The 8 Best Classic Outfits to Wear on Repeat In 2024
Lately, I’ve noticed an uptick in the number of classic outfits landing on the fashion set. But that isn’t to say that trendy fashion is fading away. Oversized leather jackets, Y2K style, high-impact colours and a fresh crop of micro-trends are already in full force for the transitional. No matter where you land on the trend-adoption spectrum, though, it’s always a great idea to have an array of timeless looks on standby. With a small collection of wardrobe capsule pieces, you can create a number of polished, easy looks that work season after season. It all comes down to some simple styling ideas. Ahead, see the best classic outfits to wear now.
CLASSIC OUTFITS TO WEAR IN 2024:
1. Blazer + Jeans + Flats
Style Notes: These wardrobe staples are the perfect pieces to throw together, no matter where you’re headed. Try the outfit with loafers, as spotted here.
Style Notes: If you prefer Mary Jane ballet flats over loafers, here’s another great blazer look to replicate.
Shop the Look:
COS
Oversized Exaggerated-Shoulder Blazer
Head to COS for great tailoring.
Arket
Cloud Low Loose Jeans
These jeans are timeless and relatively affordable—win-win.
These shoes are destined to sell out.
2. Denim Skirt + Kitten Heels
Style Notes: To make this look feel extra luxurious and perfect for cooler days, layer it with a chunky faux fur jacket. The juxtaposition of textures—soft fur against sturdy denim—creates a sophisticated edge that will keep you warm and stylish.
Style Notes: Swap out the usual top for a crisp, tailored white shirt tucked into the skirt. It elevates the whole ensemble, making it perfect for work meetings or even dinner dates. You can roll up the sleeves for a more relaxed vibe.
Shop the Look:
Arket
Regular-Fit Poplin Shirt
The building-block piece.
LOEWE
Paseo Leather Shoulder Bag
Loewe always delivers great handbags.
The classic silhouette that will be everywhere this autumn.
& Other Stories
Pointed Slingback Pumps
3. Striped Shirt + Trousers + Sunglasses + Jewelry
Style Notes: Yet again, button-downs prove their versatility. Add trousers, sunglasses, and a watch, and you’re ready to go.
Style Notes: A striped top lends a cool preppy vibe to the look.
Shop the Look:
SÉBLINE
Striped Cotton-Poplin Shirt
A sleek option that’ll never date.
& Other Stories
Wide Press-Crease Trousers
So easy to dress up or down.
& Other Stories
Angular Cat Eye Sunglasses
An all season accessory.
4. Nice Top + Trousers + Heels
Style Notes: Statement-neckline tops are having a moment but also are the ’90s staple that will never go out of style. This look couldn’t be simpler or more perfect.
Style Notes: It doesn’t get easier—or chicer—than this.
Shop the Look:
Reformation
Darra Knit Top
If you want investment staples that will last forever, head to Reformation.
Elevate any outfit with a pair of tailored trousers.
& Other Stories
Slingback Leather Pumps
Make no mistake—slingbacks are back.
5. Slip Dress + Blazer + Heels
Style Notes: For an evening look, opt for a satin slip dress, and then throw on a blazer and heels to finish the outfit. The jacket adds a great tailoring element to pull it together.
Style Notes: Keep it simple, but play around with patterns and textures.
Shop the Look:
& Other Stories
Sleeveless Satin Midi Dress
You’ll get so much wear out of this slip.
Another way to wear your staple blazer.
GIANVITO ROSSI
Tokio Glossed-Leather Pumps
6. Button-Down + Jeans + Retro Trainers
Style Notes: The styling possibilities of a great button-down are endless, but when in doubt, you can’t go wrong reaching for your most-loved jeans.
Style Notes: Just add retro trainers for a casual yet pulled-together look.
Shop the Look:
COS
Oversized Tailored Shirt
MOTHER
The Spitfire Nerdy Cuff Boyfriend Jeans
TOTEME
Double Wool and Cashmere-Blend Baseball Cap
Baseball hats seem to be cropping up a lot lately.
Converse
Chuck Taylor All Star 70 Canvas Sneakers
Converse are just as cool as ever.
7. Waistcoat + Jeans + Flats
Style Notes: Waistcoats are timeless, but they’re definitely having a moment right now. Pair with jeans and ballet flats to emulate the Instragram style-set.
Style Notes: How to pull off a comfortable weekend look that still feels intentional.
Shop the Look:
Whistles
Tansy Linen Waistcoat
A classic with a modern twist.
AGOLDE
Clara Baggy Wide-Leg Organic Jeans
To pair with the above waistcoat.
AEYDE
Uma Patent-Leather Mary Jane Ballet Flats
You’ll have these for years.
8. Knitted Dress + Pumps
Style Notes: Complete the look with a slouchy leather tote bag, perfect for carrying all your essentials. The relaxed structure of the bag balances the more fitted silhouette of the dress, adding a casual-chic element that feels both practical and stylish.
Style Notes: For a pop of colour, add a pair of striking red pumps to your look. The contrast of the bold shoes against the neutral tones of a knitted dress makes the outfit feel fresh and modern without overwhelming it. Red is always a statement, and this subtle infusion of colour adds just the right amount of drama.
Shop the Look:
COS
Asymmetric Merino Wool Dress
This cosy dress is so easy to wear.
LOEWE
Puzzle Fold Xl Convertible Leather Tote
I can’t stop thinking about this tote.
GIANVITO ROSSI
Nuit 55 Glossed-Leather Slingback Pumps
The colour is everything.
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