Allison M.

A crossdresser's thoughts on life, fashion, fabulousness, and (oh yeah) dressing up

My Willy Street Fair outfit


By now, you’ve probably read my last post about my adventures this past Sunday at Madison’s Willy Street Fair. [*gasps in shock*]  You haven’t?  Well, go on and check it out!  But since you’re here yet, let me take the time to highlight the outfit I wore for the fair.  If you have checked out that post, you’ve probably caught a glimpse of my rainbow socks as well as my blonde wig, jacket, and skirt.  Well, here’s a better look at it:

Denim and rainbows for Willy Street Fair

Let’s start from the bottom up here.  Since Willy Street Fair is known for its inclusion and embrace of participants and attendees in eye-catching clothing, I went with a pair of rainbow socks I had in my closet.  Yes, it does give my outfit that LGBT pride vibe.  If you’re thinking I wanted to stand out from the crowd, it’s quite the opposite; I just wanted to blend in.  If I wanted to really stand out from the crowd, I’d don a pair of stilts… but then, I’m afraid of heights (seriously).  On top of that, I didn’t have a fish costume in the closet (and someone was wearing one of those on Sunday already).

Let’s move on up to that denim skirt.  I have quite a few skirts in my wardrobe, mainly of the professional or sexy look.  I wanted a casual look, and last month I found this particular skirt at a St. Vincent de Paul thrift store.  The skirt looks and feels comfortable on me.  And with the weather the way it was on Sunday (sunshine with temperatures in the low 70s), it was a better choice than what I had originally considered: A just-above-the-knees leather skirt.  Truth be told, I tried on the leather skirt earlier in the morning, but that darn zipper didn’t want to zip up all the way.  And to think the last time I tried it on, it fit nicely and the zipper went up all the way. (My butt can’t be that big now, can it?)  By the way, that’s one of my male mode belts holding that skirt up.  Which reminds me of two things: (1) get a decent femme mode belt, and (2) find one where the end doesn’t hang out past the buckle so much.

Okay, now to the jacket:  This is that same trusty denim-vest-with-faux-leather-sleeves jacket I’ve had for about a couple years now, and it’s the same I wore in an early 2014 photo shoot (you can see more of that particular shoot in this album).  I hadn’t worn that jacket in a while, and I had forgotten how the sleeves feel a little bit snug on my arms.  However, it still looks pretty good on me, and it added to the casual yet free-spirited approach I wanted for my fair outfit.

Oh, and those things hanging from the front of that jacket?  Those are buttons, of course.  No, not the buttons that keep the front together on a cold day.  I’m talking about the buttons I added to the left and right sides.  Here’s a closer, better look:

Denim jacket w/ buttons

Now, I had been planning to wear this same jacket for many of my new “Allison in Madison” posts and hope that readers would notice, “Hey, there’s something different about that jacket every time I see it on her blog.”  (And I hope you would’ve noticed, because I was planning to challenge your memory recall with a quiz later on. *LOL*)  But with the cooler months closing in, I don’t really know if the jacket would be suitable for late fall and winter.  So instead of hauling out that jacket every time out, I’ll just highlight the buttons I’m wearing here.  Yes, they do have meaning with me, and I’ll start with the ones on my right side, from top to bottom:

  • That red-and-blue tie-dyed button says “Madison.”  Of course, it’s the city I live in, and it has a well-earned reputation as a progressive-leaning town, ever since at least the 1960s.
  • That black-and-red-striped button says “Bad girl in training.”  I bought that button and another one at the fair.  A button with a saying like that is so very apropos for me.
  • Also apropos is that white button with the triangle pattern just below it.  The message laid out on it says “Gender Bender.”  Of course, I fell in love with that button on first sight. (Here is a closer look.)
  • The yellow button below it says, “There are a lot more of us than you think.”  One year at a small LGBT festival here in Madison, I came across it at a station manned by a bisexual/pansexual advocacy and support group.  I thought the message was suitable for not only those who identify as bi or pan, but also a crossdresser like me.

Okay, onward to the buttons on my left side:

  • That tiny blue button just below my curl (I sure wish my hair hadn’t laid the way it did at that moment) bears the logo of the Dairyland Dolls, one of the teams in Madison’s roller derby league, the Mad Rollin’ Dolls.  The Dolls almost always have representation at Willy Street Fair (here they are again here), and it was at their station on Sunday that I picked up a couple more team buttons (which I’m not wearing here), along with that red pompom I’m holding in that photo.
  • The equally tiny button just next to that one is one I found at Ragstock in Downtown Madison, and it had it’s own cute design and saying.  What did it say, you ask?  “Rock & Roll!”  Of course, I wanted that button, because even a faux girl who isn’t into rock music just has to rock out every now and again.
  • The next button down bears an image I’m sure you’re familiar with, a rainbow-colored triangle.  The rainbow is, of course, a symbol of universal pride for the LGBT community; the triangle shape was originally a symbol of dark times for LGBTs but since reclaimed in various forms by various subcultures of the community.
  • The next button below that is another Madison button, only this was made from an old state map centered on the Madison area.  You can make out that curving red line on there; that’s the route of the Beltline Highway, the main freeway that surrounds Madison to the south.
  • The two buttons below that bear messages of marriage equality.  The white button says “Marriage = Heart + Heart,” and I found it at A Room of One’s Own, a Downtown Madison bookstore, the day after the Supreme Court ruled marriage equality was the law of the land. (A closer look at it is here.)  The rainbow button below that is one I’ve held on to for a little longer, “Happy Marriages for All (who want one).” (Here’s a better look at that button.)  Yes, same-sex couples can now marry, but these messages are still important and can never be forgotten, even when there are those who dismiss the idea that gays and lesbians can marry the person they truly love.

Oh, and yes, my blonde hair.  Yeah, it’s a little stringy and didn’t want to stay down in place.  In fact, a couple of strands got wrapped up in a cuff button on my jacket while I was driving to Willy Street Fair.  Yeah, that wasn’t fun.  I guess I gotta be careful with long hair in the future.

You can see a couple more of my fair outfit photos in my 2015 Flickr group here.  And if you want further proof that I have indeed ventured out of the house as Allison, you can see more of those photos here.  If you’re on Flickr yourself, feel free to leave a comment there.  Or if you’re here on WordPress, feel free to leave a compliment or two below.

Oh, speaking of compliments… I almost forgot (Doh!) to bring up the in-person compliments I received on Sunday.  As I was heading up the street to join in on the fair, after completely missing the parade that kicks off the Sunday festivities, I was walking past a lady in a more flashy costume, including neon strands in her hair. (In fact, I want to think she was the same person as that at the 7:15 mark of this video.)  She read me like an open book (“Yeah, it’s a guy in a skirt and a wig,” she was thinking in all likelihood), but she thought nothing of who I was and more of how awesome she must’ve thought I looked.  I know this because as we approached, she gave me this big grin and a knowing nod of her hair.  Yeah, I was blushing, and I gave her an appreciative chuckle and a grin and a quick “Thanks.”

I did get just one or two more compliments during my day at Willy Street Fair.  I think the general consensus of the crowd was, “Yeah, she’s just one of many here wearing a unique costume to blend in.”  Believing that, I really didn’t mind the lack of head-turning.  But when walking back from the fair, I was passing by the Willy Street Co-op as a family of 3 were walking out and heading towards the sidewalk.  The mother saw me, pointed at my rainbow socks, and told her young son without a hint of ambiguity, “Yes! I love rainbows!”  I was blushing further, and even more so when she told me she liked the rest of my outfit as she was departing.  In my next-to-best feminine voice, I gave her an appreciative “thank you.”

I’m sure those compliments were more of the folks recognizing that Willy Street Fair was going on and, yeah, it features people in unique costumes (like my “costume”).  But I like to think it’s due at least in part to the open-minded mindset of the people in Madison in general and in particular those in the Wil-Mar neighborhood where Willy Street Fair is held.  Still, the compliments they gave and the appreciative gratitude I felt sure helps in my confidence as a crossdresser (which was already at a peak on that day).  Which made my whole experience at the fair an awesome one.

(UPDATE 12/13/2015:  It hadn’t occurred to me when I first wrote this post that adding a composite of my jacket buttons as a banner would be a good idea.  So, to highlight my buttons further, I snapped close-up photos of the buttons and included it at the top of this post.)


Author: Allison M.

A part of the trans community ("cross-dresser" is the term that applies to me) who finds themselves much more expressive and somewhat more confident when presenting in a feminine persona. An admirer and supporter of those who are fashionable, fabulous, and friendly (LGBT or otherwise). Someone who tries to be witty and unique, but is not even remotely perverted or a pariah (I am a real human being, just like you). Using various writing styles on this blog to communicate thoughts and feelings concerning my life experiences, fashion sense, and the world at large (and maybe impressing my high school creative writing teacher who deservedly gave me middling grades).

4 thoughts on “My Willy Street Fair outfit

  1. Love the outfit, especially the knee-high, rainbow socks! By the way, did you use a bronzer? If so, it does give your skin a lovely glow! Keep posting more adventures in Madison; I would love to read them!

    Liked by 1 person

  2. Pingback: Shannon Curtis’ “Who Do You Think You Are?” | Allison M.

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