Dressing for a casual workplace, totes, & more – The Mailbag

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.

 

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.