Ask Painfully Hip: What the heck should I do with all these oversized men’s shirts?

Ask Painfully Hip: What the heck should I do with all these oversized men’s shirts?

Hi Amber and Eve,
My dad was cleaning out his wardrobe and found a dozen button up shirts he didn’t wear anymore. He gave them to me :) but I don’t know how I could wear them or alter them to make them wearable. They’re pretty large. Do you have any tips?

hi ronnie!
amber and eve passed your question along to me, (because i LOVE to sew!), so i’m going to see what i can do to help you out here. (ps. how lucky are you to get all those shirts?!?! i’m jealous!)

ok, so i’ll admit that i did a little bit of a google search on the topic before i sat down to tackle it, and i have to say that i wouldn’t wish those search results on anyone. one especially fantastic message board was plastered with sentences such as “sow the sides of the shirt smaller and cut off the collier.” (i’m not even sure what a collier is on a shirt…) and fantastic fashion advice such as: “pop the collar, belt it with a wide neon belt, and wear matching pointy toed pumps and black leggings.”
frankly, i’m hoping we can do better than that. i don’t mean to offend anyone and their personal style, but i feel like that look is just… really over-done.

amber had a really awesome idea of cutting out around the collar (collier?) and turning them into poofy halter dresses. since i always have to take things a step too far, my reaction was, “yeah! and what if you left a strip connected to the collar, to make it a t-back?!” you could do this with or without the sleeves.

the main thing you need to figure out is if the shoulders fit. this is the key to wearing any over-sized top without looking sloppy (or like you’re drowning!): well-fitting shoulders. one of my favorite thrift store finds was this over-size silk blouse, that, believe it or not, is marked as an “extra small” because it fits small through the shoulders. (please ignore the walking cast on the foot i’m trying to hide!) because of the fit through the shoulders, i’ve been able to pair it with all sorts of things without looking like i was playing “dress up.” (well… my boyfriend strongly disagrees with that last statement, but i’ve found that the best response to that is “you chose me!!”)

oversized button-down

if the shoulders fit, unless you want to drastically change the look of the shirt, you don’t have to do much sewing. if they don’t… well then it might take a little more effort. if you have any experience sewing, you can take the sleeves off, re-size the shoulders and arm holes, and then re-attach the sleeves. you can re-size the shirt by using your favorite fitting top as a pattern (be sure to remember to factor in enough of a seam allowance!). if you don’t really have much sewing experience, you will probably want to get someone to help you with this (or email me and i can give you more detailed instructions).

if you detach the sleeves, sewing them back on can be a lot of fun – you can leave them big and puffy, or tighten them up. you can leave them long, or shorten them to any length – even cute little cap sleeves. right now i’m having a lot of fun leaving the cuffs on, shortening the length to around the elbow, and then buttoning the cuff to make a puff sleeve.

to change the actual shape of the shirt, you can do all sorts of things – you could add darts in the side or vertically, and give the shirt a more feminine shape. you could also take the sides in a bit. you could sew a channel around the waistline a run a ribbon through it to create a draw-string.

styling the shirt is going to be even more of a chance to get creative. you could always go with the popped-collar pointy-toed pump/matching belt look, but i’ve been having a lot of fun trying different things – belt it high with a skinny belt, and then wear something loose and feminine underneath for spring – short bloomers or lacy vintage tap pants, tall white stockings and broken-in over-the-knee boots (or vintage woven flats?). i want to find a mini crinoline and create a very full (short!) skirt look. tighten it around your waist with a belt and roll the sleeves up so you don’t lose yourself in all that fabric! you could leave it loose and full and button a snug-fitting vintage vest over the top, or even try the corset-over-shirt look. one of the advantages to leaving the shirts loose is that you can then pair them up with very feminine pieces and not feel too baby-dollish.

Got a question? Ask Painfully Hip!

14 comments to Ask Painfully Hip: What the heck should I do with all these oversized men’s shirts?

  • Oh my gosh, that shirt look so damn cool as a dress!

  • Sal

    Damn, girl! I never would’ve thought a big floppy dad shirt could look so sexy. I’m a sewing know-nothing, but just curious: if a shirt doesn’t fit in the shoulders, it possible to remove the sleeves and make cap-sleeves from the remainder of the yoke somehow?

  • thanks guys :)

    sal – i’m trying to think of a way to turn the extra yoke into a cap-sleeve, and nothing’s coming to mind.
    this is not to say there isn’t a way though.
    sometimes having a lot of “proper” education on a topic actually limits your creativity, because you know how things are “supposed” to be done.
    play around with them! and i’d love to hear the results!

  • has a lot of tutorials for reconstructing button up shirts. I used to get tons of ideas from that site.

  • I remember that pic of you on wr, you have some great style girl and good advice on the shirts.

  • I saw a girl on the tube yesterday, wearing a big men’s shirt really well. She was very tall and quite curvy [not heavy looking, I'd guess a UK size 12? But definitely no skinny minnie - she looked like an amazon] which really complemented the look – she looked very womanly. Very simple – she just had this blue men’s shirt tucked into a pair of very skintight, ripped jeans, and open at the collar – but they were the 80s-style spray-on skintight, not the kind that wrinkle up and down the leg. And then some bright almond-toed courts. It sounds like a pretty cliched look but she wore it so well, it really stuck in the mind. She got the proportions just right.

  • Ronnie

    Hi Diana! Thank you so much for answering my quesiton – and especially for answering it so flipping well, too! I really, really appreciate it – I’m definitely going to try out a bunch of these ideas: I really love the ribbon one and I adore the dress you’re wearing in the picture (I didn’t even notice your cast :)
    Seriously, thank you sooo much! This was a great entry and I’m really grateful :D
    ps: My dad says hi and thanks, too :P

  • [...] out his wardrobe and found a dozen button up shirts he didn??t wear anymore. He gave them to me bu…Make your own Mother??s Day gift Philippine Daily InquirerMANILA, Philippines??I wanted to give my [...]

  • hi ronnie! no problem! i had a lot of fun pulling all the inspiration and ideas together!

    (and hi dad, too! :)

  • Really enjoy this opinion. Maybe mens pants website may help someone out there.

  • My kitty cat loves tuna and Dory fish, she also likes to pinch roast chicken

  • that’s kind of a cool idea for a dress.

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