We were so busy prepping style content and shooting our new YouTube series, we were unable to squeeze any new Ask He Spoke Style videos into the mix. Look for those to resume in April, but in the meantime I’ll still be answering your questions. This week, we’re talking about dressing for a Hawaiian wedding, shirt collars and sweaters, cologne, and underwear.

Hawaiian Wedding

Q: I need to shop for something suitable to wear to my beloved sister’s wedding. The wedding is in Hawaii, fortunately, but I happen to live in Billings, Montana, where they only have winter wear and colors right now. Would it be wiser to shop when I land in Hawaii? If so, it is supposed to be a beach wedding, and again I’m lost at the types of things that would be acceptable to wear to a formal event on the beach.


The ultimate men's wedding day style guide

A: What I wouldn’t give for a trip to Hawaii right now! I wouldn’t recommend waiting until you get to Hawaii to shop for something to wear. You’ll already have a million and one things to do so try to avoid adding something else on top of that. Especially something that requires more travel, and the potential that you won’t find your size! This is a great time to do some online shopping as most major retailers have just rolled out their spring collections.

You’ll want to stick to a suit in a lighter fabric – cotton, linen, or seersucker will be your best fabric options. Check out J.Crew, Suitsupply, and online made to measure companies like Knot StandardBlack Lapel, and Indochino. And be sure to check out the Style Guide for more inspiration.

Wearing Cologne

Q: I’ve been doing so much research on how to apply cologne correctly (watched your video). I asked my mom, and she told me to spray in front of you like two times, shirtless, after taking a shower. I’m just wondering if that is a good way to apply cologne because I don’t want to be “that guy.” Do you think you can give me some tips or tell me if I’m doing it correctly?

A:  There are definitely lots of ways to skin this cat. Some people, like your wonderful mother, are on to something when they say to apply it after a shower, when you skin is warm and damp. This can allow the fragrance to settle in. Personally, I like to wear it on my wrist and neck, parts of my body that are exposed throughout the day.

How much to apply will vary from fragrance to fragrance. Some are very light and you might want to apply a little more, but others, like my current favorite, are much, much more potent. If you’re not sure how much to apply, start with less and ask someone about halfway through the day whether or not they can smell it. Others are the best judges, as it’s difficult to gauge on one’s own.

Shirt Collars & Sweaters

Q: What’s your opinion about button up shirt collars with sweaters/cardigans? Do you wear them with collars out or tucked into the sweater collar and why? Also, if you do recommend wearing with the collars tucked into the sweater collar, how do you handle smaller collars that always manage to peak out of the sweater collar?

A: I prefer to have my shirt collars tucked into my sweaters. Doesn’t matter whether it’s a crewneck, v-neck, or cardigan. I think it creates a cleaner line and presents a neater appearance. The simplest solution for keeping them in is to wear a button down collar. Keeping any non-button down collar in is, as you mention, difficult. A simple solution is to add a tie to the mix. And if it’s a smaller collar, go with a v-neck or cardigan. Best to avoid the John Travolta “Saturday Night Fever” look at all costs.


Q: My question is a bit personal, but what kind of underwear do you typically wear? I only ask in that most of your pants are impeccably tailored, slim but not overly tight. My issue is when I wear slacks to work I feel that boxer briefs have a telltale band around the legs and briefs can give the dreaded “pantie line” on the rear.

A: Good question. Undergarments are a matter of personal preference, but I like to classify the major forms into three categories – always, sometimes, and never. Let’s work backwards. Never for boxer shorts. They’re bulky and bunch up way too much underneath trousers, especially jeans and slimly-taliored pants. Briefs would be sometimes, but only if you’ve got the body to pull them off. And boxer briefs, always. My personal preference and unless you’re wearing some skin tight trousers, they’re not going to show through.

As always, leave your questions in the comments, send them via email, or on Instagram or Twitter using the hashtag #AskHSS. Thanks for reading.

Stylishly Yours,

He Spoke Style


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