Turnup for What? 
If you ever find yourself waffling on whether or not you should cuff your trousers, Jesse has a great guide here that he wrote a few years ago. As he noted, cuffs are largely a matter of personal taste, although there are some general guidelines that can be good to follow. Pleated trousers, for example, almost cry out for cuffs, while flat fronts can go either way. And while you can more or less cuff anything, you’ll want to leave them off formal trousers (i.e. black tie pants) and perhaps your most casual (e.g. you can cuff your “dress chinos,” but you might want to leave them off the run-of-the-mill variety).
If you’re still left undecided, then here are two more useful guidelines.
Cuff everything. The reason is simple. You can always remove cuffs from trousers, but you can’t always put them in (depending on how your tailor has hemmed your pants). So unless you’re absolutely positive you want plain hems, err on the side of caution and request cuffs. You can get rid of them later if you decide you don’t like them.   
Think of typography. StyleForum member Parker (who’s day job is in graphic design) once suggested a rubric that I particularly like. Cuffs are sort of like the Times New Roman of menswear. They’re good for traditional, classic, and possibly staid looks. Plain hems, on the other hand, are like Helvetica, and are better suited to more modern, clean, or neutral styles. Whether you get cuffs or not just depends on the expression you want.  
To give some examples, I wear cuffs on any trousers that I might pair with a tailored jacket. So they go on grey flannels, linen pants, and dressy chinos. I also cuff jeans when I’m wearing more “classic” items, such as an oxford cloth button down, chunky cardigan, and white sneakers (as I’m wearing now).
With sleeker looking pieces, such as this black leather jacket I recently bought, I wear the same jeans, but unroll the hems. Same goes for any time I wear double black jeans, which I think of as being slicker looking than my indigo denim. 
In the end, just do what looks right to you. The only sartorial no-no is wearing cuffs on very formal trousers, such as those you’d wear with black tie. This is partly because cuffs are inherently a casual detail (they originated as mudguards) and because they interfere with the braid that typically runs up and down the legs. Aside from that, like Black Sheep said, the choice is yours.
(Photo via SpooPoker)

Linen Sport Coats for Summer
Everyone has their own pick for what they’d consider a summer essential. For me, it’d be a breathable sport coat. Something made from an open weave material — and has little canvassing, lining, or padding inside — will wear much cooler than your standard year-round wools. In fact, as hot as the weather gets in July and August, I don’t even touch my “year round” sport coats until October. 
Most open weave materials can be classified as one of two types: tropical wool and linen. More of than not, breathable sport coats will be made from linen, partly because tropical wools tend to be very smooth, so they’re reserved for suits. The upside to linen is that it not only breathes well, but it’s also a good way to take the inherent dressiness out of a tailored jacket. Nothing says carefree and casual like having a few rumples and wrinkles in your sport coat. 
You can wear linen jackets with almost anything, but I find they tend to look best with linen trousers. Something in a contrasting color, but similar weave, will make it so that your jacket and trousers are distinctive, but also in harmony. That is, pair smooth, tightly woven linens with other smooth, tightly woven linens; and slubby, spongy linens with other slubby spongy linens. A linen jacket will also pair well with cotton chinos, as both will have the same casual, summery sensibility. Between these two fabrics, you have a world of trouser options once you play around with color. 
Don’t get too hung up on rules though. Luciano Barbera once advocated wearing a linen jacket with wool flannels, and while I personally wouldn’t do it — who am I to argue with one of the world’s best dressed men? Patrick Johnson of P. Johnson Tailors is also pictured above wearing a linen jacket with denim. If you want to try that kind of combination, consider getting a jacket that’s slightly shorter in length and forgoing the tie. As usual, the danger with denim plus sport coat combinations is that they can look a bit discombobulated — very dressy up top, too casual down low. Play down the jacket by getting something that has a slightly less traditional cut, and forgo any neckwear. That way, you’ll bring the tailored jacket down a notch in its formality.
(Photo via Patrick Johnson Tailors)

Luciano Barbera's Style Tips


Luciano Barbera on style:

It’s not enough to have beautiful clothes. Lots of people have beautiful clothes. In fact, some people have too many. What is important is what you do with them. On the following pages I share some comments on how I dress and what I have taught my sons. Of course,…


Jeremy-san in his H. Lesser Prince of Wales by Orazio Luciano.
Jeremy is a particular difficult fit.  He has wide, square shoulders, a hollow lower back, and an upright posture making it difficult to create a silhouette that’s balanced and uninterrupted.
In this model, we’ve shortened the collar significantly and kept the shoulders closer to his natural shoulders which leads to a cleaner chest and a more balanced top-half  We also opened the skirt a bit to counteract his posture.
Jeremy is proof that you don’t have to let your body dictate the type of clothing that you wear.  I think it worked out well for him.
What a c00l d00d.

Vintage Leather Belts
I’m not as experienced as Jesse it when it comes to thrifting, but I do enjoy going to thrift stores. When I go, I often like to browse around for vintage leather belts - the thick kind that you wear with jeans. One of the nice things about buying second-hand is that you can get things with a bit more character. With good leather, you’ll often get something that has aged beautifully. 
Take the above belt, for example. It’s from a webpage Mister Freedom made for their “Ranchero shirts,” which are lovely, but the star of the photograph - at least for me - is the belt sitting in the middle. The variation in the coloring, the scuffing, and the scored design give the belt a certain appeal that modern workwear brands only imitate.
You can find such belts if you hunt around enough. Just visit good thrift stores or flea markets (in the Bay Area, I’d highly recommend Antiques by the Bay, which happens on the first Sunday of every month. Not only do they have a few vendors that sell vintage belts, but there are a ton of other great booths for vintage wares as well). There’s also eBay, of course, but that gets slightly dicier. Vintage leather goods can be of varying quality - either because of the quality of the leather itself, or because of how the item was taken care of throughout the years. Without being able to handle the belt, and without a brand name to go off of, it can be difficult to know what you’re looking at. Still, some of these are quite affordable, so if you get stuck with something less than ideal, it’s at least not a big loss.
The alternative is to buy something new, but from a brand that takes it inspiration from old, vintage designs. RRL and Levi’s Vintage Clothing often have tooled or painted belts that are made to look like they’re from the mid-century. You can find them at workwear-focused stores such as Hickoree’s and Unionmade. They won’t have the kind of patina that an authentic vintage belt will carry, but they’re often still quite handsome. With enough wear, you might get it to look as nice as the one Christophe Loiron (owner of Mister Freedom) photographed above (though, probably not, because that belt looks really awesome). 
(Photo via Christophe Loiron)