We have to credit Katie Holmes with the start of this trend. This summer, she was seen on the sidewalks of NYC wearing ‘boyfriend jeans’ not once, not twice, not even a few times…they were just about all she wore. To give her credit, she did attempt the look in many different ways: button up shirts, tight shirts, loose shirts. I’ve seen those photos time and again and I just can’t bring myself to like or even appreciate the style. Please understand, I’m not a Katie (or Tom) hater. I actually think Katie Holmes is quite fashion savvy. I usually like her style. But, this look was just all wrong for her. It left me thinking that I didn’t like the boyfriend jean at all.

But then, I saw a few others pull off the look:

I like the “I’m dressed casually, but I’m still trendy” vibe from these ladies. It’s still a bit feminine and sexy in a subdued way. What do they do differently that makes the look work?

How to Wear Boyfriend Jeans

1. Make sure they fit. Katie was actually wearing a pair of Tom’s jeans. This is a bad idea for obvious reasons. Find a pair that fits you through the waist and hips. You shouldn’t have to fold the jeans over with a belt to make them fit your body.
2. Wear a belt. Choose the widest belt you can that will still fit through your pant loops. Not only will this help keep your britches up as they stretch out through the day, it’s also a great accessory to match the oversized look of the jeans.
3. Wear flats. Flats are a necessity for this look. Ballet flats can work if they’re not too cutesy. The best shoes to pair with boyfriend jeans are Converse-style shoes or strappy sandals.
4. Cuff. Cuffing your jeans is kind of the epitomy of the style. Just make sure your cuffs are even. This style looks a lot better when you have jeans that don’t require you to fold the denim over before you roll them (another problem with Katie’s look).
5. Wear appropriate tops. Matching boyfriend jeans with a silky halter just won’t do. Keep the style simple with a fitted tee, a button-down shirt, a cardigan, or a small-knit sweater.

Designer Boyfriend Jeans

Shown: Current Elliott ($226), True Religion ($147)

Affordable Boyfriend Jeans

Shown: Studio Boyfriend Jean ($39), Gap Curvy Trouser Jean ($49.99), American Eagle ($49.50)

Other Ideas

Try Vintage Stores for this style. You’ll probably have no trouble find pairs of straight leg jeans (think Levi’s 501 jeans) that will fit the criteria. Just make sure they fit! Going one size larger is okay, but remember the #1 piece of advice from above!
Before you go out and buy a pair, make sure you are down with the style. I have a baggy-ish pair of Citizens that I cuffed and wore as ‘boyfriend jean’ the other day. They worked and made me a little closer to buying a pair that’s a little closer to the trend. I definitely am going to go for the cheap or vintage version, though!

So, What Do You Think?

Are you a fan of boyfriend jeans? Did you like Katie Holmes’s look? Are boyfriend jeans ‘trendy or tacky’?
Leave your thoughts in the Comments.