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Hey Sid!

Shorts 101

Hey Sid!

You ask, Sid answers

Submit a question at heysid@sidmashburn.com

“Sid, Great article a few weeks ago on shorts. Please help me out with summer shoes. I always feel a bit odd with shorts and shoes. It’s like I should be wearing pants or throwing in the towel and wearing athletic shorts. What footwear goes well with shorts in summer? (We need shorts in Houston.)” – Jared

the Sunday uniform: mocs, shorts, second-day dress shirt, coffee, paper


JB and Sid are back this week to help Jared figure this one out.

Sid: Wait is this the Jared that works for us in Houston?

JB: No, this is another Jared – Jared J.

Sid: Oh hey JJ! Okay first, do NOT throw in the towel and do NOT wear athletic shorts unless they're dazzle cloth, and you're running or working out.

JB: Wait, what? Dazzle cloth?

Sid: Joking about the dazzle cloth. that was a hot item for us at Lands End and a bit of a family joke. One of our daughters wore them to elementary school daily, even in the dead of winter. But seriously, don't be afraid of wearing shorts, because I'm here to tell you… you have many, many options! Pretty much any pair of our shorts are going to look A+ with this roll-up of shoes. Let's start with the most casual, and work our way up.

Sneakers are the obvious move on the more casual end of the spectrum, and they look great with shorts, as long as they're clean & in good condition. I love old-school, analog shoes, so one of my top choices is Diadora – an Italian brand made popular by Bjorn Borg in the 1970s. I think the Game L Low Waxed Sneaker is a white-on-white facsimile of the original Borg sneaker. Great with shorts, great with khakis, or even with a suit, particularly if you're wearing a suit with a polo. Any of the Diadoras we carry would be aces with shorts.

We also have our own Low-Top Lace-Up Sneaker in white perforated leather. It's totally unbranded and keeps a clean, low profile. White sole, white laces, white upper... with a couple of super-small SM-green hand tacks in the back of the heel. White goes with everything and I'd say, again, these would also look great, not just with shorts or swim, but with khakis or jeans or even a casual suit.

JB: I wasn’t expecting sneakers to be able to go from shorts-to-suit… is there a social threshold where you WOULDN'T wear sneakers?

Sid: You gotta let the room you're about to walk into guide you, but for anything that feels the slightest bit formal, I'm probably not doing sneakers. But one more thing about sneakers before we get there… you could also venture into hybrid territory. A Chelsea Sneaker is exactly what it sounds like: a sneaker meets a boot. It has a vulcanized rubber sole with a Chelsea shape up top. It is very, very cool-looking; a great summer shoe. And one last easy one (literally and figuratively) is the Chelsea Sneaker's close relative - the the slip-on sneaker. Slip 'em on with literally any pair of our shorts and don't spend any more time thinking about it.

Next up in the casual-to-dressy hierarchy are camp mocs. They're hand-sewn, with a rubber sole, and they’re the best backdoor shoe possible... going out to get the paper, or walk the dog, or going to the store. Even the green or the navy are great, because they're quiet and neutral, it's not like "oh! are those green! or are those navy?" - they're subtle and blend in and go with a lot more than you think. And if you want to kick it up a notch, go with the white-soled ones. They've got just a little more pop. (They were originally meant as sailing shoes because it wouldn't scar and mess up the brightwork on a boat.) But all of these are super-comfortable and are unlined - which makes the shoe FEEL like summer.

The other thing about mocs is that they are international. These would look good in India or Italy... which brings me to the next "shoe that goes great with shorts.” Driving mocs. These are unlined too, but what's different about these is that driving mocs are traditionally not a full rubber sole — it's just the nubs coming out from the leather. We didn't like that because if you run into water, the bottom of your shoe gets wet. So we call this all-weather driving moccasins, because it's got a full rubber sole with the studs. The colors are fantastic, tan and olive. And they can be very dressed up. You could wear them with a pair of cotolinos, or a pair of robust tropical wool pants, even a poplin suit with a polo shirt. But also make sense with shorts or swim trunks. The real power is how many options you've got!

JB: Stylistically when you are trying to pair these, what are you looking for? For example, take the olive colored ones...

Sid: Well, I mean, I wouldn't do those with a pair of GREEN shorts... but it’s an earth tone, so you could treat it like a neutral and wear them with any of the shorts on this page, except sage green. That will look like you tried to match but didn't quite make it. Nothing in the same color family. You could do a Nantucket kind of look with a pair of cotolino shorts , a chambray shirt or oxford shirt. That's a pretty cool look.

JB: Which mocs do you have?

Sid: I've got the brown camp mocs with the white sole. I wear them all. the. time. They're basically my house shoes. I wore them all over Italy and Portugal last week. Like I said, international.

Okay, last moc option: an espadrille riff. I’m not sure why we named these moccasins because they are really more like an unlined, hand-sewn loafer crossed with an espadrille. A mashup. These can go even dressier because of the raffia outsole. The idea was sorta low-key elegant, like what you could wear on the weekend in the country. But it can still be a back-door shoe, like the camp moc.

JB: So sneakers, mocs... would you ever recommend pairing shorts with a penny loafer or a Tassel loafer ?

Sid: A verrrry old-school preppie look. I don’t wear it often, but not because I don’t dig it – it’s just that I’m typically only in shorts on Sundays by the pool or around the house. So I’m usually doing shorts + NO shoes. But I think it's a very cool look on a lot of guys. My only bit of advice: don't wear shorts on your loafer's maiden voyage. Break ‘em in first… you want them to look more relaxed. So the answer is yes — as long as they’re not brand new.

So to wrap up... you’ve got lots of options in Houston, Jared. Sneakers, slip-ons, mocs… I can’t speak to what’s in your closet, but any of ours will look great with basically any of our shorts, as long as they’re not slightly different shades of the same color. And if you want to go a little preppier, some worn-in loafers are your friend.

From Sid

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