We walk down a road and find ourselves staring at a glass window, with a sign that said ‘Truflower and Burlington’, with mannequins prominently displaying designer suits and dresses; a wedding dress in particular seemed to be the star of the show. “Lenny, you better not try to stuff me in a fucking wedding dress.”

“Oh, what, that thing?” Lenny cackled, clearly pleased at my attitude. “Nah, fuck that, you’re a crime lord, not a Disney princess looking for true love. Though, if you were a Disney princess, you’d definitely be Mulan.”

I let out a short chuckle. “You know, I don’t think I’ve ever actually seen a Disney movie before, but I have read about how Disney ruins time-tested classics by drawing pretty cartoons and deep-frying whatever themes the story previously had in some sort of false wholesomeness just to get sales. I guess that opinion is why I’ve always steered clear of them.”

Lenny simply smiles. “I haven’t seen many myself, but I sure as hell don’t even remotely think of them as high art. They just don’t have the stones for it, if you ask me.”

I tilt my head. “Yeah, that’s what you get when you have a money-making, soul-crushing formula and a corporate machine.” While I hadn’t had much experience firsthand with it, I do understand that money tends to make people do strange and terrible things, whether in the corporate boardroom or the criminal underground. Strange things, like getting some thugs to throw a grenade into a room full of drug addicts.

Lenny simply nodded in agreement, and we walked in. “Wait, do we have an established budget to follow here?”

“I wouldn’t worry about it. The old man’ll probably see it as entirely worth the investment, in this case.” Lenny shrugs, looking around the store, well-lit with a white counter nearby a number of dressing stalls in the back. The clerk at the register is a young woman with blond hair in a dress shirt, doubtlessly to give an upper-class air to the place. “Say… I think I’ll call in Nick. He should know a thing or two about what’s fashionable on the streets.”

“So now I’ll have two boys staring at me. Great.” I sigh, looking over the outfits. Despite their emphasis on high-class suits and dresses, they had a surprising variety of formal-ish wear on display. I let Lenny get around to calling Nick as I look around, parsing through a variety of selections, silently taking in my options as they were laid out before me. I must’ve spent a lot more time just looking than I thought, because before too long Nick and Lenny walk over to me.

“So, made any picks yet?” Lenny had his hands in his pockets.

“Not just yet,” I reply, as I look over the options spread across the many racks spread across the store.

“You want us to help?”

“You’re free to bring up some suggestions, but remember, no dresses.” I snap my vision over to Nick and Lenny to make sure they didn’t get any particularly bright ideas.

And then, that’s where the dressing began.

First up, a knee-length blue skirt and a standard white dress shirt and tie. This didn’t really feel right to me, as I step out of the changing room. Nick is clearly amused, while Lenny simply chuckles lightly. “Yeah, I don’t think so, you look like a schoolgirl for fuck’s sake! More like the boss’s daughter than the boss herself.”

“Looking like a schoolgirl? That’s exactly what I was thinking, Lenny.” I sighed, looking over to Nick, who was now laughing quietly. “This was Nick’s idea, wasn’t it?”

Lenny smiles, looking over to Nick. “I certainly didn’t pick that outfit composition.”

Nick finally stops laughing and straightens his face. “Okay, okay, I’m sorry, but I had to do it. It was funny and you know it.”

Slightly embarrassed, I quickly retorted, “No it’s not.”

“I have to admit, it’s a little funny. That, and you actually look kinda cute in that outfit.”

I sighed. “Goddamnit...” That line might have made me blush slightly, but like hell I’d admit it. I stepped back into the dressing booth, sizing up my next outfit more carefully.

This one, thankfully, was completely devoid of a skirt; it’s a purple suit with a green dress shirt and tie. I step out of the booth. “The mobility isn’t that great, but this does feel a little better.”

Lenny chuckled. “I mean, yeah, it’s an improvement.”

“I dunno, a purple suit seems a little on the garish side for...” Nick trailed off, his eyes scanning my outfit again. “Lenny, did you just want her to cosplay as the Joker?”

Lenny smiled. “Well, it was worth a try. But, yeah, perhaps a little more garish than your personality warrants, June.”

I look the suit over, rolling a shoulder. “I don’t mind it much. I think I could get used to this.”

“Still, we should keep looking.” Lenny let his hands in his pockets.

I step back into the dressing booth to evaluate the third set. This was one I actually remember picking, consisting of a jacket with gold and black designs in a pattern, a crop-top shirt, and a pair of black pants. I leave the jacket open as I step out of the booth, turning to face my two onlookers.

“Yeah, I’d take orders from her. She looks pretty nice!” Nick was clearly in agreement with my choice this time around, though I had to wonder if he just thought I looked attractive enough to pull off a crop-top.

“God damn, that outfit would be… PERFECT, for an intimidating underboss, but you’re not gonna be an underboss. I’d definitely keep that outfit around, but I think you need something a little more… refined, disciplined, but still strikingly powerful. While it’s certainly good, I think you should look to do even better.”

“Thank you, gentlemen...” I bow. “I’ll be sure to take another look around and see if I can’t get something that ticks all the boxes.” I step back into the booth and get back into my normal outfit, then strolling around the store, thinking about what Lenny had said. Discipline, control, and power at the same time. I think I’ll need some basic color optimization to achieve that. I kept my shirt choice simple, a red dress shirt paired with a black suit jacket, though I made sure the shirt could be converted to either shortened or full length sleeves as I saw fit. For my tie, I sought something unconventional, audacious and personalized, so I reach for a blue and green swirly tie. This might be a little much for Lenny to handle, but I think it’d look just right.

Now for the lower half of my body. I was going to go for a normal set of black pants, boring as ever, or perhaps some normal short shorts if I really wanted to play into my gender—even though that’s not really my style, but if the boys were feeling corny, maybe they would want that—but there was one item that caught my eye. I take it off the rack; it’s a knee-length pair of black and white pinstripe shorts. Classy, yet unconventional—and a willingness to break convention could be taken as a show of force. I make my way back to the dressing booth, suiting up and stepping out to meet Lenny and Nick yet again. I can tell I have their attention, judging from their initial reactions, which can only mean I’ve missed the mark by miles or struck it dead on, and I think I know which side of the line—or in this case, pinstripe—I’m on. I let myself smile. “So, gentlemen,” I tilt my head, some part of me already getting in character, “How did I do?”

“Stylish but authoritative. You really look like you could be my boss. Also, not gonna lie, that’s a kinda hot outfit.” Nick looks away after that last comment, perhaps ashamed to admit it to a… coworker.

Lenny smirks, glancing at Nick. “I mean, he’s not wrong. But I have to say, damn, you nailed it; authority and stability with a side of panache. You look like you really could be our leader. Still, there’s one thing that’s missing...” Lenny rests his hand on his chin.

“And that is…?” I tilt my head, wondering what I possibly could’ve missed with such an amazing performance

“Well… your hair. It’s almost too casual for the rest of your outfit.”

“I’m definitely not cutting my hair, Lenny.” I cross my arms, staring at him.

“Well, yeah, it’s long and it looks really nice, but… At least consider trying to put a ponytail on it?” The pause in his sentence seemed deliberate, almost an attempt at elegance—or just him buying time for a suggestion, more likely.

“Yeah, I guess there’s no real harm in trying that out.” I nod and I step back into the stall, quickly realizing that I’d totally forgotten how to do a ponytail. I pull up a video on my phone, and after about five tries and 10 minutes, finally got one down. It didn’t look right, though, because it just made me look… boring. I undo my hair and think about how to let a little bit of my original hairstyle bleed through, and staring at my own forehead in the mirror on one of the stall walls, I come up with an idea, doing the procedure again, but letting the bangs in front of my face stay, corralling the rest of my hair around the back and into a ponytail. It looked a lot better, though I had to think that by now they were seriously questioning how I was taking so long to do something so simple.

I step out of the stall to see that Nick had wandered a few feet away from Lenny, examining a few suit jackets on the wall. “She’s back… finally.” Nick looks over after hearing him, setting the suit jacket down and walking back over. As soon as his gaze sweeps over my face, I can hear his reaction;

“God damn, that has got to be the coolest way I’ve ever seen someone wear a ponytail. It’s like…” Nick waves his hands out. “Like how I would expect a samurai to wear it!”

I can’t suppress the chuckle that pops up suddenly at the irony of his statement, combined with the childlike wonder he expressed. I look over to Lenny and see him smiling. “I mean, Nick’s not wrong. Normally when I think of ponytails I think of normal-ass women in tank tops going out for a jog, just wearing it out of a sense of utility. You leaving the bangs out on the front, though, makes it—for lack of a better word—kind of beautiful and stylish.” Something in me couldn’t help but smile a little

“That’s exactly why I was skeptical of the ponytail idea, Lenny. I decided to ad-lib a little at the last second, though.” I carry on with my confident smile. “So, what do you say? Is the outfit finally complete?”

“Yeah.”

“Oh, fuck yeah.” Nick followed swiftly on Lenny’s heels. “Well… it’s not like you need it, but you could look into getting some stockings or something. You know, for when it gets cold.”

“And some shoes, if she wanted to… but I have a feeling our fearless leader isn’t giving up her good shoes for style points.”

“Fearless leader, huh?” I raise a brow. “I have a feeling you’re really trying to oversell me here, Lenny.”

“With an outfit like that, I don’t have such a hard time believing it.”

“Neither do I, I mean, god damn does she look awesome. I can’t imagine how cool she’d look with her swords at her waist."

“Fair enough.” I roll my eyes, still putting up a half-smile. “Let’s checkout and go.”

The grand total ended up being over $150 for the outfit. Quite an investment, indeed.