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: Looking for grey wool trousers
Do you have any recommendation on grey wool trousers? I’m looking to pick up a pair, but I don’t know where to begin other than jcrew. – Buddy
Lands’ End. Take a look at their “Year’rounder” dress trousers in the tailored fit. They’re made from Merino wool, are extremely well reviewed, and have been suggested a few times in the comments here and on threads. Plus, at $79 retail, you’re looking at $50 – $60 with codes. OR… save up and go with a full suit. Instead of trousers + shirt + tie, try dressing down a new, full suit by going tieless?
Q: Interview dress for a “creative” job
I’ve got an upcoming interview at a media production company that’s known for doing really creative work. Should I stick to normal, conservative dress for the interview? Or have more fun, being that they’re known for their creativity? I don’t want to come across as a bore. – Travis
Stick with classic dress that’s well tailored, and let your talents & genuine personality show that you belong there. It’s no time to peacock (major thanks to reader, photog, and graphic designer Eric H., for passing along that article). Here’s a dirty secret about the “creative” industry. The end product might be shiny & pretty, but like any widget-maker, successful creative businesses have to operate with consistency. And consistency isn’t always fun. The doughnuts have to be made. Every day. Without fail. When a project needs to get done, you want employees/co-workers who you can take seriously and count on. Does a boutonniere, vintage tie clip, and neon orange socks (but they pop!) convey that? Probably not. They want someone who can make the f*cking doughnuts. Get the job first, then work in more creative looks later, if appropriate. (photo credit: J. Turner)
Q. Thoughts on Monk Straps?
Greetings. I found Dappered about a month ago and I really like the site. However, I’m still learning and I was wondering what your thoughts on double monk straps were? Are they a classy shoe or more casual? Leather or Suede? I was looking at these from JC Penney. Do you think they’re worth it? Thank’s in advance. – Gabe S.
First, let’s all take a moment to allow Diversification to clean up the coffee he just spit all over his laptop. You good man? Great. Gabe, welcome aboard and thanks for the kind words. No secret that monk straps get a lot of play on this website, despite the fact that many fashion-concerned fellas now consider this style to have jumped-the-shark. I disagree. They’re sort of like the well-kept stubble of the shoe world. Everyone did it, and now it’s tailing off. Doesn’t mean it doesn’t still look good. They’re a great in-between shoe. Plenty dressed up for a suit, but can be easily dressed down. As far as the JCP option, saw those in person and the leather wasn’t as good as some of the other JCP shoes. And since monks kinda draw extra attention, so-so to crummy leather isn’t ideal. Now, they’re an extra $100, but consider the Neumora from Allen Edmonds via their Shoebank. Seems like they got a bunch of those right now for $159.
Q: What’s with that weird hand on Thursdays?
So… on your roundup posts, you use this awkward hand photo… curious as to why?
– Kevin M. via Twitter
Well, they were originally going to be called, as you referred to them, “roundups”, but the herd was just not cooperating for a photo… so, there wasn’t anything to take a picture of for the top of the post. That’s why it’s called a “handful” instead. Five of the better sales (one for each finger) plus bonus sales when necessary. Handful = picture of hand. With five fingers. One for each sale. Which happens to be the same number of fingers most people have on one hand, and thus…
Q: How do I start wearing blazers?
I was wondering how you start out wearing sportcoats/jackets? I’m a college undergrad who wants to upgrade his appearance for occasions like dates or presentations. I really have no idea how to start. – Andrew
This is a completely legitimate question. After years of having the idea that jackets & suits are lame & uncomfortable (wrong) beat into our heads, it can feel odd to put one on and walk outta the house. Yet this is tricky. Because like your first spoonful of cookie butter, once you start, there’s no going back. Here’s your gateway: find an unstructured, maybe a bit rumpled, cotton blazer that looks good with jeans and an OCBD. Maybe get it brought in a bit at the sides. Don’t wear it all the time (hey look! it’s BLAZER guy!), but don’t be afraid to wear it casually. You’ll probably catch some good-natured-shit from a few mouth breathers, but their girlfriends will most likely think you look good.
Q: White dress shirts + “flashing”
I was wondering what your and the readers’ thoughts are on wearing undershirts under white button-down/-ups. Always? Depends? Full disclosure: I think I’m looking for some confirmation. I never wear undershirts, but just bought a white JCF OCBD and am on the fence about how see-through the fabric is. It looks fine to me, but I keep worrying that in the right light I’ll end up inadvertently flashing folks? – Peter
I think that if you’re on this website, you have a certain attention to detail that most others don’t have. And one thing that can be gleaned from that fact is that if you’re on the fence about it, chances are, nobody else is gonna notice. I say skip the undershirt. If you flash a slight hint of man-nip in certain light, then so be it. If you DO want to go with an extra layer, choose a grey undershirt instead of white. You won’t get those contrasting lines at the sleeves/neck. Or, better yet, wear your extra layer on top… in the form of a nice & lightweight warm weather blazer. And stay outta the fountains.
Got a question or a style tip? Send them to email@example.com. Additional answers to the above questions can go in the comments.