My Go-To Shopping Strategy (and How It’s Backfiring on Me at the Moment)

One of these days, I’m going to share a “things I DON’T do” list with you here on the blog. And when I do, #1 on the list is going to be that I Don’t Shop.

Seriously. I hate shopping.

At any given time, there are about 100 other things I’d rather be doing other than shopping. It’s not that I hate looking in stores–I don’t mind that, really, and I’m always happy to help a friend pick something out–but choosing something that actually looks good on me, and then paying for it, and bringing it home, and cutting the tags?

That’s another story.

Usually, my I Don’t Shop strategy works for me. It saves me time–because I spend the time I might have been shopping doing other things. And it saves me money, because I don’t spend any if I don’t go shopping.

But my No Shopping strategy also occasionally lands me up a creek. I’ll suddenly realize that I only have one pair of jeans that actually fits, or just 3 shirts that I actually wear and 2 of those got holes in them, and what am I going to wear to that wedding next weekend, anyway?

Through trial and error, I’ve figured out a couple of shopping strategies that work for me:

1. If I’m in a store, and I find something I like, I buy it. Period. The End.

I’m a maximizer by nature, and I’ve learned the hard way that if I let myself start comparison shopping, that process will never end. The more options I look at, the less satisfied I’ll be with my final choice.

If I find something I like, I need to buy it, take it home, and cut the tags. Immediately.

my go to shopping strategy it's backfiring now i hate shopping

2. I need to do a regular wardrobe assessment to make sure I actually have decent basics in my closet.

For those of you who actually like to shop, this will sound ridiculous. But those of us who don’t go shopping EVER (and especially if we’ve had babies in the past few years), know that it’s possible to end up with nothing to wear. I’m not talking about the first world problems version of “nothing to wear,” I mean nothing to wear besides my 3 tshirts (two with holes) and one pair of jeans.

When I fail to plan ahead, even for something as prosaic as clothing, I can create a bit of an emergency. Like now. I hate jeans shopping, so I didn’t run out and replace my jeans last year when I should have. Then I didn’t think about it all summer. When I finally got around to denim shopping last week, my size was sold out.

Right now, I’m just hoping Fed Ex brings my new jeans before I leave for the Influence Conference, because otherwise I’ll be wearing the same jeans for 4 days straight. (Not like I haven’t done that before, but my standards are a little higher for a conference!)

Sometimes I wish I loved shopping more, but that’s just not who I am. And that’s okay, as long as I follow my two personal rules to keep myself decently clothed.

Am I the only one who hates shopping?

photo credit 1, 2

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  1. You are so not the only one who hates shopping. I could have written this post.

    I’ve also learned to buy stuff if I find it and like it. And hopefully that’ll keep me from needing to look for anything else for a long long time.

    Shopping takes time away from reading. Why on earth would I want to do that??

    And now having to be responsible for clothing two other people in addition to myself? Horrors.

    • Anne says:

      “Shopping takes time away from reading. Why on earth would I want to do that??”


      I actually much prefer shopping for my kids than shopping for myself. They’re still at the age when it’s pretty easy to find clothes that fit them, and it ALWAYS looks cute on them!

      • Oh, definitely the kids are easier than shopping for myself: straightforward sizing and they don’t have a lot of opinions yet. Right now I mostly hate having to *think* about it; my daughter needs more socks. My son needs some long sleeved shirts that I don’t hate (he was gifted some but I can’t stand looking at them). They both need shoes. etc etc etc.

        Because there is so much I’d rather do then dig through a pile of shirts for the 3T size. Or figure out which shoes will fit his ridiculously shaped feet.

  2. Oh my goodness, Anne! You could have written this about me!!! I am in the exact same spot right now –and even for my kids. It’s a serious problem! I rarely go out so it makes it even worse because I don’t have time to scour for deals, and then I feel all guilty for paying full-price.

    Curious? What brand jeans do you get? I need me some . 🙂

    • Anne says:

      I just bought Express jeans for the first time in 10 years. Before that it’s been Gap and Banana Republic, and skinny jeans from Old Navy. I think my favorite pair ever were my Paige maternity jeans.

  3. I really don’t like shopping either. I find shopping for woman’s clothes is so frustrating. What fits in one size/one brand, totally is not across the board for everything. I might wear a 6 in one pair of pants, a 4 in something else, and 10 in another. No quick shopping. Frustrating.

  4. deborah says:

    I think I’d like to shop in the little turquoisey-blue shop you have pictured! Adorable!

    I like to shop, but it takes money. And space. The more stuff you have the more you have to do something with! 🙂 I’ve been working on being more of a minimalist-I’m not naturally one.

    I struggle finding summer shirts that I like, fit, look good, and are affordable.

    Crossing my fingers for you that your jeans arrive!

    • Anne says:

      I know! Isn’t it adorable?

      And guess what–my jeans are here, a day early! Thanks for your well wishes on that important issue 🙂

  5. Pam says:

    I hate shopping too. I like buying things for my kids, but not myself. I have four pairs of pants – two have holes in them and two have stains all over them from wearing them so much. I know that it’s time that I went jeans shopping too, but I’m dreading it. I hate it so much. I’d rather wear holy jeans than go shopping. Maybe after soccer season. 🙂

  6. Katie says:

    A cold front moved in and I realized that all the maternity clothes I borrowed are for warm weather, not cold weather, and not good for layering. And I still have five weeks to go and every non-maternity top I own is already skin tight. But I really, really, REALLY hate the idea of buying clothing (especially enough clothing to dress for work every day, it’s not like I’m just lying around the house or running errands–I have to go in to an office five to six days a week) that I will only wear for five weeks and then possibly never ever again. UGH.

    On the other hand, I bought a belt at Goodwill the other week that I love that does not fit me at all at the moment, but theoretically will eventually, because I am learning to follow your rule number one. And because surely every girl needs a white patent leather Levi’s belt that only cost two dollars.

    Rule number two is why I always buy an Old Navy t-shirt/cami/long-sleeve t in every color when they go on sale, because those are my wardrobe staples and I know exactly what size I need, so I don’t need to waste time in fitting rooms.

    So it’s not that I hate shopping. I just want a really good price per wear, and begrudge the fact that maternity clothes do not provide that at all (thrift stores have yielded nothing that’s not hideous, and they don’t go on sale at Real Stores that often, and even Target wants seventeen bucks for a freaking long-sleeved t-shirt!). Blah.

    • Anne says:

      Oh, Katie–I hear you on the maternity clothes!

      “Surely every girl needs a white patent leather Levi’s belt that only cost two dollars.”
      YES. That is wisdom.

      • Katie says:

        RIGHT?! Also, I realized it’s actually only four-and-a-half weeks now and freaked myself out a little. I should have just bought some earlier so I could wear them for longer. Hmph.

        I am seriously stoked about that belt. 😀

  7. Jillian Kay says:

    I’m with you. I don’t mind food shopping, or going to the garden center but clothes shopping? Yuck. Also, fitting rooms are hard with my kids and I hate to waste what precious alone time I do have trying on a bunch of stuff.

  8. Yes! Not only is this post itself fantastic, it’s incredibly refreshing to scroll down through the comments and see others who hate shopping too. I always thought I was supposed to be programmed to love shopping, and something must be wrong with me. But I HATE IT. Every time I go, I try on about two pieces of clothing, get frustrated, and call the whole thing a bust. Thanks for reminding us non-shoppers that we’re not alone!

  9. Jenny says:

    I read this amazing book a few years back and it totally changed my shopping style. I now don’t even try on anything that doesn’t fit in my body shape/style parameters. It’s called ‘It’s So You’ – here’s the link:

    Definitely has cut down on my dressing room pain. Also, jeans need to be kind of expensive. I mean,if you happen to find an expensive pair at a thrift store or garage sale in your size, by all means buy them, but don’t go into Target/Old Navy/Gap/Kohls and expect to walk out in a $30 pair of jeans that looks good. There’s a reason they’re $30…

    • Anne says:

      I need that book! Thanks for the recommendation.

      And seriously, I’m finally starting to learn what looks good on me and what doesn’t, and leaving things that I know won’t on the sales floor. It’s so helpful.

  10. Heather says:

    I think the best thing non-shopping women can do for themselves is to put a lot of thought into what looks good on them. Then when you come across the perfect thing – buy it! The only thing worse than having no clothes is having a closet full of unflattering clothes because you didn’t take the time to figure out your best colors, styles, and silhouettes.

  11. DFrazzled says:

    If I have to shop (for clothes, for myself), I love shopping at consignment stores–especially for pants and jeans. They categorize everything by size, and since we all know one brand size 10 will fit totally differently than another brand, I just pick up the ENTIRE stack of size 10 jeans and start trying them on. I have found some very flattering jeans and slacks this way, and most of the time they are $25 or less. Seriously, you get to try on 20 different brands in 30 minutes and you’re done.

  12. I’m the same. Well, specifically I hate clothes shopping for myself. I always start out intending to buy clothes.. but I try on a few things, and they don’t fit, and I get frustrated, and end up buying candles, or baby clothes, or little kitchen gadgets…

    • Anne says:

      I get this! Because for me, candles, baby clothes, and kitchen gadgets are guaranteed pleasers and a lot less stressful to buy 🙂

  13. Tim says:

    More than hating shopping, I hate returning things I shopped for.

    My ritual: I like something (shirt/toaster oven/car), I check it out (it fits/it has all the features I need/it fits), I buy it (and hope people think, “Hey Tim, nice shirt/toast/car”, rather than “Eww/yuck/what a piece of junk”).


  14. Carrie says:

    I hate shopping too, for 3 reasons. One, it’s frustrating how pricey everything decent is. Two, I think I look darn good naked but with clothing on…? disappointing. Three, it takes up so much time that I would rather be spending doing just about anything else.

    Buying clothing online for my kids has proven to be easy and fruitful, because their bodies don’t have curves yet. But for me? Nothing will fit right.

    And I am a classic “underbuyer” too like Gretchen Rubin talks about.

  15. Erin says:

    I hate shopping too. Many times I’ve worked myself up to the task of shopping only to come home with things for the kids instead. I’m a shortie, so shopping for jeans is not fun. The ones that fit my shape are usually way too long in the legs. But I’d rather wear my jeans with the pant legs rolled up than waste hours of my day searching for the perfect pair of pants that fits both my shape and height. 🙂

  16. Alas! If only I had a lady’s maid . . .

    Here’s a description from Wikipedia:
    “A lady’s maid’s specific duties included helping her mistress with her make-up, hairdressing, clothing, jewelry, shoes, A lady’s maid would also clean dishes, remove stains from clothing, fill jugs with fresh water every day, polish and dust the furniture every day and sweep the floors very slowly and carefully.”

    (long sigh)

    The truth is, if we were living in a Downton Abbey world, I would probably BE the lady’s maid, or even more likely — the laundress or scullery maid!

    I suppose it’s better to just follow your tips, Anne.

      • Tim says:

        My old boss used to go to Nordstrom’s every Christmas with a list. He’d meet up with one of their shoppers and hand it over. The shopper would sit my boss in a chair with a cup of coffee and return an hour later with everything on the list. My boss would hand over his credit card and be done with his Christmas shopping. THAT’s how a man shops Nordy’s!

  17. Lesley says:

    I love having new things, but, I am the worst about making decisions which means that shopping can certainly be stressful for me. I will admit I have a very full closet, but, I don’t wear a lot of what I have, or I wear it very little. I just bought the e-book, The No Brainer Wardrobe and spent Saturday doing a closet inventory, cleaning things out, and making a list of things I need to purchase. It was super helpful. Now I have a list on my phone with “really necessary” purchases and “wants/would be nice to have.” It helps me make decisions and saves my budget too.

    Also, as for jean shopping, here’s a strategy I use. Since I’m tall, and lengths are hard to find, I go to Gap/OldNavy/Banana online. Most of them have free shipping if you purchase over $50 of stuff. I’ll buy, no kidding, 10 pairs of jeans. They arrive at my front door, I try them all on for a girlfriend, and then I return 8 or 9 or them. MUCH less stressful than going to a store!

    • Anne says:

      Lesley, I am right there with you–I’m a terrible decision maker when it comes to clothing. I like to mull things over a bit, but it’s hard to mull for very long when you’re standing in the dressing room!

      And your jeans shopping strategy is exactly what I do. It’s the only way to shop for denim (or bathing suits!)

  18. Alia Joy says:

    I am in the major minority on this one because I love shopping but it’s something I have had to curtail because shopping actually costs money and stuff. Who knew? But I still find myself in that place where I don’t have what I need. Overbuying clothes sometimes just means a fuller closet but if I’m not intentional about outfits, I have a skirt that doesn’t go with anything or a blouse that looks terrible with jeans. I’ve done a major overhaul a la Tiny Twig, and that has helped immensely in actually having outfits without the clutter. Now book shopping is something else entirely. I can never get enough.

    • Anne says:

      Alia, I’ve really struggled with being intentional about outfits, too. That and being intentional about buying clothes for my REAL LIFE (that means no dry cleaning) are my #1 obstacles to a wardrobe that actually works.

      I thought The No Brainer Wardrobe was great.

      And ditto on the book shopping!

  19. Erica says:

    I love shopping: grocery shopping, gift shopping, shopping at the gardening center.

    I hate clothing shopping. I think part of it is because I’m short but chesty so finding clothing that look great on me. I pretty much have one pair of jeans and one denim skirt that I rotate between. I have a lot more tops, but most of them are things like t-shirts from past clubs, fundraisers, etc so not really the kind of things I should be wearing all the time.

    I really do hate the idea of looking frumpy. I made a pinterest board of outfits that I like and I think would complement my shape. I watched an extensive video on picking out jeans and have set aside a little bit of money to invest in a couple of jeans from Express that look amazing on me.

    My clothing pinterest board is a nice inspiration, and I keep my eyes out for similar clothing pieces during Goodwill Dollar Day or during big sale days. I know in advance what I’m looking for, and which colors will complement me or cuts that fit my shape so I think that really helps.

  20. Tiffany says:

    You could have been talking about me. At a conference recently, several people were talking about the book 7 and the wardrobe challenge of wearing just 7 pieces of clothing for a month. I don’t think I would find that very challenging. I hate to shop!
    My dream outfit is a pair of jeans, t shirt, cardigan that all make me look great. I’ll buy 3 sets and rotate it throughout the week.

    • Anne says:

      Tiffany, I love the idea of “uniform dressing” and it sounds like ours is pretty much the same: jeans, t, cardigan. I’ve tried to upgrade to nicer tees and blouses, and pretty, drapey cardigans, but it’s still my good ol’ uniform 🙂

  21. HopefulLeigh says:

    I like shopping but I follow the rules you listed for the good of my budget and my sanity. I’m not a Shop Til You Drop person anyway and can’t last more than an hour at the mall so if I am shopping, I want to make sure it’s worth it. Typically, I can’t find what I’m looking for when I need it, at a price I can afford. Therefore, if I find something I like (especially if it’s on the running list of things I’m looking for), I snap it up. And once or twice a year, I go through my closet and weed through it. I gather friends up for a Clothing Exchange and we bring whatever we don’t want anymore. Anything left over goes to Goodwill.

  22. Yes! I am in the same boat right now. Johanna mentioned not ever shopping and then feeling guilty for paying full price. I totally relate. I think I’ve just found a way to help me get over the guilt of paying full price – I’m never going to have too many clothes. I don’t buy them often enough anyway, so I’m no longer going to feel guilty if I spend budgeted money on something I need.

  23. Amy in Wanderland says:

    Blech. I hate shopping, too. I get disgusted shopping for clothes, but what I dread even more than that is grocery shopping. I just continue to put it off until there’s no other possible ingredient combo I can pull from the cupboard to make a decent meal. And then we run out of milk and/or cereal, and there’s no sandwich stuff left, either, and I might have pizza delivered once … and THEN I finally go to the store when I give in and admit that grocery shopping would be so much cheaper than pizza. (All that pizza is one reason I hate clothes shopping.)

    • Anne says:

      Amy, I like grocery shopping less and less as my family consumes more and more! I wish our area had better delivery options, because I would absolutely do that! Maybe one day…

  24. Joani says:

    I’m not a big fan of shopping but a few years ago I started going to Nordstom 3-4 times a year (always during the anniversary sale for one of those trips!) and their sales folks are wonderful. The clothing is more expensive than most but they are able to bring me the brands & styles of jeans to try that fit me well and are comfortable without me needing to do research myself. And they help me with tops/pants etc. If only they carried maternity clothes in the store…but then I probably wouldn’t be willing to pay their prices for something I can only wear for a few months at the most.

    • Anne says:

      Joani, this is why I wish we had a Nordstrom! Seriously, I do better shopping when I can find a really great salesperson or dressing room attendant–especially if she’s trying to help me buy clothes I’ll love and not just “sell” me.

  25. I’ve gone from loving it as a teen to hating it now. I started online shopping a lot, but if I procrastinate returning the stuff that didn’t work, then I have another,problem. Which is what has happened over the last year. Blah! I may have to start selling,on eBay as a way to clean up my mess!

  26. Julia says:

    Oooh, this is wisdom! Buy what you like when you see it and that’s it. When you don’t enjoy your shopping experience, money redefines itself, doesn’t it?

    I’m in exactly the same spot you are, perhaps the difference is that I’m secretly hoping for another baby (but that’s another story).

    Wet Seal (hellish stores with dismal quality stuff) has neat line of shirts that work for me as undershirts. Their V necks and long sleeved scoop necks have become surprisingly matchable wardrobe staples and I always buy them online – There’s NO WAY I’m setting foot on a store again.

    For my daughter, I usually give other people money and have them buy things. Sounds crazy but it works – as my sister in law and quite a few friends have children about my daughter’s age, and they go often to stores and are “in the know”, they buy good things and I approve.

    I just don’t care about buying the cheapest possible thing… money is redefined, absolutely.

  27. I can enjoy a day of shopping with my mom sometimes, but only if regular coffee and meal breaks are included. 🙂 I like to poke through a place like TJ Maxx/Marshalls/Home Goods now and then. I don’t love to try on all kinds of clothes and I especially hate to shop for pants — my weirdly proportioned body, I guess.

  28. Efficient method: getting a personal shopper. Could be free if you go to a department store that offers such things (some of the urban Macys, Bloomingdales, etc). Or if you want a wide range of stuff, pay the person. Do all your shopping in one day. She will figure out where to go, what looks good on you, etc. You will not have to shop again for years.

    • Anne says:

      Laura, I LOVED the way you covered this topic in 168 Hours! Getting a personal shopper is something I’ve definitely thought about (because I’m all about efficiency) but have never actually tried. I’m experimenting with something new–and similar–this month….we’ll see how it goes 🙂

      But not having to shop for years? That sounds amazing.

  29. Elizabeth Kane says:

    I hate shopping, but I love wearing clothes that make me feel great. Too bad that involves *actually* shopping. Now I have a bookmarked folder for when I’m online and find things I like. I look at what I’ve been bookmarking the last month, what store carries the most things I like, and what patterns/fabrics I’m attracted to before I tackle any shopping excursion to the mall. It’s like preparing for a battle!

    And I think jean shopping is the hardest shopping trip to tackle. I go back and forth trying to decide which is worse: annual OB visit or annual search for your true love jean pair.

    • Anne says:

      It IS like preparing for battle, isn’t it? And buying jeans is truly a torturous experience. The good news is that at least it can *also* be an annual thing 🙂

  30. Pingback: A Shopping Strategy for Women Who Hate to Shop
  31. Jimi says:

    My strategy is a bit different but it’s worked well for me. I don’t love to shop, especially for clothing. And I loathe shoe shopping. But, my strategy actually doesn’t address that.

    I have pretty much picked one store that I love and that’s where I go to do nearly all my shopping. For me, it’s The Limited. I work full-time, so I appreciate that they have lots of good options for dress clothes. I almost always find something that I like there. I don’t go often, and I don’t overly concern my self with sales. I just look for what I like and will wear. Now, I don’t find a ton of casual clothes there, but I spend most of my non-working hours in yoga pants and a sweatshirt anyway. 🙂

    It’s nice to walk into to the mall, go to one store and walk out.

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