I’ve been butch since birth. Sure, my mom bought me a blue dress with white polka dots to match her and my sister on Easter when I was about 7. That outfit even included a white, wide-brim hat and lacy white socks. My private school upbringing also meant wearing a skirt five days a week for the first 18 years of my life. Oh, plus Sunday for church. So that left my weeknights and weekend to express my (ahem) “personal style.” Let’s just say it was lacking. Actually, it stayed lacking until I was about 28 years old. My uniform consisted of ill-fitting graphic t-shirts (that I convinced myself were clever), jeans, and Adidas sneakers. Plus hooded sweatshirts in the winter. I know. Sigh.

Let me begin my embarrassingly weak defense by stating that I was a sheltered child. And I am not sure you know what it is like to grow up lower-middle class in a rural area. Oh and gay. I’m not throwing that out there as some special “look-at-me” card. I’m just saying that my struggle to find a way to express myself was deepened by the fact that I wasn’t even sure how to articulate my identity with words, much less with my clothing. Plop that down in a locale that is dominated by camo (and not the Nick Wooster kind either), flannel, polyester and Walmart specials, and you will begin to understand what I had to work to overcome.

The Achilles heel, though, is that I was fat. Not like, kinda chubby or a little chunky. More like, belly hanging over belt fat.  Also, really short. I’m 5’2″. Let’s all agree that short and fat is not the best foundation for winning the “best-dressed” award.

I don’t actually remember feeling any tension in regard to my dress in my early years. I wore an interesting blend of my brother’s hand-me-downs, yard sale finds and those clothes that seem sort of unisex on kids before they hit puberty – jeans, striped t-shirts, sneakers. Looking back to being a kid in the eighties, I feel like there was less distinction between the girls’ and boys’ departments when it came to “play clothes.” The first conflict I can remember is going with my mother to JCPenney’s to stock up on clothes for a week at horse camp. I was 12 and adamantly refused, after an hour of trying on every single available item, to buy shorts from the girls section. I finally wore my mother down and she reluctantly followed me to the boys’ section. There I found longer shorts in at least 5 colors and patterns and was ready with my selections after about 10 minutes. Mom was unimpressed but eager to get the whole thing over with by then. As she probably has since I was little, she thought “It’s just a phase.”

Throughout high school and the first year of college I chose clothes from the girls section but my style was firmly “sporty” and “tomboy.” I hated summer because I hated shorts. Mom wouldn’t buy me the boy shorts after that one blessed anomaly of camp clothes. So I sweated through summer in jeans and t-shirts. I remember, with utter horror, actually having to get some real summer clothes for a trip to Australia the summer after my freshman year. Mom took me to Walmart to get enough clothes to make it through 3 weeks. What I ended up with were some terrible outfits that look like maybe what my mother would have been comfortable in – stuff from the women’s department – nylon shorts, large chunk striped tank tops, and sandals that make me shudder when I remember them.  There’s a picture of me wearing this mom outfit that literally makes me sick and kinda sad to look at.  I was pitiful.

Given those experiences, it’s easy now to see why I retreated so easily into t-shirt and jean world. I found some solace in the skater jeans and t-shirts because I could buy them from the girls section (which pleased mom) and still look boyish (which pleased me). But by the time I had graduated college and in the seven years after, I became painfully aware of my stylistic shortcomings. During my senior year of college, I started thrifting men’s dress shirts and oxfords and wearing them over t-shirts in the summer and under sweaters in the winter. That look changed back to t-shirts in the summer and hoodies in the winter when I moved to the south. I thought t-shirts were the coolest thing I could wear to combat the humidity and the heat and the hoodies were a comfortable way to cover up the body I was ashamed of.

Imagine my stomach churning with that old familiar dread when I landed an office job about 2 years after graduating. Business casual dress code. Again, my mom went shopping with me.  She was really a trooper.  At this point, the choices were the plus size section in a department store and Lane Bryant. Between us, we spent a few hundred dollars at Lane Bryant which yielded a few pairs of cropped pants, some wide leg dress trousers and several button up “tops” as well as some flats for shoes. I felt more intentionally dressed than I had ever felt. But, it didn’t feel comfortable.  I felt like a drag queen in my girl clothes.

Maybe you’re thinking “Regardless of those physical, social and cultural barriers, shouldn’t anyone with some common sense figure out how to dress decently once they pass the age of 15?”

Actually, no.

I couldn’t.  I didn’t.

It wasn’t until later that year, whiling away time at my desk, I started my search for a better wardrobe. I was tired of wearing baggy chinos and sweaters. I was tired of feeling like crap every time I stepped out my door. I was beginning to embrace men’s clothing in my personal life, but dressing for work everyday was hell. Well, not hell, but it was unpleasant. This was happening in late 2007 and the early years of menswear blogs. So while I spent time trying to learn some fundamentals of being a well dressed man, in reality I was starting to dress more like a poorly dressed man. My style became something like “typical-poorly-dressed-fat-butch-lesbian” and that, friends, is not good. Let’s just say there were a lot of cargo shorts. A lot.

My frustration grew as the months passed. I was learning how to dress better but I couldn’t. I couldn’t dress well because I was too fat to dress well. Too poor to dress well. Too short to dress well. Too embarrassed by wanting to wear men’s clothing to dress well. So I kept on wearing t-shirts and jeans. I had my jeans hemmed so they wouldn’t drag and I started wearing polo shirts, but that was about the extent of my personal growth. I remember buying tickets to take my girlfriend to the theater and then realizing that would mean I needed to wear something besides jeans and feeling panic. I ended up pulling out some old khakis and wearing a button up shirt with a sweater vest. In the south. In July.  Sigh, again.

So what changed? Well, I was still fat. And short. And cheap. And a girl who liked to wear boys’ clothes. But a few weeks later, I saw a woman way larger than me absolutely killing it with her outfit.   She was dressed so intentionally and you could tell that she had put thought into each item she wore.  And seeing her caused something inside me to click. In that moment, I thought “Well, I could at least try, damnit!” And I decided to put away my fear, my embarrassment about my fat body, my shyness at shopping in the men’s department and my quiver full of excuses. I may not be able to dress to kill, but I could at least dress better.

Before long I began to feel very different. I felt an acceptance of myself that I never had before. I felt a confidence from doing things that scared me a little. I put myself out there a bit more each day and each experience gave me just a bit more steadiness. I started thrifting more and found shirts that I liked wearing. I bought a few items I had wanted for a long time. I started trying some of the things I had been reading about for over four years. And like a snowball gathering speed, I couldn’t wait to try more. I couldn’t wait to learn more about style and what that meant for me specifically.

This series is about learning to dress better.  Many of us struggle to learn the basics, the building blocks of a wardrobe, and so we struggle with having confidence in our style.  And since style is something we cannot avoid since we have to pick clothes to put on every day, I think it is important that we learn what makes us confident.

This is not about becoming some style icon or fashion forward type with all of this year’s “must-haves.”  It’s about dressing like a grown up and learning about clothing that flatters you and about feeling great when  you put together just the right outfit.  It’s not about being the best-dressed in the room or wearing things that people will always notice.  It is about beginning to dress intentionally.

Here we will cover the basics.  We will talk about fit and color and versatility and what to wear in many of the situations that challenge us every day.  We will cover wardrobe staples and accessories; we will explore various style situations, including the dreaded business casual.

And step by step, we will walk the path to being that better dressed butch.