Some questions are better answered publicly since others might be asking the same thing, or, one of you has the perfect answer. If you’ve got a style tip, question, or anything else you’d like to pass along, you can send those in here. If you’d rather your question not be featured in a future mailbag, just go ahead and say so in your email. Feel free to hit the comments with other options for answers to this most recent batch of questions. Top Photo Credit: Tracy O.
Q: What color/fabric of suit should I buy first? Then after that?

I have a good charcoal suit that fits me well, but I was wondering what to add to my suit wardrobe. Was thinking of the navy J.Crew Thompson next – but after that, I’m not really sure where to go. Should I explore other fabric types (cotton vs linen, etc)? Or just stick with wool? If I get a light-grey wool suit, is that versatile enough to use in warm weather? – Nikhil
This really depends on where you live and what you’ll use the suit for. A Navy wool suit is almost always the first choice. Charcoal or light grey usually comes next, with most picking charcoal. Those two suits are going to be your foundation. From there? Buy what you like and what you’ll get the most use out of. If you live in a warmer climate or just love wearing suits in the summer, go with a breathable suit (wool breathes too) in a lighter color with a breathable, or at least minimal lining. If you’re in air conditioning all day, explore patterns and stripes. But since you already have charcoal, navy wool is next, unless you have a pressing need for something more appropriate for summer.
Q: I work in a jeans + t-shirt workplace. Can I dress up?
I just started a new job in the gaming industry in Chicago. Everybody at my company wear jeans and t-shirts, polos, or untucked casual button-downs. When I went for my interviews, I wore a casual button-down, tucked into nice jeans, and a blazer. I have not seen anyone else wear a jacket or tucked their shirt in since then. The CEO wears t-shirts, shorts, and sandals. I’m trying to fit in, but feel professional at the same time. This week, I wore jeans, casual leather shoes, and buttons-downs, which I didn’t tuck in after the first two days. Even then, I felt like the shoes were out of place. – Dan
This is a hard one. I once got demoted/half fired from a job in a similarly casual work environment, and during the somewhat ugly downgrading process, my manager told me in a one-on-one meeting: “there’s only one guy around here who wears a tie, ever, and that’s you.” I wore a tie maybe once or twice a month. (sidenote: I hardly ever wear ties now). Anyway, the point is, you have to assimilate… to a certain degree. How? Casual canvas sneakers are going to be your friend. White Keds or grey Converse can dress down just about any outfit. But skip the tie. Layer up in the fall with jeans, V-necks, and button up shirts. In the summer, stick to lightweight pants or well fitting shorts. Keep your shoes to classic sneakers with the every so often foray into leather loafers, and just wear stuff that fits well. All the more reason to wear a suit when you take a date out on the weekend, right?
Q: Stylish cars on a budget?
What do you drive? – Greg
Other than ALL THE LADIES WILD?!? (…right) Aside from that, there was a great discussion about good looking cars on a budget awhile back over on Threads. Fellas, turning to you now. Taste in cars is pretty individual, like clothes. What do you drive? Or are you just not a car person?
Q: Thoughts on services like Trunk Club?
What’s your take on these services that send you a box of clothes hand-picked by stylists? Worth it? – Rob
Plenty of us hate going to the mall. But plenty of us also hate surprises. These services offer a stylist who picks out clothes & accessories for you based on your profile, then a box is shipped your way. You keep what you want (or none of it) then ship the rest back with a pre-paid label. But… you never actually pick out your own stuff. It’s all done for you, and as far as pricing… it seems steep. Blazers start at $300? Button ups start at $80? Sometimes these boxes get well into the hundreds of dollars, and it seems(?) like you’re paying full retail. Maybe not such a good service if you’re into assembling your own look and are into hunting for deals. This seems like going golfing and you shell out for a caddy to not just carry your bag, but also hit all your shots except for the putts. Yet it could be a terrific way to discover new brands with little to no risk since you can always send it back.
Q: Does my testosterone drop if I carry a tote bag?

I like the looks of a lot of tote bags, but they’re just too girly for a guy to carry, aren’t they? – Andy
For better or worse, men’s style is very function driven. So when we see some guy carrying a tote-bag for the sole purpose of style, it seems a little goofy. If you’re lugging a bunch of stuff into work, let’s hypothetically say… a watch to review then giveaway, a pair of shoes to shoot pictures of, your lunch, and an SLR camera, then a tote bag can come in pretty handy. Especially a Made-in-the-USA number with leather handles, wool body, and waterproof nylon bottom (sold out, sorry). So if you need one, use one. Meanwhile, it might feel more comfortable/look more masculine to just carry it by hand, instead of slinging it over your shoulder like dear ol’ Ma used to with her Pangaea purse.
OR… you could do the most “manly” (read: adult) thing possible… and just carry what you want, how you want, and not give a damn if some over-observant mouth-breather thinks your tote looks like a purse. (Above totes by Everlane. $35 – $40 and made in the USA.)
Got a question or a style tip? Send them in here. Additional answers to the above questions can go in the comments.
Stylish cars on a budget? 986 Boxster, they can be found all day long at under $15k. Being able to drop the top before you drop the hammer will make all the girls hot.
I have a 2012 Ford Focus in a dark blue. Everyone I’ve talked to about it has said that they love the new styling. Best of all, you can get a base model for under $20k.
The 2013 Fusion is also gorgeous (IMO), if you need a mid-size car instead of a compact.
Regarding how to dress for a workplace, Joe hit it on the head that it’s relative to what everyone else is wearing.
If you are looking to move up in your job (not everyone is and there is no problem with that), it’s said that you should dress for the job/position that you want, not necessarily the one you currently have. This usually means that you dress up one notch relative to what is the norm. In a casual environment, it might be just tucking in your OCBD shirt, wearing polos instead of t-shirts, or wearing the nice casual shoes (loafers, etc. like Joe mentioned). Still casual, but you become the “presentable casual guy” at the office.
From my personal experience, at my job everyone dresses casual/business casual. I usually stay on the business casual side, with an occasion tie/jacket thrown in. At work, I’ve definitely become the person that is always presentable to a client at any time (they sometimes pop by at random) and my bosses know it.
Where’s the plaid jacket from in the first post? I’ve been looking for a navy plaid blazer for a while now.
Second on the Fusion. They’ve done a really nice job on that.
Tote bag… eh. Depends on the bag and how you’re carrying it. Second Joe on that point. Granted lately I have found myself carrying a Vera Bradley purple diaper bag on one shoulder and a 1 year old on the other… so not in a position to throw stones.
After carrying a diaper bag for te past 4 months, a tote bag doesn’t seem feminine to me anymore.
Stylish car for cheap? I’d vote for a 2002 Honda S2000. Find an unmodified one ($17000–they hold their value well) and all you need to do is check up on the soft top connections, look for wheel well rust, and listen for an rattles. Have fun winding the engine up to 9000 RPM, feel the wind in your hair, and watch how your lady’s eyes get big. It’s a cone-cutter, not a drag racer, so don’t go in expecting crazy torque. (You could always add in a supercharger…mmm….)
Totes, satchels, murse… whatever you call it, it’s still for the ladies. Carry a brief case or messenger bag so you don’t look like a “Hangover” groupie. If it was fit for men in the US to carry totes, satchels or murses, they would have done it years ago and it would be part of the classical style today.
Stylish cars- New and under $30K and 4 door: Acura, Volvo S-60 (maybe), BMW 1 seres (maybe), Mazda 626.
Stylish Used (you did say afforadable): Bmw Z3/4 and 3 series (probably $8-$20 2000-2011 respectively depending on how and features etc),
I have a friend who uses trunk club.
The service is pretty personal!
You end up having conversations on why you keep stuff, and why you didn’t keep other stuff. He likes the service and the woman who looks after him.
He fully admits it is expensive though, but the more you use it, the more your shopper figures out who “you” are.a
Yeah, the S2000 is a great choice, and I don’t even like Honda. Looks great, fast, fun to drive.
That said, for the same money, you can buy a damned good Volvo S60R or V70R, which are more practical, faster, and safer. And, while they’re not as cool, girls/women are probably going to appreciate your Volvo more than your Honda roadster. Even better, you’re far less likely to get pulled over. (Trust me on this one — I’ve done 60 in a 40 past a cop in my Volvo and had no issues.)
Oh man, not a Boxster. The Boxster is one of the ugliest sports cars ever made — Porsche’s design on it was even lazier than usual, and they just grafted the front end onto the back end instead of actually designing the rear of the car.
Besides, they’re kinda slow. 😉
Then you and Danny Zuko can burn up the quarter mile. https://www.youtube.com/watch?v=wK63eUyk-iM
I tried trunk club once- way too expensive. I was clearly not thier targeted customer. But they do have really good customer service.
^this
I love my Nissan Juke.
The old boxster looks a bit soft and has always been mocked as a women’s car. I think the Cayman would be a better choice!
Says everyone that has never driven one. The same “criticism” is heaped on the Miata.
The Boxster has long been hailed as the true driver’s Porsche of current times. I would more quickly buy a Boxster over a 911.
The Juke is stylish in the way that a Bulldog is cute. They are both so homely that they are cute/stylish.
The Juke with the turbo 4 is giggle inducing when driven hard. There is something fun about getting 17 MPG from a small 4 cylinder.
At least they don’t drink oil like a RX-8. Right Joe? 🙂
Comment on the casual work environment: If you can pull this off, and are willing to be consistent, then doing a Dan Draper can be hugely beneficial to your personal brand. My first job was in an ad agency in London – about as casual as they come.
One guy had a habit of dressing up like a character out of a 1930’s movie. Silk scarves, double breasted suits, handmade shoes. Because it was an expression of who he was, rather than a costume, and because it was obvious that he felt comfortable in the outfits he was wearing, he never had any issues – indeed he went on to quite the career.
Sure the miata is cheap and can be fun to drive, but you cannot defend its styling. Awful. Plus any normal to large leaning guy sitting in that thing looks out of scale
Please elaborate. The Miata styling is classic in the same vein as the old British roadsters were classic. The car is so simple in a world of over styled vehicles.
Simple – that is true. It is essentially an ellipse. All rounded corners and soft edges. It looks like a plastic barbie car. At least an old MG had some personality (round corner headlights and the grille). I guess I’m missing the part where today’s cars are overstyled. Maybe they are all to the same extent and that is why they all look pretty generic. Granted not a fan of the Jag XKs from late 90s early 00s either.
Suitsupply Napoli fit from last year…
Congrats on the new addition though Mike!
No. Kidding. (Gotta keep the rotary happy though)
Thanks Joe!
You talk as though the Boxster is much different from the Cayman. One has a roof and the other doesn’t. Cayman has nice lines so saving a bit of weight and extra structure rigidity is a bonus.
This! I can’t tell you how many times in my life I’ve had people tell me “only you could pull that off”. Which seemed absurd to me. The only thing I’ve ever had to do to “pull something off” is to do it confidently, and without apology. I understand and respect that most folks feel the need to fit in, but if you are a little different, but do it because you LIKE to, and not because you are trying to stand out or make a point, people will generally accept that as a genuine expression, and not a stunt.
NOTE: My view is skewed by how/where I was rasied, but…
Regarding the question about stylish cars on a budget, few vehicles (IMO) exude style and value like a good ol’ American pickup truck. You can get a 8-cylinder engine, seating for 6, and tons of utliity for under $20k fresh off the lot.
If you live in a dense city with tiny parking spaces, it doesn’t make sense. But otherwise, trucks have plenty of charm that is suitable for any setting. They’re not just for farmers any more than a pair of Levi’s is. I do live in Dallas, but it’s not uncommon to trucks and SUV’s valeting at fancy restaurants. I was self-conscious about it at first, but then I saw others doing it, too.
Auto makers like Ford and Chevy have been making them for longer than our grandparents have been on this planet so at this point they’ve got winning products that they are just refining and constantly making better.
We also recently upgraded my wife’s vehicle to a 2011 Kia Sorento, and that thing is pretty darn nice. It’s larger on the inside than it looks on the outside, comes with a lot of standard features that other companies charge for, and the upgrade packages have tons of stuff worth upgrading. We got our 2011 used with all the bells and whistles (navigation/satellite radio/backup camera/chrome accents/etc) for $21k.
Sounds like a Jalop if I’ve ever heard one.
Nothing beats a Volkswagen GTI for a combination of fun and comfort on a budget.
It’s sort of in a ‘love or hate’ category, but I enjoy the Cadillac CTS.
The style has undergone little change in the last decade, so purchasing
a well-kept, low-mile mid 2000s model used in the 9-13K region will
have little aesthetic difference to a brand-spanking new one for the
30Ks – and even that is relatively affordable for a car still classified
as ‘luxury class.’ I might be biased towards the car though; I have
childhood memories of bouncing around in the boat-sized backseat of a
Cadillac.
There’s also a bustling market for truck add-ons/accessories to fully customize your vehicle, but the wrong ones will make you look like a hick (even though those are often the most fun).
I can vouch that the Miata was insane to autocross in with a little suspension & tire upgrades. I felt like a fly on the highways, but when it came to pure driving thrill, it was up there.
Touche!
Wearing shorts will make everything else you’re wearing seem more casual. Dan seems like he’s in a good position to use that to his advantage and experiment with, say, tucking an OCBD into shorts, wearing a wingtip now and then, etc. Hard to claim a guy is too dressed up when you can see lots of leg hair.
GTIs are an incredibly well-regarded car, but I can’t get past the fact they look kind of like an egg with 4 wheels and a turbo, and the whole “boy-racer” thing. It’s certainly an option though, and I’d look hard at that and the Focus ST.
I’m going to be in the market soon, so this is on my mind. My current thinking is going for a slightly used Range Rover Evoque 4d, though that’s probably even more polarizing in the style dept.
As a duly elected representative of the Mouth-Breather and Knuckle Dragger Society, it is written into our by-laws that one should carry anything they feel is necessary, but if it looks like a purse, then it is. Being a new millennium and being that there are people of many proclivities and persuasions, if you are good with a purse, then so be it.
I don’t have a problem carrying a diaper bag, holding my wife’s purse, beach purse, grocery purse or any other minor indignity, mostly because if I act like a jerk then I don’t get to do the MOST manly of activities later than night. But, I seek out something more suitable for myself. LL Bean makes some great duffle bags that have a more manly look to them.
Excellent comparison! I feel the same way. And I’ve gone from the diaper bag, to SLR bag, messenger bag, gym bag, briefcase, you name it. For whatever reason, the tote is just the easiest bag to use when it comes to accessibility, versatility, and convenience. Since the shape of the bag isn’t as structured, it can hold more than it seems. It’s also a good way of concealing whatever it is you choose to lug around. I will note though that I feel you would be treading water with the choice of colors. I use this black canvas one from Fossil which quite frankly has been my everyday bag since I got it! http://s7ondemand7.scene7.com/is/image/FossilPartners/MBG9024001_main?$datafeed_main$
Re: casual office – totally agree on taking it up just a notch. While I can get on board with dressing how you want and owning it, generally you don’t want to be the office peacock. That’s not to say you shouldn’t express your individuality with style but when you go all out in a casual office, you’re essentially peacocking and worse it can be somewhat pretentious (or at least perceived that way) as folks think that you think you’re “stunting” on everyone.
I am fine with messenger bags and briefcases of all types but I just can’t get on board with the tote bag trend.
Ah man. Missed it!
The easy answer for stylish car on a budget is whichever used Audi suits your needs.
I drive a 135i Convertible which I Iove but got way more comments when I drove a TT.
I’d be careful about dressing up in the Video Game industry.
My brother once wore a full suit to his interview at a game company, as we were taught to do by dear old mom. Everyone else wore jeans, t-shirts and sneakers. Maybe one guy had a button-up. And he said he got some odd looks. He got the job, but the boss told him to never wear a suit again.
The attire during work was the same. Everyone was in jeans and sneakers and t-shirts. The environment was more of a “garage club” setting. Not professional at all. Just a bunch of guys hanging out talking about video games. And barely any women on staff. Very Little Rascals.
If you’re the leather shoe and blazer and tie guy at a video game company, you run the risk of alienating yourself. I think the suggestions Joe made are pretty spot on. Nice, fitted jeans, classic canvas shoes, but I’d skip the dressy button-up and V-neck sweater for well-fitting polos, henley’s, etc.
But there is quite a price difference between the Boxster and the Cayman (according to my cars.com search).
Yeah. I guess I’ve been reading jalopnik too much – it’s weird to see anyone criticizing a Miata or a Boxster.
I think the real distinction is your purpose for carrying the bag. Women tend to carry purses when they don’t really need to access the contents, or could fit the items they really need in a coat pocket. The purse is an accessory that is sometimes without a truly functional purpose.
If a man has a masculine looking messenger bag, but carries it everywhere when he doesn’t need to, it’s a purse. If he carries a tote bag because he actually needs to transport the bag’s contents, it’s not a purse.
But I also think it’s totally cool for a dude to carry a purse. Do whatever you want.
I highly suggest you look through some Consumer Reports magazines before purchasing a vehicle, sticker price isn’t even near the biggest cost. They have a vehicle edition release each year, where they estimate various number of years out cost for tons of vehicles. It gives you a good idea of what vehicles have had issues with reliability and how much you can expect to spend.
Honestly, the new Honda Accord got one of the highest ratings they have given a vehicle in years, it was pretty close to perfect and it looks great. Although not the most refined vehicle, you will be able to drive that thing to dust and still resell it for good money at some point. Sometimes practicality can also be stylish.
No offense man as I know we all have different likes and dislikes, but let us not get carried away here. The Boxster was developed as the Porsche for the masses and is a nice driving car…but it is not a 911.
I just want to say: there is an art to wearing a tie so that it makes others want to wear a tie, instead of ridiculing you for wearing a tie.
You can definitely wear a tie casually, you just have to know how to do it. See Ben Wyatt on Parks and Rec, or Joseph Gordon Levitt in 500 Days of Summer (and almost everything else he does.)
I bought a 2013 Fusion back in January and absolutely love it. I get complements on it daily. Most people are shocked that it is a ford, and think it looks more like a Jaguar or a BMW. Mine is black with tan leather and 19″ contrast wheels. Highly recommended!