I need the official opinion: Can one wear socks with Sperrys?

September 27, 2013 7:34 AM

Are socks with Sperrys acceptable or a complete no-no? Not white socks - duh.

I love my Sperrys so hard and when fall comes around I'm sad I can't wear them as often.

I'm going to an event this weekend that is completely casual leaning upscale. Jeans are allowed. I'll be wearing a blazer. It will be outdoors, and the weather will be warm but crisp and in the evening probably way too cold to go sockless.

My brown sperrys are probably some of the dressier-casual shoes I have. The next level up is straight up black dress shoes which I frankly only wear with suits and kind of hate. The next level down are classic brownish/tan Clarks dessert boots.

Okay, this turned into a two-part question

a) What do I wear?
b) Are socks ever allowed with Sperrys or is that a horrendous breach of fashion law.

posted by windbox to Clothing, Beauty, & Fashion (26 answers total)

My husband wears hidden ankle socks that you can't see when he's wearing his Sperrys (he got the socks from H&M). This has solved the sock/no-sock dilemma for him.
posted by Zosia Blue at 7:36 AM on September 27, 2013 [2 favorites]

Thin dark socks. My grandfather did this all the time.
posted by JohnnyGunn at 7:36 AM on September 27, 2013 [1 favorite]

Sorry, no socks with the Sperrys. If you're allowed to wear jeans then I would go with the Clarks and a brown blazer. Actually, since it's an evening function I'd personally wear the black dress shoes and a dark blazer with jeans, but if you really hate your black shoes you can do the Clarks.
posted by backseatpilot at 7:40 AM on September 27, 2013 [4 favorites]

Sperrys worn with socks.

As you can see, it's a fine line.

I would be tempted to do something really loud and bright, so that if people do happen to notice them, it looks intentional and not sad man with cold feet.
posted by phunniemee at 7:41 AM on September 27, 2013 [15 favorites]

I love the Sperrys + striped/bold socks combo.
posted by ThePinkSuperhero at 7:43 AM on September 27, 2013 [6 favorites]

It's not a horrible breach of fashion, but it's not often done. It's fall, though, so I'd say put away the Sperry's and wear the CDBs. To me those are in the same formality level as the Sperrys, and are more seasonally appropriate. If you do wear the Sperrys, go with loud socks as other people have said. That's a look I personally like better with penny loafers, but it works with boat shoes, too.
posted by Bulgaroktonos at 7:56 AM on September 27, 2013 [2 favorites]

I wear them with a low-rise ankle sock in black. They are fine. I've also seen lots of people wear them with ankle socks... especially with jeans.
posted by Crystalinne at 7:58 AM on September 27, 2013

I would wear the desert boots before I wore visible socks with top-siders.
posted by Sara C. at 7:58 AM on September 27, 2013 [2 favorites]

I love the Sperrys + striped/bold socks combo.

George H. W. Bush agrees. Make of this what you will. Personally, I'm finding it harder and harder to hate that guy.
posted by pullayup at 8:01 AM on September 27, 2013 [6 favorites]

Yup, go with the CDBs.
posted by Dragonness at 8:02 AM on September 27, 2013 [1 favorite]

You can totally wear socks and boat shoes, provided that you're not wearing them as boat shoes--i.e., shorts on the beach, or Sunday in the park, etc. If you're wearing boat shoes with jeans at an evening function, you'll be fine.

Again, I stress do not wear socks if you're wearing boat shoes qua boat shoes. In this case, you're effectively just wearing loafers.
posted by Admiral Haddock at 8:24 AM on September 27, 2013 [3 favorites]

I'm wearing jeans, low rise ankle socks, and Sperry's today. It's my normal Friday attire.
posted by COD at 8:30 AM on September 27, 2013 [1 favorite]

I agree with Bulgaroktonos and others--the desert boots are a more seasonally-appropriate choice. That said, I also agree with people who have suggested bold socks if you're going to wear socks at all. I'm not specifically a fan of low-rise/hidden socks.

(Poppy is a good dresser, I'll give him that. Oblivious to fashion, always classic prep with more and more GTH in his old age. Style-wise, he is the George Costanza of living presidents.)
posted by box at 8:57 AM on September 27, 2013 [1 favorite]

Yeah, George H.W. Bush was a great dresser.
posted by Bulgaroktonos at 9:02 AM on September 27, 2013 [1 favorite]

Personally, I think the Clarks Desert Boots are dressier than the Sperry's. Is it summer (or otherwise over 75 degrees)? Is the party on a boat or the beach? If the answer to these questions is no, then Sperry's are not appropriate, with or without socks.
posted by melissasaurus at 9:10 AM on September 27, 2013 [1 favorite]

No, you cannot. This is one of those rules.
posted by Ironmouth at 9:15 AM on September 27, 2013

When they were popular in the 80s I always wore them with socks. However: a) I am a woman b) I am not and have never been fashionable c) mine were knockoffs
posted by interplanetjanet at 9:54 AM on September 27, 2013

I have a friend who wears socks with Sperry-ish shoes. My friend is a lovely person and their practicality and accompanying slight eccentricity of dress are two of the many characteristics I like about them. That said, it is an eccentricity, and if you wish not to look eccentric or feel that you'll be letting the side down by doing so, don't wear socks.

I nth the idea that the Clarks are as formal as the Sperrys. Honestly, I feel like the Clarks are a bit dressier as they cover more of the foot.

If I may make a suggestion: depending on your budget, why not pick up either a pair of "ranger mocs" for fall (from Rancourt if you feel like buying fancy)? They're very like tall boat shoes. Or, failing that, why not pick up a pair of brown brogues? Check eBay and consignment shops and get a good pair on a budget. It wouldn't hurt to have something robust between the Clarks and the black dress shoes.

In fact, I'll throw in a thought about a useful shoe wardrobe, since you already have half of it: a pair of nicer loafers for summer, a pair of brown brogues and a pair of black lace up or chelsea boots suited to bad weather would make your shoe wardrobe so complete! I strongly suggest consignment, classy secondhand and thrift shops and eBay for these purposes.
posted by Frowner at 10:01 AM on September 27, 2013 [2 favorites]

Muffy Aldrich says it's okay, within limits.
posted by The corpse in the library at 10:03 AM on September 27, 2013 [1 favorite]

P.S. I always knew these as "Top-Siders" or "boat shoes." Are they called Sperrys these days?
posted by The corpse in the library at 10:05 AM on September 27, 2013

I tend to call them boat shoes, but used the OP's terminology. I also wear boat shoes that aren't Sperry Top Siders so that might be part of the reason for that.
posted by Bulgaroktonos at 10:19 AM on September 27, 2013

I call them Top Siders or boat shoes, but I've only ever worn Sperry's. I've actually never heard them actually called Sperry's before.
posted by Admiral Haddock at 10:50 AM on September 27, 2013

Since I've been thinking about it: Bill Clinton is Kramer--even after all these years, he dresses like a poor man's idea of how a rich man dresses. George W. is Jerry--Crocs with socks and shorts = jeans with white sneakers. And that leaves Jimmy Carter as Elaine, which might be where this analogy falls apart.

(Mods, please feel free to delete this as noise.)
posted by box at 12:39 PM on September 27, 2013 [2 favorites]

Yes, wearing socks with your boat shoes is fine. Wearing no-show socks is better, though colder. I am wearing these with boat shoes right now.

I look forward to this thread being mentioned in Tim Gunn's next book.
posted by Sock Ray Blue at 1:01 PM on September 27, 2013

It's not even December. Roll those cuffs, show those ankles. Be strong.
posted by tapesonthefloor at 1:33 PM on September 27, 2013

Sperry actually makes no-show socks to be worn with their shoes. Admiral Haddock's advice above is correct.
posted by spaltavian at 6:05 PM on September 27, 2013 [1 favorite]