Pulling off oversized/relaxed clothing
I want to explore more relaxed/oversized fits and incorporate them into my wardrobe. I'm not really sure how to do that, since I've spent a while only wearing clothes that "fit" and generally avoided clothes that I thought were too baggy or oversized. What should I look for when doing this? Is it as simple as going a size up, or are there other things I should consider?
30 Replies
Like anything I suggest cultivating some inspo and working from there. There's a massive range of oversized and relax fits in basically any style genre you want (city for ivy for example or Armani and similar oversized tailoring from the 90s)
https://www.instagram.com/p/DGoiTq_MyJP/
just going a size up is dangerous territory
Sometimes you can size up and it will work. Sometimes you can't. In general I think it tends to go poorly tho
Yea I have found that especially as a bigger guy it really depends, just sizing up leads to things like needing to get shirts altered because they're so damn long
The cuts on clothing that is deliberately oversized end up being nicer too
Are you able to fit JP sizing?
(if you will take my advice) big pleated pants could be a good place to start since they will fit your waist and still baloon out to an oversized silhouette
usually oversized cuts still fit at the waist and shoulders
shoulders can be a bit tricky because a lot of the time they’re dropped shoulders - so they are still cut to fit a certain way but measurements get fucky
I've never looked into that. Gonna go out on a limb and say probably
imo the cheapest/easiest way to dip your toes into something like this would be too proxy a bunch of intentionally oversized cut clothing from JP, there are a bunch of JP brands available at a reasonable price point that fit oversized and can let you experiment a bit
my early proxies were a real mix of hits and misses but I’d pay like $30 CAD on average per item so it was less of a loss
Dropped shoulders feel intentional yeah but most city boy stuff (the main oversized style I'm personally exposed to) they seem to fit decently well. (this is kinda in that style vein but it's the first thing I could find on my IG feed)

Pleated pants are actually what made me want to try this in the first place
What I'm getting is to be very careful about sizing up, and opt for things that are meant to be oversized instead
yeah that’s the safest play
you can also try sizing up on like cheap button ups from eBay, I’ve had success with that but I always need the sleeves chopped a few inches
But also I've noticed that even stuff that's meant to be oversized can be hit or miss
Like some I need an XL and some I need an L
if you’re going big, too big does not exist
I may be biased
I'm not an expert in beeg like heckle is but I do think that's the most common mistake
helps to just get something wide and wear it, it changes your perspective
everything I’m wearing in waywt today for example is comically large
An easy item to find that you could try out is the J Crew giant chinos and the classic PRL chinos (not just Andrews. They're good but the have a bit of a taper, there are other cuts to explore on ebay)
I tried on the giant fits last summer and I've been considering temporarily breaking my j crew embargo to pick up a pair
if you post some more specific looks you’re interested we can try to come up with brand suggestions
I'm caught in a vicious cycle of getting wide pants, wearing them for a bit, and then wanting wider pants
Will do, that would be very helpful!
nothing much to add to already good advice, but excited to see you go w i d e r
Start with big pants and work your way up the silhouette from there imo
As someone that tried working down instead of up (which sucked) feels easier in the other direction because big pant little top is workable
And yeah like heckle said drop the inspo
widemart
breaking my slim fit curse
I love big pant little top
Gotta work on something I've been putting off, so I'll pick out some inspo once I'm done with that 🫡
My inspo folder is still very much a WIP. This is what I’ve got in terms of oversized stuff




@shrimp posted a bunch of albums in #inspiration of brands with big pants; while he likes a very wide fit seeing some of how those fits are composed may be worthwhile
heyhey
might be worth looking up fits from casey, circ, fatigue, epistrophy (and of course heckle and more jibba)
https://discord.com/channels/1116793467654381685/1117803378521673768/1338564793493098607
https://discord.com/channels/1116793467654381685/1117803378521673768/1262981880135811233
https://discord.com/channels/1116793467654381685/1117803378521673768/1260372764850917391
https://discord.com/channels/1116793467654381685/1117803378521673768/1260410736375631963
https://discord.com/channels/1116793467654381685/1117803378521673768/1260413661172994091
https://discord.com/channels/1116793467654381685/1117803378521673768/1260656473512607745
https://discord.com/channels/1116793467654381685/1117803378521673768/1260688283248103455
https://discord.com/channels/1116793467654381685/1264830040395354143/1264838321000022049
in case you're on mobile here are the usernames of people in here wearing wider/oversized stuff (not a definitive list)
circleframes
hecklebuckle
casbsp
shrimpest
_njoyer
epistrophy.
jibba9296
mike_www
audofwar
.coltar
bornebythemoon
oman121
smegmiam
search
in:waywt has:file from:USERNAME
I'm a big fan of the wides styles and clothes of:
Muji
Uniqlo
Anglan
Nike SB
Nike ACG
Harvesty
Hed Mayner
Shinya Kozuka
Sillage
Aidama
Needles
Engineered Garments
Garuda
Poolhouse New York
Joshua Samuels
If you're starting with pants and moving up, its important to know that there are many different cuts of wide pants and they all drape and move differently from eachother
@Walmart the Conqueror dive into that and ping me if you have any specific questions or need any recs
Wow, thanks for all the info!
Definitely gonna check out that inspiration and those brands
Thanks to everyone else as well