Ask Dan: Hat Etiquette, Tailoring Leather, Gifting Style

December 1st, 2014

Headwear Etiquette


Q: Hey Dan. Thanks to this site I’ve been introducing more headwear into more wardrobe (mainly classic felt & straw fedoras) and I’ve been getting plenty of complements. However, this often poses a problem when eating at a restaurant. Do I always take it off when eating? I think yes, but where to put it? Some of the tables at these NYC restaurants are about the same size as my hat…

A: Proper etiquette says that a man should always remove his hat upon entering an establishment. It’s a sign of respect and openness to others. I feel you, though, I’ve struggled with the issue of storage as well. That’s why I much prefer unstructured hats that can be rolled into a pocket. If you’re worried about crushing the crown, most restaurants should have a coat check, or at least hooks to hang coats. If you’re really in a jam, you can always wear it over a bent knee under the table.

Rolling Jacket Sleeves


Q: I often see guys with their suit sleeve buttons unfastened, for no real reason. What is the purpose of this? Furthermore, when is it appropriate to actually open up the jacket sleeves and roll them up?

A: The unbuttoned sleeve cuff is purely a show-off move. It’s for guys who’ve invested a lot of money on their bespoke jackets and want you to know…which doesn’t really have the same effect anymore now that cheap off-the-rack jackets also have working cuffs. As far as when to roll them up like surgeon’s back in the day, I never really do it. I once knew this guy who would fully unbutton the cuffs of his jacket and shirt and roll them up over his elbows whenever we went to dinner. I always thought this looked silly and a little try-hard. I keep my jacket on during dinner as well, but I don’t seem to have a problem dragging my forearms through my soup.

Tailoring a leather jacket


Q: After reading your guide to vintage shopping, I bought an awesome leather jacket. After getting home and trying it on a few more times, I think it would fit better if it were a little slimmer (I read here that leather jackets should be very trim). Is it possible to slim-down a leather jacket (specifically the midsection and sleeves)?

A: That’s a tricky one. It’s technically possible, but it depends entirely on the design of the jacket. Leather jackets often have bells and whistles that make them hard to re-cut. Basically you can’t take-in any seams that are intersected by pockets, zippers or any kind of hardware. There also needs to be enough clear space around the seams to be physically taken-in. Your best bet is to show the jacket to a good tailor, although tailor shops with the proper equipment to work on leather can be hard to find. I would recommend calling ahead before trekking through the city, leather piece in hand.

Gifting a Style Guy


Q: Dan, with the Holiday Season officially upon us, what do you get the very stylish conscious (aka “fashion picky”) man?

A: If he’s a clothes horse, I would avoid buying him clothes. He’s probably super specific in his taste, and you don’t want to make him feel awkward if he doesn’t end up wearing your gift. Instead I would aim for something that is related to his style, but not something that he has to wear (or not wear). Something like a book geared toward menswear enthusiasts or a biography on his favorite style icon. If he’s not a book man maybe a bottle of his favorite bourbon, or box of fine cigars. It really depends on his interests, but I would stick to those that are related to his lifestyle, not necessarily his fashion.


Thanks for reading. If you have a style question, you can hit me anytime using our Contact Page.

Yours in style,

Dan Trepanier

  • Terry Tomlin

    Love the new site! I’m glad that you published the hat question. I love including headwear in my wardrobe. I have some great fedoras and straw hats as well but I sometime hesitate to wear them because of the storage issue. I’ve had dinner with my hat on my knee also. My question is about traveling with hats. I’ve heard your advice about crushable hats. Back in the day fashionable women all had hat boxes for travel. Is there a male counterpart?

  • Shawn

    I’d love to receive a bottle of small-batch bourbon or a box of Padron anniversary for Christmas, indeed!

  • David Pardo

    Welcome back, Dan. You all have been missed. Good job. I love the new site.