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The Thrill of Shopping

The Thrill of Shopping

December and the Christmas season is perhaps the largest shopping season of the year with Black Friday and Cyber Monday being absolutely insane times for shopping bargains. And it is for crossdressers too as we can easily disguise our gift buying for ourselves as gift buying for others. I’ve enjoyed shopping all my life.  I’m a “thrill of the hunt” kind of person in all arenas; I love researching, digging deep, exploring all of the available possibilities. And shopping for clothes and shoes is no exception, which is why I tend to gravitate toward behemoth sites like eBay for my huntings as well as my online shops on Sister House that cater to the plus-size woman. I’m constantly excited by the transformative power of style, and enjoy investigating its trappings.

But I have many friends and sisters who absolutely loathe it: They get overwhelmed, their budgets are too tight to buy what they see and want, their sizes aren’t available at in-person shops, their personal styles aren’t represented by mass-produced lines, or they feel guilty spending on themselves instead of their families. The media loves to portray all women as shopping fiends, but it simply isn’t true.

So, do you enjoy shopping for clothes, shoes, and accessories? Why or why not? Have you always felt this way, or has something shifted over time? The opinion is mixed in the larger community of women so I thought you just might enjoy many of the responses from genetic women on their shopping experiences.

shoe shopping

• I love shopping in my imagination more than in reality. In my imagination, what I want is available, is sized for women like me, money is no object, and the choices are beyond compare. If I’m beset by insomnia, a go-to fantasy involves shopping at Barney’s–everything’s wonderful, there is no remorse. In reality, I live in a rural area with few choices. It’s an hour away to the nearest mall, and the selections there aren’t dependable. And, my size. 4′ 10″ tall, 120#, makes the shopping experience depressing and hard to not take personally. I mean, I get why manufacturers are skewing for taller women! I need only look around. I always start out with that “thrill of the hunt” attitude, but it quickly dissipates. Thank goodness for online shopping–but even there, petite choices are very limited. In order to look good, shopping has to be a bigger project than I’d like–more time, more research, more alterations. So frustrating!

* I enjoy building my collection of items that actually fit me well ( not easy at my under 5 foot size) and blend into what I understand to be my (evolving) style : ). I shop online much more than in brick-mortar stores. I window shop a lot more than I actually shop- I will spend days looking at things and even then might eventually end up returning it, but that’s what I love about online shopping, its slow and easy pace, ease of returns and watching out for items to go on sale. I have a small-medium size wardrobe but each item has been truly desired over time and very carefully selected to fit my style evolution journey.

* I love shopping, online and in person, provided that it is my sort of store. I’ve gotten to the point at which I have to tell myself that I can’t go to the thrift store until I fix up a bunch of the thrifted items sitting in my mending pile waiting for buttons or other quick fixes. I really hate being in a mall unless it is a quick mission for a specific item, because everything is out of my budget, not my style, or both. I don’t enjoy shopping if I’m looking for a specific thing and can’t find it, especially if that thing involves trying on lots of ill-fitting clothing, but I’ve learned not to do that to myself anymore. Finding jeans used to be awful, but I gave them up and I feel much better now. Finding bras was bad until I learned that I was shopping at the wrong stores. I tried different stores and read online reviews written for people with my body type, and I eventually figured out what I need.

* I enjoy the thrill of the hunt and looking for the offbeat but loathe mall stores. I thrift and buy online (ebay) but the latter is dangerous to me, with a desk job.

* I do not really enjoy shopping, but sometimes, when I stroll through the city, and can walk into stores without pressure, I might actually not find it too bad 😉

* I have switched away from in-person shopping to mostly online. A couple reasons include that in person shopping leads to too many impulse purchases and I’m trying to stick to a capsule/minimal wardrobe. Also, when I’m online I can get exactly what I want with few distractions. Having said that, I love shopping when I’m on vacation at unique stores I’ll likely never see again for “treasures” as a reminder of my time there. I also love going on etsy and ebay for finds and I *love* thrifting. I find that I can’t justify shopping at old standbys anymore–Target, Old Navy, Gap, etc–the quality isn’t there most of the time and all I can think is “sweatshop! labor violations! cheap rags your grandmother wouldn’t wear to clean the house in!” etc etc. (Just me—not trying to guilt trip budget conscious or busy moms or whomever!)  I try to spend money on the highest quality item and most eco/labor friendly I can afford. Still working on that one!

* I love shopping mostly clothes shopping because I love clothes. I really like to thrift shop because of price and the thrill of the hunt is especially good when you find something wonderful in a thrift for a really low low price. There are some very unusual things available that way too.

* No. I have a few go-to stores, both brick-and-mortar and online. Usually it works that I dream something up and know where to look for it. Then I’m done. I enjoy the dreaming-up part and the having it part but not the getting.

* Growing up, my mom hated shopping. Hated it. Clothes were utilitarian, period. But I longed for the current, beautiful, fun things I saw around me all the time. Reaching adulthood, I slowly began to realize that I really enjoy shopping, though it took me even longer to understand what suits me best and how best to shop for targeted items. Now, in my 40s, I definitely love to shop for new items, but I have parameters: most of my shopping is done online, and the vast majority of that is done at a handful of retailers I know work for my lifestyle, sizing, and price point. Occasionally I’ll stop in at a brick-and-mortar version of one of these stores if I want to pick up something quickly or to check whether they have an item that’s not online, but I don’t like to spend a lot of time physically browsing items. I will not shop at a department store; way too overwhelming & takes way too long. Every so often I’ll come across an item or style that’s an outlier to the stores I usually frequent, so I’ll go on a hunt for it (online) at an expanded list of retailers I’ve purchased once or twice from in the past, but that’s not very often. It works for me!

Can you relate to any of these experiences?

My own shopping experiences have generally been wonderful and I shop in the stores as well as online. Online shopping by far gives me the greater choices and I find that individual stores often do not carry what we see in the online shops. You’ll certainly want to check out the many columns by our Savvy Shopper in the Boutique. The Savvy Shopper shows you how to see through marketing ploys and visual tricks when shopping online or from catalogs. Following her advice can keep you from wasting your money on purchases that will die unworn in the back of your closet.

And then be sure to read our article on Sizing in Woman’s Clothing and the sizing charts by store and by brand.

And last of all, visit our Sister House shops and check our sales pages

From the Already Pretty poll

shopping with girlfriend



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