The Pocket Tomboy’s Tips and Tricks For Better Fitting Clothes

Today's blog post is a guest post written by Kayla Layne Crawford a.k.a. The Pocket Tomboy, a blogger and fashion consultant who has earned a coveted spot on DapperQ’s 100 Most Stylish list for 2017. Their mission is to help folks feel good about themselves through fashion and have fun while doing it. You can follow them on Instagram @thepockettomboy or on Facebook.

 If someone who didn’t know me had to give a description of my height they probably would use words and phrases like pint-sized, vertically-challenged, fun-sized, and even petite (shudder).

I’ve been standing at a cool 5-foot-nada since I was 12-years-old. I finally gave up hope on that elusive growth spurt that my pediatrician told me I would have back in seventh grade and I’ve finally embraced it.

There’s a reason why I’m called The Pocket Tomboy. Unfortunately for a masculine identified individual with an AFAB body, buying menswear can be a struggle at first, but there are ways to dress the way you want to and look good doing it.

Maybe you’ve been wearing clothes marketed towards cis women your entire life and you’re ready to dip your tomboy toe into the waters of the men’s department. You pick out a few items that you think would work for you, you try them on, and lo and behold nothing fits properly. You first try on a crisp white oxford shirt; it’s too long in the sleeves and baggy in the shoulders. Then you think a short-sleeve button-down will work; but the sleeves are too wide at the opening. So logically you say to yourself, “I probably need to size down,” but then one shirt pulls at the chest and another one seems to be the perfect fit until you get to the dreaded last button (You know what I’m talking about) where it’s too tight to fasten, or best case scenario you can button it, but it’s pulling like crazy.

I know your pain and I’ve been there many times before. As someone who predominantly wears clothes that are designed and made for cis men who take up more physical space than I do, it’s sometimes disheartening and makes me feel dysphoric when I look in the mirror and see my body being swallowed by something I desperately want to fit my frame. However, with minor adjustments to my clothes even without tailoring I started to look like the confident person that I am, rather than looking like a sloppy dad on vacation.


Tip #1: Roll Up Your Sleeves

I’m obsessed with short-sleeved button downs. They’re fun, stylish, can be dressed up or down, quirky (if you get one in a micro print), and can be worn throughout the year. However, putting on one of these shirts without a few “hacks” will leave you looking unpolished. First, roll up the sleeves. If you’re like me, and appreciate 1950s teenage delinquent style this will come easy to you, but even if you don’t think you can pull off this look, I’m telling you right now that you can.

Lots of short-sleeve button-downs are made with the purpose of rolling up the sleeves and feature a contrasting color or pattern hidden underneath. I recommend rolling your sleeves either once or twice to get the desired look you want or depending on how long your arms are (I’m a two roller myself). By rolling up your sleeves, the shirt becomes more fitted in the arms.

You don’t need to be hitting the gym everyday and have massive muscles to rock this look either. For shirts like these, I prefer a more structured and crisp roll. If you’re wearing a t-shirt, polo, or a short-sleeve button-down with a casual outfit, opt for a roll that is less-than-perfect and appears to be more haphazardly done. Maybe you’re one of those folks who likes to have that “bedhead” look to your hair; this sleeve roll is like that. Because t-shirt sleeves are thinner than button-down shirts, your sleeve rolls might have a tendency to fall or come undone. You don’t want to be fixing them all day or worried about them falling, after all you’re going for a cool “I don’t care” look. Do you have two rubber bands lying around? Get those and wrap one on the base of each t-shirt sleeve before you roll them up. This will keep the roll in place and nobody will see it.

While I recommend getting long-sleeved oxford shirts and dress shirts tailored, most of us don’t have the time or money to get every single one of our shirts fitted to perfection. Rolling up long sleeves is a great casual look when doing a basic roll. No, this isn’t a roll that enjoys pumpkin spice lattes and Ugg boots, the basic roll is a simple and easy way to pull off a long-sleeve shirt when the sleeves are too long. Simply fold the cuff over once and then continue to roll and pull at the fabric so it appears to be smooth until you get to the elbow. Unfortunately, you can’t rock this look with a blazer because of the sleeve bunching, but I love pairing rolled-up long-sleeved shirts with suit vests. If you’re going to do this, avoid plain white oxford shirts and go for gingham. A plain oxford with the sleeves rolled up paired with a vest can make you look like you're part of the waitstaff, whereas a patterned shirt is more eye catching. You’re done being in the background, it’s time to stand out and be proud of your tomboy style!


Tip #2: Tuck Your Shirt In

When you were younger, you probably were told to tuck your shirt in when going out to someplace special, or if you attended a school with a uniform policy you were threatened with detention from teachers for having your shirt untucked. However, if you want a shirt to appear that it fits your body better, you’re going to have to tuck it.

First of all, tucking your shirt gives a more put-together appearance. Say you have a shirt that fits great besides the dreaded last button that I mentioned earlier. Instead of leaving the shirt untucked with the last button awkwardly undone, tuck the shirt in. Because you’re pulling the fabric down when tucking your shirt in, the shirt itself will become more taut creating a better silhouette for your body. Also, nobody will know that the shirt doesn’t fit as perfect as it appears to be. Tucking your shirt also is a cure for a shirt that is too long.

I know what you’re thinking, “But Kayla, I don’t want to look conservative all the time with my shirt tucked in.” While a traditional all-over shirt tuck should be used for formal and business situations, doing a messy front tuck, half, or side tuck works for those casual moments and can elevate your style while adjusting a shirt that is too long for you. Like when rolling your t-shirt sleeves, the half, side, or front tuck should appear that it just somehow got there by the grace of the streetwear gods and goddesses, this is called sprezzatura. There are many ways to do these tucks.

For the half tuck, I tuck the shirt fully, then I grab one side and begin to pull it out until the fabric on that side begins to peek out just a little bit. The side tuck is even easier to do. Simply tuck one side of your shirt and leave the other out for a rebel schoolboy look. With the front tuck, you want to grab the hem of your shirt, fold it under, then stick the material in the front of your pants and blouse it a bit over. Again, you don’t want these tucks to look perfect like when you fully tuck in your shirt. These more casual shirt tucks are also a great way to show off a belt.


Tip #3: Fashion Tape Is Your Friend


Fashion tape is one of those not-so-secret tools that Hollywood stylists use on their celebrity clients when they’re heading out on the red carpet. It’s definitely much faster and less expensive to use fashion tape than getting something tailored. Fashion tape is perfect for those folks who have shirts that are too tight in the chest area and pull. Use the double-sided tape in between the buttons where the shirt gaps, and voila! No more chest gap!


Tip #4: Find a Place That Offers Free or Low Cost Alterations

If you’re a shorter person like myself, it’s very hard to buy jeans or pants off the rack. For the most part, I wear selvage or raw denim that is meant to be rolled up. However, I still need to get my jeans and pants altered so when I cuff them there isn’t a bunch of material being rolled up causing bunching near the knees. If you’re new to buying pants designed for cis men, be prepared for a lot of trial and error.

As a rule, I recommend going up two or three sizes that you would normally wear in pants designed for cis women and figure out what your waist size actually is instead of some arbitrary number that can fluctuate depending on what brand. If you’re located near a UNIQLO, I highly recommend buying pants there as they offer free standard alterations on pants that cost more than $20 USD, or if you want a blind stitch it’s only $5 USD. For pants under $20 a normal stitch is $5 USD and blind stitch is $10 USD. Most alterations can be done that same day!


Tip #5: Mind the Gap

So you finally found the perfect pair of jeans or chinos that fit great in the thighs, hips, and have an ideal inseam, but unfortunately the waist sticks out in the back. This is a common problem for AFAB folks who wear menswear, because men’s pants aren’t designed for bodies that have a little bit more curves. With a bit of sewing know-how you can fix this problem by placing a hidden elastic band in the waist of your jeans. There are multiple tutorials online to do this, but I found that this one is the easiest to follow (CW: Cisist Language). If you’re unsure about ripping the waistband of your jeans open, the simplest fix to a waist that gaps in the back is to wear a belt. Make sure that the belt you wear is wide enough, if you try to do this with a thin belt, it’s going to look awkward and bunch up in all of the wrong places.


Looking good and feeling good about your style has been discussed on the Tomboy Toes blog before, but once you start wearing clothes that fit your body just right and use some of these tips to elevate your style you’ll get a confidence boost as well. It’s a trite saying, but you really don’t need to be a millionaire to look like a million bucks. You can buy an expensive shirt and still look dishevelled, or you can wear a shirt you found at thrift store for a few dollars and look fabulous. It’s all about the proper fit and the small details that will make you standout and shine.



  • Kayla Layne Crawford

    These are some great questions!

    Kalen, I know what you mean when some shirts are too small and then the next size up it’s much too big. It’s the typical “Goldilocks” situation. If you’re sticking with menswear, it’s better to go for the slightly larger fitting shirt and have alterations done; it’s easier to alter a shirt that is too big than too small. Also, if you are comfortable with venturing into the women’s department, look for button ups with no darting, but are cut bigger in the chest and hips and smaller in the arms. Ralph Lauren oxfords designed for AFAB bodies are practically identical to their menswear counterparts, but with more chest and hip room.

    Tatyana, my body shape is similar. I got a bit of hipsy hipage going on too haha. I have found that for denim I’m a big fan of UNIQLO as I mentioned in this piece as well as the good old standard Levi’s, and Hudson jeans. For chinos, I highly recommend Original Penguin and J. Crew. When picking out men’s denim or chinos, I go for the slimmest leg opening possible. Avoid anything that says “Relaxed” fit.

    I hope my answers helped ya’ll! :)

  • Kalen

    I’m (for lack of a gentler word) fat, and I have a big bust. In a few years I’m going to have a breast reduction, but I don’t think I can do it for a while (I have a rambunctious toddler and he’s not going to be gentle during my recovery). In the meantime, for my back, I have to wear a bra that (unfortunately) makes them stand out even more. I used to have a pretty good collection, but pregnancy changed my body a lot, and my old clothes don’t fit anymore. It’s been a couple years, and I guess my body is never going back to its pre-pregnancy weight or shape. How do I dress well for my new size? I’m finding that the larger men’s sizes go from just a bit too snug to waaaay too big the next size up. If it’s not left purposefully large in the chest, it draws attention to my bust, but then the arms are crazy wide… Shirts are where I have the most problem right now.

  • Tatyana

    Are there any brands of men’s pants you’d recommend for those of us who are particularly hipsy? (New word!) I have a small waist and legs but pronounced hips, which would probably be a great thing if I wasn’t trying to wear men’s clothes…but I am and finding pants that will sit on my hips but not be huge in the leg is virtually impossible! (Old Navy is the only place I’ve had any luck at all.) Any tips?

  • A

    Great tips! Thank you for this!

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