The older I’ve gotten, the more casual my style has become. This. however, isn’t something I view as a bad thing. Instead, I find it empowering. Gone are the days of feeling the need to hide myself behind more statement outfits. Now, at the ripe age of 34 and feeling more comfortable in my own skin than I ever have, I’ve found there’s beauty to be had in casual outfits that I never fully appreciated before.
Of course, I still want to look classic and chic, but these attributes aren’t tethered to high heels and fanciful dresses. On the contrary, I’d argue the most classic looks are those that rely on more refined, uncontrived items which, depending on the styling, can work casually or formally. It’s something you understand more acutely with trial and error—styling ensembles without worrying about whether they “work” or not and getting a feel for what you like in the process. However, if time is short, I’ve got you.
I went on the hunt for some classic casual outfits to inspire my own looks this season—below are 11 I immediately wanted to copy, and I have a feeling you’ll want to, too. Utilising what many of us would call wardrobe “staples” such as blazers, jeans, Oxford shirts, T-shirts and simple skirts, scroll on to see them.
11 CLASSIC CASUAL OUTFITS TO TRY:
1. BANDEAU DRESS + STRAPPY SANDALS
Style Notes: Bandeau dresses burst back onto the scene last summer and are sticking around for 2024, too. Opt for a neutral style in either cotton or linen and pair it with classic accessories like strappy tan sandals and a tote.
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Reformation
Astoria Dress
Exactly what I want to wear on a hot day.
A.EMERY
Carter Leather Slides
A.EMERY are a fashion editor favourite.
2. TWEED JACKET + JEANS + MARY JANES
Style Notes: Jeans are at the heart of many a great casual outfit. Lately my favourite way to style them has been with classy pieces—namely a tweed jacket and mary jane shoes, much like Dewett’s ensemble above.
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Honestly, this could be designer.
AGOLDE
Dame High-Rise Wide-Leg Jeans
Sorry skinnies, we’re still invested in wide-leg jeans.
JIMMY CHOO
Elisa 45 Mesh and Patent-Leather Mary Jane Pumps
3. TRENCH COAT + TEE + WHITE SKIRT
Style Notes: Skirts are enjoying a peak in popularity right now, featuring regularly in the casual outfits of my favourite social media dressers. This outfit is hooked on my current go-to skirt, the white midi, which is made all the more low-key with the addition of a jersey tee and trench coat.
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& Other Stories
Buckle-Belt Trench Coat
Everyone should have a camel trench in their wardrobe.
Mint Velvet
Cotton Maxi Skirt
An all-white fit is so elegant.
4. KNITTED VEST + WIDE-LEG TROUSERS + CLOGS
Style Notes: The beauty of wide-leg trousers is that they can be dressed up or down on a whim, the latter of which is perfectly demonstrated here with the addition of a knitted vest and suede clogs. Comfortable and cool? Sign me up.
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New Look
Light Brown Soft-Knit Jumper Vest
You’ll be grateful for this come autumn.
COS
Tailored Linen-Blend Trousers
hush
Lupita Mule Suede Clogs
5. DENIM SHIRT + JEANS + BASKET BAG
Style Notes: Double denim isn’t a new trend but, after appearing on the runways of the likes of Celine, Saint Laurent and Chloé, this is a look we’re going to see a whole lot more of this season. Handily, it just so happens to be classic and casual, meaning the combination works for a variety of occasions.
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Just the right amount of retro detailing.
Hush
Katie Baggy Straight Jeans
Comfy enough for lounging.
MANGO
Natural Fibre Bag With Leather Handles
6. LEATHER JACKET + TEE + MAXI SKIRT
Style Notes: When it comes to casual outfits, no jacket style is quite as iconic nor can loan itself to as broad a variety of looks as the leather biker. Personally I think black styles look their best paired with more of just that—black. Try a fluid maxi skirt for a pairing that’s so current-looking.
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Whistles
Agnes Pocket Leather Jacket
A good biker never goes out of style.
& Other Stories
Relaxed T-Shirt
A much cooler silhouette than bodycon.
I’d wear this for evenings too.
7. BLAZER + JEANS + TRAINERS
Style Notes: When I want to elevate an outfit, a blazer is the first thing I reach for. Green is a core colour trend this season—try wearing it by way of tailoring, then offset with jeans and chunky trainers for the ultimate high/low balance.
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JOSEPH
Jaden Double-Breasted Cady Blazer
Chic blazers don’t have to be black.
MANGO
Matilda Medium-Rise Straight-Fit Jeans
The perfect length for showcasing your shoes.
8. CARDIGAN + WHITE JEANS + BASKET BAG
Style Notes: Denim goes beyond blue jeans—ecru pairs can work just as well in casual outfits and, dare I say, might even look more elegant. I love this relaxed combination featuring a roomy beige cardigan and basket bag.
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Reiss
Mink Harper Chunky Knitted Cardigan
Is it too early to start thinking about autumn?
Hush
Relaxed Boyfriend Jeans
The colour and fit are 10/10.
LOEWE
Medium Sand Raffia Basket Bag
9. JUMPER + MATCHING SKIRT + KNEE BOOTS
Style Notes: I feel like I become more time-poor by the day, so I’m always on the lookout for easy yet elegant outfits I can assemble in a couple of minutes. This look definitely falls into that category. Let a knitted skirt set do the hard work for you; all you need to consider is what shoe to wear it with.
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Bretons are back (if they ever left).
This entire outfit gets high marks from me.
10. BLACK DRESS + BLACK BAG + SANDALS
Style Notes: We’re coming into cotton dress season and I’m ready to embrace them in a big way. For ease I tend to opt for classic colours and stick to the same shade throughout the rest of my outfit—shoes and bags and all. Keep your shoes flat and your dress unembellished and it’ll strike the perfect casual/classy balance.
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Reformation
Balia Linen Dress Es
THE ROW
Park Medium Leather Tote Bag
A minimalist masterpiece.
M&S Collection
Leather Ankle Strap Flatform Sandals
M&S make some of the comfiest shoes on the market.
11. OXFORD SHIRT + DENIM SKIRT + BELT
Style Notes: I recently ordered a denim maxi skirt and was immediately struck by how much I loved wearing it. My go-to involves a blue-stripe shirt and statement buckle belt, much like Sasha Mei’s.
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Reformation
Andy Oversized Shirt
No need to size up for a “borrowed-from-the-boys” look.
Don’t underestimate the power of a good belt.
AGOLDE
+ Net Sustain Hilla Frayed Organic Denim Maxi Skirt
Up Next, These 34 Romantic Dresses Are So Chic for Summer