I’ve recently lost a fairly substantial amount of weight so I’ve had to buy a completely new wardrobe. I’m 43, size 8 now, short, curvy hourglass shape. I was a size 16 carrying weight around my middle.
I started off thinking I’d buy fewer; better quality items but it hasn’t really worked out that way. I really think think that quality on the high street is much of a muchness, regardless of cost. You need to go fairly high end to get better quality.
Most of my new wardrobe has come from Zara, H&M and New Look, with a few other bits thrown in. That’s not to say everything in those shops is good, it isn’t - you have to be choosy.
I started off by making a list of things I do eg, dog walking, watching DCs play sport on freezing cold weekends, lunch out, BBQ’s, nights at the theatre, day trips etc. I wear a uniform for work so didn’t have to think about that.
Then I thought about what I wanted to wear for each thing, including the right shoes and coat. I’ve spent so many years wearing something because it fits, not really feeling comfortable or like I’ve not got the dress code quite right.
Then I made a list and went shopping! It’s probably taken a few months of fairly regular shopping trips, lots of online orders and trying things on. If something hasn’t been perfect, it’s gone back. I want to feel like everything in my wardrobe works well for me and with everything else I own. I’ve also tried to stick to a few colours for separates so everything works together.
I worked out which shops are best for me. Trousers and jeans seem to have mostly come from M&S. I like their Lily jeans which come in extra short which works for me and their Mom jeans. I also have their jersey trousers which come in tapered 7/8 length and wide leg in a few colours. They have a bit of stretch in, reasonably heavy weight and only £15. Look good with trainers and plain T-shirt or smartened up with a blazer.
Basic T-shirt’s etc have been mostly H&M and lots of dresses from New Look - their petite range is actually really good. I’ve also got some lovely bits from Tesco.
If you’re worried about being fashionable, I think footwear makes a huge difference and can completely change an outfit.
To try and answer some of your questions, I don’t think price always reflects quality, so don’t think you need to spend more. Trousers, I’d go for jersey or something with a bit of stretch if your are between sizes. Nothing feels worse than a waistband digging in. Fashions for basics probably change every 2 years I’d say, although some items seem to look good for years. I’ve had some bits in my wardrobe for 15 years that finally fit again and look great, but most of the things I’d kept looked dated and went in the charity bag
My go to black dress was kimono style. Flared 3/4 sleeves, sat just above me knee, loose, but with an attached belt that tied at the back. Im still on the lookout for something similar.
You absolutely can be comfortable and stylish. It might just need a bit of though. Good luck OP.