A Custom Fit: Tailoring Tips For Wearing Menswear

Autostraddle o.b. tampon article series
Inspired by how happy you are that ob tampons expand all around to custom-fit your body, Autostraddle’s “a custom fit” article series will tackle how to make all the other parts of your life expand/adjust all around to custom-fit your life/self. Today Laura’s gonna teach you how to tailor stuff from the men’s department to actually fit! 

Bois and grrrls, is there anything sexier than a woman in “menswear”? I’m inclined to say “No.” Masculine or feminine, curvy or narrow, tall or short, a lady in a perfectly-tailored oxford makes me weak in the knees. But grown women looking to sport a masculine fashion can find shopping in the men’s or boys’ department to be an incredibly frustrating experience when nothing you like seems to fit your body right. Sure, you can settle for a boxy or otherwise uncomfortable adornment experience, or you can take matters into your own hands!

Good news: the only thing standing between you in your sweatpants and you as a vision in vests is a pair of scissors and a sewing machine.


Tailoring Menswear To Fit Your Body

First up: T-shirts.

There are just too many boys’ t-shirts covered in witty slogans, cool graphic designs, and dinosaurs to let a little thing like fit get in the way.
Custom Fit Autostraddle Article Series 1
The real trick to getting a t-shirt to fit you right is all in the sleeves. If you start by picking a size that fits you in the shoulders, you’ve only got to worry about the sides. Put the shirt on inside-out and find yourself a big mirror. Does it fit you throughout the body? If you like your t-shirts to hug you a little tighter, grab 3 pins per side and start making (educated) guesses at where to put them–I usually start one inch in from their seams.

Once you’ve got a rough idea, carefully take the shirt off, straighten your pins, flip it inside-out and try it on again so you can make any adjustments. They say “measure twice, cut once,” but I extend that to “measure twice, sew once” because seam-ripping is almost as fun as pulling your toenails out. When you’re all set, sew a straight line through your carefully-placed pins, cut off the excess fabric, and try it on again.

Last but not least, take a second to take a little tuck in the sleeves so they don’t stick out and give you that triangle-armed look that’s so popular among the gym-class set.

Second Up: Button-downs

Next we’re going to talk about button-downs. Or button-ups, if it suits your fancy. You might be thinking, “A button-down is pretty much a button-down. Why would I want to alter one when I could just go to the store and buy one?” My answer to you, my friend, (besides pointing out that you can buy perfectly decent cookies at the store but everyone knows homemade ones are better) is that the perfect oxford is an elusive creature. They’re always frilly or too short or just plain made for someone other than me in mind.
Custom Fit Autostraddle Article Series 1
If you can alter a t-shirt, you can fix an oxford. Just like a t-shirt, you’ll want to find a shirt that fits you in the shoulders. If you can find one that has the right length sleeves as well, you should immediately stop what you’re doing go buy a lottery ticket. Don’t worry if you can’t; finding a button-down with adequate sleeveage is a nearly-impossible feat. Just remember that sleeves at your wrists are obnoxious and that rolled-up sleeves give off a carefree sense of joie de vivre.

The main difference between fixing a t-shirt and this project is that you’ve got an under-arm seam to contend with. When you go to sew along the side, you will want to continue sewing up along the sleeve, but you will have to stop yourself. You will want to, trust me, but I’ve had the experience of wearing 3 lazily-tailored shirts and I’m telling you: don’t do it, it’s not fun! Instead end your seam when you reach the end of one side, reposition the shirt at a 90-degree angle, and then start sewing your sleeve.

Last we’re going to be turning a massive jacket into a vest-type fandango.

Lastly: The Jacket to Vest Conversion

This time we get to avoid sleeves altogether because we’re cutting those babies off before we start. You should decide how thick you want your vest straps to be and then cut accordingly, remembering to leave an inch extra so that you can hem them later.
A Custom Fit Autostraddle Article Series Photo 3
This time, you’re going to take all your knowledge from t-shirt and button-downs and apply it to fitting your vest. Just like the other two, measure, sew, and cut the sides first and then move on to the sleeves. To hem the sleeves in, fold the fabric under once and iron it, then fold it under again and pin it in place. It’s best to start sewing under where your arms will go because when you work with thicker fabrics the beginning and end of seams have a tendency to veer toward ugly.

Now you can shape the bottom of your vest. You can cut it angled, curved, or straight across, but make sure to leave a seam allowance so it’s not too short. Sew it up just like you did the sleeves and you’re good to go.

As you can see, when it comes to the right fit, it’s never impossible and it’s never too late to get it just right.

Before you go! Autostraddle runs on the reader support of our AF+ Members. If this article meant something to you today — if it informed you or made you smile or feel seen, will you consider joining AF and supporting the people who make this queer media site possible?

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Laura is a tiny girl who wishes she were a superhero. She likes talking to her grandma on the phone and making things with her hands. Strengths include an impressive knowledge of Harry Potter, the ability to apply sociology to everything under the sun, and a knack for haggling for groceries in Spanish. Weaknesses: Chick-fil-a, her triceps, girls in glasses, and the subjunctive mood. Follow the vagabond adventures of Laura and her bike on twitter [@laurrrrita].

Laura has written 308 articles for us.


  1. the only thing standing between you in your sweatpants and you as a vision in vests is a pair of scissors a sewing machine.

    This represents the exact transformation I need to make in my life!

    • This suggests that you should be able to make the vest out of sweatpants, and then go walking around with no pants on.

  2. *trans male is taking tips for turning vintage jackets into vests, and making button-ups into NOT dresses on me…

      • RAAAWR SHORTNESS. I mean I love being able to hide in things and then jump out and scare people, but when it comes to buying clothes from the men’s section, I just want my torso to not be approximately 10 inches long.

    • The only advantage to being 5ft and just about 7st, is I fit into H&M boys sizes really well and they’re really cheap. Still doesn’t make any difference to the first word people use to describe me is usually ‘cute’ though :/

  3. As a theatre person this article is interesting and hilarious. Tailor something without ripping the seams? My professor would die! :)

    • I thought the same thing. I always rip the sleeves at the armholes tailor it and then refit it, but I wonder if I’m just making too much work for myself.

      I feel like you have to pull the sleeves for a jacket, but if it’s a T or a button-up you can probably get away with it and long as it’s medium weight material.

    • Yeah, I’m usually a ran of ripping seams, but when it comes to fit, I’m usually at the end of my rope with seamripping and just go the easy route. Plus when you’re making a jacket into a vest, you don’t need the seam alliance left over from seam ripping anyway!

    • Yeahhh as a sound tech, I just very nicely ask the costumer to do it for me and pay in booze.

  4. Pingback: A Custom Fit: Tailoring Tips For Wearing Menswear – Autostraddle | secondhandsewingmachine A Custom Fit: Tailoring Tips For Wearing Menswear – Autostraddle | second hand sewing machines and more

  5. How did you know that I was just bitching at a thrift store yesterday that I really just need to learn how to alter clothing? Thank youuuu!

  6. Do you have tips for altering button downs to fit you if you’re busty? I know you’re supposed to find one where a button lines up with the biggest part of your chest, and maybe I have an abnormal torso, but I’ve tried on hundreds of button downs and none of them do this! I know there is enough fabric, because if I pin my shirts, they fit fine and don’t pucker or gape, but a solution that doesn’t involve a shiny silver dash in the middle of my chest would be most welcome!

    • Use a matching thread and sew tiny snap closures into the gap. If your stitches are small, they’ll be almost invisible, and the snaps will be kinder on the fabric than a pin anyway. A small hook+eye closure will work, too. :)

      • Yes! This is a great idea. You can also make sure just to sew the snap to the inner piece of fabric so that the stitches don’t show at all.

      • Oh, the snaps are a brilliant idea! I can never get the hook & eye positioned perfectly for some reason, so they either come undone or leave the button bands sort of curving outward right there. Thought I was doomed to either safety pins or making my own button-down shirts (which is possible, but very time-consuming and my buttonholes never look right).

        • Hint for aligning snaps: sew the male side first. Make sure yr garment is flat and dot the end of the male snap with a marker. Lightly press against opposite fabric, being careful to keep everything flat and neat. It should leave a little dot exactly where you need to center the female side. No more weird pulling! :D

    • I pin mine every day. Ha. Also some double stick Velcro can help too as long as it’s discrete.

      Like I said though, I mostly pin mine.

    • Also have you tried the J.Crew perfect shirt? I’m really busty and I have a tiny torso and it works pretty well for me as long as I pin it.

      Also when I’m pinning I just pin the inside layer of fabric on the button hole line.

    • Button plackets have 2 layers of fabric so if you just catch the inside layer of the shirt when you sew on the snap no one will see.

    • If you were to sew one yourself, it would include several darts. The larger the difference between circumference on the bust and below (i.e. the larger the boobs are) the larger the dart must be to get a tight fit. The problem with a large dart when alterering clothes is that you will lose a lot of fabric on the side and that might distort the shape of the shirt.

      So concluding it is possible to get a “man’s shirt” tailored to fit a larger chest, but it’s not so easy. If you don’t want it to be fitted as there are less difficulties. Good luck! :)

  7. Please use a stretch stitch when you mess with t-shirts and other knit situations. It’s on most sewing machines and it looks like 3 rows of straight stitches on the stitch selector dial. If you make your t-shirt nice and fitted and you don’t use a stitch that will stretch with the fabric it’ll probably break when you take it on and off.

    Also if you don’t want to do these things yourself you can find a nice tailor shop to do them for you! And everything will be done properly and beautifully. If you have a good tailor shop taking in a button up shirt should only be 10 dollars, 15 if you need to take in the sleeves too. This is extremely worth it so EVERYONE GO FIND ONE.

    I’m a senior in fashion school and I work in a tailor shop so I have a lot of feelings about this.

    Also I see many older dapper lesbians at work. They’ve got it figured out.

    • I totally agree with this.

      I feel like I’m constantly forgetting to use my stretch stick since I don’t have a serger. I always end up popping stitches and resewing on stretch.

      That being said, I avoid putting stretch fabrics through my machine like the plague. It never ends well.

      • Do you have a stretch stitch on your regular sewing machine? Most machines that have a stitch selector have one so you don’t need a serger…

    • Oooo! Oooo ooo! I have a question for such an expert as you! I’m going to be wearing a lot of festively branded t-shirts while working at comic book conventions throughout the summer (I’m an editor, and they’re from the series I edit). I’m most comfortable in v-necks…would a tailor convert a crew to a v-neck? Would it be crazy expensive?

      • I vote you cut the neck off and wear a tank-top underneath like, “Oh, this old thing? I just casually threw it on before I got here.”

        Alternative idea: cut the graphics off the Tees and topstich them on to V-necks in a complimentary or contrasting color. That’s what I do. This is particularly cool if you have a shirt that just says a couple of lines of text horizontally, because then you can sew the text back on at the very bottom of the V-neck. It looks awesome.

      • You can just cut the neckline in the shape you like, then either find an old T-shirt or buy some cheap T-shirt material and bind the neckline with that. (You know what bias tape looks like? Use an iron to make a long, skinny strip of your T-shirt fabric look like that. Then kind of wrap it over the edge of your T-shirt neckline and sew it in place.) You can either try to match the color or use a contrasting color.

      • Everyone already answered your question pretty effectively before me. Lol.

        Sorry guys I was at fashion school.

    • i’m totally doing this next time. my shirts always rip. i need a friend who is a senior at fashion school because i am but a handy went-to-fashion-school-one-summer person.

    • stretch stich would be lovely but my machine has been stuck on running stitch for the past five years because none of the buttons work anymore… So far i’ve been doing any t-shirt alterations with REALLY TINY blanket stitch which is okay but takes hours. Any other hand sewing stitches that stretch?

  8. Back in H.S. we were required to take “Home Economics”, a portion of which covered sewing. My final assignment was to make curtains to match another students throw pillows out of this funky brocade fabric we were given. I made a vest instead. It was AWSOME! I remember the teacher saying she was giving me a “C” because the stitch-work was very well done, but that it was a poor choice of project because it was an inappropriate choice of fabric and pattern for a man to wear. When I said it was for me to wear, she looked horrified. I rocked that thing for the next 2 years. Wonder what she’d say about all of these! Time to dust off the sewing machine..Thanks for reminding me I can do this stuff myself!

  9. Maybe I missed this, but who did the illustrations for this article? They’re great and I wanted to check out more work by the person who did them.

        • lizz! all of our team illustrations are BEAUTIFUL IN THEIR OWN SPECIAL WAY. there are no favorites here! except that tinkerbell is my favorite.

      • These illustrations are amazing! Laura, how did you get such great skills at drawing hot ladies wearing androgynous clothing? Those are the best skills to have.

    • Thanks Carrie! My blog’s nothing fancy, but it got some other things I’ve made/drawn on it.

  10. I wish I had the patience for this. But if the day comes that I do, now I’ll have this handy guide. Look how good these drawings look in their new clothes. I’d date these drawings.

  11. love the article, love the fact that its sponsored by OB. we’re all special snowflakes who deserve custom fitted everything!

    looking forward to the next installment in this series.

  12. Another question for all you who know how to sew! I buy pants to fit my hips, but then the waist is so big that if I tighten my belt to keep my pants up, the waist oozes out from under the belt and forms big wrinkly things. So, does anybody have any simple instructions for fixing this?

      • Oh hey that’s me! If you can go to the tailor shop and get the waist taken in.

        It’s like 12 bucks. People do it all the time.

        I could explain to you how to actually do it properly yourself, but it’s annoying and if you don’t know how to sew it’ll be really hard…

          • Honestly I know how to sew very well and I don’t have the patience to alter my own clothes. I just let someone else do it. Idk it’s just hard to take it apart, fix it, and then put it back together without messing it up. And god help you if there’s topstitching. I’d rather just make new clothes than alter existing ones >_<

    • I just did this for my sister..You will need 3/4 to 1 inch strip of elastic, Fray Ceck, sharp scissors, pin and needle & thread..
      Step 1
      Snip two holes on either side of the waist to create a casing for the elastic — one just inside the buttonhole/snap and the other just inside the button/other snap. Make sure your scissors don’t go through to the other side! Apply Fray Check to the raw edges.
      Step 2
      Thread the elastic through the casing and secure with stitches on one side. 
      Step 3
      Try on pants and pull on the elastic until you’ve got a good fit.
      Step 4
      Pin elastic in place, take off pants and secure with stitches on the other side. Trim excess elastic.
      That’s it! Totally easy! You can do this to any pants that:
      fit your hips, but are too big in the waist
      fit everywhere except that annoying gap in the back
      are made of denim without that 2% of spandex to make then snap back into shape after one wearing
      need to tide you over while you lose weight and fit into the next size

      • I’m an idiot.

        I wear BDUs at work, and the side tabs that are meant to adjust the waistband (because BDUs are made to kinda-fit a huge range of sizes while not actually fitting anyone) always slide out. I wear a belt, but, yeah, what Tali said about the waistband oozing out from under the belt.

        I’ve tried safety-pinning the tabs (the pins come undone and then my belt stabs them into my hip, looping them back through the buckles (works for a little while), just yanking them repeatedly…

        Elastic. Thank you, you have just made my work day much less annoying!

        • Cool! Glad to help. If you look at the waistline on the pants, you can feed the elastic inside the beltline between the 2 sides of fabric..Think like the tie string on sweat pants..Do you understand?

          • Yup, just like you’d put a drawstring into pants if you were making them from scratch. For some reason it just never occurred to me that you could do that with pre-existing pants!

        • I did it with my sisters jeans..Worked great! They didnlt bunch up in one place as usually happens..They just sort of gathered a bit…She is going to try it with a pair of khakis she bought..I expect it will work the same

      • After seeing these comments, I added elastic to the back waist of a pair of capris and a pair of jean shorts last month, and I’m quite satisfied with the results. I used a similar method to what Digger describes, only instead of snipping holes on either side of the waist, I picked apart inch-wide sections of the inside seams of the waistband (since I had no Fray Check and could thus make the added elastic more subtle). Thanks for the suggestion! This solves the awkward bunching.

  13. I love this!
    But, I mean, I will never actually attempt it personally.
    The last time I attempted to sew a thing, I sewed my finger to that thing.

  14. When I buy T-shirts that fit my shoulders and chest, they’re too *small* around my hips…help? I feel like making shoulders shrink would be challenging.

    • How close are they to fitting? You could just get them wet and try to stretch the bottom over something and let it dry. That’s worked on a few shirts for me.

      (That said, I’m hoping someone else comes up with a brilliant solution that I can use, because I have this same problem.)

    • It is really hard to take in your shoulders… And there’s not really a whole lot you can do because usually there’s not enough fabric to let out anything at the hips… How small is it around your hips?

    • I haven’t done this personally, since I’m a 5-foot-nothing pipsqueak on whom men’s t-shirts would fit like dresses, but I have a few alteration ideas, @postscript. They all involve changing the hemline: 1) Shorten the shirt evenly all around, either into an outright crop top or into something just short enough that it doesn’t reach the point where it gets tight around your hips. 2) Add side slits. 3) Shape the hem like the Lazy Femme tees, so that it’s long in the middle of the back and front, but shorter at the sides. 4) Shape the hem so that it’s short in the front and longer at the back.

  15. the gap has a fitted womens button down for 49.50. It’s also got a bit of elasticity but you would never know. i wear the extra small and it is still slightly big but it definitely works and is versatile in that you can wear it loose with jeans or belt it.

  16. I’ve gotten “wow you actually look gay in that” comments on it so im guessing it works.

  17. What about those of us wit GIANT TITS that want to wear the cute boy stuff and can’t because of OUR GIANT TITS?

  18. This is soo useful for all those damn unisex tees I have from volunteering and going to concerts that only have guy shirts.

  19. I have no hemming/sewing skills whatsoever but I did shop in the men’s section for clothing (above the waist) last week for the first time ever and I can’t believe I didn’t think of doing it sooner. American Apparel and H&M ftw.

  20. Random ob comment:

    I want to support them, for supporting us!

    But I’m going to need a tutorial on applicator-less tampons…including usage in public bathrooms (where it may be taboo to walk out of a stall with a bloody hand!)


    • You kind of pull open the bottom of it and there’s room to put your finger in the bottom, and then just push it in.

      that doesn’t sound dirty at all…

    • Me too! Pretty much the only good that could possibly come from my period would be supporting people who support Autostraddle. Plus no applicator=less waste.

      Then I googled to see if I could find them in France and came across an awkward personalized (they put your name in the song) apology song on their website. It was so weird and I don’t even know what they are sorry for. But I won’t hold weirdness against them.

  21. New turn-on: a woman who can sew, because I sure can’t! But I would love to do some of these things!

  22. this all looks so simple and easy but i feel like i don’t have the fingers for this.

    oy what a bad way to describe myself in front of a bunch of lesbosexy ladies…

    but wow, the things that can be done to clothing.

    my issue lies in my bust being about to pop that one button when everything else fits perfectly fine. do you have any suggestions for that besides reduction or weight loss? haha

    also that bottom button on the butto down not fitting across my hips/belly and if i go a size larger then the whole damn shirt just feels HUGE.

    also, how bout a do it yourself video featuring your beautiful self showing us how to do this one step at a time? i’d watch and take notes and maybe figure out some thaaangs.

  23. I work at Madewell and that’s pretty much all we sell, lots of menswear inspired pieces but made for girl bodies. The price point is not that cheap, but they have awesome sales and discount events. Plus their website has no shipping on lots of things. In case you suck at sewing . ;)

  24. Definitely going to drag the sewing machine out of the basement for this one…Awesome tips!

  25. Laura and the Autostraddle is officially my fashion saviour.

    Now if only I could sow…

    But for the sake of fitting into those beautiful better-patterned men’s clothes I will learn!

  26. Pingback: Who We Are: My Queer Making Story – Sewcialists

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