Hugo Boss

Author's Note: I just thought of something funny and wrote it for the Hugo Boss day of Febressuary 2022—Week 1.

Let me know your thoughts.

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"Donald!" Reddington called to the young man as he walked into his penthouse apartment.

"Red," he replied, looking around at the lavish place. "You're staying upscale I see?"

"I'm borrowing it from a friend," Reddington said as he nodded to the man with the tape measure. "I should introduce you to Oscar. He is one of the best tailors on the eastern seaboard."

"Hello," Ressler nodded at him.

"Come in Donald," Reddington gestured.

Ressler looked at the tailor and wondered why he was there.

"Oscar knows how to keep a secret," Reddington said as he watched the young man look at him. "He has been with me for a very, very, long time, haven't you Oscar?"

Oscar nodded.

"So, what are your thoughts?" Reddington asked Oscar.

Ressler looked at them both confused.

"He needs the legs tapered and the waist sits too low…" Oscar said as she walked toward Ressler and started to circle him. "The material quality is…"

Oscar placed a finger on his chin and shook his head, obviously displeased.

"Excuse me?" Ressler asked.

"Donald, you have horrible suits," Reddington said. "I know you are not into fashion, but at least tailor the cheap suits well."

"Excuse me?" Ressler asked offended as he looked at the man circling him. He paid hundreds for his suits and maybe they were cheap by Reddington's lavish standards, but they were not cheap suits.

"I think some light hand stitching down the lapel will draw out his eyes more," Oscar said as he stopped and assessed Ressler again.

"I don't need a suit or a tailor," Ressler said, offended. "I need the intel on the organization running this event Liz and I will be at tonight."

"And you will be at it in a beautiful suit," Reddington said as he gestured toward a garment bag hanging on a rack nearby.

"I have a suit to wear," Ressler said, annoyed.

"And this is a better one," Reddington said. "You will be among the wealthy, and they will sniff out a Hugo Boss suit before you take a step into that ballroom and know you are an imposter. Oscar, let's start with the pants."

"I don't need…" Ressler said as he approached Reddington.

"But Donald, you do," Reddington said as he placed a hand on his shoulder. "I have also sent Lizzie an appropriate dress. It's part of your cover and you can keep the suit. Trust me, once you wear one of Oscar's suits, you'll never want to go back. Sadly, you will have to because you can't afford another one of Oscar's suits. But maybe you can work with a tailor to replicate some of the tailoring and jazz up your suits a bit?"

Ressler looked at him angry.

"Donald, put on the pants, we don't have much time," Reddington said as Oscar arrived at his side with some pants folded over his arm.

Ressler took the pants and, angry, took off his jacket, undid his belt, and dropped his own pants, pulling on the ones Oscar had handed him. What surprised him was how close the pants actually fit him; how Reddington knew his pants size, he didn't want to know.

"I was going to suggest changing in the washroom, but I guess we're all friends here," Reddington chuckled.

Ressler stood while Oscar tailored his pants, commenting on his ass being hidden under his old suit, and that his muscular legs should be showcased and not drowned in material. Meanwhile Reddington told him about the organization as he sat and watched Oscar work his magic. The jacket came on and, again, Oscar made some mumbled comments about his shoulder's needing to be accented and not lost in the padding. Ressler shook his head, only in the world of Reddington would be get fitted for a suit that probably cost a month's salary.

He removed the suit and pulled on his own pants to sit with Reddington and eat some dinner while Reddington continued to explain the intricacies of the organization and Oscar tailored his suit in the other room.

"Shouldn't Liz be here for all of this?" Ressler asked as he cut into his steak.

"No, she needs to be naïve for this to work," Reddington said. "In this world, the men keep their wives out of the business and the wives choose to learn or hear nothing about it. She needs to be that wife to you."

Ressler nodded as he watched Oscar at a table in a room at the end of the hall stitching and sewing the suit he was going to wear.

"Thanks for the suit that's a month's salary, but…"

Reddington burst out laughing.

Ressler looked at him confused.

"Donald, that suit is half a year's salary," Reddington chuckled. "It's wool, cashmere, silk and linen…it's a Brioni bespoke."

Ressler looked over at Oscar stitching and then back at Reddington.

"That suit is almost 50 grand?" Ressler asked, astounded.

Reddington nodded. "Which is why I said, you need to keep it. It's the nicest suit you'll ever own Donald, and you shouldn't wear it in the field and running in the streets. That suit is for dates, and weddings, and special occasions. You need to keep your trim waist so you can get buried in that suit 40 years from now."

"Jesus Christ," Ressler said as he shook his head.

"The shirt is about one month's salary," Reddington said off-handedly as he gestured to a shirt hanging on the rack. "And the tie about another month."

Ressler shook his head.

"The shoes, they're about two months," Reddington smiled at him. "And, you're welcome."

Ressler sighed. "Well, thank you."

Reddington nodded in acknowledgement of his thanks.

"And I'll need this back, but you can have it for the night," Reddington said as he took off his watch and handed it to Ressler.

Ressler took the watch and switched his for it.

"Oh, and a ring," Reddington said as he reached behind him and presented Ressler with a box. "I'll need that back as well, it's just borrowed from a high end jeweller friend."

Ressler nodded and put the wedding ring on and snapped the box shut.

"Almost ready Oscar?" Reddington called over to the man. He was given a thumbs up and Reddington nodded to Ressler who walked toward the garment bag and shoe box and left for the washroom.

"We don't get another show Donald?" Reddington called after him jokingly.

Ressler chuckled and the door shut behind him to get changed in private this time.

He got cleaned up and started to dress when Oscar walked inside and handed him his suit and then left. Ressler took a moment to look at himself in the full mirror behind the door once he was fully dressed. The suit was probably the most amazing suit he'd ever worn, but $50 grand seemed a ridiculous amount of money to pay for something you wore. He noted that the cut was more flattering than what he usually wore, and the aqua tie colour did bring out his eyes, as did the hand stitching down the lapel. He had to admit it; Reddington was right.

He walked out of the washroom to hear Liz talking with Reddington in the living room of his suite.

Ressler rounded the corner and Liz turned around.

She had her hair and makeup professionally done, was wearing a drop-dead gorgeous coral-coloured dress that fit her perfectly and heels that looked like a snake. She was stunning.

"Wow, look at you handsome," Liz smiled as she walked toward him.

"You look pretty good yourself," Ressler smiled at her.

"Are you wearing two years salary also?" Liz whispered to him when she got close.

"About one years," he whispered back. "You have on two years?"

"Jewellery," Liz said. "But the shoes are almost 40 grand."

"What are you two whispering about?" Reddington called to them.

"We are comparing price tags on our ridiculously expensive outfits, that we love by the way, and you are right, we do now look the part," Liz acquiesced.

"Quality isn't cheap," Reddington said as he approached them. "And you two definitely don't look cheap tonight."

Ressler walked around Liz and saw that the one shoulder strap dress translated into a completely backless dress that left nothing to the imagination.

"Where is your gun?" he asked.

She lifted up the bottom of her dress and showed him the plastic weapon attached to her calf that wouldn't set off any detectors.

He nodded and lifted his pant leg to show her his.

"Okay, Mrs. Hopkins," Ressler said as he offered her his arm. "Let's get this show on the road."

"Your Mercedes is downstairs," Reddington smiled. "Have fun kids and get that intel."

They nodded and walked from the room and got in the elevator.

"I meant what I said, you look gorgeous," Ressler said as he placed the hand that was resting on the small of her back up a little higher and rubbed her bare skin with his thumb.

"And that suit," Liz whistled. "If I didn't have a job to do, boy, I'd be taking you home right now."

He chuckled.

"Well, hopefully these snooty people give us what we need, and you and I can have some fun helping each other take off these ridiculously expensive clothes before we have to get up for work tomorrow morning," he said with a wink.

"Promise?" Liz asked him.

He nodded and smiled.

The end.