16 Ways Your Life Can Change With a Style Upgrade

16 Ways Your Life Can Change With a Style Upgrade

Get inspired by these stories from real dudes like you.
guys style upgrades

By Taylor Davies | Last Updated: Jul 2 2019 | 16 min read

I have this blouse—I call it my lucky top—and I wear it on all my first dates. It’s pretty and feminine without being overtly sexy. I’ve come to believe it has talismanic powers that help ward off bad dates, and always gets me “the second date ask-out” before the first one is over. While it’s a style upgrade from what I used to wear, it’s been an even better dating upgrade.

Figuring out what to wear used to stress me out, big time, so much so that I’d spend half the date fussing and fidgeting with straps, sleeves and buttons on whatever shirt I’d ultimately settled on. I’d miss jokes and cues to jump into the conversation because I was too consumed with how I looked.

guys style upgrades

But finding a top that fit, flattered, and went with every pair of jeans I owned was not only a style upgrade, it totally changed my dating game. Why? Because I could “set it and forget it,” as they say.

I slip this top on and suddenly I’m like Kate Hudson in How To Lose A Guy In 10 Days—y’know, before she tries to make Matthew McConaughey dump her. I’m all eye contact, sparkling conversation, and flirty arm-touches. I’m “leaving my purse with Knicks tickets in it at his apartment as a power move”level killing it.

Before this style upgrade, I didn’t feel special when I went out.

Choosing what to wear and then following through with the date felt like a chore rather than something to look forward to. Upgrading to this (admittedly) expensive, luxurious top legitimately changed the way I date because looking like the best version of myself allows me to act like it, too.

Investing in this piece that’s “just for dates” reminded me that dressing up for those occasions could help me enjoy the experience more. When I toss on this silky blouse, I can chill, sip on a cocktail, and actually get to know this guy who could eventually become the elusive Mr. Right.

As we (hopefully?!) know by now, how we dress can change how people see you, which is huge!)

And more importantly, a style upgrade can change how you see yourself and how you act. The self-assurance and the swagger were there all along, and finally set loose in the world with a switch from “classic” to “slim” fit, or crushing a trend you’d been too afraid to try.

So I asked guys to share their experiences with something I’ve started calling, The Life-Changing Magic of Wearing Something You Absolutely F*cking Love

And guess what? The stories are so awesome. From big life changes like leaving the military or breaking off a bad relationship, to small things like the discovery of good underwear or buying a denim jacket—I was truly delighted and inspired by each and every response I got, and I hope you are, too.

Below, 16 guys on the life-changing effects of a style upgrade:

adam liebman squad

Style Upgrade #1 Invest to feel invested

“Honestly, buying my first pair of re-craftable, investment-level boots (shoutout Oak Street Bootmakers) in high school really changed my outlook on clothing. It solidified my seeing clothes as more than simply garments and instead as functional art and a means of self-expression.”

Ben Jarzombek‏ on Twitter

Style Upgrade #2 Mr. Manners

“I ended up overhauling my closet a couple years ago, and probably got rid of more than half of my clothes. I realized that dressing well and looking nice for different occasions is a form of good manners.”

Greg, 34

Style Upgrade #3 Denim Jackets & Deeper Connections

“When I first started crafting and paying attention to my style, I realized it’s an extension of me. It’s a reflection of my mood, my personality, the vibe I want to set, and helps me feel more like… me!

For example… When I put on my Billy Reid denim jacket—I know I’m cool. I feel like my raddest most bad-ass, stylish self. It was one of the first major upgrades in my wardrobe and took me 1.5 years to finally wear it but now we’re forever connected.

The next key item was a perfectly fitted grey J.Crew suit. It’s simple, classic and clean—I wear it when I want people to see me, and it’s one of the greatest tools in my arsenal.

Also, I believe that upgrades don’t have to mean big price items—I’ve become a huge proponent of second hand stores because it allows me to explore a variety of designers, test new looks and be more conscious of the environmental impact of buying new clothes every time.

“I dress up for me, so that I feel confident.”

I dress up for me, so that I feel confident. But I’ve also found that when I walk into a room ‘showing up,’ people really appreciate it. At first it was funny to be told ‘thank you for looking so nice’ but I realized that putting effort into my wardrobe can impact whatever room or setting I’m in. Caring for, evolving and paying attention to my personal style and the items of clothing that make it up has helped me feel more comfortable with myself, and non-verbally shares who I am with others. In turn, that has helped create deeper, more meaningful connections.”

clothes hanger

Frank, 31, Portland OR

Style Upgrade #4 Personality & Personal History

“In the military, fashion is an obvious afterthought, you’re told what to wear and form is certainly subservient to function. So as I transitioned out of the military and had the newfound freedom to choose what to wear, I wanted to be intentional about it in a way that I could communicate a bit about my personality and personal history.

I’ve certainly only grasped the low-hanging fruit, but I’ve found that understanding elements of style, cut, fit, and color is pretty simple and provides a huge ROI…how people look at/talk to/interact with me [has] changed—and I think I walk a little taller as a result. I’ve stopped viewing fashion as a vanity-soaked waste of time and begun to view it as a tool for creativity, self-expression, and what Amy Cuddy would call ‘presence.’”

Beau, 32, Boston MA

Style Upgrade #5 The Made-To-Measure Difference

“For me the change came when I started investing in fewer quality pieces rather than many cheap ones. We draw huge confidence from our clothes even if we are the only ones who know their quality. I now only wear Saville Row made-to-measure suits (a perk of living in London). A man’s suit is his armour and a well-fitting suit is the best investment he can make. Since I made this change in my wardrobe, I’ve been promoted twice. I guess that old adage that you should dress for the job you want rather than the job you have is true!

I’ve also invested in very good shoes—Crockett and Jones is a favourite. They look incredible and last for so many years. There’s an old English saying that fits here, it goes, “If you’re not in your bed you’re in your shoes, I suggest you invest in both.’”

Patrick on Instagram

clothes hanger

Style Upgrade #6 Put Your Best Foot Forward, Literally

“My life changed when I started taking shoes more seriously. I had  consistently received compliments regarding my taste in other areas but my shoe selection was fairly basic and confined to essentially three options: 1) something casual, 2) a leather boot, and 3) pairs of black/brown shoes that matched my dressier aesthetic. One day something clicked and I started to receive more compliments once I put effort into adding a) more options and b) options that went with multiple outfits. This, in turn, made me feel more confident and put together.”

Jeff, 32, Seattle WA

Style Upgrade #7 Captain Underpants

“I did a style revamp after a traumatic breakup, like a lot of guys, I think. But the first step towards more confidence and a really changed out look was, I sh*t you not, a different type of underwear.

Finding comfortable underwear that fit as the first step actually helped the rest of my style revamp along because it made me more comfortable and let me figure out what kind of pant fits would work for me. Plus, no one feels confident with a wedgie.”

Vic Tabeling on Instagram

Style Upgrade #8 Custom Shirts > Cargo Shorts

“Once I started buying fitted clothes, including fitted suits and custom dress shirts (I’m a little too tall for standard sizing), I knew it was time to donate/throw away any remaining baggy pieces and cargo shorts I had hiding from my earlier years.”

Vitaliy, 33, New York NY

clothes hanger

Style Upgrade #9 Dress like the grown-up you want to become

“Immediately out of college I thought my style choices helped me feel legitimate in my professional life. It allowed me to project a sense of career readiness even when I might have felt unsure myself. In some ways it helped me grow into the person I wanted to become.”

D.Urbs on Instagram

Style Upgrade #10 Out-Suit The Groom

“Earlier this year I bought a pretty expensive suit for my girlfriend’s sister’s wedding in Mexico. The biggest thing I noticed about it was that it opened my eyes to the importance of fit. This particular suit fit me perfectly. As shameful as this is, knowing what a perfectly fitted suit looks like highlighted just how poorly fitting most peoples’ clothes are.

It also felt nice to get a ton of compliments on the suit as well, which was definitely a first for me. I haven’t worn it since, but getting a couple of really great pictures pretty much justified the $900 price tag. I am pretty sure I was the best dressed person at the wedding. (Don’t tell the groom!)”

Adam, 32, San Francisco CA

clothes hanger

Style Upgrade #11 Dress For The Job You Want… Then Quit!

“Back when I was working in finance, I learned why you really should dress for the job you want. At a work conference with people from other states and branches that I’d never met, someone thought I was my manager. And it was just based on how well-dressed I was compared to him. My life changed not long after that since I ended up quitting my job in finance to work on Levitate Style full-time.”

Leo Chan, Levitate Style

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Style Upgrade #12 My Tailor, Myself

“I’m 5’6.” I finally started taking my pants to get hemmed and it not only increased my confidence, it made me feel less like a kid in someone else’s clothes and more like an adult. I stopped ignoring pants in my closet because they were no longer ill-fitting. I’m a 32-year-old biracial man, who is often misidentified as a white college-age kid. Tailoring my pants helped me feel like I’ve tat least some control in how people initially perceive me.”

Alex Hanyes on Instagram

Style Upgrade #13 Suited Up… And Up, And Up

“I was into clothes from an early age (partially because my entire family worked in the fashion industry) but still I never really dressed ‘well.’ In college I always wore sweats and Abercrombie, ha. I never cared, except when I needed to find an internship for my master’s [degree]. That’s when I decided to change that, and appreciate the clothes that were hiding in my closet, the ones I’d only wore once or twice. But unfortunately, not before I showed up to a bunch of internship interviews, at least four, in jeans and a t-shirt or polo.

I could tell I wasn’t looked at the same way when I went to my final interview in a suit. It took me six months to get it, but I got it! I got the internship then got hired [full-time], and have been promoted three times since. I really think it was due to the fact that I had a lot more confidence in myself. Now, waking up I don’t even second-guess putting on my suit. Changing my outlook has definitely changed how I’m viewed both in my personal and professional life.”

Matt M on Instagram

clothes hanger

Style Upgrade #14 Foreign Influences

“At my last job, I traveled to the Netherlands for work a few times and realized, ‘Damn, Europeans dress better, I need to dress better.’ It started out simple. No more wearing t-shirts to work.

But it evolved pretty quickly to better-fitting shirts, slimmer cuts in pants, wearing a tie on occasion because, why not! Now I feel like I can take risks and it’s fun. It’s even become a thing at work now. I work in tech, so a collared shirt goes above and beyond. So now I’m officially , ‘the person who cares about what he wears!’ Not in a pretentious way, but just in a ‘people notice’ way.”

Sean Quinn on Instagram

Style Upgrade #15 Menswear… And Beyond!

“Getting interested in menswear is what introduced me to almost everything I am passionate about. From business, reading and art, and even fencing! All of it was introduced to me through menswear in some way.

The first menswear blog I ever read when I was sixteen was The Style Blogger (now Articles of Style). It made me want to start dressing more grown up and put-together. I feel that just the confidence I gained from dressing well led me to start taking life more seriously and explore what I wanted for my future.

Long story short? I’m finishing my undergraduate degree in business administration next year, and also started my own business last year. I know that I wouldn’t be who I am today if it wasn’t for my love of menswear.”

Omar Shaikh on Instagram

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Style Upgrade #16 The Benefits of Bougie Outerwear

“The upgrade to a bougie winter coat has absolutely changed my outlook on cold in this city. Until recently, I would always layer heavily under spring coats, or find myself wearing thick, functional ski jackets when temperatures really dropped.  

I was hesitant to put the money down for a proper, fashionable, minimalist city coat at first, but I’m so glad I did. Right away, my new purchase motivated me to try a little harder with the rest of my winter outfits. The result? A big confidence boost.”

Sebastian, 28, New York NY

clothes hanger

Bonus Style Upgrade! Dress Better, Date Better

“So, I used to be totally a shorts-and-shirt kinda person. Almost every day, even to work, that was my wardrobe. I thought dressing nice would take up more of my time and wouldn’t be as comfortable. Also in my office that was relatively standard dress. Once I did change [my style], I feel like management seemed to start viewing me in a better light and I started seeing promotions and bigger opportunities open up for me.

I would also say it probably did help my dating life, too. I was constantly striking out before I changed [my style] and had much better luck when I started dressing well.”

Patrick Day on Instagram


So there you have it! Still waiting for your own style upgrade-prompted epiphany? Then allow me to loudly toot the horn of shopping with Team SG! Honk honk, it’s the best!

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Let us rescue you from shopping fatigue and sartorial apathy. Work with us to style upgrade ya, and we promise you’ll get a promotion at your job…No I’m totally kidding. We obviously can’t promise that. But we can promise the kind of personal attention and care that will make you feel like the best version of the awesome guy you already are!

If you’re ready for a lewk to change your life, or simply jump right to the end of the shopping process, give us a shout.

Taylor Davies splits her time between NYC and Sun Valley. She loves writing about menswear, overpriced martinis in dimly lit hotel bars, and cross-country skiing. Not necessarily in that order.