Upgrading: when to stop

I've noticed a trend in my shopping. Especially jeans shopping. I have some look in mind, say, high rise vintage jeans. I'll try many options and eventually settle on one. But the quest doesn't stop, and nothing is ever perfect. If I come across a slight improvement, I buy it.

To some extent this is a problem with consignment shopping. Things are inexpensive and can often be sold back to the store. Or maybe it's a problem with high rise jeans, because the fit is hard and issues aren't evident until I've worn them for a while!

I'd like to be better about this. But I suppose also, jeans shopping is just hard, and I shouldn't feel too bad, either. Maybe I'll just keep track of the actual money involved and evaluate it as I go. 

Exhibit A: high rise jeans. After my posts last month, I was basically content with the Levi's wedgie jeans, but they're honestly not the best. Then I found these Gap "mom jeans" that are exactly what I wanted, and unlike my usual habit, I cut the tags and wore them right away. They're not conventionally flattering (too much fabric in the thigh) but they're the look I was going for. 

Photo 1: the first Levi's wedgie jeans I bought (reposted from last month)
Photo 2,3: a different Levi's wedgie version I found at a thrift store, with a slightly more flattering fit (reposted from last month) 
Photo 4,5,6: the Gap jeans. I'm wearing them full length today but I folded them up to test different lengths in the photos.

I'll one or both pairs of Levi's online. I think it's time for an assessment of all my jeans.

Exhibit B: no photos yet, but I just bought another black denim skirt... Everlane's new cutoff skirt does fit me better than the Madewell skirt I bought last year, but I only wear jean skirts a few times a month, and the Madewell skirt is pretty awesome too. This one was sold out online, so definitely a scarcity thing: I found it in the store and bought it in case I decide I want it, but I can return it if not.

This post is also published in the youlookfab forum. You can read and reply to it in either place. All replies will appear in both places.


  • replied 5 years ago

    What a fascinating question.  You look fabulous in all of the jeans.  I assume you are not asking for opinions, just want to provide introspection?  

  • 3style replied 5 years ago

    What helps me most is looking at the entire wardrobe. What good does it do to buy more jeans if my bathing suit is cutting off my circulation? I find it pretty easy to cross off a category and move on to the next most urgent category. But, in the meantime if I find my jeans are really physically bothersome, I usually just try a quick fix like a different belt or tucking in a thicker shirt. If I really screwed up, well, that’s another story.

  • bj1111 replied 5 years ago

    At least you are upgrading where the next iteration has an improvement on the last. If you consign the less than optimum versions, then you have a few pennies to put toward the next-next-new and improved version.

    A related question, are you a maximizer in other aspects, or a satisficer?

  • Greyscale replied 5 years ago

    Sterling, I suppose I'm not exactly looking for opinions on the actual jeans (since I'm definitely keeping the Gap ones), but I'm curious what strategies others take in these decisions.

  • bj1111 replied 5 years ago

    I like to limit myself to 1 or 2 iconic pieces from designers I like, so I buy the one thing then I move on. The one time I didn’t, I bought a second purse because the first was not classic or versatile enough.

    I’m more likely to “upgrade” when I try out a trend that I like enough to buy a more expensive version. I don’t isually do this because I’m too impulsive and I just buy the expensive thing(s) then regret it. When i do “sample” a trend, the cheap version is usually enough that I don’t upgrade even if I like it. I just buy a new trend the following season.

  • Greyscale replied 5 years ago

    Random side note: I just figured out why I prefer button fly for high waists! (The Levi's are both button fly and the Gap jeans are zippered.) The zipper is a single stiff object that makes the front bunch oddly when you bend, whereas the buttons are separate from each other so the bunching is distributed along the fly more evenly.

    I'd noticed I had a fairly strong preference but I hadn't thought of explanations beyond aesthetics.

  • Greyscale replied 5 years ago

    bj1111, interesting points. I am definitely a maximizer (I have huge anxiety around even the smallest decisions) but, happily, once I make a decision I tend to be very happy with the outcome and hold on to the pleasure quite tangibly. I suppose this shopping dilemma is an exception because I found the upgraded options so soon after the original purchase. Usually there's no regret tied to the upgrade, unless I start worrying about money.

    I also do the thing where I try out a cheap version of a trend, and also, yes, the cheap version is often sufficient or even better. These new Gap jeans ($42 on sale) are stand-ins for a Citizens of Humanity pair I was nervous about committing to ($220), and I actually like these better.

  • bj1111 replied 5 years ago

    Then based on how you approach upgrading, I don’t see a problem unless you run out of space or money! What is bugging you about this?

  • Greyscale replied 5 years ago

    Hm. I think maybe the time spent on shopping? It becomes a bit compulsive. But then again I was too busy to set foot in a store for the past month so maybe this weekend was me letting off steam with a favorite hobby. I think I'll stop worrying about it.

  • 3style replied 5 years ago

    Not at all a criticism but.... I’m trying to wrap my head around three shopping methods for the same type of item: thrifting, mass market, premium denim. They seem like entirely different strategies for jeans shopping to me. Why choose all three?

  • SarahD8 replied 5 years ago

    Hmm, I guess you just found your answer, but I think this is an interesting question to ponder, so I'll add my two cents!

    For me, the thought process goes something like:
    -If I buy this X, will I stop looking for an X? (Question borrowed from someone here on YLF, maybe Joy?)

    -If not, how essential to my wardrobe is the item I am replacing?
    -And is the new version measurably better than the old one, and at a price point that I am likely to get my money's worth while looking for the Platonic Ideal of X?

    For example, I just replaced the mid-wash skinny jeans that I have been moaning about for months. I'm not sure this technically counts as an upgrade, as the old ones are J. Crew and the new ones are Old Navy, but the new ones fit markedly better and are SO much more comfortable than the old ones. No, they're not quite perfect, but mid-wash skinny jeans are such a key item for me that it seems worth it. The decreased frustration/annoyance during wear frankly makes them worth the price within about 5 wears.

    FWIW, I think when it comes to jeans comfort is SO important and nearly always justifies an upgrade/replacement.

    I tend to be a satisficer in most things but I can get a little pickypants when it comes to clothing -- it is not that I need the absolute best version of whatever, but I have some oddly stringent standards about what TRULY satisfices.

    ETA: 3style, I have bought jeans using all three strategies and it is ALL about finding the best pair of jeans FOR ME. Doesn't seem contradictory to me at all.

  • Sal replied 5 years ago

    Interesting - they all look great by the way...  

    I am more of a satisficer - so once I have my new jeans/new sofa etc I tend to move on.  I have made wrong calls but I just sort of accept it and make it work. 

    I have two pairs of straight jeans now - and I won't look for another pair until one of these wear out/ give up in some way.  I have one pair of black boots and I no longer like their style but I am making myself wear them when I can because they are in good condition and very practical and comfortable.  I could try and sell them and might get to that point.  But I have added new navy and brown boots during the time I have been fed up with the black ones - whereas I suspect in the same position you might have upgraded the black ones to a style you loved now.

    I also have a more random/eclectic style than you so I am less reliant on some "heavy hitters".  

    I do this more with consignment or second hand shopping when the price and item seem close - but in reality are not close enough.

  • JAileen replied 5 years ago

    I would keep looking for something too, when the thing I bought (whether I realized it or not) wasn’t perfect. I noticed this with dishes, patio furniture, and silver handbags.

  • 3style replied 5 years ago

    Well, I see thrifting as something you do because you have no other options, or because you love the thrill of the hunt and are looking for that hidden gem (to mix my metaphors ;)

    Mass market you do because it is quick and convenient.

    Premium people do for ethical, status or strong aesthetic and or fit preference. For example, my husband is really hard to fit in jeans. When I met him he had bruises from jeans chafing. Since then, he has been wearing down a stack of premium all-cotton denim that he bought when Martin and OSA was going out of business, about a decade ago. He’s starting to think about what to do next, because a few of them are getting ripped so not fit for his office wear. Seems like he can occasionally find something at BR, passable but it’s really not quite as good a fit.

  • rachylou replied 5 years ago

    I realised I had this problem when I was already the owner of two dusty pink mutton sleeve sweatshirts and was eyeing a third...

  • binkle replied 5 years ago

    I think the answer is different for everyone. Personally, I'm not a fit fiend - I just "crush" on a style and keep buying. Thus too many grey sweaters, wedge booties, etc. Eventually, and hopefully sooner rather than later, I get real with the situation, and knock it off. With time and bitter experience, I think I've gotten better.

    So from my perspective, you've answered your question - look at how much you are actually spending, think about long term life goals, and see how it all fits.

    Budgeting/finances is a deeply personal thing, and you seem a very well-thought-out person. So ignore me if necessary - I'm almost 60, and I've found that even if I'm not budgeting to a specific number, keeping track of all "spends" is invaluable - not just clothes, but EVERYTHING. Have done this for many years.

  • SarahD8 replied 5 years ago

    3style, for me with jeans it's:
    -I have a short rise and higher rises are currently trending, so what I need is rare at retail and; lower rises from a few years ago might be more common in thrift stores
    -mass market: opportunity to try on/compare multiple sizes and cuts at the same time, and duplicate if I find a rare item that suits
    -premium: I'm hard to fit so anything is worth a shot.
    Basically Angie's "no retail stone unturned" approach.

  • replied 5 years ago

    I feel like once I buy, I'm making the commitment that This Is The One for that category of need and I stop looking.

    This does sometimes cause me to feel like I missed out, when I see that a "nicer" version of something I might have liked better is sold out.

    But that doesn't bother me as much as feeling like I was impatient about making my choice.

    If we're talking about wastefulness or self indulgence, I think lifestyle is an important factor too, how many people you see, who those people are, your work, etc.

  • Suz replied 5 years ago

    All the jeans look great, but if you can get some pennies back from consigning the Levis, go for it! And you are the one who knows what truly works for you. 

    I am typically a satisficer with a few maximizing tendencies. For completer or occasional wear pieces, I take Sally's approach. If I purchase something that turns out to be not quite right, I try to make do with it -- making notes about what made it wrong so I can correct the next time. But, if it's a true essential for me (ahem, cough, like JEANs) I will probably keep looking. As you've done. I might look slowly, or quickly, depending on time available, and degree of dissatisfaction with the first purchase.  

    I am also more likely to make mistakes when I am trying a new silhouette that I have strong hopes of getting right -- one that deeply appeals to my style sensibility and works for my body type (like mom jeans for you, and probably for me, too, though I haven't quite completed my own search). It's likely I'll have to try more than one version in that case, and -- as with footwear -- the fit issues might not be immediately apparent. 

  • 3style replied 5 years ago


    Team average rise here. I sometimes buy Tall or Petite pants (or skirts or dresses) if I like the length, and never give a moment’s notice to the rise.

    I can wear any rise, as long as the pants aren’t pleated. My thing is waist to hip ratio. If it doesn’t have Curvy in the name, it’s out of the question. Chance of finding curvy thrifting: negligible.

    Premium? Haven’t tried that many, but since I am totally uninterested in jeans, meaning I see them as the pants that are easiest to keep clean, it’s hard to be motivated.

  • Greyscale replied 5 years ago

    I should note that I wear jeans 99.9% of the time, so it's really the area where I put in the most effort. Suz, I think you're completely right that trying a new silhouette leads to more false starts. 

    The exciting update: I wore the jeans today, as I said, without washing them. Not usually a problem, even with my umpteen chemical sensitivities, but these had some lingering strong odor from processing. I felt ill (headache, stomachache) all day until I figured it out just now.

    ...and now I am sitting in my office with the door closed, wearing my longest lab coat with nothing under it, so that I can actually get some work done today. (It's really no different than a shirtdress but definitely not safe for public viewing!)

  • Jaime replied 5 years ago

    I related so well to your first paragraph that the second one seemed inevitable. I have been looking for high rise jeans that fit for a long time and have had so many false hopes I can't even count them. I am currently, and surprisingly, most happy with a pair of Mango (thrifted) jeans, but when I get to NY I will be devoted some time to the jeans in Buffalo Exchange etc. I don't have the luxury of ordering a bunch online and returning the failures, so that is a factor.

    Anyway, this is just commiseration not answers. Given the complexity of personality and the number of factors that go into decision making I have to pick my battles and this is not one of them right now. 

  • Staysfit replied 5 years ago

    Hmm, interesting perspective. I accumulate lots of jeans too, but it isn’t because they don’t fit, it’s because they do fit! LOL! :-) Jeans just work for me so I buy them. It’s really length and rise that are the hardest parts, but not so hard that it’s impossible. Tops however are very hard to find........I think we all have a style holy grail. Finding tops that fit would be mine, but it doesn’t lead to an accumulation. I just can’t find any I like. I think tops rotate through my closet faster than anything because of the fit issues.

    Seriously, I think jeans fit is your holy grail. I trade up certain items also. For example, I recently had a chambray dress that I thought was decent, even excellent, but was in fact just serviceable. I kept it until I found what I now think is the perfect denim dress made by Rachel Comey. It’s a much sturdier, better made dress than the first. It’s a simple silhouette without frills but still with some detail to make it interesting. It’s easy to accessorize. Goodbye to the first dress. Will I find an even better dress? Perhaps, but I am not purposely looking, I didn’t look for the Rachel Comey dress either. I stumbled upon it. I do however deliberately and actively hunt for tops.

  • Christina F. replied 5 years ago

    I just had this same issue come up. I have some dark skinny jeans that are slightly too high rise for my comfort but otherwise great. I just bought some that look just as good and are more comfy. I go through dark jeans quickly enough, and I’ll keep them both for now to avoid laundry pile ups. They are slightly different lengths, which helps justify my decision to keep both.

  • Jessikams replied 5 years ago

    Such an interesting question! I definitely do this too, especially with jeans because I wear them alllllll the time and I love them. But truly, how many pairs do I need????

    I used to be more strict about this but then I had a learning experience. I had a cheap Old Navy jean jacket for years and I thought it filled the “jean jacket” slot in my wardrobe well enough. I didn’t love the boxy fit and found it hard to style, but I just figured that’s how jean jackets are. But THEN I tried on a friend’s Pilcro jacket and it was a game changer. Yes, much more expensive— but also much more flattering and versatile. From this I learned sometimes a different version of something is really a good idea.

  • Joy replied 5 years ago

    This is all a very personal approach. I adopted the “ will I keep looking” question because budget and closet space is limited and to keep me from buying because of sales blinders. Jeans may be an exception because I can still get lots of wear from mistakes. You wear jeans a lot, so enjoy them all.

  • Jane replied 5 years ago

    I absolutely enjoy shopping in all its guises, thrift, on line, bricks and mortar. I like to find things that feel like an extension of me, and if I find an item that I love but the thrill of finding it means I make a poor decision, I try to work through the lessons like Suz and Sal. I do feel as if I’m consumerism oriented but then I think I work in central London with gorgeous shops and so it is inevitable that I get absorbed and skewed that way for a while. I think if I worked in a paint factory I would get absorbed by colour!

    Good fitting jeans are great and I love the choices you’ve made. I love the skirt too. I’m looking forward to seeing this on you. I’d love a denim skirt!

  • gryffin replied 5 years ago

    Greyscale - I'm not sure this will resonate with you, but I will share in case it's helpful.  I am a notorious upgrader.  Usually I require an item that I am unable to find.  So it I find something "almost right" it becomes a "place holder"  I can not make the outfits I want, but the "not quite right", but really good enough nice, right, if that makes any sense, allows me to keep the item.  When I do find exactly what I want that is when I stop looking.  I do consciously try and decided in the "NQR" - do I love the new one a lot more than the other "NQR"  If not back in the box.  Also  criteria to keep, if it immediately goes into protective custody and I don't want to take it off it's perfect.  If I can pack it back up, it's not perfect.  So I have to be uber picky in these groups.  This happened with my moto jackets (plz don't ask), tux shirt, body suit, you get the picture.  In the same way I wanted the Allsaints Lucie boot (from last season they shot almost the entire catalog with those boots for good reason, gone, I know CS checked.  I bought the Frye Julia shields - more moto less cowboy/moto.  But my luck, they brought them back!!  And they are perfect.  So I have perfect and "good enough"  I'm happy the Frye's are great and I can kill them, and wear my Allsaints for special to keep them nice forever!  BTW in your not quite cowboy bootie quest, highly recommend you check out this hybrid.  Cowboy heel, pointy toe but moto/paddock buckles styling.  Unique, but not sure that's what you want.  Also incredibly comfy and TTS.  Just FYI.  But if I'm still looking after purchase then I know it's a "for now" not a "forever" piece.  If you need it fine, just know, if that's also your MO why you are keeping them and make peace with it. 


    Wont let me collect find...

  • Angie replied 5 years ago

    If the silhouette becomes a wardrobe essential, then you can keep looking and stock up. You’ll wear all three pairs, right?

  • Suz replied 5 years ago

    Eeew! Off gassing jeans?!? Yikes. 

    I have read reviews of some recent Gap products that mention this...

  • replied 5 years ago

    You wrote "I'm curious what strategies others take in these decisions."  

    This is a fascinating subject that I have actually given some thought to in the past.  I need to gather my thoughts and catch up on what others wrote.  I'll be back later.  

  • Diana replied 5 years ago

    I do this too. My problem is that at some point, if the item in question is a true wardrobe mvp, I start getting obsessed and exceedingly picky and perfectionist, sometimes to the point where I can’t find anything that’s perfect because I’m not willing to settle. Too hot, too cold, nothing is just right.
    Currently, I’m having this issue with black combat boots. I really need some new ones, yet nothing I see has the right shaft height, heel height, quality, comfort, etc etc.

  • Diana replied 5 years ago

    Oh, and ps. I’ve had the problem with off gassing black denim too. I don’t think I’m quite as sensitive as you, but it’s a gross, pervasive smell and gives me a headache. For some reason it seems to be a problem exclusively limited to black denim - not any other color denim and usually not any other black fabric. Usually I can tell right when I open the box. In my experience the smell does not easily wash or air out so it’s a dealbreaker for me.

  • replied 5 years ago

    Interesting thread. I'm with binkie.  Admittedly, I'm not a fit fiend, because I so rarely get a good fit from clothes that I no longer "expect" it, but I can get carried away accumulating versions of the same thing (denim dresses are my downfall, for some bizarre reason).  But , I think I have this problem under control now, and simply make do when things are not perfect. Money only goes so far, and accumulating too much of one thing and obsessing over getting the perfect one has run its course with me.  

  • texstyle replied 5 years ago

    I don't do this as often as I did in the past but I did at one time have at least 4 iterations of the "perfect" chambray shirt. The only one that made the cut is still not worn often. The realization was that I didn't *need* a chambray shirt after all. I've also been known to keep searching for the perfect white summer top(s). I don't have that many because luckily I've gotten better at returning things right away. But I still seem to obsess over it every summer and am disappointed when I can't find the "one." This is my last attempt for this  year and the sleeves are kind of the deal breaker - a little too billowy for my taste I guess. And it's pretty sheer and wrinkles easily, contrary to some of the reviews.

  • Bonnie replied 5 years ago

    Your perfect jeans are/is my perfect jeans jacket. I bought one three years ago and never wear it but I know if I find the perfect one, it will become a workhorse. The difference is that I haven't replaced the one I have because nothing I've tried on is any better than the one I have. Still frustrating but less expensive.

  • replied 5 years ago

    I had another thought about this - and I'm not suggesting this is happening in your case, but......I do find that when I start doing this , I'm usually barking up the wrong tree and going after something that will never be right .

  • gryffin replied 5 years ago

    That's interesting Lisa - for me it's something I really need (ok or want a lot) but I can't find the right iteration so I buy something close so I can complete the look of the outfit even if it's not quite right.  But there are still things that I can't find and others where I finally nailed it.  And no I will take those "mistakes" and their CPW to my grave but I do try and limit the amount and variations on NQR items.  Now for that 3/4 sleeve black cropped vee neck cashmere cardi for layering!!  Why of why JCrew did you discontinue it!!  Nothing has been right since!!

  • 3style replied 5 years ago

    @Greyscale, I haven’t tried this with heavy denim, but with summer weight denim, I’ve actually in the past had very basic jeans taken in by a tailor. The amazing result was that it last for years and work through many more weight fluctuations than anything that I’ve ever bought off the rack. Alas my tailor retired and I haven’t had time to find a talented new person.

  • Jenni NZ replied 5 years ago

    I will have to think hard about the underlying question but right now with the pics I feel like the scene from "The Devil Wears Prada" where Andy chokes with laughter when she can't see the difference between several belts and she gets the withering look from Emily and then Miranda Priestly gives her a talking to! Sorry Greyscale you may give me a withering look for not seeing the difference between these 3 pairs of jeans :(

  • Gigi replied 5 years ago

    I know this feeling well of always wanting to upgrade! It can be torture. I am a perfectionist in general, so this plays right into my weakness.

    My first line of defense is not to settle unless absolutely necessary. I will settle if I have a pressing need for something. This is pretty rare--it would most likely be some kind of special function or situation out of the ordinary.

    The second reason I would settle for something is if I have looked and looked, generally for at least a couple of years, for something and just cannot find exactly what I want. I will then settle IF the price is right AND I am convinced that I will wear the item quite a bit (i.e., the item will be practical).

    Once I find what I am looking for, I buy it and enjoy it...and don't allow myself to look for better versions! That is where I can really get into trouble--if I start trying to outdo my great purchase. Let's face it--you can almost always find something better (better quality, better fit, better color) if you keep looking. So I make a conscious effort to stop looking at similar items once I've bought "the one." (And as others have pointed out, asking whether you are willing to stop looking for item X once you have bought the item in question is a good way to determine whether it is indeed "the one.")

    I recently bought a faux leather jacket from Express that is about 80% what I want. I settled because I have been looking for a leather jacket for three years now and cannot find what I'm looking for. This one was on sale for $80, and the quality and fit are good. In fact, the fit is amazing, which is what is lacking in all the other leather jackets I've tried. There are a few stylistic elements about it that I'm not excited about, which was my only reservation. I will continue to look for the perfect leather jacket, but in the meantime I will likely get $80 worth out of this jacket, as I have very few jackets.

  • Suz replied 5 years ago

    I just remembered another of my strategies. I buy the thing I think is "good enough" (especially if jeans or footwear, because both are so core and necessary to my life) and wait until next season to look further. If I find I'm happily wearing the "good enough," well, then, it really was good enough! If, on the contrary, I find that I hardly wear it and whenever I wear, it feels wrong, then I let it go at the end of the season and start looking again. Oh, and I just make different outfits that don't require said item in order to do so, sometimes feeling annoyed that I don't have the piece I need, and sometimes finding new combinations that I enjoy in the closet. 

  • gradfashionista replied 5 years ago

    Even though I buy denim from multiple retailers, I frequently regret it because of fit issues. I would happily buy from Nordstrom exclusively because of their return policy, but they often don’t carry my preferred size, style, or brand. Regardless of the fabric composition, you can’t predict how jeans will stretch out with wear, and a fit that is or becomes slightly off will leave me wanting for something better.

  • Greyscale replied 5 years ago

    Conclusions: I sold the jeans from the first photo. I kept the second pair of Levi’s wedgies (photos 2&3) and my boyfriend happened to say, wow those jeans look good on you. So that’s a good sign.

    I love the relaxed fit of the Gap jeans (photos 4-6) but even after washing in my magic odor-removing detergent, they still make me feel ill. I’ll wash them a few more times but I am not happy about this.

  • Jenni NZ replied 5 years ago

    Greyscale having looked at the photos again I can manage to see that the jeans in pic 1 were not quite as flattering as the ones in pics 2/3. So that's good that you sold the first ones and also that BF likes the pic 2/3 ones so much! Sorry about the Gap ones. No suggestions :(

  • replied 5 years ago

    I bought your magic odor-removing detergent.  Have not needed it yet, but I will and I want it on hand.  Thanks for the suggestion.  

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