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

November 1, 2017


Erin Schrader

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 altogether??!” 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, especially when shopping online. Within the past year, I have started looking for brands that are sized by inches or that offer “short” as an option. 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 absolute favorite in the denim department recently? American Eagle. Their jeans are literally nearly ALL I wear anymore! They hold their shape, don’t stretch out, are super comfortable and I love that they come in short, regular, long and x-long! So many readers have purchased these and swear by them as well. I find their jeans to run true to size the majority of the time, but do recommend sizing up if you go between sizes.
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 feel Now, one of the most important things in regards to the fit and the 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 lengthwise 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 lengthwise 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 or that come in “short”.  Here’s a great example of different ways that ankle jeans can be worn.
BP sweater [size down, wearing in XS] // wine leggings [size up! wearing in short] // white tee [size down, wearing in XS] // AE Jeggings [size up if in between, wearing in short] // Military vest [size down, wearing in XS petite] // Striped tee [true to size, wearing in small] // black jeans [true to size] // converse [true to size] // lace-up sweater [true to size, wearing in small] // Patched jeans [true to size, wearing in short] // booties
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.
suede jacket [true to size] // black cami [true to size] // black coated skinny jeans [true to size] // black heels [true to size] // striped button up top [true to size, wearing in small] // vest [true to size, wearing in small]] // AE jeans [true to size, wearing in short] // black choker top [true to size] // similar grey jeans [true to size] // pink heels [true to size] // crossbody bag
When shopping online, you should be able to locate the inseam on the website. For example, look at this pair and located under Details + Care on the left-hand side [under the photos]. It is there where you will see what the inseam is [for example, the pair you clicked on should show 28 1/2″]. At American Eagle you can find the inseams by clicking on the size chart right above where you would select your size. To help you out, just note that their inseams run as follows: Short [27 inches], Regular [29 inches], Long [31 inches] and X-Long [33 inches]. Start checking this number every time you are buying jeans to know if these will be a good option for you or not.
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 a 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 are some examples of what I mean.
 One larger cuff:cardigan [true to size] // white cami [true to size] // jeans [true to size] // black tank sold out // distressed jeans [size up] // pink sandals [size up .5] // clutch // off the shoulder sweater [true to size] // jeans [size down] // booties [true to size]
Smaller Cuffs:
scarf // jeans [true to size] // booties [true to size] // turtleneck tunic [true to size] // similar jeans // calf hair flats [true to size]
Now that we have your size and inseam figured out, let’s 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.
Skinny [easiest to wear with booties and boots]:Sweater [true to size, wearing in small] // Jeans [true to size, love the small distressing] // Boots [size down for half sizes] // Sweater [size down if in between, wearing in XS] // Jeans [true to size] // Boots [true to size] // Necklace // White Cardigan [size down if in between] // Purple tank [size down] // Patched jeans [true to size, wearing in short] // booties
 Bootcut/Flare [great with heels or wedges!]:
similar cardigan // jeans [size down] // booties [size down half]
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 

29-inch inseam

30-inch inseam

31-inch inseam  

33-inch + inseam

Here’ area 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 but don’t stretch out.
+ 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 pairs 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 [and booties] lookin’ good ladies!

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