First of all let me just say I hope you can call me. That I’m still here for you to talk to and we have the kind of relationship where you respect and trust my opinions. As I’ve said a million times, my dream is that these letters are simply a jumping off point to a future conversation we can have in person. But, since we’re unable to forsee what’s ahead, I wanted to jot down a few ideas just in case.
Now, it may feel frivilous or irrelevant to talk about clothes and style but, baring world destruction, I’m here to tell you it’s not. How you visually present yourself to the world is the first thing anyone sees, ergo the first thing you’ll be judged on. It’s not fair, it’s probably not right, but it’s true. What’s inside may be what counts, but it’s the packaging that often makes all the difference. I want people to know and love you as I do but, in life, before you even have the chance to even open your mouth people will have already made assumptions about you with their eyes. It’s my goal to see you’re not starting at a disadvatage.
With this in mind, I’ve decided to do a series of aesthetic run downs. It’s strictly surface. I touched on it before when I spoke on the deeper aspects of “being a man” but this time we’re staying firmly in the shallow end of the issue pool. It’s not life or death. It’s denim or kakhis.
Dare to dream of a closet like this one from fedoras.com. Good grief…and sigh.
As you age you’ll develop and hone your own style (and there’ll probably be many a girlfriend who wants to dress you) but I feel it’s my job as your mother to let you know where to start. I don’t want you to ever feel insecure because you’re unsure of what to wear and, as far as I’m concerned, there are basics you should consider embracing no matter what your future “look” or gal pal might encourage. I expect you’ll tweak this advice to make it your own but I never want to hear about you showing up at a wedding in cargo pants or at a job interview in a ball cap.
We can do better than that.
I begin this series with a list of items I hope will find their way into your wardrobe by your mid-20’s (if not earlier). You’ll discover the best ones over time and certain trends will fill in your closet, but for now, here is my list of what I believe a grown man should own.*
Chris PIne working the right fitting t-shirt, jeans and properly sized casual belt buckle. I also love a good pair of glasses.
At least 3 PAIRS OF GOOD JEANS. Not baggy and preferably not skin tight but well fitted, straight leg, boot cut or skinny. Your jean style will depend on a combination of how your body fills out and the style of the day, but definitley invest in good denim. These days jeans can take you almost anywhere. Washes should include: a casual worn in blue, dark “dress” blue, and black. Grey and sand are also terrifc alternatives.
A CASUAL BLACK AND BROWN BELT that are your size. No flapping overhang or just making it to the first hole. Buy a belt that fits. Also make sure the buckle size balances your body type. Not too big or too small.
A DRESSY BLACK AND BROWN BELT in good shape (good quality leather, no fraying) that’s not too shiny and has a classic buckle. Europeans, and people who dress like Europeans, can get away with a covered buckle but they don’t often work on the classic American male. I’m happy to take that back if you show me the belt that proves me wrong, but for now let’s just stick with the basics.
At least 6 COOL T-SHIRTS. Well fitted. Good cotton. No logos. Personally, I like a v-neck but you might be a crew neck guy and that’s great. Beware the super deep V. It’s made for a very specific kind of man, particularly one without body hair and, looking at your Dad (and the fact that your legs are hairy as a six year old), you might want to steer clear of anything that shows a pizza size chunk of chest. The most important thing is fit and quality. You need something that breathes and looks good on you. A cotton shirt should skim your body without being too tight. It should fit your shoulders well and hit your arms at just the right location to accentuate their shape without clinging to their size. This is usually between the upper half and quarter of your bicept. Avoid cap sleeves or sleeves that go almost to the elbow. It looks wrong. Personally, I’d go with 2-3 white T’s (pitching and replacing them when they start to look tired or get yellow pits), at least one blue, one navy, one black, and one grey – light and/or dark.
Never!!! Never. Never. Never.
If you want to rock a concert T or a logo T knock yourself out, just make sure you still own a number of plain ones. People should see you, not read you. And never, ever wear a gross or rude T-shirt. It’s not funny, it’s lame, and wearing it makes you lame. Trust me on this and just don’t. Over the years you’ll find the styles and brands that fit you best and once you do, stick with them. Don’t try and reinvent the wheel. Knowing what looks good on you makes shopping easy. Rule of thumb: If more than one person compliments you on a shirt, that’s a brand you might want to go back to.
This might be a good time to mention that clothes look best on bodies that are in shape. Making the gym – or sports – a priority in your life is a great way to stay healthy AND ensure you look good in your wardrobe.
A HENLEY. Which is basically a long sleeve cotton shirt with 2 or 3 buttons at the neck. It’s a nice, casual look – waffle or plain – that says “I’m chill but still willing to make an effort.” And unless they’re worn to perfection or you (or someone else) likes to wear them to bed, you can officially let go of any High School sweatshirts or team shirt after the age of 23.**
Slim sweaters don’t have to feel conservative. They can look very cool.
A HOODIE. Seems obvious, probably doesn’t work after 50, but a great dark grey or navy hoodie can take you so many places. Casual places for sure, but still, that one piece of clothing will definitely earn it’s keep.
A NICE SWEATER. Honestly, living in California, you don’t need a ton of sweaters. A light weight, well fitted (see T-shirt) sweater can look amazing on a man. If I had my drothers I’d say, one dark grey, one black and one color – maybe blue, camel or cream. Just start with one and move forward from there. Again, personally, I like a v-neck because it looks good with a shirt underneath, but your father has some solid crew neck ones that look fantastic despite the fact I couldn’t tell you the last time he wore one.
This is an attractive man but I’m still not sure he’s pulling off this turtleneck. ralphlauren.com
A BIG, CHUNKY SWEATER. This is not essential but it’s great for trips to the moutains or say…Canada. Something wool and masculine in a cream, hunter green or dark grey. Crew neck is the standanrd here and please, stay away from turtlenecks. First, because you’ll probably sweat your balls off, and second, because unless you’re in a Michael Kors or Ralph Lauren ad, it is an incredibly difficult look to pull off without looking like an un-ironic version of 1970’s apres ski.
At least 5 WELL FITTED BUTTON DOWN SHIRTS (Read: not blousy or full). A perfect, slim white one you can wear without a tie (meaning it doesn’t have to do up around your neck). A white shirt that does do up around your neck. A blue button down (checks or plain) that you can wear with a tie but also more casually with jeans. Finally a couple casual button downs with patterns (plaid etc.) that might be a little bit hipster/a little bit country. Whichever your fancy. Men also seem to love a black button down but I find with those you either end up looking like everyone else or like the waiter or bartender, so you make that call. A button down shirt and jeans is a nice way to “dress up” without actually dressing up. It’s a pulled together look with minimal effort on your part. Add a blazer, you’re practically semi formal.
This is a big guy, but he sure looks slick in a slim fitted suit.
Speaking of blazers. You really should have a GREAT FITTING BLACK SUIT. It should fit like it was made for you and, if you buy correctly it should make you feel like a million bucks. A great black suit can double as a tux. It can be used as separates. It can take you from a job interview to a wedding to a bar. Tie or no tie, pants and jacket as stand alones, a tailored black suit is a wardrobe staple.*** And once you’ve learned to like suits, you can add as many as you choose. Nowadays you can even wear the right suit with t-shirts. It’s really a men’s wardrobe no-brainer.
4+ TIES. A dress tie with a sheen and no pattern in cream, bronze, black, or silver (just something classic that pops against a white shirt) plus 3 other ties of various subtle patterns. Once you start wearing ties you can branch out but I’d advise always aiming for classic and simple over busy and/or funny. Please no characters (unless you’re being ironic and you’re in on the joke) and use wimsy sparingly. Your Dad once totally rocked a turquoise floral tie, but it was for a very specific occasion (a Southern wedding) and definitely not an every day kind of thing.
WORK OUT WEAR. I’m not saying you need to be a walking billboard for Under Armour, just don’t cruise around in your sh*^test clothes and call them gym clothes. Once again, as soon as those pits go yellow, pitch it.
Casual, KICK AROUND PANTS. Joggers or tear aways. Something that’s comfortable but still looks presentable.
Leather jackets are just casual cool.
PROPER OUTERWEAR. A LIGHT JACKET like an army coat, or something casual, that you can swing on if it’s chilly but weighs very little and can be jammed into a bag (or ball) without fear of ruin. A wool (or if you can afford it cashmere) 3/4 CAR COAT that will keep you warm but looks slick. Your Dad currently has two of these on rotation, a camel one we had tailored (see ***) with a bit more room to go over a suit jacket, and a navy one that fits like a glove and looks amazing over a button down or T-shirt. They both look (and more importantly, make him feel) amazing. I’d also suggest a HEAVIER WEIGHT JACKET like leather. Your Dad’s worn a broken in brown LEATHER JACKET for years. It was a heafty investment at the time but, if anything, it keeps getting better with age. This year he also invested in a black one that’s more moto and less aviator. He loves that one too but it’s the brown one that gets the most play. A leather jacket can be a man’s best friend. It’s like cool sunglasses ****, able to elevate the most basic of looks to stylish extremely fast.
SHOES. Shoes are a big deal in our house. Not just because your Dad has 2 different size feet and we have to buy 2 of everything, but because shoes say a lot about a person. Men’s clothing is rather basic by nature so shoes can become an large part of your outfit. ***** The shoes I’d recommend would be: COOL SNEAKS – non-workout rubber soled shoes you can rock with jeans or shorts. RUNNERS – workout or sports shoes with excellent support for keeping in shape. COOL BOOTS – it doesn’t matter if they’re full length or mid calf as long as they fit your proportions and make you feel awesome. The right boots should, both metaphoically and figuratively, make you stand a little taller. Your Dad loves boots – Frys, lace up military, smooth side zip boots – they all work. He has one pair he currently doubles as dress shoes. Even cowboy boots rock. Whatever your style turns out to be the right boot can bring it home. Worn in is great as long as there’s no duck tape or flapping soles. DRESS SHOES. Yep. You need them. Most of the time you can probably get away with a dress boot, or lately a cool sneak (a look I’m not personally down with but is definitely popular), but there will be some occasions that call for a real dress shoe and you may as well own a pair you like. Look for ones that are slim to the foot without being pointy or skinny. A brogue or a stylish oxford can look fantastic. Get something that doesn’t look like you just went with the cheapest lace up to get it over with. Take the time to look around. Find something you can actually get behind. Unlike boots however, these ones you must keep in shape with polish and care. No matter how casual our society has become, a scuffed dress shoes still speaks volumes about it’s wearer.
Nice, seasonal clothing from a lovely inexpensive label.
SEASONAL CLOTHES – Linen pants and a linen shirt are a great summer alternative to jeans and a button down and should fit a little looser to account for the heat. Flip flops are preferable to sandles or crocs on men for, what I hope are, obvious reasons. A couple pairs of loose casual shorts and maybe even a tailored pair are great for summer and get yourself a swim suit that fits and flatters as well as a rash guard to protect you from the sun. Avoid gigantic floppy board shorts that could fit 3 people. For the winter I’d say find a good beanie, well made (warm) leather or wool gloves and a cool scarf. Everything else in your wardrobe can be used almost year round.
PROPER GITCH. Whether you’re a boxer or a boxerbrief man (which, by the way, is what the 6 year old version of you prefers), until you’ve had all my future grandchildren you should stay away from breifs. Studies show they aren’t so great for your boys and honestly, they’re a bit showy. Also, though I imagine you might go through a funny underwear phase at some point in your life, stick with plain colors – black, grey, even red is fine. White has a tendancy to look crappy (pun almost intended) and crazy pickles, smiley faces and paisley are a bit much. AGAIN, as soon as they start looking ragged, lose em! Are we seeing a pattern here?
Henley, Pea Coat, Good jeans, cool boots.
Remember, not everything has to cost a million dollars. Sure, it would be lovely to always shop at John Vervatoss or Tom Ford but there are great things at all price points. Check out the H&M of your day. Right now Express sells really nice men’s suits and you can find great fitted button down at Banana Republic or amazing quality slim T-shirt at the GAP. Check the quality of the fabric and if it passes the test, the only issue becomes how it looks on you. If it looks and feels good, it is good. It doesn’t need a $200 price tag to prove it.
If you’re going to spend money on anything start with the shoes. Superior shoes make a huge difference to the quality of your day…and your back. Then look to a proper fitted white button down. Your Dad had a Helmut Lang one he wore into the ground. No shirt has ever looked better. Finally look to the leather jacket. Those are good places to start with your money. After that I’d say jeans and suit. If you’re in shape you don’t need to spent $150 to make a T-shirt look good. It’ll look good by proxy.
Even super casual can feel pulled together. Thanks vogue men.
So, that’s that. Yes, you’ll wear baseball caps (forwards AND backwards – sorry Dad). Yes, you’ll have some questionable fashion choices over time (I’m looking at you one shoulder-ed overalls) but for the most part you want your clothes to accentuate, rather than distract from, who you are. You want to look polished, or at least, strategically casual. You want to be taken seriously so you have to appear like someone worth listening to. As comfortable as Addidas slip ons might be, no one ever took advice from anyone wearing them. You want to look in the mirror and feel good. You want your fashion choices to tell the world you respect yourself enough to care. That you’re someone worth respecting.
I’ll love you no matter what you wear but what you wear is a choice.
Choose who you want to be.
*Cavat: If you turn out to be a rockstar or professional skateboarder and your entire wardrobe consists of leather pants or baggy shorts you can skip this letter but, for the sake of argument, let’s press on.
** Acknowledge that no matter how much you love something “the time comes” for almost everything in your wardrobe. That’s you shredded jeans with no ass.
*** Your clothes should never bag or bulge. They should fit your body as if they were made for it. If something you own is good but not great or, you love something but wish it fit better, never underestimate the power of a professional tailor. A good tailor can make anything – from a dress shirt or a coat to a suit and a pair of jeans – look like a million bucks for a minimal fee.
****The right sunglasses are key. Start with classic styles that won’t break the bank like Ray Bans. You can’t go wrong with classic American cool. As your tastes and budget expand you can look at lines like Persol but you can’t go wrong with an old school Ray Ban.
Dressy shirt, nice watch, rope bracelets. Stylish can come in many different forms.
***** Men can rock a cool necklace (leather, sometimes metal, I’m not much for gold), the occasional ring (I personally like a simple wedding band, but there’s no hard and fast rule) and the right bracelet – rope, copper, leather (please no diamonds) but for the most part, mens’s accessories are pretty limited. Watches are a good place to start -the right ones never go out of style and can ultimately be passed down. Cufflinks are nice if you live that sort of a lifestyle. Tie clips are currently popular with the dialed-in hipster but not all men can pull off the skinny ties that go with it, and of course, hats which, I’m thrilled to say, have come back in style. Beenies are obvious but fedoras and their ilk are also incredibly popular these days and worn properly can really add to a man’s personal style.
When all else fails you can always look to David Beckam … or the David Beckham of your day. That man has a good time getting dressed.