Whether it be the onslaught of legging trends, the continuation of post-pandemic comfort dressing, or hybrid work-from-home life, my casual era is in full force. I’m finding myself using any excuse to dress up my choice comfort clothes. I’ve even taken it as far as going out at night. Whether it be sweatpants, leggings, lounge sets, or T-shirts, good layering and chic staples can elevate any relaxed piece.
Winter weather especially lends itself to comfortable clothing, not just for the fact of wanting to constantly cozy up and stay in, but for the tactic of layering crisp, tailored pieces with your sweats or T-shirts. Also known as me making the "dress shirt and sweatpants” Zoom look into a real capsule wardrobe.
A basic white T-shirt is something almost everyone has in their wardrobe (or should) and it can be one of the most versatile pieces. I’ve started wearing mine with casual wear, workwear, and party wear. Below are some of my favorite outfit inspirations, along with the pieces I’m eye-ing to re-create them.
Blazer + Belt + Patterned Jeans
The most polished ensemble does exist (and it involves a T-shirt). Plus, a boxy blazer, classic black accessories, and a playful pair of jeans.
Statement Skirt + Heels
Dressing up a cool white T-shirt with pink pieces is my kind of nighttime look. A retro pink shoulder bag, hot-pink mules, and a slip skirt make for the best mood-boosting ensemble.
Bomber Jacket + Sunglasses + Miniskirt
The coolest way to wear a T-shirt, period. Pair it with a pinstripe micro mini, a worn leather bomber, and killer shades.
Cargo Pants + Bright Bag + Kitten Heels
Yes, cargo pants, kitten heels, and bright accessories for 2023. This is the quintessential outfit of trendy pieces that you should consider adding to your cart for this year.
Jeans + Statement Bag + Birkenstocks
Accenting with patterned accessories is one of my favorite ways to dress up basics. Plus, dark-wash jeans always feel more elevated. Outfit complete.
Cardigan + Denim Maxi Skirt + Tote Bag
A black denim midi is an amazing investment piece for year-round dressing. Pairing it with a T-shirt and cardigan is an ideal look for a casual work day or daytime errands.
Next: Olivia Wilde Has Joined the Fan Club of Hollywood's Favorite Leggings
-
6 Fashion Editors, 36 Summer Buys—Inside Our Summer 2025 Mood BoardsEverything inspiring our wardrobes this season.
-
Striped Shirts Are Always In, But Not *This* In—These 28 Will Make Every Outfit CoolFact.
-
If I Saw You in Any of These 15 Summer-to-Fall Transitional Outfits, I'd Think You Hired a StylistNice taste.
-
This T-Shirt Trend Was "Out" for So Long It's Hard to Believe It's Cool AgainProof that everything comes back eventually.
-
This Is the Classic Black Shoe Tasteful Dressers Wear With Jeans and a White Tee to Make Them Look ChicAs seen on Molly Gordon.
-
Put Down the Black and White Pants—This Is the Richer Color You Didn't Know You NeededElegant and on-trend.
-
10 Outfits Europe's Chicest Dressers Are Wearing When They're *Not* on VacationStaying local is cool.
-
What You Should and Should Not Wear to Every Major Sporting EventFrom a Liberty game to the French Open.
