I can really identify with so much of what you are saying here.
I discovered YLF after substantial weight loss forced me to build a new wardrobe from scratch. The minute I began, I realized that I didn't have a clue how to dress my new body, or even, on some level, what I liked! I had never never in my life developed any kind of personal style (or so it seemed to me) -- and now I had to factor in a new and unfamiliar shape, which meant that the cuts that used to suit me didn't anymore. Plus, at the time, I had almost nothing to spend because my jobs were very poorly paid and we had other financial priorities.
In the past, I'd done all my shopping at discount stores, without a plan, and at end of season sales in regular stores. This had resulted in a mish-mash of clothes but not a coherent wardrobe. I was determined to avoid that mistake.
Even so, for my first year after losing the weight, I stuck pretty much to "fast fashion." I thrifted, shopped at consignment stores, and the Gap. Banana Republic and some of my consignment jackets were my "high end."
My first autumn on YLF, I tried to pay attention to Angie's guideline about buying for the climate you live in. Well...I live in Canada. My first "investment" pieces were therefore two new winter coats! I bought them both at full price and they were not cheap. (I ended up getting one at a sale price anyway, but that was a bit of luck.)
This represented pretty much my entire clothing budget. I couldn't afford to buy much more at higher price points right then. Yet my closet was still mostly empty. I would post WIWs and constantly receive comments like: "This would look good with cognac boots." Or "Don't you have a different shoe option?" Or "How about a light coloured topper with that?" And so on. People meant well, but I did not have these items and could not afford them.
At the same time, I was learning that unless I experimented a bit, I wouldn't be able to figure out what worked. So I continued to thrift for a while and do my "bargain basement" shopping -- coming up with the occasional spectacular find -- yet, I confess, also spending money on unneeded losers or things that wore out almost faster than I could wear them!
Ultimately, I had to accept that building a great wardrobe (maybe especially a great smaller wardrobe) takes time. It's not a matter for one season. It takes time and energy and planning. You'll make mistakes along the way. You'll buy things that seem great but turn out to be duds -- at both ends of the $$ spectrum. But along the way, you'll learn, and you will figure out what works best for you.
This is getting endlessly long...so let me see if I can summarize:
I'm not sure what my ratio of fast-fashion to high-end is, but now, coming up on my third autumn at YLF, I consistently aim at high quality or value for the price point.
Every season I add in a few new genuinely "higher end" items and swap them for some of my less satisfying lower end items. (Example: I trade a no-name sweater for a DVF sweater. I trade ordinary jeans for a premium pair.)
But I still do buy lower end items -- particularly when it comes to trends that I know I will tire of. Example: floral jacket from Zara (pic). I wore it to death for two months. I'll wear it a few more times this season and pass it on. No point in going high end for such an item.
And most of my stuff, especially the essential stuff, still comes from the "middle end" -- Banana Republic, J. Crew, Halogen, Ann Taylor.
Angie's guidelines about dressing for the life you lead are absolutely brilliant for helping you to prioritize your big spending and "investment" purchases. What is your climate? What do you actually do most of the time? Put your first money in clothing that answers to those genuine and practical needs. $200 premium jeans will not earn their cost per wear for someone who works in an office and rarely wears jeans on the weekend. So unless that woman also has substantial means, they probably aren't worth it. But $200 premium jeans are absolutely worth it for a woman who wears them every day -- even if her means are lower (assuming she can afford them at all).
Knowing your style goals and your style persona will give you more confidence for choosing higher end items. Example: I'm an "urban prince." One of my first higher cost items was a pair of Stuart Weitzman chelsea boots, very refined, but comfortable. That was a no-brainer for me. I knew I would wear them to the ground and love them every time I put them on. I would not have paid that kind of money for a pair of Mary-Janes, because they would not have fit my style persona in the same way, even if they were pretty and practical.
Finally, if you buy a more expensive piece and have the option to do this, bring it home and try it with the rest of your wardrobe. Return if it doesn't play well with your other things.
And last but not least, never forget the all important happiness factor. If an item truly makes your heart sing and at a lower price point the "copy" item makes you feel blah, then see if you can spring for the item you love. It might be pointing you in your best direction.
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