There are few garments as effortlessly chic and endlessly versatile as the button-up shirt. For women who gravitate toward timeless, tailored style, it’s the backbone of a well-edited wardrobe — the kind of piece that works just as beautifully in a Parisian café as it does in a New England boardroom. You can even wear one with cut off shorts while knee deep in compost in your garden, or thrown over a chic swimsuit for a preppy coastal look! Whether rendered in crisp poplin, rugged oxford, or relaxed linen, the button-up offers structure without stiffness and polish without pretension.
One of its greatest strengths lies in its adaptability. A white cotton version pairs perfectly with classic denim and loafers for weekend errands, while a striped shirt layered under a blazer elevates even the simplest trousers. Come summer, a breezy linen button-up tied at the waist becomes the ideal travel companion — comfortable, flattering, and effortlessly pulled-together. I even love a crisp shirt tucked into a midi skirt and cinched with a belt! It’s this shape-shifting ability that makes a really good shirt such a worthwhile investment.
Two of my favorites are from the small but mighty brand, Ann Mashburn.
Ann Mashburn's Boyfriend Shirt - I've owned this shirt in several colors and patterns over the years and love the white oxford version so much I have two of the same shirt! (Worn countless times, but most recently here and here!) It's the perfect piece for tucking into jeans or layering under a sweater or fabulous blazer. The large flared hemline and overlapping placket are brilliant for ensuring your button down doesn't gap - keeping everything perfectly in place! (All of my boyfriend shirts are my normal size - XS.)
Ann Mashburn's Popover Shirt - This top is a recent addition to my wardrobe and kind gift from Ann's team, and as I've already worn it 3x since it arrived last week I'm buying a second color - and maybe a third. This popover is an effortless topper for spring looks and works well as an untucked tunic with tapered pants, or tucked into high waisted, 90s jeans like I did in the photos below! I sized up for a relaxed fit, and LOVE wearing it with this powder blue sweater tied over the shoulders! (Also comes in a ruffled collar version here!)
Classic style favors pieces that transcend seasons, and a well-made button-up will age with grace. My favorite shirts all feature natural fibers, flattering cuts, and a few foundational colors — think white, chambray, pale blue, and soft stripes. These tones play well with everything and never go out of style. With proper care, your favorite button-ups will only get better with time, softening just enough without losing their shape. A wardrobe icon well worth the investment in my book!
Find a roundup of my favorite spring shirting from Ann Mashburn below (plus my new favorite mules from Ann too!) You can find all my looks featuring Ann's pieces here!
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