Layered shirts + jeans
Multiple thin layers keep you warmer than a single bulky garment. Multiple layers also allow you to add or remove clothing as needed depending on how you feel. Start with a simple tank top to keep your core warm. Then, add a t-shirt or thin blouse. Only wear one bulky layer on top (if any)—multiple bulky layers will restrict your movement and can look dumpy. Basic: a light tank top under a flowy blouse with jeans and flats, topped with a chunky cardigan or simple blazer Casual: a tank top, tee, and hoodie with jeans or leggings and sneakers Dressy: a tank top under a blouse with jeans or trousers and heels along with a bold piece of statement jewelry
Chunky sweater + linen pants
Layer breezy fabrics with chunky knits. Transitional seasons give you the opportunity to really get the most out of your closet. You don't have to put away a winter or summer favorite, you can just pair it with something lighter or heavier to suit the mild temperature outside. Basic: tee or button-down, chunky cardigan, drawstring linen pants, and loafers or ballet flats Casual: tee, chunky pullover, drawstring linen pants, and sneakers Dressy: flowy blouse or silk shell, chunky cardigan, linen pants, and heels with a chunky necklace
Trench over tee + pants
A lightweight trench coat provides coverage without bulk. When it's in the 50s, you want to be warm, but not too warm—especially if you're going to be walking a lot. The classic trench coat keeps your clothes dry without too much added weight to leave you stifling under it. Basic: a trench over a tee and jeans with ballet flats or ankle boots Casual: a trench over a tee with leggings or joggers and sneakers or rain boots Dressy: a trench over a blouse and tailored dress pants with heels
Turtleneck + trousers
A lightweight turtleneck can be just as versatile as a T-shirt. Substitute a T-shirt with a turtleneck to provide more coverage for 50-degree weather. It'll keep you warm without adding a lot of bulk. Basic: turtleneck, cardigan, casual trousers, ballet flats Casual: turtleneck, hoodie sweatshirt, casual trousers, sneakers Dressy: turtleneck, pashmina shawl, trousers, heels, statement jewelry Linda Przybyszewski, Dress Historian A turtleneck's warmth cradles you like a lover's embrace, while trousers' tailored elegance makes any affair feel special. Together they walk hand in hand through brisk autumn air, an alluring couple dancing to the seasonal rhythm.
Chunky sweater + slip dress
The sweater turns your dress into a fluttery skirt. When it drops down to the 50s, it's a bit too chilly to bare your arms and shoulders. A sweater will keep you warm while allowing you to get a little extra mileage out of your favorite light summer dress. Basic: chunky sweater, slip dress, tall boots Casual: chunky sweater, slip dress, optional leggings, sneakers or rain boots Dressy: chunky sweater, slip dress, heels, and a bold statement necklace
Cashmere poncho + jeans
A lightweight cashmere poncho or wrap adds warmth without bulk. A cashmere poncho is an investment purchase that will last a lifetime with proper care—and you can wear it with anything! This versatile piece will help you take many different outfits through the transitional seasons. Basic: cashmere poncho over jeans and a t-shirt with ankle boots or ballet flats Casual: cashmere poncho over jeans and a t-shirt with sneakers Dressy: cashmere poncho over a silk blouse and jeans with heels and dangly earrings
Oversized button-down + shift dress
Big shirts can double as lightweight jackets. Choose a shirt that's a couple of sizes too big (at least) to get the right look. To look more put together, pair your shirt with a dress in a complementary color. A plaid flannel can be a nice and unexpected touch over a solid shift. Basic: solid oversized button-down over a bold shift with ballet flats Casual: oversized flannel plus a casual shift and sneakers Dressy: black oversized button-down over a bright shift with heels and statement jewelry
Blazer + flowy skirt
The blazer adds a sharp edge that finishes off your look. When it's in the 50s, it's a bit chilly for a tee without anything else—especially if you're pairing it with a breezy light summer skirt. A blazer and a tee is a great look that helps your skirt transition into cooler weather. Basic: navy blazer over a fitted white tee tucked into a floral skirt with flats or sneakers Casual: navy blazer over a loose tee and floral skirt with sneakers Dressy: satin shell tucked into a floral skirt with heels, topped with a black blazer
Sweater vest + pants
Vests are the ultimate piece for transitional seasons. A vest keeps your core warm while leaving your arms free, so you won't get overheated. If you're buying something new, pick a solid in a neutral color and style that you can dress up or down easily. Basic: vest over a tee with jeans and flats or sneakers, with a light jacket for additional warmth Casual: vest over a tee and leggings or joggers with sneakers Dressy: vest over a blouse with tailored dress pants and heels
Crop top + high-waisted pants
This pairing ensures coverage while still being fashion-forward. You might not want to bare your torso just yet when it's only 50 degrees out, but that doesn't mean you have to leave your crop tops in the closet. Cinch up the pants so that your crop top hem falls at or just below the waist to keep out the chill. Basic: crop top, high-waisted jeans, ballet flats or loafers, and a lightweight jacket Casual: crop top, high-waisted jeans or leggings, sneakers, and a puffy coat Dressy: crop top, high-waisted dress pants, heels, layered necklaces or bracelets, neat cardigan or fitted blazer, heels, and layered necklaces or bracelets
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