Bras. Everything Bijou wrote rings true. Also swimsuits for essentially the same reasons as bras *face palm*

Shorts. I ordered and returned several pairs this summer. I didn't keep any of them. Why?

The fabric was too thick.
The rise was wrong.
The legs were too short/long.
Too much distressing.

I gave up.

OOOH! I forgot to add socks! They NEVER fit unless I am in slippers at home. Given up. I wear knee-highs, trousers socks, and hosiery. They always fit.

Footwear has to be the hardest for me. Dressy footwear is virtually impossible.

Knowing how fussy my feet are, there's almost no point in shopping online -- almost everything has to go back and that's more headache than I want to deal with.

At the same time, there's not usually a lot available locally, leaving me with quite limited choices.

Bra purchasing was also one of my favourite things, thankfully there are few shops where it is possible to get fitted and advised. This made such a difference for me!

Overall, casualwear is my least favourite thing to buy and my wardrobe is indeed lacking of certain key items for casual days , I'll need to address this soon.

Definitely footwear. I echo everything CarolS said. Since online and local don't work for me, I have to wait until I travel to a larger town to shop, and then I am rushed and less familiar with the stores. It's a miracle when I get something truly comfortable, and rarely do those look as stylish as I would like.

Footwear was on the list of my least favourite things to shop for until I bought it for comfort. It makes my life easier and my feet happier. I buy only two or three brands.

Pants, especially jeans. I always find them too stiff or too stretchy or proportionally all wrong. It seems if most of them fits properly, one part is either huge to too small - the waist, the calves, the hips, the thighs - I can never find all the right parts for me on the same pair!

Swimwear runs a close second. I am long in the body, and have a heck of a time finding one piece suits (my preference) that are tall enough. They are often bagging around the hips and waist, but still uncomfortably short from shoulder to crotch.

And bras are tough, but once I find a brand/style that works, I stick to it and, as boring as it may be, I stick with it!

Pants of all kinds. I don’t like them enough to make the effort.
I do find J. Crew fits reliably as long as they are low to mid rise. I get them cheap on ebay.
But I much prefer skirts. They are so much more comfortable & allow freedom of movement & in a relentlessly hot & humid climate, they are much cooler. I have gotten so used to the “airiness” that I really dislike anything, to be blunt, hugging the crotch or worse, digging in.

Shorts are so hard! I have bought and returned so many over the years. Finding the magical inseam number helped, but then I had to figure out the rise and the fabric and the pocket sitch, and they're as expensive as pants!

This summer I discovered Eddie Bauer Rainier shorts, and Reader, I bought four pairs.

Oh interesting! I hate going bra shopping but then just repeat the style as long as possible. Bathing suits shopping? I order online and hope for the best. Otherwise it is all the fun shopping hunt for me!

Jeans (& hard pants in general) - difficult to get a good fit for a both short & curvy body.

Bras suck too, but I bought many duplicates of the Uniqlo bra I found in my actual skin colour (so I'm good for now)

A cowlneck that is not evil !

Footwear!!!

90% of my wardrobe missteps come from buying shoes that just don’t work for me.
I don’t have fussy feet perse, I think I just get stymied with what footwear to wear with outfits. I have a vast shoe/boot wardrobe, but I probably only wear about 25% of them on a regular seasonal basis.

Bras. I have a wide torso but small cup. Big struggle.

So, I wrote a big long reply yesterday that the internet ate, alas.

I would say bras because I'm hard to fit, but honestly, I look on it as a bit of a grim challenge. I will find a bra that fits, I will!! Online ordering and returning makes it easier (to an extent).

Still on fit issues: When I was a teen, jeans were my worst. But with body changes and fabrication changes and style changes, that is no longer true. I do not find jeans shopping fun, but it's not the complete nightmare it once was. Shorts shopping is difficult, too, but not impossible.

Tall boots are also very hard to fit for me. It takes a lot of searching.

Still, on the the whole I agree with Stag Fash -- fit challenges make shopping for an item more difficult but the worst thing to shop for is the essential I truly need -- but can't find -- whether that be a pair of white shorts that meets my requirements, a bra, a swimsuit, a pair of jeans, a navy blue top with certain specifications. And so on.

Footwear for me too, except for lace up sneakers. Luckily I have loafers, a few booties and sandals that I love. I want Chelsea booties, dressier things like pumps, and 2 inch heel anything. These almost always slip on my heels, and I just don,t like sling backs.

Closed toe shoes that can be worn in wet and/or cold weather.