Few things trump a good vintage score. After all, it’s hard to beat something that’s not only extremely affordable, but unique to boot. Over the past fifteen years, we’ve seen a proliferation of identikit second-hand rails of 1990s-era denim, 1980s flannels and sports kit, as well as patterned ties and beaten-up shoes – from capital city shopping districts to small town high streets.

But while shopping vintage often brings great bargains, the stock itself can err a little too scruffy for those wanting to step it up a sartorial gear. The term ‘vintage’ itself is pretty subjective and a lot of what passes for vintage is badly made, cheap or even – *shudder* – modern clothing in disguise.

If your raids have yielded more unbranded rejects than timeless staples, then it might be time to go modern. Here, we’ve compiled a few upgrades on vintage store classics that are more streamlined, a little more luxe and destined to be future collectibles in their own right.

1. The Plaid Flannel Shirt

Step into any vintage store and we bet our Grensons you’ll find a rail of plaid flannel shirts. The broken-in fabric (done using mechanical brushing) has a plush softness but can age badly, bobbling easily and eventually bringing your look down a notch. What’s more, these grunge-infused staples often come cut awkwardly boxy – which is fine if you’re Hedi Slimane-era Dior Homme skinny, not so much if you’re anything else.

If you’re an avid flannel fan, try looking for contemporary updates from outdoor-focussed brands such as Patagonia, Gitman Vintage or NN07. These will most likely fit better (if only by virtue of the fact that you’ll have a full size range to work with) and often come in fabrications lighter in weight than bulkier vintage finds – ideal for going between seasons.

Elsewhere, on the high street, Uniqlo offers a superb selection of flannel shirts every autumn/winter, which come in both solid block-colours and classic buffalo checks. Priced at £24.90, you can afford to pick up a couple.

Lookbook Inspiration

Men's Plaid/Check Flannel Shirts Outfit Inspiration Lookbook

burton aw14bellfield aw14baldwin aw15j.crew aw15aquascutum ss16next aw15drykorn aw14allsaints august 2014cadillac autumn 2015

Recommended Styles

Men's Flannel Shirts

PATAGONIA FJORD FLANNEL SHIRTGITMAN VINTAGE CHECKED COTTON-FLANNEL SHIRTNN.07 DEXTER SLIM-FIT CHECKED COTTON-FLANNEL SHIRTUniqlo Flannel Check Long Sleeve Shirt

2. The MA-1 Bomber Jacket

Made for the US Air Force, every element of the MA-1 bomber jacket has been designed with a function in mind, from the abundance of pockets to the iconic orange lining, intended for drawing attention if your plane crashes. Or on your next night out.

While second-hand MA-1s are easily sourced, they can come up pretty bulky on a regular guy due to their fairly capacious padding. Luckily – given the resurgence of interest in the military staple in recent years – plenty of brands have saved the details and slimmed down the lining, including Alpha Industries, whose jackets are perhaps most faithful to the MA-1’s form; under-the-radar Japanese label Journal Standard, whose nylon MA-1 is brilliantly lightweight; and Acne Studios’ Selo bomber, which keeps the essential details but lengthens the silhouette for a sleeker, more streetwear-inspired finish.

There are also some solid high street options out there, with H&M and Topman providing stand-out styles.

Lookbook Inspiration

Men's MA-1 Bomber Jackets Outfit Inspiration Lookbook

drykorn aw15burton ss14h&m aw15Brunello Cucinelli SS16apc aw15allsaints august 2015next 2015original penguin aw15mango ss15

Recommended Styles

Men's MA-1 Bomber Jackets

Alpha Industries MA-1 SKYMASTER FLIGHT JACKETH&M Bomber jacketACNE STUDIOS SELO BOMBER JACKETJOURNAL STANDARD NYLON TAFFETA MA-1 JACKET

3. The Parka

It’s a well-known story: military jacket designed for extreme cold becomes beloved by mods, immortalised by cult film (Quadrophenia [1979]), is worn by an army of musicians and festival-goers alike, and ends up entering menswear history.

If you rate the silhouette and practicality of the parka but want options that differ from the badge-covered military versions that swamp vintage stores, then try a contemporary alternative.

A down-filled design – like this one from Ralph Lauren and this one from Italian outerwear specialists Stone Island – is a fail-safe winter investment and much hardier than the thin canvas styles you’ll often find piled onto racks at thrift stores. Alternatively, a coloured parka – like Woolrich’s bright red option and Patagonia’s fire engine style – puts a new spin on a time-honoured outerwear staple.

Finally, although not parkas per se, Swedish brand Stutterheim’s raincoats take the silhouette and make it fully rainproof, offering a neat, autumn-ready upgrade on this perennial cold-weather throw-on.

Lookbook Inspiration

Men's Padded Parkas Outfit Inspiration Lookbook

burton aw14calliope aw12Woolrich John Rich & Bros aw15brioni aw14j.crew november 2014digel aw14faconnable aw15next aw14primark aw15

Recommended Styles

Men's Padded Parkas

RALPH LAUREN Rover quilted parka coatWOOLRICH short hooded padded coatSTONE ISLAND BLUE MICRO REPS DOWN-FILLED HOODED PARKAPatagonia Isthmus Parka

4. The Chore Jacket

More surprising than the resurgence of the chore jacket is the fact that it ever fell out of style.

Replete with handy patch pockets, this versatile dress-up or –down silhouette is easy to layer and comes in rugged cotton that wears beautifully over time, becoming your own signature piece of sartorial history. Problem is, buying vintage means skipping that step, so you’re left with little to look forward to.

Thankfully, contemporary iterations are everywhere. If you favour a clean look, Carhartt’s chore coats in khaki and navy are smarter than anything you’ll find in a vintage shop, while Freemans Sporting Club’s take on the classic comes lightly pre-washed to eliminate shrinking and is made in America, unlike many of the mass-produced pieces you’ll find lining the walls of second-hand stores.

Men's Chore Jacket Outfit InspirationAdolfo Dominguez SS15

Recommended Styles

Men's Chore Coats/Jackets

Carhartt WIP Chore CoatCarhartt WIP Chore CoatAPOLIS INDIGO WOOL CHORE JACKETFREEMANS SPORTING CLUB CHORE COTTON-CANVAS JACKET

5. The Borg Collar Denim Jacket

Whether you call them borg or Sherpa, fuzzy-collared denim jackets are quintessentially vintage. And it’s not exactly difficult to understand their enduring appeal: denim ages wonderfully, while the contrast collar adds warmth and a certain all-American, workerwear brand of cool.

Bought vintage, they can look a little like you’ve spent a year too many tirelessly lassoing cattle on the range. Instead, try a box-fresh Levi’s version and break it in on your own terms.

Like chore jackets, these can look smarter in black, which is a difficult colour to track down second-hand. If you’re searching for a more luxurious upgrade, Burberry Brit’s version isn’t cheap, but it does come with a real shearling lining, rather than the bobbly synthetic alternative you’ll have to contend with on many older, pre-owned styles.

Lookbook Inspiration

Men's Borg Collar Denim Jacket Outfit Inspiration Lookbook

burton aw13topman aw15forever 21 aw15primark aw15drykorn aw14boohoo aw13

Recommended Styles

Men's Borg Collar Denim Jackets

Levi's Blue Sherpa JacketBURBERRY BRIT SKIPPER SHEARLING-COLLAR DENIM JACKETASOS Denim Jacket With Borg Collar In Blue WashASOS Denim Jacket With Borg Collar In Navy

6. The Tweed Blazer

Quintessentially British, the tweed blazer has – much like the double-breasted suit – joined the ranks of contemporary tailoring must-haves. But opting to go the vintage route might not be as lucrative as you would think. Many second-hand shops mix in well-made Harris Tweed jackets with 1970s-era polyester versions at the same price, with scant regard for quality.

While you might strike gold and find a perfectly tailored jacket among the rails, buying new means you’ll have access to a much wider range of colours and patterns, as well as more flattering cuts.

We rate this herringbone design from the Italian shirtmaker-turned-boutique Al Duca d’Aosta, thanks to its rich colouring and sharp fit, while the severe lines and pale grey, almost green tweed give this Acne Studios number a look-twice quality.

Buying new means it’s also easier to find trousers to match, like J.Crew’s Ludlow suit in Donegal tweed.

Lookbook Inspiration

Men's Tweed Blazers Outfit Inspiration Lookbook

marks and spencer aw13Viyella aw13zara 2012brooklyn tailorstoast aw14burton aw13ramsey aw13massimo dutti aw15ted baker aw13

Recommended Styles

Men's Tweed Jackets/Blazers

AL DUCA D’AOSTA 1902 herringbone tweed blazerAcne Studios Aron J Shet Grey MelangeJ.Crew LUDLOW SUIT JACKET IN ENGLISH DONEGAL TWEEDCharles Tyrwhitt Blue Herringbone Slim-Fit Jacket

7. The Brogues

Quality brogues can be easy enough to pick up vintage, but if you’re searching for unique details (like contrast soles), unusual materials or non-traditional colourways, you’ll have better luck going brand new.

Pre-owned brogues in brown and black are a dime a dozen, so if you want to switch things up instead, try this blue pair from like Paul Smith or these triple-welted beige suede numbers from renowned British shoemakers Grenson.

By swapping old-school for box-fresh, you can also experiment with chunkier soles, as seen on this statement pair by Mark McNairy and these practical wedge soled versions from ASOS.

What’s more, by buying new you can take advantage of many traditional manufacturers’ lifetime repair services – which means you can even pass them on to the next generation some day.

PAUL SMITH GRAND LEATHER BROGUESPAUL SMITH GRAND LEATHER BROGUES – Click To Buy

GRENSON ARCHIE TRIPLE-WELT SUEDE WINGTIP BROGUESGRENSON ARCHIE TRIPLE-WELT SUEDE WINGTIP BROGUES – Click To Buy

MARK MCNAIRY VIBRAM SOLE COUNTRY BROGUEMARK MCNAIRY VIBRAM SOLE COUNTRY BROGUE – Click To Buy

ASOS Brogue Shoes in Black Leather With Wedge SoleASOS Brogue Shoes in Black Leather With Wedge Sole – Click To Buy

8. The Hawaiian Shirt

Also known as the Aloha shirt, few items of clothing have earned themselves as bad a rap as these multicoloured warm-weather favourites. You either love the kitsch sunsets and vibrant hues – or you (painfully) endure other people sporting them.

Regardless, nothing says summer quite like a Hawaiian shirt – but between dodgy fabrics (think thin viscose and sweaty polyester), awful prints and questionable colour schemes, vintage versions can be hit-and-miss. In fact, this is one item where it’s best to buy new; designers have toned down some of the worst excesses and streamlined the fit on many designs to make them much more wearable.

For example, ASOS’ are cut slim for a contemporary feel and come complete with a smart collar that puts it much closer to Al Pacino in Scarface than Tom Selleck. Likewise, Polo Ralph Lauren takes a more muted, almost painterly print and renders it in a slightly sportier ‘popover’ style.

Lookbook Inspiration

Men's Hawaiian Shirts Outfit Inspiration Lookbook

scotch & soda ss15h&m ss12allsaints may 2015mango 2015scotch & soda ss15ovadia & sons ss13dunhill ss15allsaints ss14matalan ss15

Recommended Styles

Men's Hawaiian Shirts

ASOS Shirt In Hawaiian PrintAllSaints Monsoon Short Sleeved ShirtPOLO RALPH LAUREN PRINTED LINEN AND COTTON-BLEND SHIRTCLUB MONACO BUTTON-DOWN COLLAR PALM-PRINT COTTON SHIRT

Final Word

There’s no disputing that buying pre-owned has its perks. But sometimes the real (new and unworn) deal is what’s required to sidestep shoddy quality and awkward cuts.

Which items of clothing do you buy vintage and which will only do brand new? Are there any others worth adding to this list?

Comment below to let us know.