Top photo: Suit: Indochino Ultimate Gray Shirt: Blank Label Tie & Tie Bar: The Tie Bar
1. I plan on wearing light blazers fairly often this summer, what's appropriate to wear underneath them? Should it always be a long-sleeve button up? – Paul
Good move on the lightweight blazer. Most of the time guys are confused about their outerwear but in this case it’s the opposite. While long sleeve shirts are the standard they aren’t the only option. The beauty of a jacket is that it covers up what you don’t want to show like a stain, or a hole, etc. (do not take this as an excuse not to mend your clothes or have them dry cleaned properly).
You can wear a crew or V-neck t-shirt, a short sleeved Henley, a gauze or linen button up, or even a short sleeved madras button down. While we never recommend wearing a short sleeved shirt in a professional environment for fear of the Dilbert effect, who’s to know if you never remove your jacket?
Linen blazer by H&M | shirt by Modasuite
2. What is the rule on shoe color and style? I'm trying to break myself out of my childhood style of Volcom T-shirts, jeans and white skate shoes. I've invested in some solids and stripes for shirts, a few dress shirts and ties and I'm about to buy some chinos but I can't seem to ever match shoes. For some reason shoes are what I pay attention to most, but can't seem to bring together. – Scott
I see you’ve been taking my advice—good man. It’s great that you’re focused on your shoes. The foundation of a stylish wardrobe begins and ends with good shoes. After all, your feet are the most important tool for you getting around.
However, you may be too conscious of your footwear. You shouldn’t be matching your outfit to your shoes. Instead match your shoes to the occasion you’re dressing for and then choose your clothing. Professional environment requires professional shoes. i.e wingtips. Casual environments call for casual shoes, i.e. loafers. Speaking of matching–don’t. Matching is for kindergarten boys who are dressed by their mother. Just as your pocket square should complement and not match the colors in your tie your shoes should complement, not match your attire.
3. I love the styles of such stores as J. Crew, Banana Republic, and other prep stores. However, it seems like all of their styles are for skinny guys only. How does a 6'2″ tall guy at 270 lbs find clothes that are both stylish and made for my size? – Dan
I’ve worked at J. Crew as a personal shopper so I’ve witnessed this issue first hand. The first thing to realize is that just because the skinny, slim trend is being heavily promoted does NOT mean that you can’t find something that fits you. What it means is that you may have to look harder. There will always be a traditional or regular fit for the gentlemen who prefer not to wear the slimmer fits. At J. Crew the tall sizes won’t be found in store. You’ll have to go online for that. Most of their sizes reach up to XXL. Aside from off the rack there are big and tall stores but these are an abomination in my opinion. Most of them end up making you look like you’re wearing drapes.
Instead invest in something made-to-measure. Try Long Shot Apparel which specializes in tall shirts for men. You’ll find tall and long sizes in a tailored fit that won’t make you look like you’re wearing a bed sheet.