Everything I’ve Bullied My Fashion-Agnostic Brother Into Wearing

Give your local 20-something boy a wardrobe refresh today

Jun 18, 2026

If there’s one thing having a strong-willed older sister with a fashion job is good for, it’s getting ~~brutal~~ ~~mean~~ honest feedback on your outfits.

My little brother came of shopping-age in an era dominated by highlighter yellow sweat-wicking fabrics and blistering orange sneakers with shocking green swooshes; when pilling basketball shorts were considered appropriate dinner attire and the only metric for outfit success was how tight his Nike Elite socks were suctioned to his hairless calves.

Now, he’s just graduated college, and the boys have barely evolved: it’s reversible belts and polyester button-ups and Lululemon tech fabric “dress pants” as far as the eye can see. I feel an overwhelming compulsion to save him from this hell scape.

Thankfully, the older he gets, the more he seeks out my advice (lord knows I was gonna give it any way), and the more he seems to care about how he presents himself to the world. A natural progression for a budding young adult!

But the average 20-something man is more removed from fashion conversations than the average woman (often by self-exclusion but also because the industry doesn’t care about the demographic as much), and most are floundering to develop anything that resembles a “personal style.” Even that phrase alone is entirely played out in the femme fashion discourse, but a 22-year-old guy off the street has no clue what you’re talking about.

So how does one graduate from Dri-Fit boy to well dressed man?

It’s taken me years of subtle suggesting and course correcting and fashion-meme-sending to both subliminally and overtly influence his wardrobe. He FaceTimes me before he goes out with his friends asking which shirt goes with his pants, to which I usually reply neither, and you should probably change the shoes too while you’re at it.

When he visits me in New York, we dedicate entire days to window shopping where I throw pieces at him to try on and bore him to death explaining why the 100% cotton option is preferred over its polyester evil twin.

And at this point he’s come a long way: a month ago he sent me pictures from a dressing room asking for my opinion on a linen long-sleeve button up in a perfect shade of blue to match his eyes. I didn’t even know he knew what linen was! Let alone the color match, branching out from his reliable neutral palette into the light summer I suspect he is. Sometimes men do learn.

So this is a comprehensive list of everything I’ve bullied him into wearing over the last couple of years — me poised with my chisel and brush like a men’s department Michelangelo — and all the swaps I’ve gently (forcefully) suggested he make in his closet as his personal style begins to take shape.

this letter’s free because the info is too important to gatekeep

My 4 tenets for re-building his wardrobe:

It’s a useless suggestion unless he actually wears it. Evolution takes time, and attempting to flip his style 180° overnight would likely end up with him feeling uncomfortable and not like himself and rejecting it all (understandably so). I take small steps and work up to fashion choices that intimidate him.
Focus on well constructed basics: natural fibers when possible; classic silhouettes that won’t be out of style within a year; pieces that go with each other and don’t require a lot of thought to wear. The easier it is to put together an outfit, the more likely he is to wear it.
A little dressier the better. It’s my personal belief that men are often in general dressed too casually for things. I want him to feel good wearing a nice button-up to even a relaxed hang, and I don’t want him to treat athletic clothing like the standard option.
Basics + vintage gems = effortlessly cool. We’re still working on this… He defaults to buying new, while I default to buying secondhand, so this is one of my longer term goals. I’ll reach a new level of personal gratification once I get him to realize that the coolest one-of-a-kind pieces are vintage.

Instead of tapered poly-blend jeans, try a 100% cotton straight leg pair

Like the JW Anderson x Uniqlo Straight Jeans or Rag and Bone Fit 4 Straight Jeans

I gave him these JWA Uniqlo jeans last Christmas as an attempt to introduce designer labels in an approachable way. (Also intentionally approachable in the sense that if he liked them, he could easily repurchase in another color.)

They’re a pretty perfect straight leg — just the right width as to not feel baggy nor skinny — and they look soooo good on (wanted to keep them for myself). I chose the deep indigo shade, which seems to be out of stock, but this medium blue is the most classic, and this selvedge pair is great too.

Now that he’s into straight leg jeans, he’s recently been obsessed with this Rag and Bone style that he first tried on in-store while visiting me. He’s Rag and Bone’s #1 fan now. I’ve been planting vintage Levi’s seeds for a long time, trust that they will sprout soon enough…

Instead of trendy athletic sneakers, try timeless canvas styles

Like the Vans Authentic Shoe or Converse Taylor All Stars

I’ve been urging him away from the sneaker of the moment because they feel dated so quickly. Every few months the chatter restarts, “what sneaker are we all wearing right now!?”, and while testing out trends can be fun, it can also leave you reeling wondering whether you actually like what you’re wearing or you’ve just been influenced by an avalanche of ads.

Instead, I’ve been pushing him toward classic canvas options like Vans and Converse that (imo) never go out of style. This swap in particular was hard won though lol. I got major points when, after he initially resisted my suggestion to switch white leather New Balances for black classic Vans before we went out, a cool sales associate complimented the Vans and gave him an “I see you” kind of approval. Sisters are always right.

Instead of overpriced poorly fitting button-downs, try secondhand Ralph Lauren

Affordable and available in abundance on eBay

Red shirt ($20) / plaid shirt ($23) / yellow shirt ($27) / brown shirt ($45)

The number of links to Ralph Lauren 100% cotton button-downs I’ve sent the boy… He’s slowly but surely coming around, currently feeling more comfortable in the Abercrombie lane of button-ups than the daunting clusterfuck of secondhand shopping (fair). I let him have that — for now — as long as he’s ensuring they’re 100% natural fibers.

Instead of a corny tourist hat, try a clout-y design from a local brand

Like the ALD Unisphere Hat

Unisphere Hat in navy with a yellow embroidered globe and Aimé Leon Dore text on the front.

Hellbent on a cool New York City souvenir hat, I steered him away from somewhere like New York or Nowhere (a brand that truly confounds me because the only people who appear to be into it are people who seem to have chosen to live in the “nowhere” category). Rather, I took him to Aimé Leon Dore for their signature navy snapback with a yellow-stitched Queens design.

If you’re a New York City fashion person, this probably feels played out, but he’s not a New York City fashion person, and he doesn’t live in New York City, so it’s still fresh in his circle. It’s an IYKYK kind of souvenir — touristy in its ubiquity, but it also represents New York in a way that pays more homage to the city than a lot of other options.

Instead of a hoodie, try a zip-up sweatshirt in an interesting color

Like the Kotn Men’s Cozy Zip Hoodie

The kid loves a hooded sweatshirt. I’ve given him a few over the years (cool tie-dyes from Online Ceramics; funky graphics from Brain Dead), but I pushed him to branch out into zip-up territory and convinced him to buy a 100% cotton dark brown number from Kotn. It’s more versatile in its layering capabilities, I argued, and looks less like pajamas without sacrificing comfort. He wasn’t so sure about the color either — brown can feel scary when you’re used to wearing all black — but I promised him it was still neutral.

He later said verbatim: “Thank you for bullying me into buying this, I wear it every single day.” Dream feedback!

Instead of faux dress pants, try vintage designer

Easy to find on The RealReal

Lululemon trousers retail for around ~$150, and for that price range you can snag 100% wool Pradas ($125), cotton-silk blend Valentinos ($113), 100% cotton Loro Pianas ($128), or three pairs of Polo Ralph Lauren chinos ($38).

I got him a killer vintage YSL pinstripe suit from eBay as a graduation present that he loved, so my work in that department is looking promising. Next is to convince him that you can wear dressier trousers pants even in more casual environments.

And my wishlist for his wardrobe:

LOAFERS. I can’t tell you how long I’ve been working on this one. He sent me a TikTok recently about loafers that made me feel like I was observing an animal in captivity. Don’t get too excited… don’t scare him… don’t interfere… let him come upon the loafers on his own…
Shorter t-shirts. I’m so anti-long t-shirt shirts on men, and I’m always pushing him to pick the shortest tee in his closet. I like men’s t-shirts to hit right below the top of their pants, and I think some midriff should show when they reach their arms over their heads. Something boxier with a bit of structure looks more put together than something saggy, thin, and slouchy. He’s tall and lanky and is terrified of what he calls “the Sombr crop” (apparently the kids think Sombr’s t-shirts are comically short), and I’m trying counteract this fear by sharing reference photos of Role Model looking cool in baby tees.
More color. His wardrobe is a beige rainbow. I’ve been working hard to help him understand how to mix colors better — he doesn’t totally get how something can go together if it’s not exactly the same shade, but this is another muscle you can train. I’m hoping he lets some bright yellows, blues, and greens into his closet soon.
Vintage!!!! I’m gonna pop a bottle of champagne the day he starts shopping for vintage band tees and Levi’s jeans. Maybe he needs to be a little older to appreciate old stuff, so I hope this is on the horizon soon. I don’t really care if he ever develops a real working knowledge of trends or the fashion industry, but I’d love if he had a memory bank of people he thinks dress cool to draw inspiration from. I think vintage shopping will help introduce him to new reference material. Thankfully, though, our dad’s ‘80s t-shirts are too small for him now, so I won’t have to duke it out when he comes around to vintage.