How You Should Upgrade Your Wardrobe Each Decade
How to Upgrade Your Wardrobe for Each Decade of Your Life
While some men consider themselves fashion-forward and risk-takers with evolving trends, others prefer to stick to the tried-and-tested traditional basics to define their style. No matter how you would describe your own sense of fashion, experts recommend allowing your look to evolve along with your lifestyle. This doesn’t mean you have to toss out everything in your closet and your dresser every decade, but it does mean giving yourself the freedom to upgrade your essentials and to reconsider how your personal style can illustrate your personality, your career, and where you are in your life.
In addition to colors, fabrics, cuts, and fits, Alex Gushner, fashion expert for Boyds Philadelphia, encourages men to consider their unique shape, too. “Being cognizant of how your body changes over the years is important. Since everyone ages differently, you want to ensure that you’re dressing comfortably in a way that fits your body type and personal style,” he explains. “Depending on what phase of life you’re in and what your lifestyle is like, you can also make upgrades to your wardrobe that fit your routine during that time period.”
After all, chances are the way you dress for a first date in your early 20s isn’t quite how you’d walk into a board meeting in your late 30s. Another example: What you pack for your weekend bachelor party probably won’t fit you quite as nicely at 50.
Here, fashion pros offer their best advice for upgrading your wardrobe from your 20s to your 50s and beyond.
Bid buh-bye to those fraternity T-shirts and sneakers worn through the soles, and greet the beginning of your professional wardrobe. At the start of your adulthood, Brice Pattison, the fashion director of The Black Tux, recommends men start building their basics. These will become the pillars of your style moving forward, and while they’re not cemented in stone, they will ensure you have classic go-to’s for any occasion.
He suggests owning two pairs of quality dress shoes, preferably made by craftsman such as Alden, Church’s, or Crockett & Jones. When your entry-level salary is meager, it’s tempting to buy inexpensive options, but Pattison urges men to opt for quality. If you don’t want to drop the hard cash? “You can buy them used from Grailed or eBay to save money and then resole them for life,” he suggests.
In terms of clothing, it’s important to try many styles and fits to determine what feels good, looks great, and gives you the most confidence. In your early- to mid-20s, Gushner recommends developing two wardrobes: one for your work life and one for social life. “I recommend a few staple items for your professional day-to-day: a slim-fitting, solid charcoal suit, five to seven dress shirts, a solid navy blazer, and three pairs of slim dress pants,” he explains.
When you’re not in the office, Gushner says to impress your date. Think casual — but well composed. These could include a solid pair of simple sneakers — he suggests ones from Common Projects or Golden Goose if you’re willing to spend, with Reebok and Converse offering great options under $100 — and two pairs of nice jeans, plus a handful of fitted shirts. We suggest starting at Mott & Bow, H&M, and Amazon’s Essentials and Goodthreads collections for some great options that won’t put a big dent in your entry-level budget, but will still have you looking great.
One last point Gushner adds about this decade: “Since your 20s can be a decade of back-to-back weddings, it’s also [a] good time to think about investing in a nice tuxedo.” With formal attire becoming more available and affordable, it’s easier to have one on hand. Because who doesn’t love the classy guy who shows up in his own tuxedo?
If you’ve hit and passed the big 3-0, you’re no longer fresh in your career and are likely thinking about many lifestyle shifts in the years to come. Whether it’s branching out and founding your own company or working tirelessly toward the vice president title, careers go through a transformation in this decade. For many men, so do their relationships, considering the average age of marriage is 29 for men. These are pivotal, metamorphic years — and your wardrobe should express that.
“Your 30s bring a heightened sense of self-confidence and a paycheck to match,” Gushner says. “You’re established now and so is your personal style, but there’s still room to experiment with trends.”
He recommends thinking about how you dressed in your 20s. What worked, and what didn’t? Be honest with yourself, since Facebook and Instagram won’t let anyone forget about the wins and blunders of years past.
“It’s a time to upgrade since you’re starting to settle down and it’s time to dress the part,” Gushner continues. Try experimenting with more luxe options for your career, like a double-breasted or three-piece suit. His top picks are ISAIA and Canali.
Pattison reminds men not to forget about their accessories, including high-quality sunglasses and a staple leather jacket. He suggests opting for a quality version from Lewis Leathers, Vanson, or Schott NYC. For your other staples to last you through your 30-something decade, we suggest shopping Taylor Stitch, Bonobos, and Uniqlo.
If you’re in your 40s and you are feeling like you’re in a bit of a funk, that’s not a surprise. Whereas it’s a time in a man’s life where there are a lot of questions about life — past, present, and future — Gushner warns men it’s no coincidence it’s also the trickiest decade for your personal style. “While you were still capable of pulling off some bolder, trendier looks in your 30s, now it’s more important than ever to stay true to your personal, more simple style,” he explains.
Think about those guys you’ve likely seen at some point who tried to keep up with what the younger generation was wearing (that was you then). In your 40s, you start to run the risk of having your associates — or your children — thinking the same of you.
“Don’t be the guy who overreaches and tries to pull off younger looks that just aren’t appropriate,” Gushner urges. Leave the wide, oversized sweatshirts, loose-fitting tanks tops, and gym-only style joggers for your workouts or when you’re relaxing at home.
Pattison suggests men switch to straight-cut jeans, without embellishments. "Part of the value of a jean, in my opinion, is the ability to repurchase the same product with minimal risk of having to shop for a substitute,” he says recommending Levi's as the unmatchable historic denim icon, A.P.C. as the original minimal fashion jean, and RRL for its design anchored by traditional materials and construction.
“This is the time to stop trying to dress hip and dress simple, in high-quality clothing that, most importantly, fits you precisely,” he notes adding that by now, you’ll likely have some brands you’re loyal to — his favorites are Canali, Ravazzolo, Scuderi, and Mr. Porter — but you can keep things fresh by adding new pieces seasonally, or playing with color. Other brands we like that offer great, sophisticated styles at a more modest price point include Massimo Dutti, Gant, and Rag & Bone.
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Your 50s and BeyondGettyImages
If two words could define your hop over the hill, Gushner says they would be “comfort” and “luxury.” You have your eye toward retirement, your kids are likely out of the house, and you’re ready to invest in the finer things in life.
In terms of wardrobe, Gushern says to “think understatement vs. overstatement.” This means being purposeful with what you wear, but also ensuring it gives you the self-confidence you might be struggling with during this decade. “I recommend Brunello Cucinelli and Ermenegildo Zegna suits, jackets, and sportswear for classic and elevated looks that fit your comfort level,” he shares.
This is also a time to consider what colors you’re wearing — especially if you intend to travel more during this decade, according to Pattison. He suggests thinking carefully about anything that isn’t a shade of navy, blue, khaki, black, olive, or white. Why? A classic and timeless color palette lends itself to looking more sophisticated since the pieces aren’t “trendy.”
Plus, it just makes everything easier — from getting dressed to travel and laundry. “Your wardrobe should overall be solids only,” he recommends.
With the right upgrades and elevations over the decades, by the time you hit retirement, you’ll have a style that speaks directly to who you are and allows everyone else to recognize your sense of self, too.
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