This title may be a bit ambitious, but my sweet (and fashionable) sister, Kara asked me to do a post on what tops to wear with different styles of jeans. So, after doing a ton of research, here are my findings. Hint: grab a cup of coffee… this is going to be a LONG post!
I’m going to start with wide leg jeans- since 1. that is what I’m wearing today 2. they are totally back in style 3. you may be wondering what the heck to wear with them.
I’ve worn these once before, paired with a cute striped top as seen here. Today, I’m pairing them with a black camisole and a VERY old blazer. Seriously, I think my 17 year old was an infant when I bought this at White House, Black Market. But, after all these years I still love it. It has that classic, Chanel inspired look that will never go out of style.
In my before photo, I paired it with a blouse that is oversize and a jacket that was too baggy for this style of jeans and clunky boots. The trick with wide leg jeans is balance. Since you are big on bottom, keep the top somewhat fitted or simple. My cropped jacket doesn’t overwhelm the pants. You don’t want to look like this photo below. While she looks comfy, it’s also a messy look.
I would say with wide leg jeans or pants, do not wear peplum, tunics or oversize tops. Unless you are super skinny, avoid long jackets. Stick to slim tops, or a fitted blouse. Off the shoulder top is popular with wide pants. Or a striped sailor shirt with boatneck collar would be cute. Try a tank or plain fitted v neck shirt (like I did today). Shoes really matter here- think heels, pointy toe or very minimal tennis shoes like Converse or Superga. Below are some inspiration outfits for you to consider.
Now let’s talk about skinny jeans- since you all know they are my favorite! One of the nice things about skinny jeans is you can basically wear anything with them! They are so versatile.
An oversize sweater (or tunic), skinny jeans and booties is a great, casual look! Jackets and blazers over a tank or camisole look cute with skinny jeans. A long cardigan over t shirt works, or consider a statement blouse or button down shirt. Be sure to add a skinny belt. Another option is a boxy blouse to create a little shape on top. As for shoes, try neutral sandals, or pointy toed heels look gorgeous. Ballet shoes work as well. For a more casual look, wear simple tennis shoes. Below are some inspiration outfits I found on Pinterest.
Moving on to cropped jeans! Cropped jeans can be a skinny cut, a wide leg cut, or a straight leg. As with skinny jeans, any top works with cropped. Cropped straight leg cut is a good alternative to the skinny- they are still dressy, but better for many figures.With cropped jeans, it’s all about the shoes! Ankle boots, flat sandals, tennis shoes, ballet flats, pointy heels. Anything goes!
Boyfriend jeans are a must have for most fashionistas (although truthfully, I’m still trying to find some that I love). Boyfriend jeans are usually really faded, distressed with holes at the knees. They fit somewhat baggy, but have a straight leg. They are often rolled at the cuff. For date night, pair with a super feminine top and heels. Otherwise, pair with t shirt or fitted sweater and tennis shoes or ballet flats. Try a crew neck sweater and loafers. A graphic t and blazer would be a super cute outfit. Below are some inspiration photos:
Making it’s way back into style is the bootleg cut. I do not own bootleg jeans, but now think I may need to get some! They are a great jean for a curvy figure. With bootleg jeans, try an off the shoulder top, or something somewhat fitted. One rule with bootleg is always wear heels, boots or wedges! No flats! For an edgy look, try a graphic t shirt and a bohemian cardigan. Or for a classic look, a button down blouse tucked in with a wide belt. Add a cropped jacket to show off your waist. Or maybe a flowy blouse- but not too flowy (no Seinfield references!) Remember, the jeans are the main attraction in this case. The top should be understated and not compete with jeans. No oversize sweater!
One of the things I noticed in my research is that you can wear basically anything with jeans! There aren’t any rules- just go with what you think feels and looks right. But try to think about proportions, big on bottom = small on top and vice versa. Remember, darker denim is dressier, so for a casual look- for for a washed or faded color. For evening out, go for a dark wash or black jeans. And in my opinion, white jeans are in style year round.
That’s all I’ve got for you today. I’ve got to get to work (teaching 4th grade today)! Wish me luck… and please comment with your favorite style of jeans and what you like to pair them with.
Everyday Mom Style 
Thank you Megan! I love seeing all of these options and inspirations. So helpful and just what I needed as inspiration for Spring!! You look adorable today. I bought that same jacket with you and still have it too!! LOL
You’re the best!! Love and miss you!
your little sis
xoxo
Love you so much! And please know you are my inspiration- you are the most stylish person I know! 🙂
Great post. Now I’m all ready to go out jeans shopping!