The 5 Jackets I Wear on Repeat, and the Outfits I Always Wear Them With

If you're an avid Who What Wear reader, you might've seen my article series on how I've never managed to catch the accessory bug. Of course, I can appreciate a well-crafted bag or beautiful shoe as much as the next person, but when it comes to parting with my cash, they leave me a little cold. (I know, I know, coming from a fashion editor, this is practically heresy.)

Sorry, shoes—my heart simply belongs to something else, and that's jackets. As anyone who knows me (particularly, my husband) can attest to, I have a bit of an infatuation for all thing outwear. In my small one-bed flat, not only do they take up roughly 50% of my wardrobe, but they also hang off every door, chair or shelf (or anything that can bear a coat hanger), due to hanging space in the aforementioned cupboard reaching critical levels. Whoops.

No matter how many I own, I'll always find myself reaching for a jacket when browsing in Zara or sifting through the rails at a vintage market. It might have something to do with the fact that I love winter dressing, and when the mercury drops, all you can see is your outwear. A good jacket can transform an outfit, whether it's a blazer with a white tee and jeans, or a leather biker over a floaty summer dress.

Although I probably own over 20 jackets, there are five particular styles that get the most airtime in my wardrobe. The majority are over three years old (with a couple of newbies thrown in), and there's even one winner that dates back to pre-uni. From an Arket blazer to my statement Saks Potts jacket, scroll down to see the five jacket styles I wear on repeat.

The Leather Jacket

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(Image credit: Joy Montgomery)

Style Notes: I bought this longline biker from a sample sale around three years ago, and for some reason, it's become my go-to for travelling, as it's hard-wearing but also warm thanks to the padded lining. It looks good with everything from jeans to Topshop's silken slip skirt.

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The Checked Blazer

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(Image credit: Joy Montgomery)

Style Notes: This Arket blazer is a more recent acquisition (a Christmas present from last year), but it has already proved itself worthy of a spot in my top five. Fitted at the shoulders but boxy in fit, it also hangs so well, which makes it look far more expensive than it is. It's ideal for when I want to add an androgynous edge to an outfit—as seen in the above outfit from London Fashion Week.

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The Statement Piece

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(Image credit: Joy Montgomery)

Style Notes: I patiently waited for this Saks Potts showstopper to come on sale at the end of last year and finally managed to nab it at a fraction of the price. I've never looked back. Out of all my jackets, this is the one I receive the most compliments on. Yes, it's quite bold, but that makes it a perfect pairing for the simpler staples in my wardrobe. It makes any outfit feel 100 times more fun.

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Related: All I Have to Say About These High Street Dresses Is "Wow”

The Black Blazer

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(Image credit: Joy Montgomery)

Style Notes: I know I've already included a blazer in this roundup, but in my mind, a classic black style occupies a very different space in my wardrobe to my checked iteration. Bought for a mere £50 in TK Maxx back in 2014, I've worn this Theory blazer at least once a month ever since—now that's a good cost per wear. I often pair it with black trousers as a suit, or with jeans and heels for an evening out. It's just the right balance of grown-up, smart and timelessly chic.

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The Military Jacket

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(Image credit: Joy Montgomery)

Style Notes: This jacket was bought almost 10 years ago, in the days when Kate Moss was the style icon du jour. A bargainous £15 from H&M, it's living proof that you can find affordable pieces on the high street that will stand the test of time; it's just about choosing sturdy fabrics and styles that won't date. This has been a long-standing favourite to throw over a "nice top and jeans" pairing. It's fitted and flattering, and let's face it—military style never really goes out of fashion.

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