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
awburkey
awburkey2d ago
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/
scottfrasercollection
Let there be sun. Valentino 95’.
From scottfrasercollection
Instagram
heckle
heckle2d ago
just going a size up is dangerous territory
awburkey
awburkey2d ago
Sometimes you can size up and it will work. Sometimes you can't. In general I think it tends to go poorly tho
Gazoo
Gazoo2d ago
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
heckle
heckle2d ago
Are you able to fit JP sizing?
ginsoul
ginsoul2d ago
(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
heckle
heckle2d ago
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
Walmart the Conqueror
I've never looked into that. Gonna go out on a limb and say probably
heckle
heckle2d ago
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
awburkey
awburkey2d ago
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)
No description
Walmart the Conqueror
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
heckle
heckle2d ago
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
Gazoo
Gazoo2d ago
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
heckle
heckle2d ago
if you’re going big, too big does not exist I may be biased
awburkey
awburkey2d ago
I'm not an expert in beeg like heckle is but I do think that's the most common mistake
goofus
goofus2d ago
helps to just get something wide and wear it, it changes your perspective
heckle
heckle2d ago
everything I’m wearing in waywt today for example is comically large
awburkey
awburkey2d ago
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)
Walmart the Conqueror
I tried on the giant fits last summer and I've been considering temporarily breaking my j crew embargo to pick up a pair
heckle
heckle2d ago
if you post some more specific looks you’re interested we can try to come up with brand suggestions
Walmart the Conqueror
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!
baek
baekthis hour
nothing much to add to already good advice, but excited to see you go w i d e r
adaptation
adaptationthis hour
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
Walmart the Conqueror
Walmart the ConquerorOPthis hour
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 🫡
Walmart the Conqueror
My inspo folder is still very much a WIP. This is what I’ve got in terms of oversized stuff
No description
No description
No description
No description
zeometer
zeometer18h ago
@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
Shrimp
Shrimp18h ago
heyhey
zeometer
zeometer18h ago
might be worth looking up fits from casey, circ, fatigue, epistrophy (and of course heckle and more jibba)
Shrimp
Shrimp18h ago
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
Walmart the Conqueror
Wow, thanks for all the info! Definitely gonna check out that inspiration and those brands Thanks to everyone else as well

Did you find this page helpful?