Bras by about a million votes. I have literally spent hours trying on all sizes, styles and price ranges- the ones I settled on were the size I usually wear but they don't fit perfectly. I did go into a specialty store and there they were, bras in my size in plain view and ... more than 1! But, they were 120.00 each:-( Really?! Maybe I'm just too cheap and behind the times. Is a C30 or C32 too much to ask for in a more mainstream, affordable brand?
End of rant.

Bras and swimwear, no doubt!

Bras and underwear, purely for logistics reasons. I'm lucky to have found a brand and series that works. But tracking down all the pieces and getting them shipped to the U.S. takes a lot of time and attention. My Belgian pusher can supply most items, but manages to jinx every shipment. Hip-briefs I ordered in March arrived in September; fortunately, the bras in that set were still going strong.

Each season, I choose a line and color from which I buy two different bras (one moulded/t-shirt style and one unlined with seamed cups) and six bottoms (a mix of hip-brief, short/hotpant and thong). That's where the major, major annoyance comes in: it's become nearly impossible to find all of these items from one shop or on-line supplier.

I used to actively support B&M stores with my underwear purchases, because the proprietors helped so much with fittings. But a few years ago, the manufacturer changed its inventory policy (or whatever it's called in the fashion world), no longer allowing shops to return unsold items. So boutique owners stock limited sizes and colors. Worse, many proprietors and SAs push items that don't fit perfectly, and even suggest "coordinating" bottoms from other lines. With a straight face. Ugh.

Undergarments is the *one* category I never mind spending money on. I wear it for more hours each day than any other item of clothing, it affects the fit of anything I put over it, and I feel the fabric against my skin, my very own skin. Whatever shape my body is in, putting on nice underwear sets (or undressing to find them) makes me feel fantastic. Hard to imagine how so many women so easily compromise in these areas (perhaps without experiencing it?), but to each her own.

Oh, and for another reason: the unpredictability of color options, specifically reds. For a few years, they were too orange or too burgundy. This year, finally a pure red ...but look at the pattern:
http://www.lace-lingerie.com/c.....es=so_chic
Not a motif I need on my undergarments, when there's already a live one running my life!

Swimwear and dress pants. Dress pants never fit me correctly, and the ones that do are always too short. Very frustrating!

I'm not a big accesory shopper-- either I have no idea what I like or what I would do with it, or I have something in my mind and can't find what I want. Usually my happiest purchases are gifts or things I stumble across.

I have problems fitting pumps and flats and don't own either, which is problematic since you can't wear open toe footwear, sneakers, and boots everywhere. Pumps cause issues when I need to wear a dress or skirt in a non-boot/bootie appropriate situation . . . as for flats, in the summer I crave a closed shoe with an open vamp, but no luck. Part of it is that my toes are very long and I have one that starts very far back on one foot because of contracture from an old injury.

Jeans-- because of length issues-- so many brands don't come in long enough lengths except in one basic bootcut style. I want straights and BFs that are long enough . . . in different fits and washes and in premium and non-premium options. I end up wearing a lot of basic bootcuts.

Similarly, I often have issues finding sleeves long enough --- I NEED AND LOVE LONG SLEEVES! I shouldn't have to layer everything over a proper-length L/S tee. There are pitfalls to being almost 5'9" with even longer arms and legs. Plus, I don't even look particularly tall because I'm proportionately curvy.

Right now I'm battle some IT blues . . . but I also have a very curvy rear and thighs. It is very easy to look unbalanced either way, amd conventional wisdom doesn't necessarily apply (i.e. ITs should show of great legs).

I also HATE paying for prescription medication, basic non-luxury toiletries, vitamins, etc.

Unlike most ladies I enjoy shopping for utilitarian items, basic tees, bras, undies, socks, swimwear, and gear. I love my gear! And PJs/Loungewear--- all feel like special treats, and most don't break the bank (with the exception of bras) so my inner tightwad is happy.

Dresses and dressy shoes. I always think I ought to have one such outfit as a stand-by, although for what occasion I don't know. My eyes glaze over as soon as I hit the dress department because most look ugly to me. Same goes for dress shoes. Just not interested.

Bras and jeans for me too. It's so hard to get a good fit in either.

Like a lot of people have said, I hate buying swimwear. I will try to wear a suit into the ground before I buy another.

I have zero interest in swimwear. I don't use the pool at the Bachlorette Pad, I generally only get as far as the tiki bar at the beach, and bottom line is I wear swimwear maybe once a year. Maybe. I have one suit I got from Lands End a few years ago and although it isn't setting the world on fire, it is good enough to keep me from shopping for anything new!

Gymwear is also challenging because I hate to spend the money, but I think I have gotten over that this week. I bought a pair of Athleta capris and oh my goodness gracious they are so so so much nicer than my usual on-clearance-at-Target gear!! Who know my booty could look like that? So I decided to bite the bullet and stock up -- after all, I'm in the gym almost every day and it makes sense to wear something that makes me feel great, right?

I hate spending on and shopping for lounge wear! I hope no one catches me unawares in my *lounge wear*

All the bra shopping frustration makes me hopeful that my friend's new bra store in Oakland will do well. She's going to carry a really wide size range. I'm going to check it out as soon as she opens this spring. I'll let YLF know how it goes, in case any bay area people are interested.

I honestly can't think of a darn thing that I don't like buying! Everything feels like a "treat" to me. Love that!

MaryK, you have a POOL? And a tiki bar?

*packs bag*

*Girls' weekend at Mary's!*

I find it really hard to buy trousers long enough and in the style I want (I'm only 5'6" but they seem to be short as standard in Britain!)

And I hate buying summer clothes, I never feel quite right in them and summer here tends to be a few sporadic days of very hot then back to cool and drizzly.