5 Ways to Wear a Vest (aka Waistcoat)

Midlife women wearing menswear inspired vest and boot cut jeans.

This fall, many of the trends are holdovers from last year, which is reasonable considering we barely had a chance to wear any of them. So keep wearing your shackets, lug sole boots, and wide-leg denim. Late last year, the sweater vest grew in popularity, and this year it is a strong trend for fall. The trend evolved to include menswear vests or waistcoats, and I am here for it.

There is something very empowering about donning a menswear look. Women turned to pants during the suffrage movement, and we have never looked back. As recently as the early 1960s, women were chastised for wearing pants despite adopting them during WW2 while working in factories. The late 60s and 70s freed us of many societal fashion norms, and women began to experiment with other menswear looks. By the 80s, menswear style was trendy, and women wore power suits, vests, and trousers as staples in their wardrobes. Now vests are back in a big way.

Each time the vest or waistcoat trend comes around, I hop on. Vests are an easy fashion item to add to your existing style.  So when the trend popped up recently, I went on the hunt for the perfect vest. My goal was to find a vest that could work alone as a top or with all my favorite pieces. This time around, the vest had to be long enough that my belly would not show.

Right now all types of waistcoats are popular. There are double-breasted vests both long and short, a traditional suit vest like I am featuring in this article, and cropped versions of both. I generally stay away from anything double-breasted. It adds unnecessary bulk whether buttoned or hanging loose.  The long vests remind me of the early 90s and I just can’t do them again. Those were some rough years for me.  I prefer to stick with the classic menswear vest that will stand the test of time.

The Perfect Vest

After several unsuccessful attempts, I found the perfect vest for midlife women. The Anthropologie Menswear Vest is perfect. The vest is 23″ long and made of polyester. It is not stiff, and the drape is lovely. This vest works both opened or closed. I am wearing a size medium. A vest should fit snugly but consider how you will wear it. This vest has enough room to add another layer underneath.

Despite my picture below, a vest should be worn with the last button open. Apparently, buttoning the last button makes you look like a rube or country bumpkin, just in case you weren’t familiar with the rube term like I was. These are fashion rules primarily for men’s suiting, so apply them or not. When I wore this outfit out, I found it easier to sit with the bottom button undone. So despite not being a slave to fashion rules, I am nothing if not practical, and the bottom button rule appears to be born of practicality.

The vest is available in black and navy blue. When I set out on my search for a vest, I wanted a tan or white vest, but despite finding some great color options at Aritzia, the vests showed half my belly. So I opted for black, which is my go-to color for most items.

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Women wearing a menswear inspired vest

Menswear Inspired Vest Outfits

Outfit #1: Vest + Blazer + Bermuda Shorts + Slides

With the little bit of summer we have left, I wore this outfit out to lunch with my friends. I love the contrast of a tailored vest with distressed shorts. The shorts offer a bit of irreverence to the more structured vest. The shorts I’m wearing are the Frame Le Slouch Ripped High Waist Bermuda Short. Honestly, they aren’t that high-waisted with an 11″ front rise. These days an 11-inch rise feels downright mid-rise. My happy place is a 9 or 9.5 in mid-rise, but they are all but impossible to find.

My slides are by Vince Camuto and are the perfect way to get in on the woven leather trend without breaking the bank. At just under $100, these slides look far more expensive and are incredibly comfortable. In addition, they look great with shorts, trousers, and dresses.

Midlife women wearing a means wear vest, blazer and shorts

Outfit #2: Vest + Button Up Shirt + Joggers + Loafers

I’m feeling a bit like Annie Hall in this outfit, honestly. All I need is a hat and tie. By keeping it simple, the outfit looks less like a costume and more casual. Am I the only one who is sick of hats due to so many influencers wearing them all the time wrong? No? Just me. I may spend too much time on social media.

If you are looking for the perfect white button-up shirt, check out the Madewell Drapey Oversized Boyfriend Shirt. This shirt is cotton and Tencel, making it structured but not stiff. The fabric is not see-through, which is hard to find these days. My pants are the rag & bone Engineered Joggers. I love these pants. The joggers have an elastic waistband in the back but a five-pocket silhouette in the front. They are so comfortable, and no one has to know you are wearing stretchy waistband pants. It is the little things that make me so happy. I love them so much I picked them up in two colors.

My loafers are by Vagabond Shoes. They are killing it with the modern styles. The quality is fantastic, and the price is reasonable. I have been slowly adding more and more of their shoes to my collection. These loafers are buttery soft with a perfect lug sole. They are available in a rounded toe like I am wearing or a square toe if you want to go with that trend.

Outfit #3: Vest + T-shirt + Bootcut Jeans + Boots

A vest can spice up a simple jeans and a t-shirt outfit. I added a belt, pointy-toe booties, and a fun bag for a casual girls’ night out look. I could also wear this vest closed over the tee or buttoned up alone. Both would look fetching with my bootcut jeans.

My jeans are the AG Angel Bootcut. I’ve linked a darker wash as mine are no longer available. The darker wash is dressier and more on-trend right now.

Midlife women wearing menswear inspired vest and boot cut jeans.

Outfit #4: Vest + Dress + Loafers

Add a vest to your favorite dress to bring new life to it. In all honesty, the vest with this dress isn’t my favorite, but I didn’t have another dress that would work in my closet, and I wanted to give you this option.  I think the dress would work better if it had 3/4 sleeves or long sleeves. I like adding a vest to a shirt dress or over a flowy bohemian maxi dress to add a little structure.

Maybe I need a new dress to pair with this vest for the holidays. What do you all think?

Midlife women wearing menswear inspired vest over a dress.

Outfit #5: Vest + Straight Leg Denim + Slides

Don’t pair your vest with skinny jeans. It just doesn’t work. The proportions are wrong. Instead, add a vest to your favorite pair of loose, straight-leg jeans. The loose bottoms balance out the structure of the vest in the same way the shorts above do. Honestly, this is my favorite look for fall.

To warm this up as the temperatures dip, I will add a tissue turtleneck. My favorites are from J.Crew. They wash and wear well and are perfect for layering. If you want something more trendy, add one of the popular semi-sheer print styles. There are so many pretty ones on the market right now, like this AFRM Zadie Print one or this sparkly one by Jonathan Simkhai.

Midlife women wearing menswear inspired vest and boot cut jeans.

A vest is a quick and easy wardrobe update for fall. It is a versatile piece that allows you to make dozens of new outfits from your existing wardrobe. When you find the right vest hang onto it.  The vest trend is sure to be back again. Because vests are such a specific item, the styles don’t change over time. I wish I had taken my advice. I had the most fabulous houndstooth men’s vest back in the early aughts that I found in a vintage store. It is long gone now. I am not good at hanging on to things. I really don’t like clutter. To learn from my mistake, I will be keeping this vest until I die. 😂

If you are interested in more fall trends check out my Obsessed with Clogs post.

I would love it if you followed me on Instagram for my everyday outfits or on Pinterest for my fashion inspiration. StyleDahlia is a fashion and lifestyle website with a modern take on midlife. We hope to inspire you to step out of your comfort zone, try new things, and live your life in full bloom.

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StyleDahlia is a fashion and lifestyle blog with a modern take on midlife. We celebrate the beauty in everything whether it be fashion, travel, or home. StyleDahlia offers and honest take on aging, fashion and everyday. Our hope is to inspire you to see beauty in the little things, step out of your comfort zone, try new things, and live your life in full bloom.

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