Ladies, I need help! I feel like I used to know what to wear. I mean, it wasn’t too hard – throw on a pair of skinny jeans and a cute top and I was good to go. But now they’re telling me that my skinny jeans aren’t cool anymore, and there are so many new styles and lengths of jeans that it’s just all a little overwhelming. Plus, I work in a high school where dressing cool can gain me bonus points with the students, so I need to look good! 😉

I have slowly introduced a few new pairs of straight-leg and bootcut jeans into my wardrobe, but I still feel like I don’t have quite enough pants to keep me from running back to my skinnies.

I recently had a bunch of Gap/Old Navy rewards to use, and Old Navy was having a great sale, so I went crazy and bought 5 pairs of pants/jeans that are out of my comfort zone, with the intention of returning some. But now I need help deciding which ones to keep!

So I guess this post is like the opposite of what an influencer would do. I’m not an influencer, I’m an influencee. I need you guys to be my influencers and tell me which of these pants look good and which I should send back immediately!

Option 1: Olive Extra High-Waisted Wide-Leg Jeans

I do have another pair of beige wide leg jeans that my daughter convinced me to buy, and I’ve only worn them a few times because I feel like I’m trying to pass myself off as a teenager in them. I do get compliments from the teens when I wear them, but are 40-some-year-olds wearing these too?

Option 2: High-Waisted Wow Wide-Leg Jeans

Again, not used to the wide legs. Do they make me look stumpy?

Option 3: Extra High-Waisted Button-Fly Cut-off Straight Jeans

So these I actually ordered in a tall because I was afraid they would look too short, and they ended up being too long so I had to roll them. Does that look dumb? Should I try getting them in a regular? Or should I ditch them altogether?

Option 4: High-Waisted Wow Loose Jeans

Now it’s hard to tell in this picture, but these are on the shorter side. They hit just above my shoes. I know that’s the style now, but I can’t get it out of my 90’s brain that they’re not “high-waters.” I always had longer legs, so I’ve always struggled getting jeans long enough so they wouldn’t look dorky. So now that it’s the style, it’s taking me awhile to come on board.

Option 5: High-Waisted Pleated Chino Ankle Pants

I switched it up here with a beige top because I didn’t have any shoes that looked good with a black top and these pants. I thought my Nikes looked weird with these, and I don’t have any decent black shoes. What do we think about the pleats? I’ve always thought they were unflattering, but I know they’re making a comeback. And the length? These are ankle pants, so obviously they’re supposed to be shorter, but are they too short?

So please, ladies, influence me! Comment here or on my facebook post and let me know your thoughts! Be honest! I can take it. 😉