How To Wear: 4 Different Types of Jeans

How to Wear: 4 Different Types of Jeans

I had a request to write a Fashion Friday post about what to wear with different types of jeans.

I’m always up for a challenge, so I’ll tackle this one, but I have to make one caveat. Every body is different — not everybody, although everybody IS different. But every BODY is different too!

So what might work for me might not work for you. Styling an outfit is all about creating the illusion of proper proportion, and we all have to experiment a bit to figure out what works best for us. But. There are some general rules of thumb to keep in mind, and I’ll share those with you. If you know the rules, then you can break them, right? Well, at least the fashion rules. Don’t you all go out now and hold up the Apple store at gunpoint.


Let’s give it a shot.


Skinny jeans are pretty popular right now, although they’re not the best look for everyone. I do think most women can pull them off, but it does require a little more effort than a basic straight leg or boot cut. We used to say to pair skinny jeans with a voluminous top or tunic. But these days, skinnies really can be work with any style of top. It just depends on the look you’re going for, AND your body type. So if you are pretty evenly proportioned, you can wear a fitted top, a loose top, long top, short top, blouse, sweater or tee with your skinnies. Really, anything goes, you lucky duck.

skinny jeans with blouse and cardi

If you carry your weight in your hips and legs, you want to wear a longer top that glides over your hips to create a more even proportion.

skinny jeans with blousy top

Shoes are also a big factor here. If you carry your weight on your top half, you might want a chunkier shoe or boot to balance out the top and bottom of your silhouette. If you love ballet flats, try rolling the skinny jeans to create balance. This is a great article on how to properly roll your jeans.

Boot-Cut Jeans or Straight Leg Jeans

There’s often not a big difference between boot-cut jeans and straight-cut jeans these days. Both tend to be more forgiving than skinnies and can be dressed up or down depending on the occasion. I don’t care for voluminous tops with boot-cut jeans. I think they look better with fitted tops. If you are bottom heavy, go for a top with squared-off shoulders or ruffles to create balance. If you’re top heavy, wear tops that are fitted through the waist, and make sure they aren’t too short. Here are a few looks that work.

jeans with cardi

In this case, I would tuck the front of the blouse in or it could look frumpy.

straight leg jeans with heels

Loving this longer fitted sweater with bootcut jeans. The bulk of the cowl neck helps balance out the wider leg.

bootcut jeans with fitted cowl neck sweater

Trouser Jeans

I still consider trouser jeans a dressy/office look. Because they’re so wide at the bottom, I feel they need some structure on top. Try a fitted blazer or form-fitting blouse. Heels are always a good idea with trouser jeans; they elongate the leg and make you appear taller and slimmer.

How to wear trouser jeans


Boyfriend Jeans

Then there’s the boyfriend jean. This style takes some panache to pull off well. I encourage you to peruse Pinterest for ideas and make your own look. Generally boyfriend jeans tend to look best with tops that are tucked in but not too tidy. A feminine blouse helps them not look too sloppy, and heels are often shown with boyfriend jeans, but I think they’re too fussy for most of us. I’d probably pair them with ballet flats, or if I went for a more casual top, they’re cute with a pair of Converse sneakers.

boyfriend jeans


What is your favorite type of jeans? And what’s your best tip for styling them to be flattering for your body type?

Also, if you’re looking for help building your wardrobe, I highly recommend Trunk Club, a personal shopping service by Nordstrom.

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17 Responses

  1. “Styling an outfit is all about creating the illusion of proper proportion, and we all have to experiment a bit to figure out what works best for us. ” I don’t know why this hit me this morning because I think I subconsciously knew it but it really made sense to me today! Also, I’m definitely not cool enough for either the trouser jeans or boyfriend jeans but I wear the mess out of the other styles all winter!

  2. I love the cowl neck sweater. Very well proportioned. I have to again say how helpful your Fashion Friday posts are. I really have used almost all your advice over the last few years and feel much more “put together.” Thank you!

  3. OK….I have heard of boyfriend jeans…..but don’t know what they are. Are they loose all over? What body type do they best fit….or is that in your post and I missed it? I am a pear shape and unfortunately skinny jeans don’t work for me unless I wear my boots…..helps my drumstick legs (aka skinny calves look more proportioned).

  4. Oh, well, my closet doesn’t seem to fit any of those…it’s full of “mom jeans” as my kids put it…lol! Love checking out the styles and getting ideas, for whenever I get to finally update the wardrobe =)

  5. You’ve done it again….Terrific post…thanks for educating me! Now I feel like I could actually have a successful shopping trip.

  6. I’m going to put in another vote for an actual definition of a boyfriend jean please. I’m not sure I really know what they are either. What makes it different than a straight leg jean?

  7. Love this! Great advice! I get nervous about wearing flats with trouser jeans because I’m so short..what are your thoughts? I tend to shy away from the 1 pair I own because its so hard wearing heels in NYC!

  8. I bought some narrow calf ones at New York a few years ago by a company named Slimcalf boot. I love them because I can adjust so they always look nice whether wearing over tights or thick jeans.

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