Hmmm.. Great question!
I'd buy:

- a great pair of tall, tough boots for winter (preferably a mid-tone mottled gray, I think)
- black, narrow-leg trousers for working conferences
- a great pair of dark wash jeans without fading or distressing. Also for winter.

Runners up:

A replacement pair of boyfriend-jean type shorts
More comfy shoes (a pair of nude-ish sandals, and a great pair of oxfords)

I'm in pretty good shape for winter. Things will have to live up to a pretty high standard to get in my closet. Mine are:

1. pewter puffer

2. Asymmetrical split hem sweater in navy

3. winter boots, haven't decided on exact style

I really can't think of a thing or 3 things that I want just now...I have shopped and have some great pieces ready for fall...Other than wearing those, I can't think of a thing...
Great exercise...

I'm quite happy with my wardrobe particularly after a recent mini-spree, except for the shoe section, but I do still have a dream list of things I'll snap up if I come across them while thrifting (and it's bigger than three). If I had to limit it to 3 though, I'd probably opt for:

1) a pair of knee high boots in medium grey or taupe;
2) another pair of shoes: either flats or ankle boots;
3) a sleeveless, round necked, knee length fit & flare medium grey dress in either linen or tropical wool with a silk or acetate lining.

All 3 would really extend my closet's versatility/fill holes that I notice!

Gray leather (not suede) mid heel pointy toe boots (not Western style)
Fuchsia or hot pink wool blazer or mid-weight jacket
I have not yet identified a purse for fall but I feel that it will be iPad capacious and black, burgundy or dark red. And it might have a lot of hardware and studs.

Shoes shoes and shoes. Not boots, not sandals, but actual shoes, well made, quality, versatile, wear with pants of a dress shoes. One in black, one in navy, one in nude, which given my skin tone, is like saying one in unicorn.

The perfect white jean.
A warmer weather top to freshen my S/S wardrobe.
Birkenstock sandals for walking.

Yes, this makes me twitchy just thinking about it. But my three would be, assuming they exist:

--gold zipper boots. Of course.
--a new medium sized cross body bag for weekend running around town (I have lots of bigger bags for work but I like a slightly smaller one for weekends and traveling).
--a new heavy winter wool coat.

Give we are mid winter here and heading hopefully towards spring....

1. Tan flattish comfortable but trendy sandals that look good with a dress, shorts and loose trousers.
2. New handbag also in tan, mid size and wonderful leather.
3. Denim jacket, maybe blue, maybe white?? Suspect I might need two casual toppers as this part of the wardrobe is very empty. For spring to autumn temperatures. My cardigans feel wrong now...

Others
Black silky t shirt that works for layering but okay on its own, so flattering cut. I will wear under my kimono, with patterned trousers and sometimes with jeans and a statement necklace. A workhorse item.

New maxi dress, elegant in styling. The least necessary item. A jumpsuit could fit this gap.

Thanks, fun exercise! My shopping won't be too different to this although there will no doubt be a couple of wild cards as well!

Thanks, this has helped me focus!

What I really need is:

Replacement straight leg jeans
Machine washable tops

I have other 'needs' but I could postpone them for the rest of the year if necessary and get by with what I have.

Boy, that's tough. I guess I could keep going with my sellotaped puffer. I'll need a new pair of bakery shoes and winter boots. That leaves one item to play with... grey plaid jeans, I think.

1) Blush leather moto jacket
2) Citron Green leather satchel
3) A fabulous fitting pale pink hi-low knit top

Didn't even have to think about this - these things have been on my list for a long, long time!

Mo, your posts are so great at keeping a girl focused!

1. Black leather low-heeled booties suitable for teaching kindergarten!
2. Dark wash high rise skinnies - also suitable for teaching k!
3. Long lightweight cardigan - you guessed it!

My style is very casual but some pieces I know won't work teaching little ones so I'm making some adjustments.

I'd like something in pool table green - scoop neck sweater, tunic, sweater dress?

I'd like to try out a wristlet, perhaps in mustard or cognac.

I'd like some kind of shoe in a smoky aqua, maybe an ankle boot because they give my feet a whole lot less trouble than anything else.

Actually, this is my reality, thanks to a tight budget and a taste for better quality clothes. The three things I'm planning to purchase for Fall are: a new pair of slim boyfriend jeans in a darker wash, ankle boots and a great sweater. Fortunately, I work in a very casual office, so I don't have to have a separate work wardrobe. Still working up the courage for a WIW!

This is a difficult question. I think mine would be:
1) metallic shoes (loafers, oxfords, etc)
2) black booties to wear with jeans and dresses
3) non-formal dress for winter that can be dressed up or down

I'm pretty happy with my jeans, bags and coats. I always want more sweaters but I probably don't need more at the moment.

I have a very tentative list. If I don't find versions of these things that are absolutely fabulous, I can skip them and buy something else that is. I can do without these, but here goes:

1) cashmere cardigan, crew-neck, traditional cut (like J. Crew) in a neutral color that works with allllllllll of my clothes, Winter or Summer (tall enough order for you?)

2) almond toe chelsea boots that are flat and super comfy. Not sure what color or texture I'm looking for. Must play well with skinny jeans!

3) some sort of wallet that let's me go handbag-free, or another bag, or something in that category. I'm not sure exactly what I want.

I won't freeze without the cardigan. I have other options.. In fact, I might not find that a cardigan will slide over my stiffer long sleeved shirts. If it doesn't, I'll just regroup.

I can live without the chelsea boots. I don't have any boots at the moment. If I get cold I can wear DD's chunky white court Nikes (that she played tennis in one season) and pretend like I'm doing the sporty luxe trend.

A new wallet or bag is not a dire necessity either. I will not shop just to check this off my list. It has to be love. All three of them do, actually. But those are three I've been thinking about, and I'm not twitching......yet!

Need?
1. Strapless bra (believe it or not, it hasn't warmed up enough here for
this to go to the top of my priority list...yet...
2. Capris or shorts for warm-weather, outdoor exercise walks, in a color
other than black. (Can I throw in a non-black exercise t shirt, too?)
3. Warm, wool coat for winter.

This is an effective exercise in clarifying needs vs. wants, Mo!

I'm planning;
1. Brown ankle boots
2. The ever elusive white button down that doesn't require a cami
3. A new watch
4. New eye glasses

My HEWI - blue pants suit (I have tried on a lot)
The perfect warmish rain-proof coat to replace 3 coats I currently have.
A fabulous top - open to all comers just needs to be able to dress up or down & travel well

Need? Nothing really.

Keeping an eye out for, and would definitely get use from:

-a replacement cool toned pale pearl/ash gray cardigan, not waterfall, not over-sized, silky synthetic and/or merino wool knit since my current one has subtle stains that have resisted my washing and dry cleaning. (I found the perfect one at a thrift shop but when I tried it on noticed the single moth hole, sigh. I found a nearly perfect one at Macys, but it was only in their clearance section, and the right size had a snag.)

-comfortable but fashion forward mid-tone to pale gray booties with minimal heel, can be worn in damp weather, can fit an insole. An option would be gray spectrum animal print too if it was the right one or two-toned booties. Higher mid-ankle vamp that will cover socks.

-a dark chocolate/espresso leather bag. Can have texture (for example faux alligator). No bling, minimal hardware (silver), interesting shape (fashion backpack, vintage look cross-body satchel, bowling bag, or very modern look), will weather well and look good if the shape relaxes.

I have two or three other fun things I'm keeping an eye out for that would slot nicely into the wardrobe, but they aren't load-bearing pillars if you know what I mean.

Lyn*! You had me look up Canada Goose Parka and I am not absolutely smitten with this one in "redwood."

And there would be my entire winter wardrobe budget! Yikers. But it would be worth it, given I take the triain/bus at least one way to work every day I work in winter. (4-5 days/week)

I also thought I might get another pair of winter boots--my current ones look a lot like hiking gear--I'd love some sleek leather ones--no clue about calf height!

A warm sweater or two would not go amiss. I have no idea what I have to wear for winter. I've spent the last two winters very warm.

I would buy one very warm wool sweater, one very warm heavy maxi skirt, and one silky button-down blouse in navy or black. I struggled not having these things last year (or not having enough for my climate) and am hoping to find something suitable this year.

1. Black booties. To replace some that I thought had seen the end of their lives last year, but a cobbler saved them - a bit of a HEWI (have since bought a couple of pairs that are close but not as versatile as the ones that are dying) but I think a pair of black leather Petty's might be the answer.
2. A black asymmetrical tunic sweater, like my Joie one, but maybe different. Maybe not.
3. A red or cobalt wool winter coat.

Easy. I'd get a black turtleneck sweater a layering long sleeve tee and a summer tee. I have a few more items on my list but if needed they could wait til January eg new bra, some clothes for high summer.

I am reading everyone's response with great interest. I wish I knew what I need. I surely have needs even in that silly huge wardrobe of mine.

This makes me very twitchy but I do need:
1. A new down parka because my cat decided my old down parka was a very cozy liter box last year.
2. A medium length rain jacket that has some warmth to it. I only have a very thin jacket right now which doesn't work when it's chilly outside.
3. Gray or black medium high boots.
Thanks for getting me focused. I need to plan for these expenses which is challenging when all the Fall pretties come out!

I really had to think about this one...

1) black skinnies
2) black hunter rubber boots, kids version (I'm short LOL)
3) summer top

I don't need much if anything at the moment. But these 3 things would help my closet out quite a bit. I hope to at least have the skinnies by this fall. We'll see... we are adding on a bathroom so any and all money has been going towards that rather than clothing.

This is a great exercise! I sort of did this the other day, pulling out my summer clothes to see what I needed when Spring arrives (please let it be soon!). All my summer clothes are only 1 year old, so I didn't really have any desperate needs. However, I did want to shift into wearing white and pastels and I am really enjoying the crop top trend, so I wanted to add another one to my wardrobe. My list:
1.Replace white wide leg pants from last summer (pilling and worn hems)
2.High-waisted white pencil skirt
3.White crop top
I found all three items yesterday when I was wandering through the shopping centre checking out the new season fashions, so I put them on lay-by and will have it paid off and ready to come home with me by mid-September. I was really happy with the lay-by plan, because it means I CANNOT be tempted by other pretties, as I have already committed! There is a certain freedom in that.

Wow Sharon, wish for it and it will come, huh? Talk about self-fulfilling prophecies.
I'm glad this was a good exercise in focusing for many of you. And I get it for those of you whom this makes twitch!
Also fun to see who is very specific and who is more general in their list.