Special thanks to Nordstrom Rack for working with us to make this post possible!
It’s the most wonderful time of the year.
No, I’m not inflicting holiday music on you already. I meant stylewise – fall has always been the most anticipated season for well-dressed men, because fall means layers and more options, which means more clothing combinations and more thoughtful ensembles.
And whenever your wardrobe is undergoing any kind of expansion, it’s always a good chance to upgrade the essentials that you find yourself wearing the most. If you're reading this, I know you’ll be glad to hear that leveling up from your Old Navy basics doesn’t have to entail big price tags. There are ways to upgrade without spending too much more – the trick is knowing where (and how) to look.
I’ve struggled with this myself. Finding a great deal can be hard enough, but trying to search for that rare in-store gem that’s – A) a quality bargain that B) fits – can be such an insufferable ordeal that I’d rather pay full price (I know, pardon my French). That’s why I never liked sifting through the rat’s nest of off-brand items in a bargain bin, let alone entire war zones like Ross or Marshalls, with their motley merchandise chaotically scattered all over the store (as one of my favorite comedians Sebastian Maniscalco says so eloquently of TJMaxx: “Looks like a bomb went off in there”).
So, if you’re anything like me – and you prefer to do your deal-hunting from the comfort of your iPad – you cannot sleep on Nordstrom Rack, one of our go-to destinations where you’ll find higher end items that sell for a lot less. Most of these are items originally sold at Nordstrom, which only carries respected brands, so you can rest assured you’re only seeing quality name brand items at Nordstrom Rack.
Since everything is priced to sell quickly, you may not always find your size. Nordstrom Rack addresses this with a comprehensive filtering tool where you can input your sizing (for waist, jacket, shirt, neck, etc.) which will then only show you results with availability in your size. This makes deal-hunting even more efficient and painless – and heck, I'd go so far as to say I actually enjoy it now. The only downside? Not a lot of material there for my man Sebastian.
To make things even easier, we’ve rounded up a collection of our favorite fall essentials, all from high-quality designer brands – and all bargains.
(Check out our 5 Hacks at Nordstrom Rack for Finding the Best Deals for more in-depth tips on getting the most out of their site).
A nice work jacket like this in an understated color like olive brings out the rustic charm of pretty much anything you wear with it. Point of interest: this one has a rugged corduroy collar.
Navy gingham is a dress shirt essential. This – as opposed to say, a plain white dress shirt – gives you extra mileage with the potential for more casual pairings (like a denim jacket). This shirt also features the polished look of a smaller-scale check making it just as easy to wear with a suit.
If your Target chinos need an upgrade, consider these chinos with a button-tab closure that adds a slightly dressier, European look. Slim fit and fine cotton twill with a bit of stretch for added comfort from a designer name.
The packable jacket is the utilitarian triumvirate of action-ready outerwear: lightweight, warm, and portable. You can roll it up and stuff it in a bag without worrying about wrinkles. And even with all its practicality, it works great as part of a smart-casual look.
Perhaps the most essential shirt you can have in your closet, from Brooks Brothers, one of the most classic names in American clothing. The light blue and the bold chambray texture – as well as the button-down collar – makes for ultimate versatility.
While its textured crepe sole and overall ruggedness gives off strong work boot vibes, the classic style and rich suede of the upper makes these the kind of shoes that might actually prompt people to say “hey, you clean up pretty good.”
As far as lighter weight outerwear goes, this sleek jacket is a classic in the stately Harrington / Eisenhower style, which, given its military roots, is not at all difficult to look smart and clean-cut in.
This field jacket is by Barbour, the British luxury brand that has been around for over a century. While this is a stylishly outdoorsy jacket very much in the “countrywear” aesthetic they’re famous for, it looks especially urbane in black.
A knit shirt like this adds a touch of class to your shirt game, as well as versatility. Don’t let its luxurious pima cotton piqué keep you from rocking it with even your most casual pairings.
It doesn’t get more classic than a pair of Chucks. These are modeled after the original vintage Chuck Taylor All Stars of the 1970s, the predecessor of the modern sneaker. While most standard Chucks are made of canvas, these are a step up – in suede.
Slate & Stone promises “elevated fashion for the modern man,” which their tastefully understated designs have consistently delivered on. Being that we just recently heralded the black long sleeve polo as the answer to feeling bored by polos, this is a smart way to upgrade.
There are few ways to achieve impeccable ease with such… well, ease, than with penny loafers. These are on the more refined side (especially in suede), yet casual enough to slip on (without socks) for that lazy Sunday drive.
The ideal casual pant is comfortable and lightweight enough for daily wear, and is capable of contributing to a clean-cut aesthetic when you need it to. These pants check all those boxes – plus, they’re cut in a flatteringly slimmer straight-leg without being restrictive.
A highly versatile casual boot thanks to its classic construction and classic looks, married with some rugged details – like the patina and light sole of a work boot which adds a touch of rough-and-tumble.
The soft knit terry of this hoodie reminds us that quality athleisure continues to blur the line between “casual” and “gym”. You may never have thought of splurging on a hoodie – but when you consider how often you wear one, it starts to make a lot of sense.
The shawl collar is often overlooked in the sweater world, which is exactly why people will take notice. It’s also surprisingly versatile, so you can dress it up with a tie, or dress it down with a simple t-shirt.
Upgrade your trousers (or your blue jeans) to a solid wool blend like these ones from Brooks Brothers, the oldest men’s clothier in America. Dark grey is an essential choice that you can build an entire fall wardrobe on, for both the office and after-hours.
These work trousers have a classic lived-in fit that you can easily wear during the week or on the weekends, and with WFH still going strong, what's the difference? Dark neutral brown makes it work with just about any color palette, even black.
This wool topcoat is a statement, and a classic one at that. Its understated blue-and-grey check pattern allows you to wear it with a wide range of colors you likely already have in your closet. We also dig the attractive, modern slim fit.
Vans Ward Sneaker, $49.97
The side-stripe signals the laid-back SoCal heritage of Vans. A classic and minimalist low-top sneaker like this gives you a lot of versatility in that you can wear it with just about anything – from summer shorts to a fall smart casual. This one features a rich, attractive gum sole.
This topcoat in charcoal herringbone is a timeless outer layer that makes any ensemble more dignified, no matter how casual the layers underneath.
There’s an appealingly minimalist swag to this chore jacket in subtle military green, which keeps things simple with four placket buttons, a single chest pocket, and unadorned side pockets.
The leather jacket is an essential for both the fashionable and rebelliously casual. Upgrading often means making a statement – and you can do here with a genuine shearling trim which makes this jacket reminiscent of classic aviator bombers, but with a modern slim-fit and sleek moto styling.
A stylish upgrade for your flannel, this ups the ante with its robust but soft cotton-silk blend, which lends to its deluxe look and feel. Also smartens things up with a chest pocket and button-down collar, a la oxford.
The warmth of a chore shirt with the added comfort of 100% woven cotton, and the placket stripe adds a subtle flair.
An essential suit in an essential color. This suit is even more versatile than the photos may suggest, as grey can also handsomely match with brown shoes (not just black). Zoom in to appreciate the subtle, tonal plaid pattern.
Ralph Lauren has long enjoyed rarefied status as a globally recognized American luxury designer (not that the name needs an introduction). You can’t go wrong by stepping up your game with their light grey sharkskin suit – arguably the most versatile type of suit you can own.
Business casual can (and should be) cool. This piece helps achieve just that with its light textured brown in a breezy, classic fit.
We picked this stretchy blazer because of its refusal to compromise comfort in the name of looks. Even though it’s knit, its high-quality double-faced construction will likely make you the best-dressed (and most comfy) guy in the room.
Zegna is a preeminent Italian fashion house and top-rated in terms of expertise and customer experience. Their unique sunglasses feature a rare combination: the classic look of tortoise frames in the style of aviators.