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Meg’s Most Loved: Year-Round Clothing Favorites

I’m asked about my personal favorites all the time. My favorite jeans, the pants I travel in, the sweaters worth buying, and the pieces I reach for when I need to get dressed quickly.

So I’m bringing those recommendations together in one place.

Today, we’re starting with clothing and the seasonless pieces I rely on throughout the year. These are the classics I consider best in class, regardless of what is currently new or in season.

As we move through the year, I’ll update Meg’s Most-Loved with the seasonal staples I wear and recommend most. Throughout the rest of this week, I’ll share my most-loved shoes and bags, accessories, and undergarments.

Meg’s Most Loved: Clothes

Shop My Favorite Clothing Here

Perfect White T-Shirt

COS Slim Raglan Cotton T-Shirt | $39.00 , J.Crew Vintage Jersey T-Shirt | $34.50 , COS Clean Cut T-Shirt | $45.00

There are plenty of great white T-shirts on the market, but these are the three I reach for most:

COS Slim Raglan Cotton T-Shirt | $39
The fitted option, with a short, snug sleeve that makes it especially good for layering under blazers and jackets.

J.Crew Vintage Jersey T-Shirt | $34.50
Easy to wear on its own or under a sweater, with a banded neckline that holds its shape nicely.

COS Clean Cut T-Shirt | $45
Slightly boxy with a more substantial feel, making it especially good worn on its own.

Shop the COS Slim Raglan Cotton T-Shirt, J.Crew Vintage Jersey T-Shirt, and COS Clean Cut T-Shirt

Classic Denim

MOTHER Mid Rise Dazzler Ankle | $238.00 , J.Crew Denim Trouser Jean | $158.00-168.00 , MOTHER The Hustler Ankle | $258.00


Jeans are the most-worn category in my wardrobe, and I own dozens of pairs. But these are the three I could not get dressed without:

MOTHER Mid-Rise Dazzler Ankle | $238
One of my most-worn jeans, with an incredible fit and a versatile wash that works in every season.

J.Crew Denim Trouser Jean | $158–$168
The perfect dark-wash trouser jean. I own two identical pairs: one kept long for heels and another hemmed to wear with flats.

MOTHER The Hustler Ankle | $258
A slightly cropped jean with a subtle kick flare that works especially well with flats, sneakers and sandals. I wear mine most often during the spring and summer.

Shop the MOTHER Mid Rise Dazzler Ankle , J.Crew Denim Trouser Jean , and the MOTHER The Hustler Ankle

Bottoms

Quince Washable Silk Skirt | $69.90 , AGOLDE Parker Long Short | $148.00-158.00 , AYR The High Hopes Pant | $165.00

Outside of jeans, there are a few staples I rely on throughout the year:

Quince Washable Silk Skirt | $69.90
Every time I put this on, I’m so happy I have it. I pair it with a simple white tee and strappy sandals in the warmer months, then wear it with a cashmere sweater and heeled boots in the winter.

AGOLDE Parker Long Short | $148.00–$158.00
I keep shorts on hand all year so they are easy to pack whenever we travel somewhere warm, and AGOLDE makes my favorites. They are expensive, but the fit is excellent. These are classic and clean, and I also own the distressed version. I live in both pairs at the beach.

AYR The High Hopes Pant | $165.00
These look like clean-lined trousers but feel like sweatpants. They are incredibly comfortable and ideal for working from home, travel, or any time I want to look pulled together without wearing anything restrictive.

Shop the QUINCE Washable Silk Skirt , AGOLDE Parker Long Short , and the AYR The High Hopes Pant

Knits

J.Crew 2025 Rollneck Sweater | $98.00-128.00 , Quince Mongolian Cashmere Tee | $44.90-49.90 , J.Crew Perfect Cashmere Cardigan | $178.00-188.00

Knitwear does a lot of the work in my wardrobe, especially once the weather turns. These are the sweaters I rely on for their versatility, quality and ability to work year after year:

J.Crew 2025 Rollneck Sweater | $98–$128
A classic, cozy sweater with a distinctly ’90s feel. It is easy to wear with jeans, trousers or over a button-down shirt.

Quince Mongolian Cashmere Tee | $44.90–$49.90
Quince makes beautiful sweaters in quality fabrics at accessible prices, making cashmere something you can wear every day instead of saving for special occasions. The short sleeves make this especially useful during transitional weather and for layering.

I also love, though they are not pictured, the Quince Mongolian Cashmere Oversized Crewneck Sweater and the Quince Mongolian Cashmere Crewneck Sweater, which is only $50. Both are excellent everyday options and further proof that cashmere does not have to be reserved for special occasions.

J.Crew Perfect Cashmere Cardigan | $178–$188
A good cardigan in a classic color will take you far. Wear it over a tank or T-shirt, button it and wear it as a top, or layer it over a button-down shirt.

Shop the J.Crew 2025 Rollneck Sweater , Quince Mongolian Cashmere Tee , J.Crew Perfect Cashmere Cardigan , Quince Mongolian Cashmere Crewneck Sweater , and J.Crew Cashmere classic-fit crewneck sweater

Dresses

Ralph Lauren Belted Cotton-Blend Shirtdress | $155.00 , Tuckernuck Chloe Dress | $298.00

In my humble opinion, a shirtdress will take you far. It is one of those rare pieces that works for the office, dinner, an event, or an ordinary day, depending on how you style it.

Ralph Lauren Belted Cotton-Blend Shirtdress | $155.00
This is the classic, practical option. The belted silhouette gives it shape, while the cotton-blend fabric keeps it comfortable and easy to wear. Add flats or sandals during the day, then switch to a heel when you want it to feel more dressed up.

Tuckernuck Chloe Dress | $298.00
The Chloe is a more elevated take on the shirtdress and the kind of piece that makes getting dressed incredibly easy. It looks finished with very little styling, making it especially useful for dinners, showers, luncheons, and any occasion that calls for something special without feeling overly formal.

Shop the Ralph Lauren Belted Cotton-Blend Shirtdress and the Tuckernuck Chloe Dress

Button Downs

THE SHIRT The Boyfriend Shirt | $157.00 , Lands End No Iron Button Front Shirt | $74.97

If you know me, you know I love a button-down shirt. I wear them on their own, layered under sweaters, open over tanks and tees, and even as a swimsuit cover-up. Few pieces in my closet work harder.

THE SHIRT The Boyfriend Shirt | $157.00
THE SHIRT makes fabulous button-downs, and they are worth the investment. The Boyfriend Shirt has the relaxed fit I want from this style while still looking crisp and intentional.

Lands’ End No Iron Button Front Shirt | $74.97
I also love many of the button-downs from Lands’ End. They are well made, easy to wear, and typically under $100, making them an excellent option if you want a classic shirt at a more accessible price.

Shop THE SHIRT The Boyfriend Shirt , Lands End No Iron Button Front Shirt , and THE SHIRT The Short Sleeve Shirt

Jackets

Barbour Allerston Water Resistant Waxed Cotton Jacket | $500.00 , Quince 100% Organic Cotton Denim Jacket | $49.90 , Barbour Annandale Quilted Jacket | $220.00

A few classic jackets are all you need to get through the beginning of fall. These are the layers I reach for year after year because they work with almost everything and only get better with wear:

Barbour Allerston Water-Resistant Waxed Cotton Jacket | $500
An investment, but one you will have forever. The waxed cotton offers protection from the weather, while the classic Barbour styling works just as well in the city as it does for a weekend away. Wear it over sweaters, button-downs and simple tees throughout fall and again in early spring.

Quince 100% Organic Cotton Denim Jacket | $49.90
A classic denim jacket at an excellent price. The straightforward cut makes it easy to layer over dresses, tees and lightweight knits, and the 100 percent organic cotton gives it a more substantial feel. This is a true wardrobe staple.

Barbour Annandale Quilted Jacket | $220
Lightweight, timeless and distinctly East Coast. The quilted design adds warmth without bulk, making it ideal for transitional weather. It is casual enough for everyday wear but has enough structure to pull an outfit together, whether you pair it with jeans, trousers or leggings.

Shop the Barbour Allerston Water Resistant Waxed Cotton Jacket , the Quince 100% Organic Cotton Denim Jacket , and the Barbour Annandale Quilted Jacket

Stripes

Boden Olivia Long Sleeve Breton | $49.00 , AYR The Early Mornings Tee | $145.00 , AYR The Divers | $135.00

There is nothing like a striped shirt. I wear them year-round, and these three offer slightly different takes on the classic:

Boden Olivia Long-Sleeve Breton | $49
A timeless Breton stripe you can wear in every season. The classic shape works with jeans, trousers and shorts, either on its own or under a jacket.

AYR The Early Mornings Tee | $145
A more relaxed take on the striped tee, with an easy fit that looks especially good with jeans. It has enough presence to stand on its own without needing much else.

AYR The Divers | $135
With a neckline closer to a boatneck, The Divers feels a little more refined than a traditional crewneck tee. Wear it with jeans or trousers and add a blazer or lightweight jacket when you need another layer.

Shop the Boden Olivia Long Sleeve Breton, the AYR The Early Mornings Tee , and the AYR The Divers Tee

Blazer

TUCKERNUCK The Diana Blazer | $298.00

It is funny that with all the shopping I do for myself and our community, I have found only one blazer I truly love:

Tuckernuck The Diana Blazer | $298
The Diana is beautifully cut, comfortable and easy to wear without feeling stiff or overly corporate. Available in black and navy, it works especially well with jeans or trousers and a simple tee, button-down or lightweight knit. If you want one dependable blazer, this is it.

Shop the TUCKERNUCK Diana Blazer

Want everything I recommend in one place?

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If you are looking for something specific, or want reliable options without the overwhelm, this is where I start.

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