So, it’s denim season. 
 While I’m as basic as they come about all things Fall, the thought of squeezing back into a pair of last year’s jeans – or worse, actually braving the mall to go jean shopping – makes me feel a bit queasy. 
 As we all know, I pretended to be a fashion blogger a few weeks ago and I knew I wanted a pair of distressed black skinny jeans for one of my looks. Sigh. 
Time to pull on my Spanx and hit the fitting room.
And because I love you all so much, I thought it would be super fun to snap terrible fitting room selfies and share the process with you, if only so that you can avoid the terrible lighting and potentially soul crushing adventure that is jean shopping.
With that pep talk under our belts, let’s begin.
Here’s how I approach the nightmare that is the hunt for the perfect pair of jeans:
I invest my time, effort and cash in one or two pairs of staple, high end denim.
Mid-rise, dark wash, no whiskering or fading, straight leg, slim ankle. 
Season-less, timeless and worth a bit more cash so you score a quality that will last.
My absolute favorite pair is the Hudson Nico Midrise Super Skinny jean. I’ve owned the same pair for three years plus and love them. They will always be flattering and will never go out of style, making the cost worth it for me.

 photo originally published 4.3.15

Once I have my base pair stashed safely away in my closet, I choose to buy trendy styles in a (much) friendlier price point. Old Navy, Target and American Eagle are my go to’s for anything boyfriend, ripped, faded, tapered, flared, jeggings or in a unique color. And let’s be real – I don’t want to spend a ton of time tripping over myself in a poorly lit fitting room or being bothered by a pre-teen sales girl, so my strategy is to blow into the store, grab anything in a wash and rise that I think might be remotely flattering on me (so nothing low rise, no one at Mother’s Morning Out needs to see my lower back tat) and hit the fitting rooms.

My latest run was to Old Navy in the hopes of scoring a new pair of slimmer fit boyfriend jeans and the aforementioned pair of distressed black denim.

I spent approximately 45 minutes in the store (including the longest line ever at check out), tried on 7 different pairs and walked out with one (and should have purchased another).

And, in the name of keeping things real, I’m showing my true sizes so you can get an idea of how one of these looks may work on you, if you are as blessed in the butt department as I am.

ready??

First up, the boyfriend skinny ankle
on the model:
On me:

I really wanted to like these but I thought they were just too loose in the back, making them look dumpy and not even remotely put together with my tee and flats (which is how I would wear/style them in real life). Also, something was happening in the crotch area that was bordering on not flattering.

Hoping I could keep the look of the boyfriend cut and lose some of the bulk, I sized down to a 10. Sadly, I lost enough length that I thought the jeans looked cropped and not just cuffed.


the butt is better though.

 
Ultimately, I wanted the length of the 12 but the tighter fit in the rear of the 10 so I had to pass. 
I did give the same fit another try in the distressed wash and the crotch issue only got worse! 
Boy Friend Skinny Ankle Distressed
(on crazy sale for $18.50)
On the Model:
 On me:
I can’t take my eyes away from the issue.
Buzz, your girlfriend. Woof.
Sadly, I really do think this is a great pair of denim and at $18, I honestly wish
they fit me better. I would rock these way too much. Obviously, I didn’t
purchase. 
 Basically, I’ll try on any pair of boyfriend because I think they can be a bit tricky to find the perfect blend of comfy/loose but not baggy/frumpy and you never know when you’ll get lucky. I hit up the Boyfriend Straight in a super light wash with a distressed knee and thought they were comfy but really similar to my Target pair. 
On the model:
On me:
Yet again, I have some sort of crotch issue happening, which I’m choosing to
blame on extra material and not some sort of physical deformity that I’m
just now noticing. 
The wash
was probably just a bit light for my liking (bordering on ’90’s) but if I
didn’t already own a similar pair, I would have sought out a slightly darker wash and given them a try, but alas, it just wasn’t worth it for a pair that looked so similar (and less flattering) than I pair I already own. 
In case you haven’t heard (from every style blogger on Instagram, over and over again) Boot Cut is back! If you find the right fit, the boot cut can elongate the leg and slim the thigh and nobody can be mad about that. I think I still have a great pair of flares laying around from a few years back but to avoid the humiliation of trying to get into them, I tried on a dark wash pair of the Curvy Bootcut Mid Rise .
on the model:
on me:

I was really torn over this pair. I thought the wash was great and the length was perfect for heels but something about this cut just wasn’t right in my hip area. In fact, I think my hips look completely different in the top left and bottom left photos, which made my decision process even more confusing. I will say that I found these incredibly flattering in the butt. In all honesty, this may have been worth trying on with heels but I rarely wear heels in my real life so I decided to pass. If you have a big butt (like yours truly), these will fit you so well. My tummy felt pulled in and my butt was rounded and smooth – if only that hip area had worked out, I would have pulled the trigger on these.
The pair I was really hoping would be a win were the Rockstar Mid-Rise Super Skinny Distressed 
in black/stow away.
on model:
On me:
These came home with me but I made one crucial error. And I know better. I decided to round up and purchase the size 12. Huge mistake. Old Navy denim is a great price point but you get what you pay for and, in my experience, ON jeans stretch out like crazy while you’re wearing them. The 10 felt just a teeny bit snug but I should have grabbed those, knowing that I wanted the black skinnies to have more of a streamlined look.Overall, I love the length (I cuff them with booties) and the price makes me happy. If this look is out next year, then I know I will have worn them enough to justify their price point by the end of this season.
So, it turns out that the last pair that I grabbed, The Diva Skinny, are no longer available online, which is sad because they look great on and I should have bought them.
Originally Skinny Jeans 

If you took a peek at the tag, you’ll notice these are actually short in length. Yes, I’m 5’9″ but sometimes I’ll try on a short so that I can wear them with flats. They hit me right at or just the teeniest bit above the ankle and I’m a fan. This pair turned out to be super slimming and comfy – I didn’t buy because they actually look a lot like my investment pair but if you see these in your store, size up and try them on. 
Ok, there it is. My rapid fire, totally un-styled, terribly photographed attempt to find a pair or two of trendy jeans for fall.  If I can do it, you can too. Now go forth and order online, since I did all of the dirty work for you!
and p.s. while this is in no way a sponsored post, affiliate links are used.