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: Tucking sweaters?
Question about the sweater tuck… Many of my more trim fitted thin sweaters often lose the elasticity to their waistbands so I can’t fold them over properly and they look strange hanging down.Yes I understand this might be a sweater by sweater call, but I know it might look better if I tuck it in. But it feels strange. Is there ever a time where tucking in a sweater is appropriate? – Chris
The Great One and Ovie seem to favor this look… but that’s a different kind of sweater. The sweater tuck seems to fall into the same category as the disheveled chino cuff roll. Both perpetuated by J. Crew, and both seem to be a little too artificially sloppy for most. Like wearing a watch on the outside of a shirtcuff, or a denim jacket under a blazer, once you start mixing up the order of layers it gets pretty hairy. 99% of sweaters are too thick to tuck in all the way around. So tucking in one side would be the strategy… but does that ever really work? I say let it hang.
Q: Thoughts on the JC Penney Harris Tweed Blazers?
I’m surprised y’all haven’t featured JCPenney’s Harris Tweed jackets since the price drop. They’re on sale for $150, and the code NOVSAVE drops the price down to $120 with free shipping. You really can’t beat that price for real harris tweed. I don’t own one but people who have are complementary about the shoulder, armholes, and cut. The code’s one of those 15% under 100, 20% at $100, and 25% at $200. – Justin
Good call by Justin. Those first popped up in the fall preview post, but sorta fell off the radar. Last year’s “classic fit” blazers from Stafford were pretty off. These don’t seem to have made their way into all (many?) stores, and… where the heck are the 38R jackets? Nothing smaller than 40R? Damn.
Q: Bucks and Chukkas on a College Budget
I’m looking at getting myself a pair of suede bucks and a new pair of chukkas. I’m a college student, so I’m on a tight budget. I really like the look of the JCrew’s Kenton suede bucks and the Alden 1494 suede chukka. Any ideas on what would potentially be more in my price range? Especially on the chukka? I really like the hard bottom on those. – Colin
Bucks and Chukkas are two styles that’ll get a lot of use on a college campus, so nice picks Colin. Hat tip to LosRockets over on threads for digging up this deal on these Made in the USA Walk-Over bucks. They ship free with SHIP75. But $120 is still triple digits. A super cheap option would be these from Bass
Q: Blazer wearin’ in a decidedly un-blazer world.
I live in a sleepy beach town in Florida. How does one get in to wearing blazers and sport coats out and about when you are 100% assuredly the only person to be seen all night wearing one? If I head out on the town Friday night, hitting up maybe four or five different places, I’ll be lucky to see more than a dozen guys wearing dress shirts that are actually tucked in. It’s made me think I’ll never actually be able to wear blazers. – Dustin
The less structure = the less formal. The more rumpled = the more casual. So take something like the Merona Kensington (pictured above) and pair it up with jeans. And consider sticking to jeans until you get super comfortable with your new sportcoat-wearing self. Even the most casual sportcoats can look a little too dressed up with chinos or cords. For the shirt, go with casual poplins or OCBDs instead of stark white dress shirts. Drinking a beer instead of the decidedly crisp yet well balanced Pinot Gris might help fight off the “look at stuck-up dude” vibe too.
Q: When is a shirt too cheap to tailor?
Is there ever a point where a shirt is ‘too cheap’ to tailor? I’m a tall guy with long arms and a thinner build, so absolutely nothing fits me off the rack. Even when I find the mythical 16.5 36/37, the sleeves fit fine, but I could house half of Ringling Brothers in the extra material around the torso. That puts me in a position of needing to get every single shirt tailored if I want to look good. So what’s the cutoff point? Do you spend $30 to get a $30 shirt tailored? – Also Dustin
Here’s the thing about getting used to wearing blazers Dustin… you can get away without tailoring all your shirts at the sides. BUT, to actually answer the question, there is no line. This is sort of like owning a beater of a car that works great but you feel weird about putting any money into it for maintenance. I’ve got a 1991 K5 Blazer with so much rust you can see through the floor in some parts in the back. It didn’t pass emissions and needed a few hundred bucks worth of work done on it. But the thing ALWAYS starts no matter the weather, it’s a 4×4, can pull down a house, and it comes in handy for moving big stuff. If you like the shirt and need the sides taken in? Doesn’t matter how much you paid for it off the rack. Like the $30 Merona Ultimate Shirts seen above.
Q: Matching shoes for groomsmen?
I’m getting married next July, and I’m having my groomsmen buy a navy suit (colors are navy and pink). I don’t want them to show up wearing different shades of brown shoes, so as part of their groomsmen’s gifts I’ll be buying them a pair of shoes. Do you have any suggestions for brown dress shoes in the $50 – $75 range? I have 8 groomsmen plus myself. – Nick
First, congrats on the upcoming wedding Nick. Hope the day goes stress-free for you. Second, groomsmen now have to have matching shoes? The wedding = broadway musical production thing is really getting… detailed. I think it’d be good to consider just having them wear whatever pair of dark brown shoes they happen to have. It’s more likely they’ll have dark brown compared to a tan or walnut. And you can always ask. If they majority of your guys don’t have brown dress shoes (totally possible in our increasingly-casual society) then your idea to pick them up a pair as a gift makes sense. But $50 – $75 is pretty tight for a pair of suit-worthy shoes. Try the Claiborne Wallis from JC Penney. They’re sort of a less-fortunate man’s AE Kenilworth. Make sure your guys try these things on BEFORE the big day. Shoe sizes can vary greatly (especially the jcp offerings) and you don’t want the day to arrive and someone can’t get in their shoes.
Q: Robe suggestions?
Starting to explore the idea of getting a robe. Any suggestions? – Jack
More of a pajama pants + hockey jersey guy myself, so you’re askin’ the wrong person. Whatever you go with, don’t think too hard about it. It is, after-all, a garment meant to be worn when you’re at your most relaxed. So if you want to go full Apollo
Got a question or a style tip? Send them in here. Additional answers to the above questions can go in the comments.