4 Ways to Style Boyfriend Blazers for the Win

Blazers have been a favorite of mine ever since watching “What Not to Wear”. Of course, it didn’t hurt that as a dentist, I felt more professional in this item. Yet when I retired, I did what many retired people do, and gave away much of my workwear.

Fast forward to starting this blog and realizing that our clothing is MUCH MORE versatile than we think. Too often, we categorize a clothing item, and that creates a roadblock to styling it.

I used to do this (and maybe you do too)

1-Call an item dressy or casual

2-Refer to it as workwear or weekend wear

3-Put shirts in my workout drawer yet they could be worn as normal shirts

I’m sure there are more, but the key is to stop labeling our clothing, and just wear it!

Here are 3 ways to wear the bigger blazers, and there's another different option on my site.

How to Style a Boyfriend Blazer

Now the rule of thought with how to style a boyfriend blazer would be to make sure the clothing you are wearing it with is fitted. This goes with the rule that if one part of your outfit has volume then the other part is streamlined so you aren’t overwhelmed with your clothes.

And it’s a good guideline, but I want us to start realizing that sometimes rules are meant to be broken. There are times when wearing 2 voluminous pieces can look great. I experimented with that concept when wearing a pair of culottes.

Insider tip: So no matter what fashion rule you hear, read, or think about, always remember that there are exceptions to the rules. Or in your mind start calling them guidelines instead.

The 3 of us came to this idea of how to style boyfriend blazers by pairing them with a dress, a skort, wide jeans, and shorts. That doesn’t mean there aren’t many other ways to style them. Wear them with any style of jeans, with skirts and even with pants.

How to style a boyfriend blazer with wide jeans

Jodie-Wide Jeans and Oversized Blazer

Jeans: Molly Bracken~~ Blazer: Ann Taylor-preloved~~Vest: LOFT~~ Bralette: Belong Lifestyle~~ Shoes: Rag & Co- DSW~~ Scarf: Vera-thrifted~~ Purse: from Bealls

This example is breaking the guideline of loose with loose since the boyfriend blazer is oversized and so are the jeans. Yet I did keep the pieces under the blazer more form-fitting.

I purchased these jeans many years ago. They are the brand Molly Bracken which I liken to Betsey Johnson’s style but not always as colorful or whimsical. These jeans are probably my first pair of wide-leg jeans and they were included in how-to wear that silhouette of pants many years ago.

This blazer was handed down to me by my bestie when she passed away. I wore it a lot during my working career, and I kept it because I liked having the longer style to wear as a coat, especially with dresses. Even though I don’t wear black much anymore, it can be lightened up with other items.

The vest is also from my working days and I paired it with a bralette. I used the green of the scarf and the green in the shoes to bookend each other.

If you don’t want to wear a bralette, a camisole or Halftee is another option. See Halftee styles here and use code Jtouch20.

Dress: AGB Dress-thrifted~~ Blazer: Fashion Bug-preloved~~ Shoes: no label~~ Earrings: Happiness Boutique c/o~~ Purse: made from chewing gum wrappers-thrifted

Charlotte Wearing a Dress with her Boyfriend Blazer

Charlotte recently found this boyfriend blazer at a garage sale in the neighborhood. It’s such a perfect color for the summer and pairs well with her fair complexion.

For our assignment on how to style a boyfriend blazer, she paired it with a floral dress.

I think a blazer (both oversized like a boyfriend one or even a shorter one) is a wonderful option for any dress that needs a layer. You don’t always need to grab a coat from the coat closet.

Boyfriend blazer and colorful dress

We were talking about this dress because it’s a thinner, silk material and my mom doesn’t usually wear her skirts this short. But I was so impressed that she was comfortable wearing it this day since she has wonderful legs.

And while most of the younger generation doesn’t wear half-slips anymore, my mom was commenting that she did wear one with this dress.

This is a great example of how the proportions work wonderfully with the length of the dress. The blazer is 2/3 of the area of clothing, while the dress only shows 1/3 making it an ideal proportion.

Insider tip: Remember that even proportions are a guideline. I don’t follow them all of the time, but if something seems wonky with an outfit, consider changing the proportions and see if it’s better.

Related post: Comparing side-by-side examples of different proportions for outfits

Skort: Croft & Barrow-Kohls ~~ Blazer: Pretty Garden- thrifted~~ Top: Chicos ~~ Shoes: Coasters- Payless~~ Necklaces: 1-Stein Mart & 2-thrifted~~ Bracelet: thrifted ~~ Purse: no label

Lesley-How to Style a Boyfriend Blazer with a Skort

Lesley calls this an “Arizona suit” with a skort instead of a skirt or slacks. She says: “It’s sorta professional but remove the blazer and jewelry and it can hike or play pickleball, although I’d switch to sneakers in that case.

This outfit would work for a business, church presentation, or medical appointment. For date night, you could easily change out the t-shirt to a cami and the wedges to heels for dinner or a matinee at the theater.”

Match your boyfriend blazer to a skort for a suit look

Red is a fabulous color for Lesley and maybe you’ll notice if you look closely that the blazer and skorts are not exactly the same shade of red. It’s very darn close, and definitely a good pairing.

And instead of just wearing a neutral color t-shirt under the jacket, Lesley wore a yellow one. Color combinations are the easiest way to change up a look.

How to style boyfriend blazers for older women

Now make sure to head over to my site to see the 4th way of styling a boyfriend blazer along with a ton more photos.

How to style a boyfriend blazer for grown women

Photo credit: Rob Filogomo

Thank you

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Jodie Filogomo
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