A Complete Guide On How To Buy And Wear The Jeans Of Your Dreams

I've never been a jean snob nor really gave much thought to length, comfort, and overall fit as I have always been more concerned about two things - price and price.

It wasn't until the past year or so when I started to find myself frustrated on how to actually wear the jeans I owned. Most of which were way too long, baggy in the places you didn't want them to be baggy and the only thing I wanted to wear were tall boots to cover the awkward "do I roll these up? do I roll them under? do I go naked and just forget about jeans all together??!" And don't even get me started on the option of getting them shortened or hemmed. Oh hail no, ain't nobody got time for that. Because hemming hasn't been an ideal option for me, I've had to really look at what makes up a great pair of jeans for me and my body type.

As I have gotten a little older, wiser and comfortable with what I feel and look good in, I've discovered some tips that have helped me buy the best jeans for me that fit perfectly, that I know how to style every time and that still fit within my budget. Today we're going to unravel all of those things. 

Let's start with the most important in my opinion - fit. For years I've turned to Target and Old Navy for jeans. While they were okay and definitely budget friendly, I wasn't ever confident in my sizing as it could range from sizes 0-9 which got to be slightly confusing. Within the past year I have started looking for brands that are sized by inches. By doing so I have been able to narrow down exactly what pant size I need 99.9% of the time. A HUGE help to me has been the Nordstrom True Fit Calculator. After filling out the questionnaire one time, it shows me what my recommended true fit would be for every pair of jeans that I am looking at on their website. Luckily, it hasn't failed me yet. One thing I have done before is I will order two sizes [my typical size is 26, however sometimes 27 fits just a tad better] and then get them, try them both on and return the one that doesn't fit how I like. Be sure to only do this when ordering from websites that offer free returns. 

Another recommendation I would suggest is to read both what the website says to be true about sizing but also what the reviews say from those who have purchased the jeans that you are interested in. This can be a huge help when people share their height, weight and what their thoughts were for how they fit and felt. Now, one of the most important things in regards to fit and length is this - the inseam. GET TO KNOW WHAT YOUR PREFERRED INSEAM IS! Your inseam is going to be different from mine, even though we may be the same height. It all has to do with the length of your legs and believe me, owning jeans that are way out of whack length wise will deter you from ever wearing them or feeling confident and comfortable in when you do wear them. Here is how you can figure out your preferred inseam: 

1. Get out your favorite pair of jeans that you own length wise and lay them out flat 
2. Measure from the bottom of the crotch seam down to the ankle seam
3. This number is your preferred inseam

Things to think about when it comes to inseam and length - you will most likely want to own jeans with different inseams. Currently, my favorite length of jeans are those with an inseam of 25-26 which hit above the ankle [for reference I am 5'4 and have average length legs]. I have found these to be the easiest pairs of jeans for me to wear as I can easily wear them with flats, heels, wedges, athletic shoes and ankle booties. While I love a rolled up look, I love not having to touch a thing even more. Because of this I try to locate jeans that have "ankle jeans" in the title. Here's a great example of above the ankle jeans and the different ways they can be worn. 

plaid top [size down one] // white tee [true to size] // jeans [true to size] // converse shoes
cardigan [true to size] // black tee [true to size] // jeans [true to size] // wedges // purse
black tee [true to size] // jeans [true to size] // black and white striped flats [true to size]

You will also want to own jeans with a longer inseam for times when you are wearing shoes with height. For me personally, jeans with an inseam of around 27-28 are perfect for heels. Anything 28 or higher for me is either going to be rolled up or rolled under. We'll get to that more in a second. 

When shopping online, you should be able to locate the inseam on the website. For example, look at this pair and click on Details + Care on the right hand side [under check store availability]. It is there where you will see what the inseam is. Start checking this number every time you are buying jeans to know if these will be a good option for you or not. 

Now that you hopefully know what your desired inseam is, here are a few pair of jeans for each range that I would suggest. 

24- 26 inch inseam 

27 inch inseam

28 inch inseam

29 inch inseam

30 inch inseam

31 inch inseam


33 inch + inseam

So what do you do if you already own jeans that are a little too long yet you don't want to have them shortened by a seamstress? Easy! You have two options - either cuff them up or roll them under. Two years ago I rolled everything under. These days I gravitate towards rolling them up. This is going to be a personal preference - if you prefer a cleaner look I would suggest folding under. When doing this try to keep the height right around your ankle bone as that is typically the most flattering point for your jeans to hit. Also be sure to of course make sure they are lined up evenly. I typically sit on the ground and put both legs out flat next to each other to compare the length and make sure they are even. Here's an example of jeans that I rolled under to keep a cleaner look. 

tank from stitch fix // jeans // sandals 

If you would like a little edgier look or the inside of your jeans have an seam worth showing off [this is something you should be mindful of when deciding between rolling up or folding under - for example, the jeans shown above have a very plain and clean inside seam so they wouldn't look right if I did cuff them up]. When deciding what you want your jeans to look like cuffed up, you have a couple of options - you can either keep to smaller rolls or folds [when doing this I typically roll twice] or do just one large cuff. Boyfriend or straight leg jeans are definitely more conducive to smaller cuffs while skinny jeans can typically look great with one larger cuff. Here's some examples of what I mean. 

One larger cuff: 
cardigan [size down one] // white tee [true to size] // jeans [true to size] // wedges
cargo jacket [size down one] // white tee [true to size] // jeans [true to size] // new balance shoes

Smaller Cuffs:
turtleneck sweater [true to size] // similar jeans // flats // purse
cardigan [true to size] // black tee [true to size] // similar jeans // michael kors slip ons

Now that we have your size and inseam figured out, lets talk style of jeans. Everybody is going to have a different preferred style for your body type. The most common styles are going to be skinny, boot-cut, flare, boyfriend and straight. To give you an idea of which is which, see below. 

cardigan [size down one] // white tee [true to size] // jeans [true to size] // booties [whiskey brow leather] 

pullover sweater [true to size] // similar jeans // heels // purse

turtleneck sweater [true to size] // similar jeans // flats // purse
turtleneck sweater [true to size] // similar jeans // heels 

                            cardigan [true to size] // black tee [true to size] // similar jeans // wedges 
                  cardigan [true to size] // black tee [true to size] // similar jeans // michael kors slip ons

top [true to size] // jeans // purse
cargo jacket [size down one]  // baseball tee [true to size] // jeans similar // booties

Here's a few tips for selecting your style and fit based on your body shape: 

+ Regardless of your shape, the stretchier the denim typically the more flattering. These are my favorite pair of denim that have a nice stretch with a butter-like feel. 

+ Pockets flatter your booty. The larger they are, typically the more flattering they can be. 

+ If you have shorter legs, try flared legs as they can elongate your legs - especially when paired with heels. Another popular style for petite people to wear is cropped jeans. 

+ If you are curvy, gravitate more towards a high rise jean. If you are more straight and narrow, stick to a mid or low rise jean. You may also want to consider looking for a more straight leg jean the curvier you are. 

Typically you won't figure out what you think looks best on you until you try them all. I have learned that my favorite styles that I feel best in are skinny and flare. Boyfriend and straight don't flatter my figure in the slightest and boot-cut are hard for me to pair with shoes. 

Moving on - denim wash. This will also be a personal preference, however I would recommend darker washes for figure flattering purposes. Lighter washes typically look a little edgier to me while darker washes have a more classic refined look. I would recommend having medium to dark washes for the majority of your jeans [I think you will find these are most versatile], one or two pair of a light wash jean, one or two pair of black denim as it's a staple all winter long and one or two pair of white jeans that will last all spring and summer long. One thing you may want to avoid is an overly blue denim wash. The bluer the wash the harder it is to pair with tops. At least that's been my discovery. 

Phew - there we have it friends. Any questions drop them below in the comments or ask em' over on my facebook page. I'd love to hear any suggestions you may have! Cheers to our legs lookin' good ladies! 



  1. Excellent guide. Great tips on inseam, length and style.

  2. Love this! Thank you! I've been an Old Navy Jean girl for as long as I can remember.. it's always hit or miss. I'm going to try the Nordstrom fit calculator to help me really find my correct size. Now Im sure I will regret passing up those denim deals during the anniversary sale.. haha. But I did enough damage anyway. :)

  3. Great tips hun! Finding jeans is such a nightmare! x

  4. Fabulous work!
    P.S Can you please follow me back?
    Blog: www.glaringwaves.blogspot.ba
    Facebook: www.facebook.com/glaringwaves

  5. Love your blog and this post! Do you mind sharing the paint color on your walls? It's exactly what I've been looking for!

  6. Shopping for jeans is as awful as shopping for a bathing suit!!! Thank you for this guide. I'll definitely be using it soon.

  7. Thank you for this post! It's life changing for me! So helpful. Do you pin your jeans when you roll them?


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