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.
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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.

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 329 articles for us.


  1. 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.

  2. 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.

  3. 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!)


    • 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.

  4. 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.

  5. 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 . ;)

  6. 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!

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

  8. Pingback: Guest Post on the Sewcialists! – Clara & Co.

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