The Expert: A User's Guide to Chelsea Boots
Sleeker and more modern than ever, the Chelsea boot works just as well with a suit as with beat-up jeans.

Here, Grenson creative director and CEO Tim Little's three tips on keeping your boots looking good.

Rule 1: The Right Pants Are Key
"You want a narrow pants bottom, so that the pants sit tight, just a little way up the leg of the boot. You need to see just enough of the elastic gusset to know it's a Chelsea boot—otherwise it just looks like a very plain shoe."

Rule 2: Invest In Shoes Trees
"They help shoes keep their shape, but they also stop them from cracking, because the leather doesn't crease as it dries out. If you can, try to find trees with a high instep, as the Chelsea's shape is all about that gorgeous curve running up the front of the boot from the toe."

Rule 3: Avoid Quick Fixes
"My pair goes back to the Grenson factory, where they are re-lasted. There are also some very good independent guys around—just be sure to ask if they put the boots on a last as they repair them. Most don't, so you end up with a nice new sole but a misshapen upper."

Clockwise from top: Ermenegildo Zegna ($725). Tod's ($1,875). John Lobb ($1,695). Bally ($750). Grenson ($395). Church's ($570).

Trust us: It isn't just for Ivy League professors anymore. The classic fabric is looking thoroughly modern in slim-cut pieces that smarten up any wardrobe.

A Brief Glossary
Harris: A high-quality, hand-woven tweed, rougher than other varieties. Originally made with pure virgin wool in Scotland's Outer Hebrides.
Donegal: Known for its thick slubs of colored yarn woven into the fabric. Also called Irish tweed.
Herringbone: The most classic tweed pattern, introduced in the 1800s. Recognizable by its characteristic parallel lines that form V shapes.

From left: Jacket ($748) by Mark McNairy New Amsterdam, sweater ($775) by Marc Jacobs, pants ($385) by Michael Bastian, shoes ($1,060) by Church's. Jacket ($228) by Express, shirt ($360) by Patrik Ervell, jeans ($298) and shoes ($598) by John Varvatos. Coat ($1,498) by John Varvatos, sweatshirt ($650) by Trussardi, jeans ($310) by G-Star, shoes ($420) by Wings + Horns. Suit ($568 for jacket, $298 for pants) by J.Crew, shirt ($60) by Express, tie ($150) by Alexander Olch, shoes ($745) by Saint Laurent by Hedi Slimane.

1. Proof that incorporating tweed into your look doesn't have to mean putting on a suit and tie. Made for color-phobes, a snap-button jacket like this one adds texture and pattern in a minimalist way.

2. Forget the itchy stuff your mom used to force on you. This shirt and blazer are cut from plush, higher-end weaves that are undeniably comfortable.

3. Never worry about getting this nubby fabric wet—it's made to repel water. A dress coat like this one can withstand the elements while elevating even the most casual basics.

4. Wearing a tweed suit without looking like a codger is simple. Just opt for an expertly tailored, contemporary cut and pair it with a can't-miss white shirt.

No denim packs more attitude and effortless cool than a pair of black jeans. Light or midnight, this season they're the only ones that matter.

Why, When, and How to Clean Your Jeans
Frank Pizzurro, owner of Brooklyn Denim Co., weighs in: "We are not big fans of never washing your jeans. When they're caked with dirt, the fibers break down, which causes the fabric to rip easier. Our suggestion is to wear them three to six months—this will maximize the fades without destroying the fabric. At that point, wash in cold water, inside out with a small amount of mild detergent, rinse thoroughly, and hang dry."

From top: Levi's ($58), Surface to Air ($210), Simon Miller ($265), Acne Studios ($350), Dior Homme ($790), Jean Machine ($190)

Fall's richer, more luxe shade of tan adds polish to any outfit. Wear it with gray, navy, or black—just don't dress head to toe in it.

Blazer by Boglioli ($1,450), sweater by Sunspel ($182), shirt by Hugo ($145), pants by Paul Smith ($700), toggle jacket by Saint Laurent by Hedi Slimane ($2,590), backpack by Krisvanassche ($1,307), shoes by Louis Vuitton ($1,090).