Interesting thread
I was overweight for a good few year's, back around 2007-2010. Classic case of getting too comfortable in a relationship and working on the road and in / out of hotels a lot. At the time I hated going cloth shopping, those mirrors in the changing rooms are very unforgiving!
Skinny jeans, slim fit etc. were all coming in, plus I have a short inside leg at 29', that combined with an expanding waistline made for far less choice. I decided to do something about it and took up running. I'm still not what you would call thin, but sit at around a 36' waist and generally a medium size top, sometimes large depending on the fit which I am happy with.
When I find clothes I like and that I feel look good, it makes me feel better about me. Gives me a little boost in confidence which I see as being a positive and good thing.
I like jeans, wear them all the time and in a variety of styles from skinny, to straight, to boot / flared leg. My go to brands are Diesel, G-Star, Replay, all really comfortable.
Tops wise I do like a hoodie Lacoste and Replay, love a good fleece, have in the past year come across Finisterre and their 1/4 zip which are really well made and warm, downside is their recent (and completely ludicrous) price hikes have meant these are unlikely to be anything but a sale purchase from now on. I do love big knits and roll necks to, a high quality cable knit being a particular favourite, although these tend to be very expensive so I always look out for a bargain on these. During the summer I am Polo top wearer, Next, Ralph Lauren, Lacoste being the usual suspects. I love a good shirt too both sort and long sleeve, but more of the casual variety - John Lewis, Ralph Lauren, Lacoste, Replay etc. Footwear is a mix of Adidas Gazelles in a variety of colours and smart casual shoes
I do like a bit of colour, yellows, orange, and yes pink too!
As others have alluded to, I buy quality brands as they tend to last a lot longer and I'll wear most things out and if I no longer wear them, they either go to charity or my partners Dad! I am not anti high-street brands at all though, recently brought a great suit from Next for a funeral, John Lewis and House of Fraser all have good own range items. For me it is often a case of if I like it, it's not too expensive, fits well and looks good I'll buy irrespective of where it's from
I purchase everything exclusively online these days and couldn't tell you the last time I brought any clothes in a shop