Unsolicited advice is the worst. Unless it’s done anonymously over the internet, with the best of intentions… and then maybe it’s okay. Maybe. First we started with the rookies. Then it was advice for those who have been at this for a bit. Today is for those who consider themselves “experts”.

#1. Resist getting weird.

“Boring” doesn’t mean bad to all. Or any.

So you’ve got it pretty much figured out. Awesome. But there’s a threshold one risks crossing. At some point, normal becomes boring, and the risk is you start reaching for extremes just to keep yourself entertained. At first, some will probably think it’s charming. Cute even. But left unchecked, you quickly spiral into the realm of inappropriate and flat out bizarre. It’s The Depp Effect. And then, it’s tough to be taken seriously. Most of us use style as a tool. Keep in mind what purpose you’re using that tool for.

#2. Pass along knowledge & your opinion… when asked.

 If they didn’t ask, then don’t offer your advice.

A lot of us have probably been asked at one time or another from a friend or acquaintance to provide some sort of advice on style. And that’s a flattering thing to be asked. If they didn’t think you looked good, they wouldn’t ask. And we all remember what it was like starting out. It was hard. Embarrassing even. And many of us didn’t WANT to ask someone where they got their shoes, or why their suit looked so good. But just because you think someone might want to ask a question or two, doesn’t mean you should preemptively answer them. You’re not their personal stylist, and most of the world finds the topic of men’s clothing excruciatingly boring. Wear it. Don’t share it. Unless asked, then yes, absolutely.

#3. Keep it in perspective

Musta been the dysentery.

This is different than #1. This is less about the wardrobe and more on how much time/effort/money you spend on it. If the first thing people will say about you when you die is: “He was so well dressed.” Well then, what the hell?

Unsolicited advice is the worst. Unless it’s done anonymously over the internet, with the best of intentions… and then maybe it’s okay. Maybe. First we started with the rookies. Today is for those who have been at this for a bit. Finally, we’ll wrap up with advice for those who consider themselves “experts”.

#1. Develop a great relationship with a Good Tailor

Somewhere between beginner and intermediate, we all figure out that having our suits, blazers, shirts, etc… tailored is often (always?) a worthy investment. But always using the faceless tailoring department at a big box store or dry cleaners is sorta like having your hair cut at Supercuts. And no, that’s not a criticism of the talents of the person wielding the scissors. The downfall is having a different person doing the work each time, and never developing a relationship… and thus… good communication, with that person. You want someone you can get to face to face (and garment to garment) with. They’ll see you, get to know you, you’ll get to know them, and you become a team. They’ll come to respect you, and how you feel your clothes should fit.

They’re stunningly similar. Consistency + communication = great results.

#2. Get good at taking care of your stuff

Just like when you were a kid, you gotta put your toys away. Even if you’re on a strict budget, your clothes will look better and last longer if you get proficient at maintaining them. That means getting good at laundry (i.e. reading tags, not shrinking stuff, finding  good detergent), ironing, taking care of your shoes, and storing all of it properly. It takes time. Lots of practice. You may sometimes wash a blazer, forgo shoe trees for your best dress shoes, or use crappy hangers for everything. Even sweaters (nooooo!). It’s a process. Respect what you’ve earned to acquire. But don’t forget to get out there and use it. Don’t be Cameron’s Dad from Ferris Bueller.

Oh look. Must be Sunday afternoon.

#3. Limit asking for style critique from strangers on the web

Short version: Trust yourself. Long version: When starting out, the web and its communities can be a big help. But the risk is you end up becoming part of the cycle of cyber-menswear-addicts who spend more time looking at pics of suited-up strangers on the web than going out and living their life. Pictures on the web, usually either photoshopped to death or alternatively with poor lighting, shadows galore, and bad angles, don’t give the correct representation of what something looks like in-person anyway. Put a still image within a frame and every little tiny imperfection is going to stand out. Post something that’s 90% awesome on the web, 95% of the viewers will crush that negative 10%, while 99.999% of people in public would never think anything other than “wow, that dude looks sharp“. This seems hypocritical coming from this source (a website) but when in doubt, log off.

Unsolicited advice is the worst. Unless it’s done anonymously over the internet, w/ the best of intentions… and then maybe it’s okay. Or totally not. Anyway, this one is for the rookies. Up next is advice for those who are well on their way. Then we’ll finish this series with (unsolicited!) advice for the self appointed style experts.

#1. Try a size down

Left: Medium. Fine, but a bit boxy.  Right: Small. Fitted, but not tight.

It doesn’t hurt to just try a size down. There’s something about the “you’ll grow into it” clothing strategy that somehow sticks with men as we go from adolescent to adulthood… and sometimes real far into adulthood. We think that anything relatively fitted won’t be “comfortable.” Horse feathers. Clothing that fits isn’t tight. Nor is it loose. It skims the body. It doesn’t cling to it. So try a size down in shirts, pants (inseam and waist), and especially suit jackets, blazers, and sportcoats. You’ll look stronger and leaner. Here’s a few tricks that can help land the right fit.

#2. Get good at shopping smart, but don’t buy something just because it’s on sale.

Cole Haan’s Lunargrand in “Red Multi Mosaic Camo.”
The fact that they were $248, and are now $129.95, means diddly-poo.

For those of us who aren’t rookies at this dressing-better thing, think of the collective cash we all burned along the way. Only pay full retail if you REALLY want it, and you just can’t wait for a sale. Yet at the same time, don’t buy something you only think you might wear, simply because it’s marked down. This is especially true for items that are close to your size, but not actually your size. If it doesn’t fit, or can’t be tailored to fit, don’t pick it up.

#3. Go Slow

And suddenly, all of Frank’s co-workers at the salvage yard stopped talking to him.

It’s awfully hard to go from cargo shorts + graphic tee guy, to three piece suit guy overnight. It’s a process, and by jumping in head first, you risk looking out of place. There will be disappointments. And there are plenty of reasons as well as opportunities for a guy to dress well. But that doesn’t mean you have to start wearing a tux every night for dinner. Work up to it. Want to start wearing blazers more often? Pick up a cheap, cotton sportcoat, and get it tailored. Wear it out to dinner here and there. You’ll get there.