The Psychology of Clothes Shopping for the Unfashionable Woman

9:00 AM

I don't know about you, but the problem isn't dragging myself off the couch, into the car, and into the Goodwill parking lot. That's tough, I'll admit...but the real battle begins as soon as I walk inside.



I come in with a game plan: skinny jeans. A pair of nice skinny jeans like my head RA and my roomie and every college girl everywhere wears with their Toms and hipster sweaters. It takes me a couple years, but eventually, I catch on to modern clothing trends. I'm still wearing high-waisted jeans, but I'm learning. I'm getting there.

Skinny jeans. Not the kind that squeeze every curve into plain view. Not the kind that makes me look like I'm entering middle school. Not trendy, not sexy, just collegiate. I don't have Toms or hipster sweaters, but maybe in a couple of years I will. And I'll need a pair of nice, collegiate skinny jeans to go with them.

In the few years I've been clothes shopping on my own, I learned a couple of rules:
  1. If you love something, don't ask your sister's opinion on it.
  2. If you're uncomfortable wearing it, don't buy it.
  3. If it doesn't fit you perfectly, for the love of closet space and all other things good, don't buy it.
Ladies, perhaps you can sympathize. I come it at 5 feet, three-and-three-quarter inches. I'm short. I'm small. (I possess no curves whatsoever.) And everything nice in Goodwill comes in size 8. I'm not a size 8 by any stretch of the imagination. Still, I always, always, always convince myself that somehow this oversized dress or jeans or skirt will fit me. Maybe it'll shrink? Maybe I'll binge on a bag of cool ranch Doritos? Maybe my sister can alter it? It never shrinks, I'm still tiny, and I go back to school before my sister can alter it. 

In my dresser and in my closet, nothing fits. I safety-pin my skirts, I belt my dresses (actually, I stopped belting my dresses because I can't make the belts tight enough). I wear my roommate's clothes a lot. And I continue to buy size 8 clothes. It's just so cute.

Shopping is psychological warfare. Hear me, future clothes-shoppers. Hear me, unfashionable women such as myself. Hear me, anyone who ever struggles with this problem: don't buy something that doesn't fit perfectly. Don't, don't, don't. Don't compromise. You'll regret it. You'll look ridiculous. You'll get tired of the safety pins popping off and your skirts puddling around your hips. 

I never thought I'd give fashion advice, but there you have it. 

I also tend to buy things I don't actually like. I come into Goodwill, snoop around for a cute dress, and come away with something kind-of cute that I might wear if I analyze the situation for five minutes like I do in the store. (Yes, it's size 8.) In real life, I throw on something and am suddenly aware of all its imperfections: it's too long, it's too big, it's too oddly colored, it's too not-my-style. I used to think my style preferences must change as much as my leftover adolescent attitude. I now realize it's because I buy things that might somehow be cute and stylish and am later undeceived when I actually have to wear that bag outside of the store. 

Just because it's in Goodwill for $4.99 doesn't mean you should buy it. Case in point.
The other thing I struggle with -- to get serious here (not that buying properly-sized clothing isn't serious) -- I struggle with branching out into clothing I used to find immodest. Like skinny jeans. Or shorts. Or tank tops. I don't know how to shop for them without caving in and buying a regular t-shirt or size 8 capris that I'll never wear in public...or going the other way and buying something I'm ashamed of wearing for different reasons. The Goodwill dressing room is a closet of temptation, I'm telling you. It's where my old life and my future life -- whatever I want that to be -- collide. I get identity crisis in that dressing room. What do I really think is modest or immodest? I run through all the people I could possibly offend and all the people I could possibly shock and all the people who would be impressed. Can I wear this at school? In front of my professor? In front of my roommate? In front of my mom? 


Scottie dog turtleneck -- not impressive

Apparently reds -- particularly Marsala -- are the newest color trend?
I once called a girlfriend while shorts-shopping for the first time ever. My boyfriend was of no help due to his upbringing among only brothers. "How short is too short?" I cried. "I don't think it's too short, but I was homeschooled. I don't know these things. What are the manmade guidelines that will prevent me from offending a normal person?!" 

"Rule of thumb, literally," she said. "The shorts need to go past your fingertips." And that's the rule I swear by. 

I didn't phone a friend during skinny jeans shopping, but I did call in my sister. I always shop with people for this very reason -- a neutral person who won't freak out about my style preferences or try to shop for me, whose job is solely to answer the question and allay the concerns I'm worried about. 

"Does this look too weird?"

"Yes."

"Is this too tight?"

"Yes."

Problem solved. They also can hold all the rejects I pile into the corner. I went into the dressing room with five pairs of skinny jeans, and I came out with one great pair that's not too long, not too tight, with real pockets. I actually like it, it's not size 8, I'm not worried about immodesty, and it will look great with Toms and a hipster sweater. 



What are your clothes shopping tips? Do you battle with these psychological shopping problems?
I'd love to hear your comments -- I'm still new to this shopping thing!

p.s. Check out my sister's recap of our adventure and leave her a comment!

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24 impressions

  1. Heehee. I'm glad you're past the Goodwill polo-shirt stage. ;)
    And just for reference, I can wear a size 8. But I don't think I'll take any of your reject clothes from past thrift sessions. :)
    But I can always use extra scrap fabric. ;)

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    1. (Wait...are we actually discussing our clothes size on the internet?!) I was always embarrassed into not wearing the clothes I bought when you younger sisters refused to touch them. *awkwaarrrrd*

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  2. Lol, Bailey. Don't worry, I've also bought too many clothes that were too big, hoping to fix them up. And they just sit in my closet until I decide to give them to a charity (actually, they probably go right back where they came from). I also understand the thing about modesty, and wondering what to wear around who. Maybe you could write about it? I'd be interested to hear your thoughts; it's a subject I've thought at lot about but haven't found many people who came to the same conclusions I did.

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    1. I wonder if the Goodwill workers recognize the same clothes coming back again and again as bad shoppers like me buy them and good sisters like mine return them right back where they came from. Though, as my sister said, my old clothes get ripped up by creative seamstresses in my house. ;)

      Oh, gosh. Modesty is so hard for me to talk about as a category! I suppose I could give my own personal convictions about particular items of clothing (like the past-the-fingertips rule for shorts). Is that what you're talking about?

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    2. Could you give your personal convictions on items of clothing, like how you went from exclusively wearing skirts (right?) to wearing jeans? What was your line of thought, and how did you match your convictions with Scripture? (Not that there's a specific scripture on skinny jeans and skirt wearing, obviously, but still...:) )

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    3. If you're interested in reading such an article, ladies, I'll write it!! If anyone else is interested, feel free to email me or leave me questions here on this post!

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    4. As our family and I have gone through this transition (from all skirts to pants) in the past two years or so, I'd be very interested in hearing your thoughts and process as you went through it.

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    5. I've got a trilogy of posts written up for next week: why I decided wearing pants didn't count as cross-dressing, what I think about a girls' responsibility to not cause her brother to stumble, and my personal do's and don't's about what I wear. Sounds good, ladies? :) I'm encouraged by your interest! I can't wait to hear YOUR thoughts too!!

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  3. One of my shopping rules is, if you don't love it, don't buy it. This is because I know there are so many things out there that I love that I can't waste money on something I don't. If you look at it and say "eh...", don't buy it. I definitely agree with your first two rules; they are both ones I try to keep in mind myself. I got this really fun pair of pink and purple chevron shoes that my sister hated. I loved them, and in that instance, I didn't care what she thought. :) And yes, if you're uncomfortable in something; you'll never wear it. It will sit in your closet haunting you until you get rid of it.

    But I love your sweater with your new skinny jeans. And the picture of you and Bethany in the dressing room is too cute!

    Also, I'd love to hear (read, I guess) an article about how your convictions about clothing changed. And my sister agrees with me. :)

    (And I think it is pretty stinkin' awesome that you left a comment on my brother's blog. Yes, that was random, and it's late and I'm a little slap-happy.)

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    1. Chevron is amazing. I have nothing in chevron. But those shoes sounds TOTES ADORBS. Thank you for echoing the "don't buy it if you don't love it!" So true!!

      Well, I thought your brother's post pretty stinkin' awesome...hence the comment. ;)

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    2. I'm a sucker for chevrons; whatever it is, if it has chevrons, I love it. I might have a problem...

      Your trilogy sounds good; I'm looking forward to reading them!

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    3. I was shopping today at Bed, Bath, and Beyond and saw a chevron pillow. I thought of you. ;)

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    4. Awww, thanks-I'm sure I would have loved it! haha

      (And I'm increasing the length of an already long reply train...)

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  4. Well.... I have.... Not a hard time shopping.... Ever!!!! ;D Well, that's not entirely true, but you get the idea. Most of my clothes come from Goodwill, so yeah. ;)

    Well, I don't have any clothes shopping tips, but I know what does look really fashionable (for me anyway) is like a black, flowy pencil skirt (that comes right under the knees) and a nice sweater (I prefer black for that too. ;D ) Then you get one of those scarves (any color. I like purple, blue, or pink best. :) ) Then finally you wear black tall boots with it. It looks awesome!!!! :) But I don't know, it's kind of complicated, and you might not like it. ;P

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    1. My roommate dresses EXACTLY like you!!! I love the classic black look, and I bet you look stunning in it. I only have black snow boots, though. :'( Someday I need to get myself some nice tall black boots, and then I can put together the outfit you suggested.

      And high five for Goodwill shopping!!! :D

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  5. I'd like to know your journey from one modesty standard to another, too. It's happened to your younger sisters, too. It's good not to be legalistic in dress or any matter, but certain principles of modesty are good to hold onto without throwing the baby out with the bathwater. It takes creativity and thoughtfulness to find a style that's just right for one's own self--pairing up femininity, basic modesty, and cuteness (it's okay to want to look cute or beautiful--I think that's how God created females to be!), but without necessarily trying to look like everyone else or imitate the trends of the day. I still cringe over low-waisted, tight jeans--ugh.

    Okay, I realize I'm a middle-age mom and frumpy by the younger generation's standard, and I don't expect my growing-up daughters to dress exactly like they did in the 2000's, but I'd be interested to hear your thoughts. How do you decide how much skin showing and degree of tightness is okay, personally?

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    1. @ Mama - actually, you do have a style and I don't think it's frumpy at all. ;) And you're actually educated on styling/blow-drying hair....unlike all of us. Seriously, we missed out on all the big-hair secrets from the eighties. Someday, you need to show me how to hot curl my hair. If I ever cut it. :)

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    2. I too love your style, Mama! I know we don't see eye to eye about the practical application of our beliefs on modesty, but I think you'll agree with almost every principle I use to shop!

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  6. High-waisted jeans are THE fashion now, gurrrl!! lol. I personally hate them, but they're everywhere in the mall.

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    1. JEANS? I mean, I knew the high-waisted ripped booty shorts were in style. I didn't know my years-old jeans might count. Woohoo!! ;)

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  7. Oh I never know what to buy either. I ask my sister to tell me. But I don't like skinny jeans because they are uncomfortable. I am waiting for the loose bell bottom ones to come back in, which my sisters think is a really bad idea. And yes I would love to see a blog post about what your personal modesty standards are and why! That always interests me :)

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    1. Bell bottom jeans are so much fun. I actually have a rip of flare-bottom jeans, and I think they're the cutest kinds of jeans! (Mine happened to be ripped in the knees. Oh, wellllll....)

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  8. I HAVE THAT SAME SCOTTIE DOG TURTLENECK. weird. wow. and I actually really love it and wear it out in public though now i'm pretty sure i'll never wear it again. It's one of those things that's questionable, ya know? Everytime I wear it I wonder if it really looks like a pj top or if I'm just imagining it. then I end up wearing it anyway. not anymore . . .

    I like skinny jeans just not the tight ones (which I guess defeats the purpose of them? not sure) because they're so uncomfortable. I went through a phase where I loved thrifting and buying clothes online so I got a bunch and now I haven't bought any clothing for months. I just wear the same things. It's hard to know what's "modest" or not . . . but usually I feel a certain way when I know something is immodest for me personally so I take it off. Can't really describe it, but I just know. Oh and asking your brothers helps, too. just a tip.

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    1. YOU CAN STILL WEAR YOUR TURTLENECK!!!!! DON'T LISTEN TO MY DISDAIN!

      From what I understand, skinny jeans are just a cut of jeans. They don't necessarily need to be skin-tight. (They're really uncomfortable if they are. Blegh. :P) But you do have to peel them off...which is weird. Like a Chinese finger trap, as blogger Esther Anderson described them.

      I too go by my gut a lot. If I'm uncomfortable with it, it's a no. A BIG no. And I don't ask the men in my life for their opinions on my clothes because I don't believe modesty is about dressing to keep men from stumbling. More on that later. ;) But guys are great at pointing out stupid styles that girls get crazy over, which is always super entertaining!! Oh, and this isn't to say that asking guys for their opinions on modesty isn't helpful, but I would ask a brother's opinion for the same reason I'd ask my sister's, if that makes sense.

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Hit me with your best thought! I'm very interested in your unique perspective. If you'd like to discuss things in private, feel free to email me! :)