Best Casual Fashion Brands for Single Men in Their 40s and 50s
Reginald Murray Williams started making boots in a shed in 1932 and the design he settled on, a single piece of leather wrapped around the foot with one seam at the back, is still the thing his company sells 90 years later. That is the standard worth applying to a wardrobe at 45. A brand earns a place when it makes the same good item every year, in a cut that suits a body that has changed since university, at a price that does not require a story to justify.
Country Road
The Australian option most men default to, and the default is sound. Country Road covers the middle of a wardrobe well, which means the chinos, the merino crew necks, the oxford shirts and the unstructured blazers that go from an office to a bar without a change.
The cut is slightly generous through the body compared with the American brands, which suits most men past 40 better than a slim fit does. Sizing is consistent between seasons, so a size that worked last year will work this year, and that is a more useful property in a brand than novelty. It also means the whole wardrobe can be replaced by attrition, one item at a time as things wear out, instead of in a single expensive afternoon.
Faherty
An American brand built around soft fabrics and a coastal look, run by twin brothers, with a stated commitment to transparent production. The knitwear and the flannel shirts are what to buy.
Faherty is the answer to a specific problem, which is the weekend outfit that has to work for a walk and an afternoon that might turn into an evening. The silhouettes are looser than most of this list. That makes them forgiving, and it also means one size down is often correct. The prices are higher than the fabric weight suggests, so the sale periods are when to buy, and the flannel is worth waiting for.
Rodd & Gunn
A New Zealand brand with heavy fabrics and a strong physical presence across Australian shopping centres, which matters because this is a range that has to be tried on. The jackets are cut for a wider frame than the European labels assume.
The house style is country weekend, so the wax jackets, moleskin trousers and heavy knits are the strength. A man who spends time outdoors will get more out of this than a man who lives in a flat and eats out, and that is a reasonable filter to apply before walking in.
Buck Mason
Founded in Los Angeles in 2013, Buck Mason built its reputation on one product, a heavyweight slub-cotton tee cut long enough to stay tucked and thick enough to hold its shape. The denim and the chore coats came afterwards.
This is the brand for a man who wants to look considered in a t-shirt, which covers most of what a single 45-year-old does on a weekend. Age-gap relationships are common enough now that any given room is mixed, and someone looking for a sugar daddy and someone hoping for a second marriage will read the same 3 things off an outfit, which are fit, condition and evident intent.
Uniqlo
The correct place to buy everything that does not need to be interesting. Crew neck tees, merino jumpers, oxford shirts, chinos and the packable down jackets are all made to a standard well above what they cost.
Scale is the reason. The Uniqlo owner reported revenue of about ¥3.1 trillion in the year to August 2024, and that volume buys fabric development that a small label cannot fund. The catch is fit. Uniqlo is cut for a narrower frame, the sleeves are short on tall men, and anything structured should be tried on rather than ordered.
Levi’s
The 501 is the only pair of jeans on this list that needs no explanation. Jacob Davis and Levi Strauss patented riveted work trousers in 1873, the 501 lot number arrived in 1890, and the modern version settled into its current shape in 1947. Levi’s 501 blue jeans passed their 150th year still in production and still selling.
For a man in his forties, the 501 solves the problem of jeans that are trying too hard. A mid-blue wash with no distressing and no logo on the pocket will go with everything else here. Buy them slightly long and have the hem taken up, because the factory hem is cut for a taller average than most men are, and 20 minutes at an alterations counter is the difference between jeans that look bought and jeans that look owned.
R.M. Williams
Everything else in the shop is secondary to the boots. One piece of leather, one seam, elastic sides, resoleable for decades, and they work with jeans, chinos and a suit, which almost nothing else does.
Ownership matters to some buyers. In 2020 Tattarang, the investment company of Andrew and Nicola Forrest, bought the iconic bootmaker RM Williams back into Australian hands for about $190 million, after a period under an international private equity owner. The clothing range is competent. The Craftsman boot is the reason to walk in.
Todd Snyder
The most expensive name here and the one that behaves most like a designer label. New York cut, Savile Row references, and knitwear and outerwear that account for most of what people spend.
Todd Snyder belongs with the cool menswear brands that fashion editors buy for themselves, and the pricing matches that position. Buy 1 piece and stop there. A single Todd Snyder jacket over Uniqlo basics looks better than a full outfit from anywhere in the middle of this list, and it is the cheaper way to arrive at the same effect. The knitwear is the other place the money is justified, since a good merino crew neck holds its shape for years and a cheap one pills across the forearms by the second winter.
The Finished Wardrobe
Picture the result on an ordinary Thursday. Dark 501s, a heavy tee, a pair of Craftsman boots that have been resoled twice, and a jacket that cost more than the rest of it combined. Nothing on the body is new, nothing is branded across the chest, and every piece fits because it was tried on.
That is 4 items and roughly 6 shopping trips spread across 2 years. It will still work when the man wearing it is 58.
