Boyfriend jeans have become mainstream and I am thrilled about it. We desperately needed a basic jeans silhouette with a roomier fit. Over the years, skinnies have become tighter and tighter as denim fabric became stretchier and stretchier. Straight legs and bootcuts are still tight, but not overly so. And wide legs remain a fringe look. Boyfriend jeans give us a wider denim assortment, and that’s how it should be. 

We are living in an age of casualization where descriptions like “casual chic” and “easy elegance” and “relaxed polish” make complete sense. The juxtaposition of opposites is one of the directions in fashion and this in itself is liberating and creative. For example, mix ultra casual pieces with dressier ones. Luxurious fabrications with distressed textures. And looser fits with tailored items. 

So here is an ensemble formula that begins with a casual pair of boyfriend jeans, matches them with easy tops, structured toppers, and allows the footwear to give the outfit its personality.

The components of the ensemble:

Boyfriend Jeans

Remember that boyfriend jeans needn’t be extra baggy and slouchy. Find a bagginess threshold, waistline, wash and length that suits you. Roll the hems or wear them unrolled. 


I’ve chosen soft tops like a basic blouse and pullover with an inset printed silk panel, both of which are roomy to create a relaxed vibe. Comfortable and forgiving. Layering tees and button-down shirts are other options. Wear them tucked or un-tucked. 


I’ve kept the toppers structured and dressy to create a sophisticated juxtaposition against the casual jeans and relaxed tops. Think leather jackets, blazers, military looks and Chanel-esque jackets. Or any jacket that is at least semi-structured. 


I’ve shown 11 on trend options here, some dressy and some casual. Each style of shoe can be worn with any combination of jeans, top and topper depending on your style preferences and the dress code of the setting. Pattern mix or stick to solids. Add colour or stay neutral. Here are your footwear options to wear with rolled or unrolled boyfriend jeans: 

  1. Casual Booties
  2. Mid-Calf Flat Boots
  3. Slipper Flats
  4. Pointy Toe Pumps
  5. Pointy Toe Pumps with Ankle Straps
  6. Low Heeled Pointy Toe Pumps
  7. Flat Oxfords
  8. Peep Toe Booties
  9. Converse Sneakers
  10. Wedge Sneakers

Finishing Touches

If you tuck your top, by all means wear a belt. I’ve chosen a clutch, but your bag choice is whatever floats your boat. Add jewelry as desired. 

As with all the formulas, I sow the seed of an idea. The next step is to substitute the items so that they work for YOUR style. After all, fashion is what we buy, but style is how we wear it.