I don't. My preferences are so changeable that even "classic" or "timeless" items can fail. I won't wear things I don't like and I'd rather risk paying a little more, or missing out on something, than have to address the shame of wastefulness!

Absolutely, but my climate is pretty mild so many things I buy are almost year round. The other thing is my style is pretty basic/classic so I will stock up on things I know I will wear over and over. I don't know that I'd buy a statement piece a year ahead because those are more trendy and I'm not sure that I would still be on board by the time the season rolled around. Your sweaters look timeless and perfect for your style so I think you are on track!

It is really interesting because a few times I have bought items on websites such as the Outnet and Net-a-Porter (like Deb mentions) - being of a designer brand that I could not get locally or at that price. However these have been in the main statement pieces and my success rate has been poor, and even discounted, expensive. So whilst I may enjoy looking at web sites such as Net-a-Porter and Matches fashion my desire to take a leap and buy items is limited.

For me, getting items from Boden, JCrew etc have been much more successful, likely because these have been more classic and basic pieces. All three new sweaters are going to be fine to wear to work and on the weekend and my style only changes marginally from year to year.

The short answer is : "no". The item would have to be pretty darn special to warrant buying for another season , and I can count on one hand the number of times I've done it for that very reason.

Just to be different, I will say a big YES. I am working toward a 100% second hand wardrobe (not including undergarments) and I take things as they come, while keeping an eye on what is coming up. Definitely not a strategy for everyone, but, for example, some of my best coats have come at the end of winter and I have waited 7 months to wear them. Still worth it.

Yes, I buy ahead.

I would only do this because my size doesn't change.
And I keep Pinterest boards that remind me that my style doesn't change much either.

I keep a running (constantly updated) Pinterest board with styles I like. I keep them organized by having separate boards for each type of weather ex: hot/warm weather, cool weather & cold weather.

Before I buy ANYTHING, I check to see if it is on my board (in several variations/instances). If it's not, I know that I probably won't still want it by the time the season rolls around - in which case I won't buy ahead.

This is the first year that I wish I hadn't made several NAS purchases. Like many of you, I buy undies, basics, and one or two special items. This year I jumped in but better choices for me came along later in the season.

It's rarely a mistake for me to buy a sweater or jeans that I won't be wearing for several months.

I wish I were better organized.

My most successful off-season shopping is usually buying F/W items on end-of-season discount in late winter/early spring. I continue to get a lot of mileage out of cold-weather clothing in March and April, so my usual rotation can start to feel a bit stale. It's nice to do a refresher late in the season, and often I can find things I've had my eye on for months marked down considerably.

I do not have good luck shopping for winter while it's summer. My summer season is short and I want to enjoy it, not spend it shopping for and thinking about the long winter ahead! To be fair, I don't shop much in the summer at all; I try to be done with my summer shopping by early- to mid-June (end of school year). I tend to travel a lot in the summer and don't like dealing with return windows when I'm in between trips. Labor Day sales in early September are usually when my shopping picks up again.

Definitely something that is very personal. Shevia and luck3 have a strong sense of what works for them, to buying ahead is not a risky proposition. It will be interesting to see how this works out with these sweaters.

Bijou, I like your selection. I hope they work out well for you!
I do some pre season shopping, but it is limited. I will check NAS for fall and winter wear, usually outer wear.
If I need to replace or want to gift a pair of LL Bean boots, those need to be purchased very early, because they often sell out.
I will be looking to purchase a pair of Bos and Co boots as soon as they are available again. See photo below. I wanted them for Christmas, but they quickly sold out in white.
When I get to shop with my twin, I will purchase mostly preseason items, those are usually on deep discount.

I think part of the reason it worked for me, prepping for this move, is that I never went out with the intention of "buying things for a year or more from now". The things that I bought in advance are things that really called to me, so they fit my style (even though "my style" is still emerging, I'm building it around the things I like best, so some of those lightweight sweaters, for example).

I do, and I think it makes sense for us because if you are interested in US or European labels you kind of have to buy them in the season that they are available ie the northern hemisphere season. I generally start looking actively at what’s available O/S towards the end of their season, when many items are on sale. That’s generally anything from 2-6 months ahead of when I’d actually be able to wear it here. Local labels I buy in season. I rarely buy a year ahead at the end of winter in our local season sales or in NAS. That’s too far ahead for me and I already over shop for winter. But I’d consider it for summer because our summers are so long and so hard on clothes. And I’m such an under-shopper for summer that if I found something I really loved towards the end of summer I think I’d take a chance that I will still love it next summer.

Your jumpers are lovely. I’m sure they’ll be hits when the weather gets cooler. Feels like a long way away now

I don't. I keep track of wardrobe holes and what works well with my style but I find it difficult to get excited about off-season clothing. Now the complication for me is that I go to Florida for 2 months in the winter so my winter becomes another season. I don't actually buy that much in Florida unless it is really special or a big need (my jeans suddenly wore out).
What you have purchased looks like classics and would well with your style. The cashmere from Boden is such a great price and gets great reviews.

Actually, planning ahead is always a good idea if you constantly change your wardrobe every season or occasionally. It saves you from too much time consumptions and a lot of hassles. However, practicality wise- sale items usually show up when the season is near or during peak days!

I have but less and less so. Even though my style is pretty consistent, small tweaks each year/season mean that preferences change just enough that out-of-season buys may not become workhorses. I think I’m just too fickle!

I’m learning too that this no longer works for my daughter either. When she was younger we often bought off-season, especially for pricier items. I can usually still get sizing right (she just turned 9) but her style preferences are ever-changing now! The girl who used to be all about dresses, would now live in sweatpants

Kerry, that is so true of kids. One of my BFFs was lamenting when he took his triplet 14yo daughters shopping that only a few months ago they were all about skinny jeans, and now they all want super high-waisted styles. Teenagers are so fickle!

I hadn’t really thought about this before but of course if you are a Southern Hemisphere girl buying from a northern retailer you are buying out of season aren’t you.l don’t tend to but I have bought winter sales stuff in the summer but I never know what I will feel like wearing until the relevant weather arrives.l guess this means that I am an emotional shopper rather than a good planner.

Hm, the definition of "seasons" is funny. I don't like that seasons start in stores a couple of months before they start weather-wise. I hadn't thought of it before, but I suppose one way around that (assuming stores in the S Hemisphere do that too) would be to buy from there, getting winter things before your winter, when it really is winter here, like in February. hmmmm

I have been thinking about this a bit more as I finished up my tracking for the year. A removal of worn items at the end of a season, if they have been limping along for a while, means they are not available when that season comes next time. So then a small judicious purchasing ahead can mean there is a reasonable wardrobe to start that season with, along with multi-year items. As our winter clothes start appearing say in start of March, I don't need to buy then because I have enough. As winter goes along, the stuff will start to go on sale in mid-season, so I could get something then if I had found a gap. Case in point: last winter, I had ditched my only warm loose cardigan in winter 2017 as it was a 2008(?) purchase which was getting a bit worn plus was not all that flattering I felt, having learned more since 2008- it sort of went straight up and down hiding any shape I have. I had other things like jumpers and jackets and thin layering merinos. But I did miss a warm cozy cardigan. So when I saw the lovely bronze one in August at half price, I pounced. And I wore it 37 times from then until early December on the cooler Spring days. That has made the $95 cost ( rather than the full price $190) so reasonable.
This strategy does mean you won't get the new stuff at the start of a season that really sings to you. But the point is, you still could. And I also find that as an eclectic dresser a lot sings to me, far more than I could actually either afford or get a chance to wear. Sometimes it might not sing so much in a few weeks or months. So it might be better sitting on a Wishlist on a site rather than in my closet. And if it still sings in a few months, and my size is there which it may well be, then bonus it may be on sale by then.
I know my strategy would not work for Angie who is an unusually small size. But I am a common size ( NZ/Aus size 14 which is US 10 I believe) so often they make plenty in my size. I'm only a small size for shoes.

Jenni you make a very good point. I pounced on the Boden cashmere because it was reduced to half price and I know I will not find anything in Australia at that price once winter commences. In addition, basic crew neck knits are something that I love to wear (and wear out because pilling is generally such an issue), so I am pretty confident that these will be worn. As for the striped sweater, well that is so fun, I could not resist.
How wonderful was your bronze cardigan! Hoping that the bronze boots will be equally successful for you.

I am a mixed bag on this!

First and foremost is to battle “ sales goggles” at all times. Trying not to buy something on sale that doesn’t fit any plan - even if it looks great.
I too have more problems buying NAS cold- weather items in July because it’s harder to put the item through rigorous try- ons with my winter clothes or to be really in tune with whether I already have “ enough “.

Exceptions might be HEWI footwear— if it feels superb right out of the box and I can tell by comparison that my feet are happier than in my older items. I was very picky and returned NAS booties that were not 10’s and later bought different booties and loafers at full price after looking around a lot.

Finding things in “ my colors” or HEWI fabrications can often work off- season. I try to tune into what have been “ enduring styles” for me.