7 Rules for Shopping for Jeans

by Chloe Jeffreys · 33 comments

in How to Shop for Jeans, pp, Style

Thank goodness it was fall and not spring when I went to San Francisco.

If it had been spring then I might have been compelled to write: “How to Shop for a Woman’s Most Hated Garment: The Swimsuit Edition.” And then you’d be subjected to my stomach in a bathing suit instead of my butt in jeans.

But the shopping gods were gracious and it was fall in San Francisco and nary a swimsuit in sight.

So I did the next most hated thing: I went shopping for jeans.

Ever since I was in Paris–and saw them everywhere–I’ve wanted to get a pair of trendy skinny jeans that would look great on me. It took time and effort, but I think I was successful.

While the rest of this article is about buying jeans in general, the skinny jean has some rules all its own.

First of all: Be prepared.

These puppies are tight. You have to put them on like pantyhose.

When I did find a pair that I felt fit me, Nicole (my saleslady extraordinaire) told me in no uncertain terms that I’d have to go one size SMALLER.

I was shocked. And I balked.

Quickly a cadre of sales ladies gathered around  my backside assuring me that indeed these perfectly good-fitting pants were TOO BIG.

So down a size I went. I could hardly get on the pair I eventually bought, but now I see that Nicole was right. I’m glad I followed her advice.

These pants stretch out and as I was vehemently warned: You cannot reshrink them in the washer or dryer.

In fact, attempting to shrink them in the dryer has the opposite effect since it degrades the Spandex.


Also, not every fashion looks good on every body. The strong taper of the skinny jean accentuates the butt. Wear with caution.

So, without further ado, here it is, my Seven Rules for Shopping for Jeans. 


RULE #1: Choose a store that has a large selection

Don’t waste your time shopping in stores that have a limited selection or don’t carry your size.

And unless you KNOW that a brand really fits you, like I know that Express Editor pants fit me like a glove, choose larger department stores that carry lots of different styles and labels.

I decided to do this piece when I realized I would be at Macy’s in Union Square because I figured that a 7-story Macy’s had to have one pair of trendy Skinny Jeans that would fit me.


RULE #2: You get what you pay for

A good pair of jeans is a wardrobe workhorse. Dressed up or down, jeans can take you everywhere from the PTA meeting to the annual Office Christmas Party (I’m wearing my new jeans to the Office Christmas Party this year).

We all have to live within a budget, but jeans are so fundamentally important to a good wardrobe–and carry such a huge potential for a low Cost per Wear Ratio–that they are worth spending a little extra to get a good-fitting pair.

Katherine Finney at The Budget Fashionista explains Cost per Wear Ratio like this:

“Total cost of the item/ estimated number of days you’ll wear it = the cost per wear

For example, if you spend $500 on a great winter coat, wear it for about 100-150 per year over the next five years, it’ll cost you about $.67 to a $1.00 every time you wear the coat. The more you wear the coat, the lower the cost per wear. On the other hand, the trendy top you bought for $20 at your local OldNavy, that you wear only three times before throwing it out, costs you around $6.50 everytime you wear it, making it almost SIX times as expensive as the coat.”


Rule #3: Enlist Help

Take a trustworthy friend shopping with you (Return the favor by going shopping with her in the future) and enlist the aid of a knowledgeable salesclerk.

Shopping for jeans correctly can be a physical test of endurance because , and I’m not kidding, you are going to try on LOTS and LOTS of them.

It’s exhausting enough pulling pants on and off without having the additional stress of having to re-dress to go back out to the sales floor searching for more jeans to try on.

Start the shopping session by discussing what you are looking for with the salesclerk and your friend so that everyone is clear.

Collect some jeans to try out,  and then park yourself in the dressing room and have your trustworthy friend and your knowledgeable salesclerk do all of your running for you.

On my shopping adventure I didn’t have a friend with me, but I had Nicole:

Nicole is a Denim Specialist who has worked for Macy’s for seven years. She knows her jeans. Undauntingly patient, Nicole joined my crusade and helped me try on 20 Pairs of Jeans until I found the perfect pair.


Rule #4: Jeans are all about the butt.

The purpose of jeans is to make your butt look good.


If they don’t make your butt look good then DO NOT BUY THEM.

I can hear you say from way over here,  ”What if the jeans I try on do not flatter my butt?”

Then you need to remember the most important rule of them all:


Rule #5: It’s not you; it’s them

One reason women have such a hard time shopping for clothes is because we’re so conditioned to believe that our bodies are flawed. When we try on clothes and they don’t fit right we automatically blame ourselves.

This is wrong-thinking.

Because a pair of pants doesn’t fit you doesn’t mean that there is something wrong with you. Take them off and try on another pair until you find a pair that fits you. That’s all there is to it.


Do NOT emotionally engage with every damn piece of clothing you try on.  


I tried on one pair of jeans that were simply too tight. They were so tight that I set off the anti-theft alarm trying to pull them up.

This was embarrassing.

The pants were too small which doesn’t mean that I’m too big.


Rule #6: Plan to try on 20 Pairs of Jeans before you find one pair that fits

Back in my frumpy-dumpy days, I had all the wrong-thinking I’ve been talking about.

I would go into a store, pick out however many articles of clothing that were allowed in the dressing room. I would try on those things and pick the best fitting from the lot.

Because I didn’t understand that bad fit wasn’t about ME, and because I didn’t enlist help from a friend or the salesclerks, I would get tired and discouraged quickly and settle.

What I ended up with was a hodge-podge of ill-fitting clothes.  And I hated shopping because it was so unrewarding.

Those days are over.

Now I go shopping with the clear intention that I’m going to try on lots of clothes and that MOST of them won’t fit me and/or I won’t like them.

That’s okay.

How can I know if I don’t try them on?

So with that in mind, here I am trying on  19 Pairs of Jeans: (yes, I said I tried on 20, but I’m saving #20 for last)


Rule #7: Don’t Settle

Do not walk out of the store with anything less than perfect. This is hard to do especially after you’ve invested a whole lot of time and effort trying on 20 Pairs of Jeans.

I know you feel that you wasted time trying on that many clothes and leaving with nothing, but you can’t buy yourself back the time by settling.

If you don’t find something you like, do yourself a favor and walk away. It’s okay. Better luck next time.

Some additional tips:

To make the sheer physical ordeal of trying on clothes easier, remember to wear yoga pants and slip-on shoes. (you can see I didn’t follow this bit of advice, but I let Nicole do ALL the running around so I only had to undress once.)

Take a pair of shoes that have the height heel you are planning to wear with the jeans. (this was easy because just before shopping for the jeans I bought the shoes. hehe)

And here’s the results:



Jeans: Citizens for Humanity Cropped Thompson Skinny Jeans $176.00 at Macy’s; Shoes: Michael Kors Gibson Platform, Slate $175.00 at Macy’s; Shirt: Essential Stretch Long-Sleeved, Red Laquer $49.50 at Express

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{ 29 comments… read them below or add one }

December 25, 2013 at 11:46 am

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Jill S.
December 7, 2011 at 8:08 pm

Okay, so I didn’t try on 20 pairs of jeans. But I did try on 5. Or, okay, 3. But two pairs got “second looks.” (Being in the middle of Nowhere’s-ville Nebraska, I would be astonished to find a place that even carried 20 different kinds of jeans.)

But I tried to keep your words in mind, and the pair I bought was NOT the pair I would normally have purchased. I didn’t tell the hubby – we’ll see if he notices and says anything.

Thanks for the tutorial!


Stephanie, The Recipe Renovator
November 16, 2011 at 1:50 pm

Great story, great tips, and you look ah-may-zing! I too just went and splurged, asking for help from a saleswoman who actually knew jeans… she assured me that they looked good and weren’t too tight and they would stretch out… and by golly, she was right. And I feel great when I wear them! Just wish I could wear heels.
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November 16, 2011 at 1:11 pm

Never mind the jeans its those heels that caught my eye, they are pretty special
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November 16, 2011 at 8:25 pm

No doubt about it, the shoes are sweet. I L-O-V-E them. But at 5 1/4″ they are for sure the highest shoes I’ll ever wear.


November 16, 2011 at 6:29 am

Girl, you look fabulous daaarling! The shoes rock too!! :)
ps I like the new header.


November 15, 2011 at 9:42 pm

Can I just say that your butt looks really good in those jeans?

I agree that you get what you pay for most of the time. My most expensive pair of jeans (I paid $140 on sale) are still my favorites. Unfortunately (or maybe fortunately) they’re now my “fat” jeans, as they’re too big. One of these days I’ll splurge and get a smaller size.

I really enjoyed this post and I think you look fabulous. :)


November 15, 2011 at 9:38 pm

You. Look. Marvelous!! I showed this blog to my DH- Mr.’ jeans critic’ of the family- and announced (after answering his question as to WHY I was having him look at pictures of you in your skinny jeans, lol) that you are my new mentor. He approved, lol. You rock!


November 15, 2011 at 3:29 pm

I logged onto the big old home computer JUST so I could come check out your posts. ;-)
BTW – I really liked #4 on you. And I’ve never paid more than maybe $60 at the Gap for a pair of jeans. I do love Gap jeans…
Fun post!


November 15, 2011 at 8:21 pm

You most certainly can get wonderful jeans for much less than $175. I have before and I will again. My very favorite jeans in the world are a pair of Levis that I picked up at a JCPenneys several years ago. I’m going to cry when those jeans die.


Kristi R.
November 15, 2011 at 12:02 pm

It was interesting to see how many were wrinkly on the leg. The whole outfit looks great! So glad you found the shoes and pants that look good too.


November 15, 2011 at 2:34 pm

My thighs are proportionally bigger than my waist which means that pants that fit me around the waist tend to be too tight in the thigh. But if I get pants big enough for my thighs then they gap at the waist and give me plumber’s butt.

I just have to try on lots and lots of pants before I find a pair that fits.


November 15, 2011 at 6:11 pm

What about those of us with a FAT ASS? FAT STOMACH? Skinny legs? And how tall are you? As much as I love the look, at 5’9, I can’t wear stilettos. With my bad back, frankly, I can’t wear heels.

I do, however, appreciate the quest to smarten up one’s wardrobe and look. I’m actually moving away from denim (my lifelong love) and filling my closet with trousers. They look MUCH better on me.

Classic. Smart. Chic.

I’ll take it. :)
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November 15, 2011 at 8:20 pm

Having seen almost every episode of What Not to Wear over the years, and watching Stacy and Clinton dress every conceivable body type known to womankind, I believe there is a jean for everybody.

But I also like Express quite a bit. Editor pants have long inseams for you tall girls.


November 16, 2011 at 8:39 pm

I like Stacy and Clinton. They don’t demand everyone look like a fashion model.

Stacy definitely champions the…”try jeans on until you find a pair that fits”…..mantra.

I guess I’m seeing myself in business suits and trousers after graduate school. It’s a change for me.

You look good in the skinny jeans. I have two daughters who look FABULOUS in them (both of them are very tall and very lean). Mom, on the other hand, is no longer built for skinny jeans.
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November 15, 2011 at 9:33 am

And all I can come up with is a cat-call “DAMN. GIRL!” You look incredible.

Another helpful tip when jeans shopping: Wear support-type pantyhose. They’re slippery and they help the jeans to slide on and off more easily.
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November 15, 2011 at 9:35 am

That is a good idea!

Wear whatever underwear you are likely to be wearing under your jeans.


November 15, 2011 at 9:15 am

I didn’t get the luck you did, but I was ok with the jeans I got. And my husband thinks I am smokin in them.

I didn’t have saleslady so I had to get dressed after trying on 10. But I did stack 20 in a cart and left them at the entrance, so I didn’t have to go all the way out to the floor.

Once I went on a date with dh to the new shopping center; it had a Neiman Marcus. Wow, I had no idea what it was like for rich people to shop. I happened to be at my lowest weight since puberty, it was when my baby was about a year old. The sales lady tried desperately to fit me into a beautiful dress I tried on- it was gorgeous, but the smallest size she had was a 6 and it was too big. She tried to tell me she could get it altered for me- but it was knit in the round and had no seams. I was able to firmly tell her no thanks. Only after she finally left us (with drinks) for me to change back into my clothes did I glance at the price tag. Really? People spend over $600 on a knit dress???
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November 15, 2011 at 9:30 am

This is why it is good to take a trusted friend with you if possible. Salesladies have an agenda and can’t be trusted to be honest with you. If I’d had my druthers, I would have had my daughter with me. I can always trust her to tell me the absolute truth.

But a good salesperson knows her stock and a career salesperson, like Nicole, should be able to steer you in the right direction.

This is the most I’ve ever spent on a pair of jeans in my life. I’ve had theories about jeans’ shopping and I wanted to try them out. I also wanted to interview a professional salesclerk and get her input.

At the very beginning, I told her I was doing this article and wanted to pick her brain. I asked her, “How many pairs of jeans do you think a person should try on?”

Her answer?



November 15, 2011 at 6:21 am

Love the jeans, Chloe! You look smokin’ hot!


November 15, 2011 at 9:30 am

Thanks, Stacy.

These pictures take a little of the blow out of turning 50.


Susan in the Boonies
November 15, 2011 at 6:02 am

The last pictures look lovely! Great job, Rachel.

You look stunning in those jeans! Absolutely fabulous!

And I never buy anything these days unless when I try it on, it makes “me” look like I’ve come alive. And yes, sometimes I have to weed through a mountain of possibilities before I hit paydirt. Good shopping takes time, and dedication. Don’t settle.
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November 15, 2011 at 9:32 am

I want her camera!!!

She did a great job and we had a blast. (okay, I had a blast).

I do have the best daughter in the entire world.

I forgot to bring tromping shoes, so she had to help me totter down the nature trail until we found the place to take the pictures.


November 15, 2011 at 5:13 am

Love the top! Love the jeans! The shoes make my knees hurt just looking at them!

I might agree with you about the purpose of jeans “to make [my] butt look good” except that I have different jeans for different jobs. The painting jeans come up higher so passing children are not scarred by seeing painter crack (plumber’s crack?) etc.

Sometimes (just sometimes) jeans are to cover up the thighs and butt and knees so that I don’t get cold or get a ticket for indecent exposure. ;-)


November 15, 2011 at 9:23 am

I also have jeans to paint in and to wear to rake leaves, etc. But I never go out purposefully shopping for jeans like that. Those jeans tend to evolve out of the jeans, or other pants, I have that don’t fit properly anymore or have gotten stained or that are out of style.

When I go out shopping for jeans to wear out and about then it is all about the butt.


November 15, 2011 at 5:06 am

Yay for the last pair! Absolutely my favorite ones. Thank you, this was a very encouraging post, next time I won’t start crying in the changing room…
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November 15, 2011 at 9:33 am

Don’t cry, Anna!

I spent many years hating the dressing room and hating myself. It is so freeing to let that go.

If something doesn’t fit, take it off. That’s all.


November 17, 2011 at 6:01 am

I consider these jeans like a red sports car or an affair with one’s secretary: a symptom of my turning 50 and thumbing my nose at the world.

I’m excited to see where your endeavors take you, Mags. You’ve always been a huge inspiration to me.


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