Should I or shouldn't I buy... (clothing item)?

Didn't feel like making a whole thread for this but what should my next major purchase be? I have some extra money for once and instead of buying a lot of cheap stuff I would rather put it towards a single quality item.

My choices are

Very Warm Outerwear
Bag
New Jeans

I already have all three however I feel that they can be improved. I'm tired of wearing the same oversized puffer jacket every time it's too cold/wet for me to wear something else. I'm also a college student and right now I have a pretty cheap messenger bag and would like something more aesthetically pleasing and of better quality. Also I currently own some APCNC and they're ok, I feel very meh about them.

Currently I live fine with all of my current items but I feel like I should put some improvement in those areas. I'd like to hear advice on what my major purchase would be? I can save up about $200-300 for these.

Which should I opt for? (keep in mind this will probably be the biggest purchase of mine for the next couple months)

^outerwear generally being on sale right now, thats what i'd go for

Well, you could probably pick up a new bag and a good pair of jeans for $300 right now. There are plenty of sales on pretty standard jeans, and Property of... bags are pretty nice for a casual look and the prices are accessible. I saw a good selection of the messenger/cycling bags in Sydneys in Toronto, and they are carried at a large number of retailers and online at their own site, as well.

I would leave out really warm outerwear. Unless there is something you really have your eye set on, the stores are pretty low on all winter stock.

http://www.oaknyc.com/men/jeans/acne-mic-wall-grey Do these fit true to size? If my waist is 33 for dress pants will these fit good?

Originally Posted by PinkPantser

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^outerwear generally being on sale right now, thats what i'd go for

I'm leaning towards outerwear but the reason why I might hold back is because it's something that for me is seasonal and would last me for years and years (since my current jacket has lasted me through the past 4 years) so I feel that it's something I could wait on.

Originally Posted by LA Guy

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Well, you could probably pick up a new bag and a good pair of jeans for $300 right now. There are plenty of sales on pretty standard jeans, and Property of... bags are pretty nice for a casual look and the prices are accessible. I saw a good selection of the messenger/cycling bags in Sydneys in Toronto, and they are carried at a large number of retailers and online at their own site, as well.

I would leave out really warm outerwear. Unless there is something you really have your eye set on, the stores are pretty low on all winter stock.

Jean wise I am looking at something real nice and not the generic entry level raw denim so my eyes are currently set on Somet, possibly AndeWhalls, not quite sure yet. So I don't think I can do a bag + denim.

Bag wise I'm leaning towards Filson.

I understand I'm being difficult but I'm semi-unsatisfied in all three departments and I'm deciding which ones I am most unsatisfied in, but the advice so far is appreciated.

Sperry Top-Sider Striper

in really good condition for about $200

What are the tumor lumps in the back for?

^^ If you're looking at the ones I think you are, they are the first "defective" version. Apparently the silver coating cracks really easily.

Originally Posted by robin

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What are the tumor lumps in the back for?
Mini parachutes so that when you jump really high you can still land softly.

Originally Posted by robin

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What are the tumor lumps in the back for?

weed, i think

Originally Posted by Curious_George

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Mini parachutes so that when you jump really high you can land softly.
Sounds rad. You should kop them then Kodiak.

Originally Posted by PG2G

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http://img211.imageshack.us/img211/6264/ss09018zg3.jpg
Yes.

I like this too