Food & Wine Thursdays: How To Dress When Going Out To Dinner

There was a time when getting dressed for dinner meant putting on your dinner jacket or evening gown and sitting down at a tastefully appointed table to be served grey meat and table-side Caesar salad by closeted homosexuals.

Thankfully times have changed. The line between “fine” and “casual” dining is very very blurry and one’s appearance is judged on fashion and style rather than “appropriateness” and formality.

And where our waiters are out and proud.

There are some basic rules for what to wear when going out to dinner, and I now set them forth thusly for posterity.

I’ll be speaking mostly about what men should wear, since I don’t really know too much about women’s fashion and men, generally speaking, need the most help in dressing for dinner. A couple basic rules for women:

1. When in doubt, wear a dress. I don’t care if it’s a gown or a cute little retro hipster thing, you’ll always look good in a dress that fits you.

2. Strappy tops, skinny jeans, and stiletto heals are for the club and/or going out for cosmos with your girlfriends after seeing Sex and the City 2: Electric Boogaloo, not for dinner. Seriously, you don’t look like Miranda, you look like a tramp.

On to the men:

1. A well-made solid colored t-shirt, stylish jeans, nice shoes, and a sweater or sport coat will work in 99% of instances.

2. Shoes are key. If you’re going to wear sneakers they need to be distinctive and scuff-free. No jogging shoes or hiking boots (unless you’re a lesbian). And don’t wear black leather oxfords to dinner. Save those for the office.

3. If you’re going to wear a sport coat and jeans, make sure you’re wearing a true sport coat, not a suit jacket. It looks terrible. If you’re to wear a t-shirt and sport coat, wear a very casual sport coat. Something made from cotton with patch pockets or vaguely safari-style is good. You can also opt for something nice but unconventional like a workman’s jacket, Eisenhower jacket, or unadorned leather jacket. Wool jackets should pretty much always be worn with a collared shirt.

4. Unless you want to look like a 70 year-old man, never under any circumstances tuck any shirt other than your undershirt into your jeans. There are many nice collared shirts available that are darted and square-cut for this purpose. Do not wear a belt with your jeans if you can avoid it. Conversely, always tuck your shirt in (and wear a belt) if you’re wearing slacks to dinner.

5. If you wear a jacket to dinner, leave your jacket on at the table. Especially if you are dining with a lady.

6. Do your research. If you’re going out to dinner at night in the city at a restaurant with white tablecloths where you think you’ll be spending $50+ a person on dinner, you can never go wrong with a jacket and tie. Period. Nobody’s going to think you’re cool because you went to the French Laundry in your True Religion jeans and English Laundry shirt you freakin’ douche bag (see Women’s Rule #2)! At any nice restaurant after dark you’ll never be out of place in a jacket and tie. And you can always take off your tie and unbutton your shirt a couple buttons if you really do feel overdressed.

7. No shorts, no short-sleeved button-up shirts (just roll up your sleeves man!), no sweatpants, no athletic gear/sports team/designer logo t-shirts (go either solid/pattern or hipster ironic), no Velcro (ever), no sandals with socks, no white socks, no parkas/ski jackets/any coat you’d buy at REI or the North Face, no $5 digital watches (unless chosen very deliberately as part of a campy/ironic ensemble or featuring a calculator), no baseball/trucker hats , and no hats in general worn at the table.

Most importantly…

8. Dress consistently! Just because you’re wearing slacks and a collared shirt doesn’t mean you’re “dressed up” and just because you’re wearing jeans and a t-shirt doesn’t mean you don’t look “nice.” These are standards that have been set for people under the age of fourteen and should remain such. Don’t wear your dirty scuffed Rockports with a jacket and tie and don’t wear Allen Edmonds bluchers with jeans and a t-shirt. Don’t wear a long-tailed dress shirt untucked with jeans and don’t tuck a pastel “South Lake Tahoe, California” t-shirt into your khakis.

But if you must tuck your novelty t-shirt into slacks, at least have the decency to complete the ensemble with an appropriate woven leather belt, and Tevas worn with white gym socks.

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About David D.

I'm a wine professional. Like a real one who makes most of his living in wine and have for most of my adult life. I also write, but you can see that.
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