Ask Chris: Any Briefcase Recommendations?

12 items in this article 2 items on sale!

Chris Black has returned to The Strategist with a monthly column to answer all of your burning questions — from super-specific style predicaments and workout and tennis recs to foolproof host-gift ideas that will get you invited back to the beach house.

The briefcase discussion came up recently on an episode of How Long Gone with stylist and costume designer Heidi Bivens, so I have been mulling it over. Unfortunately, the briefcase feels like something from a different time, replaced with adult backpacks and messenger bags. I say we bring them back.

I have always loved this design from Japan's Porter-Yoshida. The navy nylon is chic and a nice change from the typical black, and it has enough storage for your laptop, legal pads, gum, cords, an extra pair of briefs, sunglasses, keys, a bottle of Mountain Valley sparkling water, etc.

This thing got rinsed during the 2012 menswear boom, but I think it's time to bring it back. The twill can take a beating and wears in really nicely over time. This will hold all your office stuff and look respectable while strolling down Fifth Avenue. Just don't pair it with a buffalo-check flannel!

I love all of these — I really do — but you can't beat leather. The front-pocket flaps are simple and sophisticated, it will hold everything (there is a hidden back pocket), and you can even monogram it.

New York Magazine readers are going to love this: The classic Prada briefcase is worth every penny. Sorry! It's chic, practical, and can be dressed up or down. It's made from Re-Nylon, a functional material and vehicle of experimentation produced from recycled and purified plastic trash recovered from the oceans. That explains the cost! Live a little.

I love this question because almost every single brand is cheaper than Loro Piana. Wanting to look chic and logo free has become somewhat of a trend with silly names that I will avoid using thanks to a certain television show I don't watch. I will, however, recommend a few brands that make simple, beautiful clothes that will never feel dated.

I have mentioned Stoffa a handful of times over the years of doing this column. They make tailored, timeless clothing that will age gracefully and not totally destroy the bank. The short sleeve polo is a standout, bridging the gap between casual and formal. Gently tapered with a semi-spread collar, it would look appropriate on the riding mower in July or on Barry Diller's yacht in August.

Any diehard Loro wearer keeps a pair of white jeans in rotation. This pair from Rubato mixes Ivy style with a dash of European elegance. No whiskering, holes, or extra adornment — just made-in-Japan, 100-percent-cotton, five-pocket jeans that will last forever.

I got to visit the Saman Amel atelier in Stockholm a few months ago and was blown away. Every detail was just right: the furniture, the lighting, the cup they served coffee in. The clothes are no different, expertly executed in cut and fabric. The Amo Trouser has a slightly wider leg and comes in brushed royal-flannel wool in a muted taupe.

[Editor's note: Saman Amel lists all prices in euros, so the price shown here is an approximate conversion to U.S. dollars.]

The quarter-zip sweater is a must-have, and this version from New York's Salie66 hits all the right notes. Done in a normal fit out of durable merino wool, it comes in navy, black, or ivory and will serve as a nice addition to your wardrobe.

These teens are looking pretty crazy. Comfort has taken hold, and we need to steer them back on course. No one should be uncomfortable, but Crocs are not shoes. They are barely acceptable for shuffling to the bodega at midnight. There is a way to be young, cool, and put together without looking like your parents dressed you.

Joggers are not the only comfortable pair of pants available, a hard lesson for some to learn. J.Crew (full disclosure: my client) makes amazing, roomy chinos in a variety of colors. I wear a pair all the time, partly because they are much more comfortable than my vintage Levi's.

This overshirt lands somewhere between a flannel and a jacket, perfect for spring and fall. It's simple and roomy and will look good with jeans, chinos, or even … gulp … joggers.

This collared half-zip sweatshirt is a step up from the hoodie. Feels relaxed but not hoodie relaxed. Wear a simple T-shirt underneath or a button-down.

It doesn't get more classic than this. This will last forever and only get better with age. It's a nice step up from sneakers, but it's not a loafer or a boot. Hopefully, he has at least heard the Clash before. I assume you are a good parent!

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