How To Wear A Vest

20-somethings will probably get their midlife crisis early once they know that Y2K fashion is now deemed ‘vintage.’

It was known as the ugliest phase in clothing history, but due to the rising popularity of low-waisted jeans and Juicy Couture, we’re inclined to think otherwise. In its defense, the early 2000s was a nostalgic time filled with great music, movies, and pop culture. 

You can thank TikTok for Y2K fashion’s exponential growth. Typically dominated by zoomers and Alphas, this virtual community resurrected this dying trend, turning it into this years hottest fad.

If I were to pinpoint one garment that ranks high in popularity, I’d say it’s the vest. If you have yet to jump onto the Y2K bandwagon, you’re probably wondering how to wear a vest. 

Take this as a sign to crank up the Spice Girls in your CD player and reinstall that inflatable chair. I’ll teach you how to wear a vest using 10 outfit ideas. My style guide may or may not cover topics such as:

  • How to wear a vest casually
  • How to wear a vest women’s edition
  • How to wear a vest men’s edition

History Of The Vest 

For some, the vest is commonly dubbed the ‘comic sans’ of clothing. Often cheesy in aesthetic, you’d be surprised to know that this particular garment holds a royal lineage

It originated in Persia during the 17th century and was first documented by diarist Samuel Pepys. King Charles II quickly took hold of the trend, as he became a leading model in sporting the iconic vest. Worn by the gentry, gentlemen viewed the sleeveless garment as a ‘modest’ alternative to lavish clothing—ironic, right?

Waistcoats soon became synonymous with the Victorian corset—as they were considered indispensable in terms of gendered clothing. As time went on, they became shorter and more complicated in structure in order to accommodate the lifestyle and trends of the upcoming modern age. 

Nowadays, vests are considered optional. They’re not regarded as an intrinsic part of formalwear anymore. Plus, their recent revival is partially due to the Y2K resurgence. 

What Is A Vest?

A vest is simply a sleeveless top. Typically constructed with a button-down front, this particular garment is usually worn over another piece of clothing, such as a collared shirt. 

It’s worth mentioning that there are two types of vests: the formal and informal fit. The latter is generally made out of denim, leather, polyester, or wool. If you’re prepping for a fancy event, fabrics such as twill, tweed, or silk are notable alternatives. 

When To Wear A Vest

As previously mentioned, vests can be worn formally or casually. With the resurgence of Y2K fashion, the typical vest is viewed as an everyday necessity, as it’s used to jazz up an outfit. 

Most trendsetters pair it with crop tops, tanks, or by itself in order to achieve that early 2000s finesse. For fancy events, wearers will usually opt for more ‘elegant’ fabrics such as silk or tweed. 

Given their sleeveless nature, vests are considered summer/spring garments. Of course, this may not apply if you intend to layer it with other clothing. 

How To Wear A Vest

It’s not a simple matter of ‘grab, wear, ‘n go.’ Vests require a bit of styling prowess to pull off—unless you covet the ‘substitute teacher’ look.

Thankfully, the fashion gods are on our side. If you’re wondering how to wear a vest, I’ll share some trendy OOTDs worth considering. 

10 Outfit Ideas With A Vest

Opting for the ‘substitute teacher’ look isn’t a bad idea, so long as it’s kitschy—not cheesy.

For instance, this Y2K-inspired look is quite charming in aesthetic. Composed of a tapestry vest, a loose white button-down shirt, a brown mini skirt, and a pair of black loafers, it definitely has a bookish look that’s less nerdy and more romantic. 

The cropped hem of the skirt helps to keep the outfit youthful and playful while the shoes exude that classic collegiate girl vibe. Ideally paired with a tote bag, this ‘how to wear a vest’ contender should definitely sit high on your list of OOTD ideas. 

Nothing screams art teacher vibes more than a horse vest. I can practically imagine the outfit now, as it’s typically paired with a wool turtleneck, an unflattering midi skirt, and a pair of boho flip-flops as a wild card.

If you happen to own a stallion-printed waistcoat, don’t throw it out just yet. With a bit of tweaking, it can definitely act as a statement piece. 

Case in point, this Instagram-friendly outfit features a horse vest paired with a relaxed white button-up shirt, a set of matching trousers, and a chunky beige belt to help accentuate the waist.

Somewhat romantic in aesthetic, this OOTD exudes a sense of ‘90s nostalgia without relying on bright colors and patterns. 

If Belle happened to live in the late 1990s, I’m fairly certain that she’d swap her usual blue dress for this bookish ensemble.

Composed of an embroidered geometric vest, a white puffed blouse, and a black high-waisted skirt, this romantic look manages to combine ‘90s finesse with collegiate core. 

In retrospect, these two aesthetics are known to be quite cheesy, so it only makes sense that they’d be paired together.

To further enhance this ‘how to wear a vest’ contender, I recommend wearing a chunky headband, frilly socks, and black loafers to really emphasize that vintage preppy look

Most choose to wear their vests without any underlayers. While it’s considered an acceptable look, I totally understand if you’re not comfortable showing your shoulders or arms. To help keep things semi-conservative, I suggest wearing a leather jacket over top. 

Meant to juxtapose the formal look of the waistcoat, a motocross coat helps to add a more streetwear touch to the final look.

Plus, the white tennis skirt adds a flirtatious element to the outfit. Of course, you can always swap it with a pair of distressed black jeans for a more grunge-inspired ensemble. 

Let’s not forget the ever-iconic sweater vest! Considered a closet staple for fall, this sleeveless cable knit can help add a stylish touch—as well as another layer of warmth—to your outfit. 

For example, this chic look features a white, knitted vest with a loose button-up dress shirt, a pair of chunky white boots, and an oversized black tote bag to help contrast with the bright tones of the OOTD.

Simplistic in design, it’s regarded as the perfect mix between classic Parisian fashion and New York City glam. 

Plaid sweater vests are often cheesy in aesthetic, which makes them hard to style.

So, instead of pairing the vest with modernized garments such as jeans or leather pants, I suggest opting for the corny route.’ You know what they say: two negatives make a positive. 

This outfit is considered a prime example of this phenomenon, as the kitschy nature of the vest paired with the brown corduroy pants is quite charming when put together. Complemented with chunky Doc Martens, it definitely passes the vibe check. 

Is it just me, or does this ‘how to wear a vest’ contender scream 1970s John Travolta to you?

Seemingly reminiscent of the black leather-clad garments that Danny loves, this outfit features a motocross waistcoat, a white tank top, mid-rise jeans, a belt, and a pair of cowboy boots for some Western twang. 

It definitely exudes those quintessential bad boy vibes due to its semi-rugged aesthetic. So, if you love to intimidate, this is the ensemble for you. 

Also reminiscent of ‘70s fashion, this bohoinspired outfit is perfect for hippies, flower power believers, and those who frequent expensive coffee shops. 

The lax nature of the brown vest paired with the cream button-up shirt is perfect for no-nonsense days, thanks to its loose silhouette. Accentuated with fitted black jeans and matching loafers for a touch of class, this OOTD manages to strike the perfect balance between comfy and casual. 

Aside from his music, Tyler the Creator is known for his unique taste in fashion. Here, he’s sporting a bright blue vest, a white graphic tee, khakis, and a pair of red Chuck Taylors. Deceivingly simple, the colored waistcoat does wonders by brightening up the outfit. 

Plus, the bucket hat adds the right amount of late ‘90s nostalgia, which cannot be accomplished with a regular baseball cap or a fedora. If you’re prepping for the cold season, I recommend swapping the tee for an oversized hoodie instead. 

Utilitarian in vibe, this bold outfit does its best to emphasize the versatility of the puffer vest. In bizarre fashion, it’s layered on top of a trenchcoat, which is usually considered a no-no in the fashion world—but this model seems to pull it off.

Paired with brown trousers, white sneakers, a crossbody bag, and a yellow hat, it’s considered a strange but chic mix of Safari fashion and New York City corporate

What Type Of Vest Outfit Can You Get?

Given their utility, remind me again why vests were considered cheugy for so long.

Sure, the early 2000s practically destroyed the classic element found in waistcoats, but I’d like to think that vests have made a significant recovery over the years. Plus, today, we’re spoiled with hundreds of modernized updates. 

For those hoping to streamline outfit coordination, next up, I’ll share some trendy OOTDs in this ‘how to wear a vest’ style guide. 

  • The preppy look: This core aesthetic usually involves embroidered vests, button-up shirts, midi skirts, and trousers. Often kitschy in design, most of these outfits exude a classic charm that’s hard to not appreciate. 
  • Streetwear finesse: Those who own a utility vest or a puffer waistcoat will definitely make use of this core aesthetic. Try pairing this garment with sweatpants or an oversized hoodie. 
  • ‘70s boho: Think of bell bottoms, flower power tees, and relaxed vests. This core aesthetic is all about exuding those lax, hippie vibes. 
  • Y2K glam: Considering that the vest is intrinsic to late 1990s and early 2000s fashion, it would be a missed opportunity to not include this category on this list. In terms of matching garments, I recommend opting for low-waisted bottoms and crop tops. 
  • Complete formalwear: As previously mentioned, vests can be worn formally as well. They’re typically paired with a blazer, a button-down shirt, a tie, and tailored trousers. 

How To Choose The Best Vest Outfit

The vest has yet to dominate the fashion world. Most trendsetters and brands are quite hesitant to incorporate this particular garment in their collection, given the frivolous nature of clothing fads.

With that in mind, finding the perfect vest is quite a difficult venture. You’re left with two options: good ol’ thrifting or supporting your local indie brand

While it’s easy to buy a $5 vest, it’s not a recommended option. Fast fashion brands are notoriously known to skimp on quality control—so it’s common to find uneven hems, delicate fabrics, and loose threads in construction. 

Instead, I suggest opting for reputable, sustainable retailers that utilize premium materials such as leather, denim, or organic cotton. Customers should also look out for any additional features, including pockets and buttons. 

Additionally, the fit is also a point of concern. As a general rule of thumb, customers should always opt for tailored garments

Oversized garments or tightly-fitting waistcoats are typically unflattering and uncomfortable, which is why it’s important to always try on your vest in person. If you’re limited to online shopping, taking a peak at the size chart is always a recommended practice. 

Design is another factor worth considering. Ultimately, you should settle for a vest that aligns with your current aesthetic.

For novice trendsetters, opting for neutral tones and traditional silhouettes is always a good move, as they’re relatively easy to style. Of course, this may not apply to maximalist fashionistas who prefer bold prints and colors. 

Price-wise, vests can retail for as low as $30 to as high as $1,000, depending on the brand and the design. As always, I suggest sticking to a limited budget to help prevent overspending. 

How To Style A Vest Outfit

Getting your hands on a new piece of clothing usually entails some worry. “How do I wear it?” “What garments go well with it?” and “What designs are available?” are a few common questions that arise.

You can rest assured that a vest doesn’t require an expert level of styling prowess to pull off. Instead, it only needs a decent degree of confidence and creativity

Next in this ‘how to wear a vest’ guide, I’ll tell you about some trendy ways to style this particular garment. 

  • The classic button-up shirt: Considered the go-to garment for vest-centric outfits, the collared shirt offers a touch of sophistication needed for academia-themed OOTDs. 
  • Fitted trousers: Preferably high-waisted, wearing a vest with tailored pants can help you look more distinguished and mature. 
  • Good ol’ juxtaposition: If you own a leather vest, try pairing it with a lacey white blouse. The contrast between the two results in a unique outfit. 
  • A crossbody bag: I can’t put my finger on it, but vests and purses go intrinsically well together. 
  • Loafers: Given that vests are often cheesy and corporate in aesthetic, wearing a pair of chunky loafers can help balance out the final look. 

Fashion Tips To Avoid With A Vest 

Those familiar with the vest probably know its controversial past. There’s a reason why it’s considered cheugy for so many trendsetters, as it’s been styled with several bizarre outfits.

If you’re not fond of early 2000s cringe, I’ll share some fashion tips to avoid with a vest. 

  1. Off-the-shoulder blouses: Given that vests are sleeveless, it seems counterintuitive to pair them with an off-the-shoulder top. 
  2. Sweatpants: It’s worth mentioning that sweater vests and joggers can go well together. Instead, I’m referring to embroidered waistcoats and tracksuit bottoms. 
  3. Over-layering: From the get-go, wearing a vest with a blazer or leather jacket on top is an appropriate look. That said, donning an additional cardigan or a tank underneath may look too overwhelming. 
  4. Oversized vests: The extra-large look should be exclusive to sweaters and t-shirts only. Wearing an XXL vest when you’re a size 2 may result in a boxy silhouette. 
  5. Denim shorts: The casual nature of cropped denim paired with the semi-formal look of a vest is a prime example of a fashion faux pas. 

How To Take Care Of A Vest 

Vests come in a wide variety of designs. And puffers, vintage embroidery, and leather waistcoats typically come with different care instructions. So it’s important to double-check the laundry tag of your garment. 

Those made out of regular cotton and polyester can usually be machine-washed with lukewarm water and gentle detergent.

On the other hand, those constructed out of delicate fabrics may require special attention. In addition, after rinsing, it’s always a good idea to let your vests air dry to prevent shrinking, wrinkles, and ripping. 

Best Places To Buy A Vest 

Before I conclude this ‘how to wear a vest’ style guide, I’d like to share some store recommendations for readers to check out: 

  • Farfetch 
  • Nordstrom
  • Mother of Pearl
  • Patagonia 
  • Your local thrift store 

Final Thoughts

From initial observation, vests are considered an exclusive item among the fashion elite. And it’s easy to get imposter syndrome when surrounded by style-forward influencers and celebs.

That said, the beauty of fashion is its inclusivity and diversity. You’re basically allowed to wear whatever you want—whether it’s considered cheugy or in style. 

After viewing the 10 outfits that I’ve featured, here’s to hoping that you know how to wear a vest. Versatile, semi-practical, and chic in design, it can act as the final cherry-on-top to your OOTD.

Looking to up your fashion game? We’ve got you covered:

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