Our We Try Before You Buy series aims to take the stress out of shopping and eliminate the number of Post Office visits you make each month to return failed online orders. We test new-season buys and styling ideas so you don’t have to, and this month our editors have styled looks that revolve around Tommy Hilfiger’s Tommy Icons, showcasing how they’ll be styling the edit’s three hero pieces this spring.
I guess I’ve taken uniform dressing quite literally here by pairing a classic linen Oxford shirt with a pleated skirt and buckled Mary Jane flats—so much so that a stranger asked me if I was heading to school (as a teacher, I think), which I totally took as a compliment. This reaction speaks to the easy and instantly recognisable collegiate mood that these particular Tommy Hilfiger styles exude when worn together (and separately). The “me“ twist, though, is that after buttoning up the soft, breathable striped shirt as usual, sans tie, I went ahead and knotted the hem to define my waist. It just felt a bit more casual and less bulky than tucking the shirt, which would ruin the lines of the fluid cream skirt.
I’m tall too (5’11”), so I was thankful that the shirt’s arms are long enough that I wasn’t forced to roll them up if I didn’t want to. Neither stiff nor stuffy, the relaxed silhouettes of this decidedly smart outfit move and flow really nicely together, and I shied away from black for once to embrace lighter blue, white and cream tones. I did revert to a chic black ruched-leather bag, though, which is roomier than it looks and adds a graphic edge. And by throwing another print in the mix via my black-and-white snow-leopard-print shoes, there’s a point of difference compared to the sea of zebra-print shoes around right now.
I’m tall too (5’11”), so I was thankful that the shirt’s arms are long enough that I wasn’t forced to roll them up if I didn’t want to. Neither stiff nor stuffy, the relaxed silhouettes of this decidedly smart outfit move and flow really nicely together, and I shied away from black for once to embrace lighter blue, white and cream tones. I did revert to a chic black ruched-leather bag, though, which is roomier than it looks and adds a graphic edge. And by throwing another print in the mix via my black-and-white snow-leopard-print shoes, there’s a point of difference compared to the sea of zebra-print shoes around right now.
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Regular Fit Bengal Stripe Pure Linen Shirt
£110
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£140
Snow Leopard Print Buckle Ballerinas
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£180
Soft Leather Crossbody Bag
Tommy Hilfiger Spring 26
THE LOOK
T
he endurance of “preppy” style is worth studying. Rooted in the tailored blazers, button-down shirts and polished loafers traditionally worn at Ivy League colleges, the nostalgic pull of our personal academic journeys is definitely a factor. My own boarding-school days have certainly rubbed off on my personal style, as I’ve worn
and owned many pleated skirts and academic knits over the years, although my actual uniform was Tudor-style and very British. Whilst certain brands stay faithful to the upper-class American design codes and heritage that define preppy style, their more progressive peers remix them so the timeless aesthetic skews fashion-forward. Still, not all traditionally preppy pieces are equal. It’s the distinct spirit and superior craftspersonship that distinguishes them, and no one puts a more modern or captivating spin on it than Tommy Hilfiger.
Ever since the American designer launched his namesake brand in the ’80s and shaped the evolution of modern prep style as it stands today, the same three pieces have cropped up in Tommy Hilfiger collections. The Oxford shirt is characterised by its collar buttons and Oxford cloth material. Originally designed for elite leisure sports like tennis, polo and golf, the polo shirt is essentially a knitted, button-up T-shirt with a collar and button fastening. Finally, there’s the cable knit, which started life as fishing gear before soaring to new levels of high society. Yes, they’re enduring status symbols, but what makes these comfortable pieces iconic is their supreme wearability and that they’re always ripe for reinvention.
Whether from the current season or one of her vintage finds, Klaudia wears all her cotton Tommy Hilfiger shirts in the same approachable way.: left unbuttoned and worn open over a tank top, because the shirt is the cherry-on-top layer she turns to in place of a jacket for spring. It’s a clever move and an extra comfort when shedding heavier winter styles and darker tones as it gets warmer, ensuring she still looks stylish and put-together. “I don't like to be overly ‘girly’ or ’boyish’, and the shirt gives a balanced look that’s kind of my vibe,” she explains. “I love the stripes and how soft the material feels; it’s not at all stiff.”
Colours were a careful consideration, too; off-white trousers, a blue tank top and burgundy trainers to go with the shirt’s pink stripes. Klaudia says she cannot overstate how important the shirt’s fit and length are, especially for tall girls (she’s 5’9”), because it’s relaxed rather than oversized. Or why it’s such a versatile hero that’s worth investing in, as she excitedly reels off more shirt outfit ideas. “I’d also tie the shirt on my waist to make it into a skirt layer with jeans,” she adds. “It’s a cool way to add texture that’s actually very practical, because you’re covered if it gets cold.”
THE OXFORD SHIRT
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£90
Relaxed Fit Flag Embroidery Oxford Shirt
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£55
Contrast Trim Ribbed Slim Tank Top
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£160
70s High Rise Wide Leg Jeans
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£100
Suede TH Monogram Low Profile Trainers
Look 1: KLAUDIA
Look 1: Felicia
PREPPY COOL
RELAXED
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£160
Pleated Linen Blend Midi A-Line Skirt
Sponsor content created with Tommy Hilfiger
2 Fashion Insiders, 6 Looks— These Preppy Staples Are Our Favourite Tommy Icons
WE TRY BEFORE YOU BUY
the polo shirt / dress
the cable knit
the oxford shirt
For spring/summer 2026, the Oxford shirt, polo shirt and cable knit are officially crowned “Tommy Icons”. Tagged with Tommy Hilfiger’s signature flag logo, everything from the colour to the silhouette and fabric has been tweaked just enough to feel fresh but familiar. The high visibility of these three cornerstones of American prep also seems very aligned with both extremes of the current style spectrum. At one end, it’ll be easy for capsule-wardrobe builders to embrace and upgrade these essentials, as they know they’ll earn their place in a solid rotation. And at the other, the pick ’n’ mix dressers amongst us can clash the heritage and sportiness that these pieces radiate with contrasting outfit references to their heart’s content.
With the help of fashion content creator Klaudia Kedziora, I trialled all three Tommy Heroes by creating memorable looks that showcase more of Tommy Hilfiger’s new arrivals. The goal was to incorporate our favourite Oxford shirt, polo shirt and cable knit of the season into our everyday spring wardrobes, and the truth is, they work as hard as they play. Keep scrolling to see what we picked and how we styled it.
Tommy Icons
AUTHOR: Felicia Pennant | Photographer: Jameela Elfaki
STRUCTURE
Fully buttoning up this Tommy Hilfiger polo shirt was a revelation for Klaudia. She usually leaves at least one button undone, but admits that she looked “neater and much more chic” with the collar fastened. The fitted polo shirt looks really good tucked into her wide-leg jeans and smarted up with loafers, instantly elevating it from a familiar staple to a sophisticated T-shirt alternative. It’s still light but looks more structured. “I'm wearing the navy with stripes, which is such an iconic look for spring,” she says. “I feel like I'm in the Hamptons, about to get on a really fancy boat and drink a lot of champagne.”
Klaudia’s default style setting is casual, so she believes that the genderless polo shirt is an easy bet. The classic item to reach for when you’re unsure about what to wear, it’s a strong foundation when building memorable weekend looks. “Wearing a long-sleeved top underneath is quite noughties, and would look cute,” she notes. “I would probably also put a cable knit on top, over my shoulders, and do pink with the blue so the colours aren’t too samey.” This elevated outfit feels especially coordinated because the indigo-wash denim matches the navy of the polo’s darker stripes, and it's styled with a beige trench jacket and a tan shoulder bag.
THE POLO SHIRT
POLISHED CASUAL
Look 2: KLAUDIA
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£150
Patent Leather Cushioned Loafers
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£160
Selvedge Mid Rise Loose Straight Leg Jeans
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£75
1985 Regular Fit Pique Polo Shirt
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£180
Water Repellent Collared Relaxed Short Jacket
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EFFORTLESS
ELEGANCE
Look 2: Felicia
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£180
1985 Pleated Sleeveless Midi Polo Dress
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£300
Timeless Wool Blend Relaxed Double Breasted Blazer
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£160
Leather Block Heel Penny Loafers
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£85.00
TH Monogram Tote Bag
THE LOOK
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Tommy Hilfiger has been reviving and reinventing the timeless polo shirt since the ’80s, and this season, it has extended into a sleeveless pleated dress that falls to mid-calf in clean, fluid lines. It’s the same knit-like pique texture and same tipped collar, but the design team has clearly considered which proportions are most universally flattering and cross-generational. Naturally, I’m hooked, because dresses are my favourite clothing item of all; they’re instant outfits that require very little brain power to pull off. This one is on the smarter side of casual, and even before I paired it with a gorgeous pair of off-white heeled loafers, this anti-trend dress looked most polished with all six white buttons done up.
I’m clearly in an “embrace colour” phase, because I couldn’t resist this firework red hue that is a brand signature, but one I’d actively avoided as a Blue football fan (if you know, you know) in the past. However, this elegant dress is more tennis-coded anyway, and I know it would transform into an entrance-maker (doubled-breasted blazer optional outside of work situations). I must call out the drawstring waist, too, as another sporty detail that enhances the dress’s shape, because it ensures the fit-and-flare skirt sits exactly where you want it. You can tie those lace loops into the biggest bow, as a different belt just wouldn’t work as well.
Klaudia opted for a beige cable knit here. The neutral tone always holds its own as a springtime palette-cleanser, and it’s safe from the potential (red wine) spillages of winter. Without any outerwear on top, the jumper’s admirable warmth and traditional surface pattern are fully on show as the last layer standing. Below, a fluid, silky skirt dials up the playful movement, in a deliberate attempt by Klaudia to lighten up and move away from her go-to jeans, whilst white sneakers inject a contrasting sporty twist that feels very current. The blue of the mini bag is still tonal but bold, adding another spark to this low-key look.
Move over, chunky knits, because, as far as Klaudia is concerned, these “cute” cable jumpers are finer, lighter and amongst the hardest-working pieces in any wardrobe. They’re so easy to wear that there’s no need to overthink it. “You just chuck on a cable knit (or two), and you look great. I could have these jumpers in so many different colours, because the texture is beautiful and they’re really high quality,” she says. Day or night, season to season, she can’t think of a moment when she couldn’t wear one, which is just as well. “I get overstimulated when I have too many layers on, and going into softer textures and layers feels so much nicer than just wearing rigid knitwear all the time.”
THE CABLE KNIT
SOFT STATEMENT
Look 3: KLAUDIA
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£180
The American Icon Suede Tote Bag
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£90
TH Monogram Satin Trainers
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£140
Midi A-Line Skirt With Linen
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£120
Cable Knit Crew Neck Jumper
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BOLD
CLASSIC
Look 3: Felicia
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£120
Cable Knit Crew Neck Jumper
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£75
1985 Regular Fit Pique Polo Shirt
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£140.00
High Rise Denim Flare Midi Skirt
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£130
Mixed Texture Metallic Trainers With Leather
THE LOOK
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When I chose this juicy orange cable-knit jumper as my preppy cornerstone, I was in a “go bold or go home” kind of mood. You can’t miss it or fail to admire the incredible raised surface pattern, and this sunny colour certainly brightens up dull days. It’s dopamine dressing at its cosiest, and to find the most complementary tone to complete the look, I spun the colour wheel and landed on navy. Specifically, the same striped navy polo shirt that Klaudia wore, only layered underneath the regular-fit organic cotton knit, with the collar folded over the crew neckline and the hem staggered for a pleasing visible pattern clash. A white Oxford shirt peeking through would look great, too, along with any kind of roll neck for a more retro vibe. I can also imagine a world where this fine-gauge knit helps an oversized suit really pop off.
Whilst I don’t do jeans, I live for A-line denim skirts, and the dark indigo wash of this one continues the navy theme. As put-together as this looks, it’s the silver trainers that push this ‘fit firmly into “weekend” or “running errands” territory, because they won’t hinder your step count. As it gets hotter, that cable knit can be artfully tied across your shoulders or around your waist, so the effect isn’t lost.
Klaudia’s Tommy Icons
Felicia’s Tommy Icons
