Here's How to Style Your Boyfriend's Clothes With a Cool-Girl Twist

This year, much has been made about the debate on whether or not having a boyfriend is embarrassing. I am firmly in the camp that men are embarrassing, period. But I am open to the idea that boyfriend embarrassment can be circumstantial, and I would say that the humiliation can be reduced to almost non-existent if you manage to expand your own wardrobe by borrowing your boyfriend’s clothes.

Before I met my boyfriend, he was struggling to find his personal style. He dressed like most of the other men that he knew—all of whom never really worried about updating their outfit rotation. And that’s what the power of the patriarchy being on your side gets you––less stress and a healthier bank account.

Anyway, now that we have been together for the last two years, I have given him a makeover worthy of an Anne Hathaway montage. He wears prints and colors, albeit conservative ones, but he’s willing. He even scours the Real Real on his own! His fashion glow-up is one of my greatest achievements.

Yes, I helped him to elevate his style because I love clothing and I think dressing well helps you to show up more confidently in the world. But selfishly, I also benefit. When he acquires more clothes that I like, my closet concurrently grows. The pieces I have access to multiply. Living together helps, but even spending time with a partner who will occasionally leave things behind at your place is a great way to maximize your closet.

The easiest way to do this is with jackets, coats, sweaters and shirts. I like a lot of my clothing to be oversized so I don’t mind that my boyfriend is physically larger than me. However, fitting into his pants can be tricky. While I could theoretically wear his bottoms, the cut of menswear does not usually support having hips or junk in the trunk—both of which I have been abundantly blessed with.

In this month’s column, I’d like to show off the clothes I’ve stolen from my boyfriend, and how I’ve styled them.

I went to prep school, so I love a classic rugby shirt. This one from Noah NY is my boyfriend’s most colorful closet staple. He was very intimidated to wear it at first, but pairing it with neutral pieces—like green cargo pants and brown boots—makes it really digestible and easy. I added my tiny Louis Vuitton Speedy bag because I like the balance of something small and feminine while I am dipping my toes in the menswear pond.

While men’s jackets are typically roomier in the shoulders and arms, I don’t mind at all. In fact, I’m used to the oversized silhouette because most of my vintage blazers boast a similar construction. So, it should come as no surprise that my boyfriend’s Todd Snyder jacket found a place in my closet. Cut from Italian wool, this piece is super luxe.

To give the jacket some shape and dimension, I styled it with a mini skirt and a belt. Defined by a polished appeal, it’s a versatile outfit that can work for a range of occasions, whether I’m heading to a book signing or a dinner.

We got this shirt at Costco! Yes, you read that right. I can shop anywhere, I promise. For a similar alternative, I’d suggest the Banana Republic version included below. Pro tip: Banana Republic offers an affordable menswear selection that’s extremely stylish.

I paired this printed top with a sweater from Linder Sport, which is technically a menswear brand. This under-$100 style comes in several colors, and I love it so much that I bought two.

While you likely can’t tell, I’m wearing Uniqlo HeatTech under my look. I live in Wisconsin and temperatures have been below zero several times in the last week, so layering is essential.

To finish off the outfit, I added a pair of cozy pants and a Gucci bag.