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: Slim, Suit-Appropriate Wingtip Boots?
I’m looking to buy a pair of brown or cognac wingtip boots to wear with suits in the fall and winter. But I haven’t been able to find a pair that looks as dressed up as a nice pair of Oxford Wingtip dress shoes such as the Allen Edmonds McAllister. The Allen Edmonds Dalton, Florsheim Hawley and Gaffney, Wolverine’s Addison and the Aldo/Mr. B’s Blake don’t quite fit the bill. The Allen Edmonds Fifth Street isn’t a wingtip, but it does have some nice broguing. Any suggestions? – Matt
Three things will dress up a boot: #1. A slim heel & sole, #2. No reinforced metal eyelets, #3. Closed, true oxford lacing if you can find em’. But boots are meant to be tough. And wingtips/brogues also have a rugged past. So a slim suit-worthy brogue boot is sorta the Porsche Cayenne of the shoe world (only, the shoes look much better). Stick with the Fifth Street if you have the cash. They’ll look just fine as long as you’ve got some weight to your suits this fall (no breezy tropical wool.) Otherwise, there’s this ultra-cheap option from ASOS, and these from Hugo Boss are 40% off (down to $143.40) through today, 10/4.
Q: Building out the Business Wardrobe?
After not landing the start-up job from a couple months ago (thanks again for the Style Debate about it), I’ve since been employed as a consultant. So while before, I was wondering how dressy is too dressy for a casual workplace, I now come to you with the opposite problem: how should I prioritize building out my dressed-up business wardrobe? I have two suits, a charcoal grey Alfani Red, and I just invested in BR’s Tailored suit in Navy (absolutely gorgeous and fits so good off the rack…). I’ve also purchased a couple pairs of all-wool, trim-fit, flat-front dress slacks. What’s next? Classic Navy blazer? Tweedy sport-jacket? How should I build out my business wardrobe from here? – Caleb
Congrats on the job! Start with two more suits if you can afford it. One light grey, and one with a noticeable pattern like a chalk stripe of subtle/shadow plaid. It’s always easier to dress down something dressed up than to do the opposite. A plaid or bold checked shirt plus a knit tie with a nice suit makes it more friendly and less stiff. And there’s always tieless, layering with sweaters, etc…. It’s hard to dress a tweedy sport-jacket up for a boardroom presentation. Meanwhile, it’s better to spend a little more on the suit and skimp on shirts and ties (Target is your friend). SuitSupply just added some more terrific options to their $399 line. If that’s too steep, wait for a One Day Sale at Macy’s, hit BR with some coupons, or keep an eye out for all wool suits on Overstock.com.
Q: Do you bowl?
Was just reading the recent article about the Lands’ End Canvas Rugby… and this has nothing to do with the shirt, but more rather the pictures you took. You wouldn’t happen to be a bowler, would you? - Jeremy
Nope. Although I do believe Pete Weber’s “who do you think you are??? I AM!!!” moment will go down as one of the greatest nonsensical celebratory outbursts in sporting history. Per the pics: Didn’t have a rugby ball, and the bowling ball was the closest thing on-hand at Dappered Headquarters. Came with the bag I carry my lunch in. As for the pin, that’s another story.
Q: Watch under $100?
I like watches, but I just don’t have the desire to wear anything expensive. My father was once robbed of a very expensive watch, and that might play into my reluctance to buy & wear a watch that’s more than $100. That said, what’s the best watch out there for under one hundred dollars? - Stephen
It’s hard to go wrong with this slim, simple, elegant but not girly, silver dial dress watch from Bulova. The band is awfully thin, but the timepiece itself is great. Get a solid springbar tool, a couple of different bands, and maybe even a striped NATO style band (yep, even on that dressed up dial), and you’ve got one watch that can pull off multiple looks easily.
Q: $1500 Wardrobe Part II?
Will you be making another $1500 Wardrobe Series? Honestly, it was one of my favorites… and now that I have the money, another one would be awesome during the holiday sales season! -Mike
Sure. How’s November sound?
Q: Symphony-date-worthy suit needed. NOW.
I’ve been sucked into attending the Symphony next Friday as well as a musical within a week or two after (she’s beautiful, I can’t say no). The last time I purchased a suit I weighed 210lbs. I’m now 175lbs. I’m just under six-feet tall. If worse comes to worse I could wear my old suit but I’d definitely look like crap. I want to look good for her and I’ve worked hard to lose the weight so I’d prefer something well fitting and slim. I don’t have a reliable tailor so I need something that’s going to fit off the rack. Help? - Cory
Congrats on the date and the weight loss. You’ve slimmed yourself down into what should be the perfect shape for a 40R / 32×32 or 33×32 Banana Republic Tailored Fit Italian Wool Navy Suit Jacket & pant. Keep an eye out for a 30% off sale these next few days (they run them often) and you can land it for $353.30 total. It’s as good as a fused suit gets. Great fabric. Offer her your arm and once she touches the sleeve she might not want to let go. Also, don’t clap until everyone else starts applauding at the symphony. Just when you think they’re done playing and you’re supposed to applaud, they’ll start right up again. Must be one way the tricky upper-class spot us well dressed serfs. UPDATE: BR just launched a 1-day 25% off $150+ sale w/ BRSTEP25. Not the best promo overall, but not bad if you’re in a pinch and need a suit. Credit to Michelle in the comments for the tip.
Q: Dappered for women?
I am happy to say that between Dappered and Effortless Gent, I’m slowly but surely becoming a well dressed man. My wife was complaining the other night about how its easy for guys because there is “less to dressing a guy” than with a girl, and that its hard for her to keep up with what’s in fashion for women. Are there any blogs out there similar to yours or Effortless Gent for the ladies? Help me out and you’ll make me a hero! – David
Thanks for the kind words David. Dappered does have a better half. It’s fullclutch.com. Now as far as there being “less to dressing a guy“… well…
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