The Big Preppy Gay @thebigpreppygay - Tumblr Blog

"Your new life begins today Vincent, you are now a pristine preppy boy. I've taken the liberty of upgrading your wardrobe. You will only wear collard shirt from now on. Pastel polos always tucked in. Chinos and loafers, your nice belts. It all feels so much better on you, don't you agree?" "Yes Sir" Vincent said, with a wide smile emanating from his face. There wasn't a single thought other than total obedience, and that was so swell, just how he liked it. It was just earlier that day that the rugged boy who went by the name "chaz" had run into a well dressed older man. He was dressed in a crisp white shirt, blue tie and jacket all tailored to him. He spotted the boy trying to act tough, trying to be cool. Once the older man, now known as "Master" had hypnotized Chaz on the spot, he began to reprogram him and change his life for the better. His new name was Vincent, it suited him much better. He lived with Master as his obedient servant, nothing but obedience for good preppy boys like him. Of course his wardobe had to change, tracksuits and ripped jeans are not suitable for a good preppy boy. Pink polos now lined his new wardrobe. Beige chinos lay neatly pressed, waiting to have a belt wrapped tightly around them. Oxford shirts, crisp white shirts, all ready to be worn on a different occasion.

But most importantly was masters brainwashing. 3 hours, daily, of course. Nothing less to make Vincent the perfect obedient boy he is suppposed to be. He always wears his preppy uniform now, his favorite is the pink polos, because it makes him feel even more submissive. It matches the pink cage that master put on him to help his training.

His hair is slicked back using the strongest hypno gel. Not a strand is ever out of place, just how master likes it. Vincent is his servant, and toy for when Master invites other dominant men around to use Vincent, and Vincent loves every second of it. It deepens his training, being used while dressed properly and locked up.

At the Gym his polos are tight fitting to show of his muscles, a good preppy boy should be in shape after all. But he always looks formal.

Vincent ran into one of his older friends once, and they were rather confused as to what had happened, but seeing Vincents blissed out face and demanour, they were intrigued. So Vincent invited them back to Masters house, where after examination by master, they were put in a deep trance and made to be just like Vincent. Masters army will continue to grow, if you ever run into a pristine preppy boy, you could be next...

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What made you decide to wear formal clothes?

My origin story! The full version is that I'm from the UK and went to a school that had a formal uniform. I didn't wear it properly because I was obviously far too cool for that, until my maths teacher made me fasten my collar and tighten my tie. That was an awakening! Since then I have enjoyed menswear, but I was always too self-conscious to fully go for it.

I had phases in my early and twenties where I tried, but I didn't make it last. Now I have the self-confidence to wear what I want. That doesn't answer why I wanted to dress this way though.

One part is just getting a bit older - t-shirts and tracksuits look a bit tragic on a 30-something. But the real motivation for me is how I feel, how I see myself, how it shapes my behaviour, and how others see me. All of which impact each other in a positive cycle. I love the masculine shapes of menswear, enhancing our torsos' taper and accentuating our shoulder line. I love how understated classical tailoring is. It's all about the quality of the cut and fabric not flashy details. I find that version of masculinity, quietly confident and unobtrusive, deeply attractive.

Moreover, I like the associations of formal western clothing. To me a suit has always been associated with being put together, bringing your A game and being serious about something. We wear them for when we want to show we care. I associate them with a kind of restraint and self-control, the details are considered and buttoned down or tucked in place rather than everything thrusting forward in some stretch fabric. When I wear a tie it brings those associations to my mind and I'm more self-aware, but not self-conscious. I want to live up to the associations the clothes hold, associations of capable, disciplined, traditional men.

I'm a conservative guy in a some ways (well, a lot of ways really if not for the homo to bisexuality), and I like the call-backs a suit has to previous generations and maintaining their traditions. I like wearing something my great-grandfather could have worn 100 years ago and participating in that instead of trying to make my "own style," which, coincidentally for almost everyone who does it, looks very much like someone else anyway (but invariably more embarrassing to look back on than classical menswear). And I like knowing that when I interact with others, be they colleagues or neighbours or people at church, when I'm a suit with a big smile I look every inch the pleasant young gentleman. It would be a bit delusional to pretend there isn't an aspirational aspect to this too - I am British after all - and dressing this way is bluntly associated with higher class people. I have never really identified with working class culture and escaping upwards is something I have enjoyed in different spheres.

Essay over!

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Impossible not to feel good in a double breasted jacket, I must love anything that makes me feel broader. Back into something closer to my normal uniform today, although the pink in the shirt is very indulgent with the classic navy combination. Sometimes I notice my mood and demeanour shift with my clothes, I might be feeling quite laid back in my gym gear and then when I get changed I shift into a more...rigid? Impatient? Disciplinarian? Version of myself, I guess the clothes put me a frame of mind where an insistence on standards kicks in harder.

I'm on a new gym split, doing upper/lower over 4 sessions a week and I am feeling it in the best way. I reached a good upgrade in my personal best on deadlifts this morning which is great, although going down the stairs after a hard lower body session isn't always the most pleasant sensation! I want to progress much further but I know that making incremental progress each session is the way to get there, based on what my body can currently do. I will get there!...And then promptly set a new goal of course.

baldingbaldy

Hard working baldy!

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09/01/2026

The way I dress has changed a lot over the last year. A year ago it was like this, a handed down pair of track suit trousers, trainers, and a t-shirt. I worked fully remote so I could get away with staying in my pyjamas most days, putting the trackies on when I went out. This was how I met my friends. It was low effort and sad.

Around April 2025 I decided to make a change. I had gotten into a rut I wasn't dressing or presenting myself as I wanted, I didn't like how I looked in the mirror at all - sloppy, undisciplined, and like an overgrown child. I started by buying a polo shirt and some chinos, pictured. I loved the look of the polo, but I was painfully aware that it didn't drape quite how I wanted over my body. I began exercising in earnest for the first time shortly after which has been one of the biggest positive changes I have ever made: go and start lifting the heaviest weights you can if you don't already, your life will improve. The chinos and polo looked out of place with trainers, so I bought these loafers to look more cohesive. At this point I began to gain a lot more confidence and ambition with my self-presentation, a virtuous circle was forming of confidence in my body and that I could wear the clothes I liked. A colleague reacted to me wearing a polo for the first time on a video call by saying "No dressing gown today? I think this is the first time I've seen you in a collared shirt!"

Preppy gear became my default. Button up shirts were mixed in, and by October/November I had the confidence to start adding a tie into the mix.

This was my outfit today. The shirt is pink and white striped, although it doesn't quite show on camera. I loved the tightness of the collar around my neck throughout the day and structure of the jacket. This feels right now. I have started to feel something is missing when I'm not wearing a collar en route to the gym, the only times I haven't been in a tie for the last week. This is how I should be. And it's how I am becoming. This week hasn't felt difficult at all, I feel more settled on being properly dressed than I did at the start. With incremental change we achieve a lot over a longer period of time, and eventually the new habits we make around clothing form dispositions - it's wrong for me not to be wearing a tie, I need more respectful and polite like a proper suited man and so on. I wonder how long it will take before I skip a day...maybe I won't?

suitedboi92

Saturday.

No meetings, no obligations, no reason to dress up, except that it matters to me. There’s something about putting on a proper shirt and tie that changes how I move through the day. Sharper mind, better posture, more focus. Discipline isn’t just what you do when someone’s watching. It’s what you do when no one else cares. This is my take on a slightly more casual weekend dress code: subtle pattern dress shirt, solid tie, and brown pleated dress pants. Let me know what you think.

suitedboi92

“Sunday prep”

While most settle for sweatpants and hoodies, I know what is best for me. Starched shirt, pressed trousers, proper tie. Not only because this is my calling, but because I refuse to let comfort be the excuse for complacency. We have normalized dressing down to the point where showing up polished feels radical. It shouldn’t be. If I can inspire even one person to reconsider what ‘casual’ has cost us as men, our presence, our confidence, our self-respect, then this journey is worth sharing. Leading by example, one ironed crease at a time.

sartorialboy

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FROM FULL HEAD... TO MPB. FEEL FREE TO COMMENT!

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From a full head of hair to MPB. Your comment? Feel free to write it here!

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PROUD. FULFILLED.

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05 BLEACHED FRINGE. End of the before-and-after series. Which picture is your favorite? Feel free to comment here. Your feedback motivates me to keep going!