How To Style Preppy Outfits For Every Season

Want to wear preppy outfits but don’t know how? Check out how to style preppy outfits for every season.

Recently, I rewatched the series Gossip Girl and was blown away by the stunning preppy outfits featured in it.
In my opinion, the preppy style has a timeless appeal that blends sophistication with a sporty aesthetic you can rock year-round. It’s also a look anyone who wants to look put together can pull off.
In this guide, you will learn tips on how to style preppy outfits and see outfit options that Blair Waldorf and any Gen Z will approve of in 2025.

What Is Preppy Fashion Style?

It dates back to 20th-century Ivy League uniforms, tennis clubs, and the sophisticated East Coast. It’s known for clean tailoring, quality fabrics, and understated style. Think sweaters, blazers, and pleated skirts.
The style has evolved, though. It’s not as super polished as what you would see on campuses or even Gossip Girl.
And if you’ve been on TikTok, you must have seen Gen Z’s take on the preppy style featuring cropped trench coats, silk scarves, bow-tie collars, rolled-up sleeves, straight-leg high-waist jeans, etc. Think “Clean Girl” meets “Collegiate Cool” and wearable.

What Are Preppy Colours?

If you are thinking of what colours to wear with this aesthetic, you can’t go wrong with these:

Navy
Cream
Camel
Grey

These colours are the base of the preppy look. Then add accent shades like red, Kelly green, pinks, or sky blue to make your outfits pop. Don’t also forget patterns like Breton stripes, checks, and argyle.

When dressing in these outfits, follow the 70/30 rule. This means:

70% neutrals (Navy, Cream, Beige, Grey, Black)
30% accents (Red, Green, Pink, Yellow, Blue)

This makes everything blend beautifully for every season.

Do Preppies Wear Jeans?

Yes! You can wear jeans with this style. I always keep it simple by wearing dark wash, ecru, high-waisted jeans with my loafers and blazer.

You should also go for fabrics that give you the look. Think cotton poplin, Oxford cloth, cable-knit wool, cashmere, tweed, linen (my favourite, especially on hot days), and silk print scarves.

Must-Haves For A Preppy Capsule Wardrobe

To build a preppy wardrobe, invest in the following basics to get started:

Tops and Knitwear

These are the backbone of any preppy wardrobe. Invest in Oxford shirts, striped T-shirts, rugby shirts, and bow-tie collar tops.

Don’t forget layers like cable-knit jumpers, cardigans, and cricket sweaters.

Bottoms

Opt for comfy and polished pieces here. You can’t go wrong with chinos, tailored trousers, pleated skirts, and shorts. For casual preppy looks, choose straight-leg and ecru jeans.

Dresses

This is also an essential you need in your wardrobe. Shirt dresses, knit midis, A-line minis, and tennis-inspired dresses are perfect year-round and suitable for work and weekend errands.

Layers

This is the most important part of this aesthetic. Invest in quality pieces like a blazer, trench coat, quilted jacket, and pea coat.

Shoes

Preppy shoes never go out of style, and you can wear them for years to come. Opt for loafers, ballet flats, brogues, boat shoes, and white trainers. On cooler days, swap them for riding boots.

Accessories

Accessories can take your outfits from meh to wow! Some pieces to instantly level up your preppy look are:

Silk scarves
Pearl or gold jewellery
Headbands
Sunglasses
Crew socks
Structured handbags

Preppy Outfit Ideas For Every Occasion

Whether you’re going to the office, running errands, or going on a movie date, this aesthetic has something for everyone.

Work

Navy Blazer + Cream Trousers
A navy blazer is essential because it adds a preppy touch to your ensemble.
Pair it with a striped tee, loafers, and a silk scarf knotted around your neck. Finish off with pearl studs for an elegant look.

Shirt Dress + Cardigan
Stick to a neutral-coloured one and add a belt to nip in your waist.
Then layer a cardigan and ballet flats. This outfit is simple to put together in minutes.

Weekends

These options will help you stay casual and comfortable without looking scruffy.

Polo Shirt + White Jeans
A classic polo shirt paired with white jeans and boat shoes is the perfect pairing. Brighten it up with gold earrings and a canvas tote.

Varsity Jacket + Straight Jeans
A varsity jacket has long been a staple of this aesthetic, and you can style it easily with straight jeans and trainers.
They are perfect for coffee runs or meetups with friends. It has a modern preppy vibe Gen Z loves.

Smart Casual

I love these because I can wear them for dinner or a date.

Silk Blouse + Pleated Midi Skirt
This combo is laid-back but super chic. It’s ideal for lunch dates.
Start with a silk bow tie collar blouse, then add a pleated midi, and finish off with Mary Janes and a small clutch.

Roll Neck + Tweed Midi
This is the perfect outfit for autumn. Pair it with tights to keep you warm while the loafers maintain the preppy touch.

Evenings

You can rock your preppy clothes in the evening and still look glam.

Black Knit Dress
Go for an elegant look by opting for a black knit dress. This dress looks incredible with pearl studs and a sling bag. Add red lipstick to bring a pop of colour to your look.

Velvet Blazer + Dark Jeans
This blazer with dark blue jeans adds a luxe touch to your look. Style it with a satin clutch and heels. This beautiful outfit is perfect for dinner or a low-key night out.

Travel

When on the go, you need comfy outfits that look put together. This aesthetic is perfect for that.

Breton Tee + Chinos
I can’t do without my Breton tees and chinos when I am traveling. They are so comfy. Pair them with trainers and a cardigan for a perfect travel ensemble.

Best Preppy Outfits For Body Shapes

You will look your best in these clothes when they fit your body shape.

Petite

If you’re petite, cropped and fitted pieces will look great on you. Wear cropped blazers and high-rise skirts and trousers to lengthen your legs. Avoid oversized pieces that can overwhelm your body.

Tall

Tall gals, you’re in luck. Show off your height with longline blazers, wide-leg trousers, and midi or maxi coats.

Curvy

Curvy ladies, show off your curves in A-line skirts, fit-and-flare dresses, and scoop necklines. Don’t forget to add a belt to show off your waist.

Athletic

Athletic ladies, choose preppy outfits with flowy and soft fabrics. Think pleated skirts, soft knits, and belts to accentuate your waist. Also, add accents like silk scarves or pearl earrings to soften your look.

Final Thoughts

That’s it! I hope these tips and outfit ideas will help you get the preppy look we all love.
Which one was your favourite outfit? I would love to see it in your comments below!