The 7 Fall Wardrobe Essentials Every Man Needs, On Two Different Budgets
By Jared Paul Stern / September 26, 2019 1:03 pm

Curating a wardrobe that you’ll be able to wear for the next 20 years will of course require an investment. So if you can’t afford to do it all in one go, we recommend acquiring legacy pieces one at a time, deliberately — the kind of stuff that will serve you well thanks to its durability in terms of both construction and aesthetics.

While tastes may change, great style never goes out of fashion, so avoid anything overly trendy and instead focus on sartorial building blocks that can anchor any outfit, no matter the occasion. So below, we’ve picked out the seven wardrobe essentials you can’t afford not to own.

A couple notes before you begin: for each item, we’ve identified options at two different price points. Why? Well, we don’t all make the same amount of money, for one, but we also don’t all have the same priorities. Maybe luxury watches speak to you in a way that a more affordable option never could. Maybe you appreciate the craftsmanship of a blazer that’ll set you back over a grand, but your lifestyle is such that you wouldn’t get much wear out of it.

The point is, these are items around which you can build a great fall wardrobe, regardless of how much coin you drop on ’em. Check your bank account and your social calendar and choose accordingly.

Navy Blazer

The navy blazer will always be a sort of Swiss Army knife in a gentleman’s style arsenal. The way to make sure you’ll want to wear it for a decade or more is to opt for soft tailoring and ditch the gold buttons. 

British designer Paul Smith’s take in pure cashmere (left) is unlined and elegantly casual with horn buttons and patch pockets.

The Grayers Poindexter (right) is made of heathered cotton canvas with a touch of stretch, making it one of the most comfortable blazers you’ll ever slip on.

Blue Oxford Button-Down

White shirts are a bit stark for everyday wear. You’ll find a soft blue to be a much more versatile ally whatever the season. 

Proper Cloth’s American pima cotton version (left) is, as they put it, “hardy, remarkably soft, and incredibly resilient.”

Brooks Brothers’ Red Fleece label (right) offers the pitch-perfect slimmer version of the shirt that literally became an icon of American style.

Grey Cardigan 

Executed correctly, a cardigan with some visually interesting details can serve you as well as a sport coat in many situations, and make you look that much more interesting to boot.

Thom Browne’s Aran Cardigan (left) is hand-knit of Irish Donegal wool and mohair in a dashing cable stitch pattern with his signature sleeve stripes and ribbon trim.

Cable stitching also adds visual appeal to this heavyweight, three-season cotton shawl collar number from L.L. Bean’s Signature line (right).

 Olive Suede Shoes

Suede shoes literally toe the line between ruggedness and elegance, and while brown is always a safe bet, you can give your autumnal style an upgrade by opting for olive green. 

British brand Trickers holds a Royal Warrant from the Prince of Wales, and these wingtip boots (left) are as appropriate for an English country house party as a Brooklyn house party. 

Olive suede also works well in a more casual silhouette like the cool Bradley collab from Los Angeles brands CLAE and March LA.B (right).

Waterproof Jacket

Speaking of seasonally appropriate items, a waterproof jacket is as essential as you can get. Here again, olive green will stand you in good stead in a number of settings. 

The Barbour Beacon (left) in classic waxed cotton is part outer layer and part blazer, allowing you to wear it over a cardigan or with a knit tie, and look very 007 either way — Daniel Craig sported a version of it onscreen.

L.L.Bean’s Upland jacket (right) is a perfectly suitable, affordable alternative that will work just fine for people who don’t need to go all in.

Steel Dive Watch

A brand new stainless steel Rolex Submariner (left) is impossible to come by these days, which says a lot for a watch that was designed 65 years ago. Like the Porsche 911 it has been refined a bit over the years but never bettered. 

Pre-owned Submariners from the late 1980s and the 1990s are your best bet at getting in on the ground floor, so to speak, and it’s an investment you’ll never regret for a moment.

The Black Bay (right) made by Rolex’s “little brother” Tudor might be a starter luxury watch for some, but it has enough presence and precision to keep you arriving on time for many years to come.


 Blue Knit Tie

This may be the last tie you’ll ever need to buy, or the beginning of an artfully curated collection, but either way it’s indispensable for the modern man of style. We find black a little too severe, but dark navy just right.

The ultimate in classic silk at just the right width with the perfect gauge knit for an added layer of visual interest is from Ralph Lauren’s top-drawer Purple Label (left). Cary Grant would be proud.

For cooler weather you can’t improve on this attractive alpaca and wool number from Suitsupply (right), the affordable Dutch brand that has prompted an entire generation of men to dress better.