Fashion Advice for 20-Something Guys
After I recently noted that half of my readership is made up of guys, male constituents have been writing with requests for posts. Several have specifically requested fashion advice for 20-something guys. I like the idea, because the blogosphere is divided into male fashion blogs and “how to be good with women” blogs – and they don’t overlap at all. In fact, the latter group has a tendency to claim that looks don’t matter.
Nothing could be further from the truth. Research shows that what a man is wearing dramatically affects the way women perceive his attractiveness. While it is accurate that women prize kindness and intelligence more than looks when seeking a relationship, those qualities are not measurable at first meeting. If you want to make an impression that leaves a woman wanting to know more, your appearance is very important. The mistake that I see young men make most often is dressing like college kids when they should be dressing like upwardly mobile men.
Consider this fellow, recently profiled in the Boston Globe. Ethan Gilsdorf realized he needed a “middle age makeover” when he was still dressing like a college kid in his 40s:
Ethan’s not a bad looking guy, and he certainly seems friendly. But he’d be invisible to most women with his Joe Shmo look – scuffed boots, baggy old jeans, and a dark shirt hanging out. Look what happened when the salesperson at a clothing store picked out some clothes for him:
No doubt he was coached on his posture, but look specifically at the difference the clothes make. Ethan has a very nice torso, and the fitted clothing shows off his trim athletic body. Fitted pants in interesting colors make him look more stylish. And I like those shoes!
What’s most noticeable is the huge bump in self-confidence he seems to have experienced. Now Ethan looks like someone who would get noticed by women at a social gathering. This look is also appropriate and attractive for guys in their 20s.
Here’s a photo of my 26 year-old friend Parker Cote, who has gradually shifted his look away from the old college uniform:
The letter sweater is a nod to retro college Americana, but he’s added light gray jeans and a pair of red kicks. The look is fairly conservative but still interesting, and it radiates self-confidence.
In fact, that’s one of the two best reasons to dress with flair – making that effort signifies that you take pride in your appearance, which is something that requires self-confidence. And research shows that what you wear can have a profound effect on how you feel about yourself.
Studies in the field known as “embodied cognition” have shown that the clothes people wear change their self-perception and their behavior. From Enclothed Cognition, Journal of Experimental Social Psychology, Adam, H., and Galinsky, A. (2012):
“Clothes can have profound and systematic psychological and behavioural consequences for their wearers,” the researchers said. Future research, they suggested, could examine the effects of other types of clothing: might the robe of a priest make us more moral? Would a firefighter’s suit make us more brave? “Although the saying goes that clothes do not make the man,” the researchers concluded, “our results suggest they do hold a strange power over their wearers.”
Polishing your look does not need to be very expensive. In the U.S., we have many reasonably priced clothing suppliers that can bump up your look without a large capital outlay. Over time, you can acquire quality pieces as you are able. Start with H&M, J. Crew and The Gap. You can also find some great looks at Target.
Essential Upgrade #1: Jeans
The first thing you should do is get some nice fitted jeans in a dark, indigo wash. Save your baggy old pale denims for washing the car. The Art of Manliness, one of my favorite blogs for men, sums it up well:

“Faded & Distressed Jeans to Dark & Clean Denim
A man moving into the professional world wants to ensure his denim is less conspicuous and dressier. In fact, with the common acceptance of dark colored denim in many workplaces, you may find jeans to be the de-facto uniform at your place of employment.
Low-Rise Jeans to Mid-Rise Jeans – Men in excellent physical shape are often drawn to jeans cut low. You’ll want to migrate towards the classic and universally flattering mid-rise fit. Not only does this better proportion the torso for the man approaching or over thirty, it helps insulate you from the effects of a slowing metabolism (aka increased midsection). Low rise jeans and even a slight gut are a bad combination.
Skinny Jeans to Straight or Relaxed Fit – Similar to the reasoning above–skinny jeans compliment a lanky build. However, once you start adding weight and filling out, those same jeans make you look like an over-the-hill 1980’s rocker and should be switched out with a classic straight fit or if you’re heavier, a relaxed cut.
Skinny and low-rise jeans are trendy and hip, but a young man transitioning into manhood should start investing in style pieces that are masculine and classic.”
In addition to dark denim, jeans in neutral colors and corduroy look good. Khaki trousers like the green ones Ethan has on are a good staple.
Essential Upgrade #2: The Button-Down Shirt
When you’re meeting new women, avoid wearing t-shirts, especially those branded with sports teams, bands, your favorite beer, etc. In general, your wardrobe should be moving toward shirts. Dress shirts or casual collared shirts in flannel look great.
Essential Upgrade #3: The Sweater
Retire the hoodie when you go out. You’ll look good in pullovers of all kinds and cardigans can also look very sexy on guys. Look how Adam Driver rocks a button-down shirt and crew neck sweater in this recent Gap ad. By letting the tail hang down he radiates cool, not preppy:
His jeans are fitted but not “skinny.” This is the look you’re going for.
Essential Upgrade #4: Shoes
Shoes should be neat and polished. Business Insider has a great chart that pairs shoes with clothes:
My only suggestion is that you don’t buy any new chunky sneakers, except for running. Branch out.
Essential Upgrade #5: Blazer
You should own at least one blazer or sport coat – it’s an awesome look for a date. Pair it with anything, especially jeans!
How To Wear A Sports Jacket With Jeans
Essential Upgrade #6: Outerwear
For casual you can’t go wrong with North Face or Patagonia. For a slightly dressier look, I love duffle and pea coats, preferably in navy:
The scarf is a great look too. Here’s a tutorial on all the ways a man can tie one.
Putting It All Together
1. Fit
SayWhaat correctly noted that most men wear clothes that are too big. Clothing should be fitted. Pants should fit at the sides, with no sagging in the crotch or bottom! Women will find a fitted shirt far more attractive than a boxy one, because it reveals the chest and shoulders:
One last thing about fit – if you’re not in great shape, you may feel that it’s not worth it to buy new clothes. This is wrong. You should wear clothing that fits you well even if you are working to improve your fitness. Good fit insures your looking your best by playing up strengths and downplaying weaknesses. A good tailor is useful too – it needn’t be expensive, many dry cleaners offer tailoring.
2. Layer
Reader Sassy said that layering makes a man look put together and capable. See Adam Driver above, or these ads from J. Crew.
Notice too how there’s a slightly mussed up touch in each photo – a shirt tail hanging out a bit, a shirt or sweater tucked in here but not there. It’s very fashionable and women see this as a sign of your having style.
3. Style
I’ve focused here on a mainstream, all-American look because it suits the greatest number of people, is readily available and is affordable. By all means, if you’re operating in a niche market, adopt that look instead.
Following these basic guidelines will catapult you to the best-dressed group of guys aged 21-35. If you can develop your own personal look over time, all the better. That brings me to the other reason it pays to dress with flair – it signals creativity, and women dig that.
Thanks to Say Whaat and Sassy for their input. Here are some additional resources you may want to check out:
Dressing Sharp & Casual: The Comprehensive Guide for Young Men
Clothes Make the Man (Reddit male fashion advice)
Questions from the guys?













