Things I Think My Brother Should Wear
THIS IS A NICE POST ACTUALLY.
About two four many weeks ago, I came upon this wonderful post by
Unfortunately for my brother, I am neither kind nor genuine.
In this post, I will roast his fits back to mall brand fitting rooms.
No but in all seriousness, I actually really appreciate how my brother dresses and how he’s managed to put together a sort of uniform that works for him + his career. Here are some of his fits below:
Some things to consider here:
He works in a career where he can’t really have visible logos.
He’s in his mid-20’s so he’s in process of making sense of what he likes / doesn’t like.
He’s admittedly not nearly as consumed by the menswear landscape as I am.
His uniform is pretty consistent, no real ‘out there’ pieces or concerning purchases.
I’d say his clothing choices are conservative middle, sort of like an elevated & self-aware post-college frat bro who is extremely informed about how the patriarchal institution is working against minorities & women and doesn’t give off any weird bro energy that would have women worried about him spiking their drink. (Good job there buddy!)
His rotation is pretty standardized with the GAP / Abercrombie mall brand revivals, with some sprinkling of thrifted clothing and assorted shoes. Proof below:
SO THIS IS A GREAT START. A lot of people have to reconcile their brother’s wearing Yeezy Boost or those evil red hats — I’ve gotten lucky with none of that nonsense. The challenge here isn’t to redo his wardrobe, it’s to begin to include some pieces that are (1) better quality (2) will last well into his 30’s and (3) won’t become obsolete as the trend cycles roll forwards. That last one doesn’t really matter too much as I genuinely don’t think he’ll fall victim to the next batch of hyper-extreme trends (and I say that in a good way).
Let’s start from the bottom up.
Footwear:
Tommy tends to lean towards the good and faithful basics here, think Sambas and Doc Marten loafers. Although he will occasionally deviate from that path ever so slightly, we aren’t trying to reel him back in from paying resell prices for a retro’ed Jordan 1.
For sneakers…let’s pass on these. Not that I think sneakers are bad, but a nice grey 993 will be the staple for most guys and for good reason. I don’t care too much about these / not too worried about his taste here.
Since he likes loafers, I think there are a few options that would give him the same look as the Docs, but with some additional benefits. For a little extra $, you get the Solovair Classic Tassel loafer which is [arguably] the same shoe just manufactured better & by the original makers of Docs; fascinating read about how that all came to be exists on their site here. For the same look but the addition of a Vibram sole, Pompeii has the Modena loafer, a shoe that I cannot seem to escape from seeing online. I cannot vouch for their quality, but a quick tell that a brand has put some thought into their product is the additional of the Vibram sole, it’s a like a guarantee that you won’t slip and fall + that these will last more than you think they will. He could also benefit from trying his hand at a pair of hard bottom G.H Bass Weejuns, which come in every single color combination possible. They also offer rubber bottom options + lug soles to get those extra 2” which makes allllll the difference for the 5’10” guys. Finally…my personal choice and something I myself will likely scoop this year, the Paraboot Reims. Now if you’re good at math, you might have noticed that you could buy all three pairs above for roughly the same price as these. “But Mariano will these last three times as long?” — ACTUALLY, YEAH, PROBABLY. The price here comes with the legacy, and the legacy is really, really good. I myself own two pairs of their Michael shoe and they’ve been worn to weddings, funerals, parties, dinners, birthdays, church, in the rain, in the snow, in the 100º days, and even recently to salt my driveway. Paraboot is one of those brands that you just sort of fall into and suddenly become a loyalist for life; it’s very likely that I will be buried in a pair of their shoes. And although the look might seem a little more rounded / chunky than he’d like, I know after walking all day and getting home without any sort of pain he’d grow quite fond of them.
I know he doesn’t wear boots, but I think he should. It might be the look that gets to him, or the fact that he tends to wear his jeans cut a little shorter, but I think he’d understand the hype the second he stepped into a pair of Blundstone’s. Their 558 model is the classic rugged boot, while the 063 model is its dressier brother; I think either would fit him nicely. I’m partial to the 990 model myself, which is a steel toed death machine that gives off Prada Brixxen boot vibes but for guys who aren’t scared of getting a little dirty. The fact that I nearly daily steel toed boots without any complaints or physical anguish should be a testimony to how well built these boots are. I think going the Austin Butler route would also serve him well via the Red Wing Blacksmith. He might even benefit from the Ranger boot that GH Bass puts out, a very classic look that not many people can pull off. Both of these require HEAVY WEAR TO LOOK GOOD SO MAYBE IT MIGHT BE WORTH DOING THE STOLEN VALOR ROUTE AND BUYING A USED PAIR.
Pants:
I THINK most of his pants are from Abercrombie or the Gap, which both offer some pretty good offerings; the creative teams at both seem to care about product. I think it might be worth transitioning to some really good denim and good chinos that he could wear out to nice dinners AND to work meetings.
I would love to see him get a good pair of denim that he can wear into the ground, and the orSlow 105 fits that exactly. Based off of a vintage pair of jeans, they fit as if they’ve been worn in and the color of this pair is wonderful. He can also walk into Self Edge or 3sixteen but I don'’t think he would care / benefit from the raw selvedge craze as someone who is always on the move.
I also think the Todd Snyder offerings in the pants department are INSANE. I love their vintage straight fit chino which you’d be hard pressed to find something as good for $148. Is this a little more preppy than what he usually wears? Maybe. But Todd Snyder is one of those brands that grows with you and looks good in your mid-20’s as well as your mid-40’s. Quality is there and Todd is a true menswear fanatic.
The only other thing I would be curious to see him to is step into the vintage military world, the whole bigger pant / smaller shirt combo. I think there are so many places to go and get good vintage clothing, but you have to deal with the fit issues / smells / stains, etc. — reproduction is the way to go. FrizmWORKS actually has their own version of the iconic OG-107 pants that they sell as their jungle cloth fatigues for $155. This with a good white t-shirt tucked in? Very young Marlon Brando vibes.
OH — Dickies 874 might also be incredible. Sure they’re $30 and likely made by slave labor, but they’ve been a go-to for years for good reason as they exist in that sweet spot of affordable and reliable. It’s a good loose look to pair with some t-shirts.
T-shirts / Tops:
I think the wave here is plain t-shirts, and good ones.
I don’t subscriber to the Merz B Schwanen love, and for the ~$100 price it feels excessive. Lady White Co offers their two pack of t-shirts for $110, which still feels like a lot at $55/shirt but with the incoming tariffs it feels like [garbage] shirts will be priced as much anyways. Why not give the $$$ to our good Canadian neighbors instead?
If you still feel loyal to America, Manresa offers a 3-pack of shirts for $58 (which I will likely order myself soon). This is one of those brands that I cannot personally vouch for, but a lot of menswear guys I follow do. Does that mean that they’re being flowed shirts so they owe loyalty??? Maybe! But I think the product might actually speak for itself. Hey Tommy, go order these RN.
For long sleeves my default is the trusty thermal. This fits great under a sweater, or a chore coat, or a denim shirt, or a denim jacket. If you’re looking for reliability, LL Bean is the way to go. Now, is $90 the best price for a thermal? NO. But this is one of the few thermals you’ll be able to wear for a decade. I think part of shifting Tommy’s wardrobe is shifting to these legacy brands that will cost more today but last longer tomorrow.
*** ALSO LETS ENJOY GRAPHIC LONG SLEEVES. I am very partial to First Port, which I’ll be writing about soon. The whole vintage looking prep shirt is very much Tommy, and I think they integrate well into his wardrobe. This long sleeve they made feels very wearable and useful and will look good with shorts into the summer and also good with a jacket in the fall and spring.
In terms of button ups, people really undervalue chambray as an option for the spring / summer. Light + easy to wear + ages great, this one from Buck Mason is well worth the sub-$175 price. I don’t love the look of chambray when new, but it ages great and looks better with time. Again — he (or you) can go vintage, but make sure you know your measurements; I have an old LL Bean chambray shirt from the 90’s that I love as much as my daughter.
Outerwear:
I only have three real desires here: (1) chore coats and (2) waxed-barn style coats and (3) denim jackets.
For the chore coats I am reminded of Bill Cunningham’s allegiance to the blue French coats, especially for all the pockets + practicality of them. As someone who does photography and video work often, I think Tommy would benefit from a type of coat like this. My personal fave is from Le Mont St Michel that you can get from Huckberry, or their site for more colors. I know the $275 is steep, but these are the types of coats that get better with age, last for decades, and people opt to repair over and over as they get damaged. There is always the vintage option but the measurements are always really weird and off (in my experience).
I think the best waxed style that would fit Tommy’s built would have been the Barbour x J Crew jacket that is all but sold out. I know he doesn't love the longer coats and so the Spey model from Barbour might be the way to go (assuming you can find one in stock). Most people think these look too short, but you need to see it styled like it is here by @thedenimdentist on instagram to see how great it can look. Slight crop + tucked in t-shirt + nice jeans = a full look.
For denim jackets, the Lee Rider is the way to go. The best versions are the vintage ones that go for a little more, anywhere from $75-125; this one is from the 70’s and is $100. He could also hunt down a Storm Rider which has the blanket style inner lining if he wanted something warmer, but otherwise the standard one is fine. I like Levis classic jackets too but they do tend to run longer and as a 5’10” guy it might not be a good fit for Tommy. The only other option is to spend $$$ and get something solid from 3Sixteen. Their Type 3s denim jacket is iconic and will outlast every trend cycle, but you are also spending close to $300 for it. (WORTH IT!)
Accessories:
Tommy loves his hats. Specifically, he love his (1) sports hats for teams he doesn’t care for and (2) instagram start-up brand hats as well — no shade to either, but I think there are smarter options. Hats are an easy way to show loyalty to something — a brand, a team, an idea, etc. without having to spend $$.
WHR has a cult-like following and I understand why. Their unique approach to hats with a bungie strap in the back is the right mix of whimsy and daily-wearability. I am quite partial to this corduroy hat they offer. Noah also has some incredibly subtle hats, this Anchor 5-Panel is similar to their main cap but subs out the cross for a naval design. The navy color will be extremely easy to integrate into his wardrobe. Wythe also makes incredible hats; I own one of their chain stitched hats in green but I feel like Tommy would do well with this blue one.
…besides that I literally cannot imagine him wearing anything else as an accessory, which I don’t think is a bad thing.
WELL THAT IS THAT. I’ll do an update if he ends up wanting to try something form this here list, but if you’re someone who wants to have an article written about you and your style — hit me up and lets do another one of these.
Thank you for the mention. I'm so honoured SITMBSW can be considered anyone's all time fav. What a compliment!
This was a great read and love to see Paraboots get a mention. Though I am sorry to your brother for somewhat causing this well-intentioned style roast of sorts. If it's any consolation I'd say he dresses a lot better than the mid-20s guys I know.
can confirm the manresa tees are nice