes no sense to put the short sleeve over the long.

But I don’t care.  Because I love it.

It’s a great idea to put a little extra effort into your off-time style, but those who can’t think of a single guilty pleasure risk being a little too dressed up a little too often.  Someone who feels actual guilt about their guilty pleasure takes clothes way too seriously.

Maybe it’s the thing you put on after a really long day.  Or maybe it’s that item of clothing you’ve had for fifteen years that you still love and can’t bring yourself to send to Goodwill.

We all have one.  What’s yours?

Comments

  1. Hoodies. I love them. I know they don’t look “wonderful” — but dear God they feel so good.

  2. That look is very college circa 1995. Maybe you could throw a plaid flannel over top to complete it.

    Sometimes I go out in my pajamas. Usually when I wake up at 11 on a sunday.

  4. I have these terrible sweaters from American Eagle. They’re this huge, loose knit that looks like chain mail, are grey like chain mail, and pretty much can’t be washed except in the sink, so they get longer and longer. The arms go to my fingernails. But they are still the softest sweaters ever, and the best movie day on the couch clothes I’ve got.

  6. My black Jack Purcell’s. They’ve been to four different countries, are beat up as all hell, and look great (and are super comfortable – sorry, wingtip shoes, you have to take a break once in a while).

  10. In high school, I had different colored thermal undershirts I used to serve this very purpose.  I guess if I had to say my “guilty pleasure” would be hoodies… currently in the market for a slimmer one to replace a ton of huge ones I tossed recently, suggestions?

  11. Old t-shirts, long sleeve or otherwise. Collected them at events and such through college, nicely broken in and soft. Can’t help wearing them (even if it drives the wife nuts b/c there are holes in the underarm)

  12. I would try Gap. I picked up one on sale last year. It’s slim and you’d be surprised how dressed up it can look. Going through the store now I see similar items. I’m pretty sure they’re all zip up, but I prefer that to the pull-over anyway. 

  15. i wear old reebok pumps – black, white, purple, and blue. They are huge and very 90s….. they do not belong on anyone 25 or older, but i still love them…..

  17. My secret identity is as a winter outdoorsman. So I’ve got a lot of stuff in my wardrobe that wouldn’t impress anyone at Style Forum – knee-high hunting boots, Gore-Tex ski shell, softshell jackets, fleece jackets, insulating jackets, technical long johns, knit ski caps, balaclavas, gaiters, those Burton snowboard pants that look like jeans, plus about a thousand pairs of $10 Kinco’s gloves in various states of disintegration. Yeah, I am one of those guys who wears a red ski jacket and Kinco’s gloves.

    http://www.famousinternetskiers.com/media/sam/09_10/3rd%20TR/IMG_6490.jpg

    I’ll admit to occasionally wearing some of these items in “the real world” as well.

    I do the old t-shirt over a long-sleeved shirt as well, but I generally save that for lazy weekends around the house.

    Or for wearing under a few layers of jackets….

  18. I look pretty awesome in a pair of cold-weather running tights, too. Especially when it’s REALLY cold and I bust out the wool-socks-over-tights look.

  19. Thick, old, too-big flannel shirts, with jeans. Nothing feels better for around-the-house.

  20. I still rock my Pumps as well. hah I have the original ones, and some baby blue ones with white in them. I also still rock my occasional Air Jordans, Nike Airmax’s and Nike Airstabs. But those are on super rare occasions. I jus wont ever get rid of em.

  22. An old pair of beat-up grey Vans classics with holes on the top of the toe area on one of them.  They are the most comfortable shoes I own.  

    I love Vans.  They are simple, comfortable and come in many colors.  I sometimes feel like I should move on from wearing them since I am 30, but I think they fit my style without looking too much like a Hipster.  I often will wear them with Gap skinnies (Gap skinnies are usually not as skinny as the Levi’s) or slim fitting pants (sometimes cords) with a button up and V-neck sweater combo.  I think it gives off a laid-back feeling with the outfit. 

    So anyway I guess Vans are my guilty pleasure.

  23. I have these old, baggy, paint splattered cargo shorts I’ve had for many years that I wear during the summer a lot. They’re not amazing looking but they are so damn comfortable and breathable. I haven’t gotten around to finding a replacement and probably never will.

  24. A seriously too-big-for-me striped sweater that I’ve had for more than a decade and that goes to mid-thigh and about six inches past my fingertips.  It’s my I’ve-got-a-cold-and-don’t-wanna-go-anywhere uniform, over pajamas.  Usually while wrapped up in a down comforter on the couch and watching old movies.  Far from fetching, but so comfy!

  25. Yes!  Those are awesome.  Are they vintage or the newer releases?  I see those on Jackthreads every so often.

  26. 1.) Thrift store tshirts:  Love ’em.  Seriously, I can’t ever see giving that up.
    2.) Baseball hat:  When I don’t feel like wetting my hair, using product, and combing.
    3.) Vans authentics beat to shit w/ holes:  They just look better that way.

  27. Basketball Shorts
    College T-shirts – Gotta rep the Buckeyes.
    And since I live in NY, snow country. The above, with hiking boots and a carhart jacket for walking the dog all winter. 

  28. Oh – this Billabong t-shirt I got as a freebie one time. It has some moronic graphic print on it but I swear to god it’s the most comfortable, best-fitting t-shirt I’ve ever owned. It actually makes my upper body look muscular, which if you’d seen me in person, you’d know is no mean feat.

  31. I picked up an Alfani hoodie from Macy’s that fits me really well (tall / slim). You could also try H&M.

  34. a black Hugo Boss sweater with a zip up collar. Yes, it’s a BOSS, but I treat it like a ugly dog for the past 10 years I’ve had it. I rarely wash it, so it’s wrinkly and it stinks. I roll up the sleeves or let them drag a bit too much so the edges are tattered. With the collar up I look like a douche. With the collar down I look like a prep.

    but I love it. wear it over a button up, a polo, a t-shirt, or nothing underneath. Chinos, trousers, jeans, shorts it seems to go. boots, clogs, loafers, trainers, flops, even bare feet at the beach. it’s my armor, my weapon, and shield.

  36. Flip-flops!  I go through a pair of Rainbows a year.  I know it’s a faux pas, but I love wearing jeans and my hemp rainbows on a warm, lazy day. 

  37. I regularly wear these: http://www.ebay.com/itm/REEBOK-20TH-PUMP-EASTER-US-11-RICHES-BODEGA-HUF-UNDFTD-/320604460029?pt=US_Men_s_Shoes&hash=item4aa583d3fd#ht_3565wt_1139

    Of course, I bought them at retail, and not $500 for a used pair.

    They don’t belong on anyone at all, but I love them too much to stop wearing them. 

  39. My red an white pumas! I swear when I wear them I can physically feel the ground since the sole has been so worn out, but I still love ’em. The main problem is that I can only wear them during the summer since they are made of such a lightweight fabric.

  41. Not to go all Grandpa Joe, but, they don’t make t-shirts like they used to.  Best fitting, best quality, best material t-shirts are almost always at the thrift store.

  43. My Adidas Samoas, A long sleeve baseball t, my 7 yr old worn fitted baseball cap, and a light pir of gap vintage fit…just for running to the grocery or playing with my 2yr old son on campus on a saturday afternoon

  45. My off-time quick winter look: beanie, hoodless zip-up fleece, sleeves pulled up, t-shirt, gym shorts, and Chucks. So what if my legs are cold? Head and feet are warm.

  47. I have an old midnight blue adidas zip up sweatshirt from a ten years ago. It’s got only a thumbnail-sized logo on the chest, and great build quality (both of which they need to go back to in their apparel). Over the years it’s faded, which looks great, and gotten some holes along the seams of the arms and the cuffs. I took it to a tailor, and the lady seemed confused as to why anybody would want to save it, but she sewed up most of the holes as best she could. I don’t wear it out for anything more formal than grocery store runs, but I’ll keep it around until one of us dies.

  48. they are new releases… not sure how long ago I bought them, but definitely post-y2k years.

    here they are: http://www.searchyoursneakers.com/reebok-court-victory-pump-bring-back-package.html

  50. I guess they’ve been trying to remake the original and it’s slated for 2014?  According to the interwebs.  Blasphemy?  (Half the awesomeness of the TV show was the intro music.  Queen yo.)

  51. I bought a distressed Batman t-shirt because the one I had previously actually became distressed and ragged from so much use.  I try to sneak it under my clothes when I want to feel like a superhero

  52. fall/winter – Hoodies. Distressed comic book superheroes t-shirts. 

    summer – Birkenstock Jesus sandals. Cargo shorts. 

  54. I think mine would have to be my beat up, holey cargo shorts. I don’t wear them out, but I usually have a pair on Saturdays and Sundays after I wake up. They are comfy hold a ton for if I’m working in the garage.

  55. The kinco’s are real.  Stupid warm, perfect for that kind of thing (and if you’re reading FIS, you’re my guy).  We wore out pair after pair when I was a snowmaker.

    Outdoor chic, baby.  It’s its own styleforum.

  56. I have this raddy pair of Addidas basketball shoes that make my feet feel so damn good. And I picked up a pair of desert combat boots from the factory (Bates) before I quit working there. I wear them when I want to feel a little extra manly.

  57. I have noticed more than a few Wisconsin references since I’ve been following Dappered. What is your tie to Wisconsin – current resident, alumnus of the university, born there and lucky enough to escape?

  59. I love my Abercrombie Hoodies and Sanuk Sidewalk Surfers. http://www.sanuk.com/hemp They’re sandals with a shoe upper built on top. Most comfortable shoes I have ever put on my feet. I have them in Hemp, boat shoe, and lined boot for winter… Oddly enough people ask me where I got them all the time. 

  60. My hoodies around the house. And my Nike Baselines that I wear far too often. Both items have a time and place that I like to spread a bit farther since I like them so much.

  61. I too like the old tshirt over a long sleeve tshirt – I’m wearing a white long sleeve t with an old red Inzer tshirt over it right now.

    I’m also a fan of cargo shorts and a hoodie.

    Both are for lazy days or days I’m only going to leave the house to go to the gym or run to the grocery store.

  65. My guilty pleasure is probably my topsiders. Not that they’re unstylish for casual wear, but I probably wear them a bit too much. Just so comfy and easy to slip on when I’m hitting the grocery store.