Ok I had a bout of insomnia at about 3-4 am this morning and I pondered.
I got it wrong. I'm sorry.
Let me try again.
You have a dichotomy in your style. It's built in your moniker, Urban Warrior Princess. At times you play up different aspects. When you channel the Warrior you play up your strong shoulders and arms. When you channel the Princess, the oversize waif feeling works.
Am I closer?

I don't feel all that comfortable in oversize actually. I do have a select few pieces, but overall it's not really my thing. The pieces I do have, I have to sort of make peace with some aspect - the khaki maxi dress I need the movement of the draped pockets to break up the tent like nature, and my swingy dalmatian tank I was mortified of the side view but enamored enough of the front and back ones to let it pass. Both these pieces have spaghetti straps, to show skin for balance as well. The one silk sack dress I had I only wore a couple times and then cut it down to hopefully make a tank out of it.
We are both of similar size, me being slighter larger but barely out of petites. So I don't think it's a size thing at all. More what's psychologically comforting.

Interesting. I am wearing more oversized stuff and I like it. Some of it is items that were orphaned because they felt too oversized as recently as last year. SO am I wearing more oversized stuff beacause:
1. I am up a size and appreciate the comfort.
2. I am up a size and oversized looks better on me than it did when I was down a size.
3. Oversized is trendy and now looks better to my eye
4. Some combination of the above?
Oversized is tricky on a bigger frame (5'11" and about size 14). On one hand being tall accomodates the extra drape and fabric well, but Anna has apoint about looking bigger in bigger clothes.

AnnaG, that totally makes sense! Also, it explains why sometimes the monikers are really helpful. It makes me wonder if I need to revisit mine.

Fascinating discussion. Una does have a dichotomy to her style. Go, urban warrior princess!

To answer your first question, Una, I like oversize because of the feel primarily (yay comfort!) but also because the right oversized item takes advantage of the parts of my body that I like (the slender athletic bits) and obscures the rest. The key is, of course, in the cut and fabric. The "right" oversized item has to suggest the shape underneath, otherwise it is spectacularly unflattering.

Call me crazy, but I've never found oversize to be that comfortable, especially for everyday out-of-the-house wear. The excess fabric tends to get in the way when you move, and the fit at points like the shoulders or the waist is not close to the body, so the garments always have to be moved back into place during the day. Maybe this does have to do with figure type and where things hang from / are anchored at.

I think I am with Viva on this one- I like small doses of oversize tempered with a more fitted lower half and sometimes a topper that can reign- it -in.
And I need to be able to see hints of outline underneath to be at peace with it.
Love the shirtdress on you Una!

I admire it on others but similar to Janet feel it is not my best look as I have broad shoulders and hips, with a slimmer waist. I also can find the excess fabric annoying.

I do wear volume but with caution.

Janet took the words right out of my mouth RE: why I find oversized or shapeless garments a challenge. I've only recently started wearing really soft, oversized button down shirts not tucked in over skinnies or pencil skirts when I want to try an oversized look; the fabric has a lot of movement so I don't feel like my figure looks like a giant, wide block underneath.

Oh fun!

I love oversized looks too, and I feel good in them both physically and psychologically. Physically, in summer I love that the fabric billows away instead of touching me. I love that oversized blouses always have room for my shoulders & that full skirts (although not sure if they're really oversized) let me stride along. Psychologically, I like the waif thing as well. But I also feel as if I'm thwarting the (conventional) male gaze, and that makes me feel good too. hehe Relatedly, I find that oversized looks can neutralize shorter hemlines/lower necklines. For instance, in summer I like mid-thigh (and higher) shorts. By wearing them baggy (and w chunky flats), I feel psychologically comfortable exposing that much leg, as the bagginess makes my already thin legs look more gawky than anything and hides my bottom. Whereas when I want to play up my legs/bottom, I go for skinnies that show off the curves.

I do see the how wearing oversized can also be its own type of sexiness, as some posters have mentioned. It's just not how I personally deploy the look. I actually love body con as well; it's the in-between tailored styles that I seem to have the biggest issues with and end up feeling frumpy in. Somehow, those styles have just enough ease to hide my (small) curves but not enough to make it look intentional. I love the tailored look on other women, but I never feel good in it myself.

Fascinating discussion!

I love oversized looks -- both on others, and (sometimes) on myself. I also like (some) bodycon looks -- if the fabric's stretchy enough, that's just as comfortable as oversized, for me, providing I can "de-bombshell" the look. And I love tailored fits, too. Assuming they fit perfectly without constricting.

In terms of the look of the thing, I do need to take care with oversized looks that they are not too drapey -- that will drown me. Sometimes I don't even care about the look, though. I bought that super oversized J. Crew cashmere sweater despite the fact that it looks like a tent on me from the side. It felt so great, I just didn't care. I promptly wore it about 20 times in its first month. I ended up wearing it as LOUNGEwear as well as regular at-home wear. Which tells me that I definitely love the feel of oversized! For summer, I also bought an oversized dress and some very fluid tops.

I do think Laura brings up an excellent point, though, and one I almost forgot. Oversized can be inconvenient and a bit tricky when you have to layer jackets and coats over top, which in my climate I often do. Unless of course the coat is similarly oversized!

Oh, the oversized top with coat issue can be a dilemma! Especially if it's any kind of voluminous sleeve like a dolman. I have yet to find a generous roomy coat that I really like on me.

I am wondering if it is true that every girl has at least one oversized shirt ...... for those days when you just want to be extra comfy and for when you want a change from wearing skin tight outfits that are so tight that breathing can sometimes be a challenge (ie certain party outfits)

Thanks for all the replies! And Anna, thank you for coming back and clarifying - that makes much more sense to me. Will be back later to comment as my sister and her kids are keeping me busy but wanted to say that Mo's mention of psychological comfort really resonated - that is just what I feel in oversized looks. Xoxoxo and back soon!

Oversized have one postive and one negative..!!!!

postive is that it will be most comfortable as everyone knows..!!
and negative is that it damages looks of the ffabric but for some it also doesnt matter..!!

Echoing what's been said---freedom of movement, comfort, escaping the body com look, particularly during weight fluctuations, and letting the skin breathe. But even oversized items can fit well and hint at ones figure, particularly during movement. My "fancy" LBD that I always pack is an oversized sill V-tunic and I love both the comfort and the aesthetics--a few critical darts make a flattering difference.