How to style: oversized boyfriend t-shirts

I go through these phases where I get really into — pretty tops, statement-y tops, “fun” tops, tops that get me excited to get dressed — that feel, in and of themselves, like a whole outfit.

I go through similar phases with pants, only it’s less proactive (I hate buying pants because I hate trying on pants because dressing rooms make me sweaty) and far more whiny. I get mad that I have no cool pants, , no party pants.

But all it takes is for me to see one person in ye olde “jeans and a tee” to make me think, That is the most genius outfit I have ever seen. 

In the same way that other people’s pasta orders always look more delicious than your own, regular old “jeans and a tee” on someone who isn’t you have the capacity to appear genius. It’s a bit of green-grass syndrome, sure, but mostly, it’s a combination of personal style, personal taste, novelty and individuality. If you’re ever bored with your closet, invite your friends to come over and put on a fashion show of your clothes; I guarantee you’ll see your wardrobe in a new light.

To get ahead of myself before I start to get sick of jeans and tees again, I asked nine women to show me how they style the as they interpreted it (which means when someone texted me, “Are white jeans okay?” and another asked, “Does it have to be a T-shirt or can it be something else entirely?” I said, “Sure, whatever you want.” The ice cream question was mandatory, though. Keep scrolling to meet the jean-iuses.

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Senior Fashion Editor and Instagram Wiz at

How would you describe your style to someone who knows nothing about “fashion,” who has no idea what you look like/who you are/what you’re about?

Describing my style is always challenging; it depends on who I want to be when I wake up that day. Some days I want to be ladylike in a gingham dress and slingback pumps. Other days I want to wear a suit or coordinating separates that feel cool but look polished. Either way, I always have fun with it. I want to feel good and I’m not scared of trying new things or wearing something that people might not “get.”

Jeans and a tee: What’s the magic that makes it work for you? Does it have to be specific brands, the styling, tailoring? Tell me your secret recipe.

I think it’s really about the fit (like most clothing). I only wear high-waist jeans because they just look sexier, so they have to fit right, and sometimes that means getting them taken in at the tailor or belting them. I prefer a looser fit through the legs, and right now I’m loving cropped flares.

Where are your favorite jeans from? 

are my favorite, but I have to give honorable mentions to , and

Where would you wear this outfit?

I’d wear or to hang out with friends.

Purely because it’s summer: What’s your go-to favorite ice cream/fro-yo/cold non-dairy order?

I’m completely obsessed with the lavender ice cream at .

, , , , Latino jewelry on Bowery (ask for Tommy) necklace

Founder of PR and Creative Agency  and creator of sustainable goods line

How would you describe your style to someone who knows nothing about “fashion,” who has no idea what you look like/who you are/what you’re about?

I would say my style is entirely inconsistently eclectic. Sometimes I’m drawn to or with (which comes from growing up in New England), but I also gravitate towards boho/traveler prints, shapes and . And then, of course, who doesn’t love a minimal, norm-core and/or streetwear moment? In terms of fit, I’m kind of short and pear-shaped, so crop tops and cropped jeans are generally more flattering.

Jeans and a tee: What’s the magic that makes it work for you? Does it have to be specific brands, the styling, tailoring? Tell me your secret recipe.

It’s super versatile. In my mind, I immediately think of classic, no-fuss, ’90s supermodels in high-waist jeans, but there are so many more options out there now. For tees, I gravitate towards anything super soft from to . I love . And nothing that bunches at the hips — that’s the worst. For denim, my favorites are vintage Levi’s of course, but I’ve been considering splurging on a pair of the vintage cuts at their Soho tailor shop or . In terms of tailoring, as long as it doesn’t flatten my butt and still fits through the thighs, almost anything can happen below the knee: flared, tapered, straight, take your pick.

Where are your favorite jeans and tees from? 

I frequent the shops and spend ages there, since I’ve been really trying to quit fast fashion, but can’t be spending all that contemporary designer money.

Where would you wear this outfit?

I feel like I could wear this pretty much anywhere, weather permitting — work, date, barbecue (must be very careful with sauces and condiments), under the sea, etc.

Purely because it’s summer: What’s your go-to favorite ice cream/fro-yo/cold non-dairy order?

Does the horchata boba tea from count? If not, in Bed Stuy. My friend Selena just took me there for the first time — they use honey as a sweetener, collected from the bees on their roof. And it’s a very convenient three blocks from my house.

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Content Consultant and Writer

How would you describe your style to someone who knows nothing about “fashion,” who has no idea what you look like/who you are/what you’re about? 

I would most definitely describe my style as “all over the place.” I am always really inspired and stimulated by everyday life and what I see. It can go from to to . It’s completely intuitive and dictated by the following factors: weather, mood, itinerary and desired outcome.

Jeans and a tee: What’s the magic that makes it work for you? Does it have to be specific brands, the styling, tailoring? Tell me your secret recipe.

I think, for me, in all the crazy clutter of my wardrobe, jeans and a tee (more specifically, ) is such a source of sartorial stability. I like the and I buy ten packs on . They are the best. If it’s actually tees, then it’s logo designer tees ( are a current fave), vintage music tees and skate tees. Jeans are such a saga so if I find a pair that works for me I have to go for it. I bought off a shoot from the stylist because it’s so rare they look any good on me. are great for evenings out. I also have that are really good. I guess the formula is that it CANNOT just be that. It needs something to take it further. Jewelry, a bucket hat, bum bag, a corset on top. Something to just make it wrong/right.

Where are your favorite jeans/tees from? 

, Vintage 501s from , Dover Street Market Tee shirt bar…

Where would you wear this outfit?

Drinking a frozen Dark ‘n’ Stormy at .

Purely because it’s summer: What’s your go-to favorite ice cream/fro-yo/cold non-dairy order?

Always and forever, Soft Serve.

, ,

Hair and Make-Up Artist 

How would you describe your style to someone who knows nothing about “fashion,” who has no idea what you look like/who you are/what you’re about?

My style is very intuitively driven. I don’t really (try) to be fashionable at all times. I don’t think there is a (yet). I wake up in the mornings and get dressed very randomly; funnily enough, jeans and a T-shirt have been my favorite outfit recently. This would have never been my thing half a year ago. It would have been too “easy,” but I have come to love it deeply. For now. I honestly never know when my mind will change.

Jeans and a tee: What’s the magic that makes it work for you? Does it have to be specific brands, the styling, tailoring? Tell me your secret recipe.

The magic has come to me just recently. I used to only wear and wide-leg jeans, but at the moment, my jeans have to be very tight. The magic of it, for me, is that you can pair jeans with any top. Literally any top. There is no top in the world that doesn’t go with jeans. A pair of jeans works so well with a white tee but also with the strangest, or . You can fancy jeans up by adding or fancy jackets or tops. I don’t think the brand matters. I take them all.

Where are your favorite jeans and tees from? 

I wear , , , , ,  and . For shirts, there really are no limits. I wear , , , vintage (maybe from a flea market in Rome), (my friend’s brand that unfortunately no longer exists), , , , , , , , . It really is endless.

Where would you wear this outfit?

Everywhere. To the playground, to a lunch date, dinner date, to the movies, for a meeting, to the lake, to get my coffee, to go food shopping. The usual!

Purely because it’s summer: What’s your go-to favorite ice cream/fro-yo/cold non-dairy order?

Stracciatella and lemon sorbet.

and , , vintage earrings from

Content Creator/Host of the

How would you describe your style to someone who knows nothing about “fashion,” who has no idea what you look like/who you are/what you’re about?

I would say my style is “California geometry.” I love shapes and textures and a funky silhouette, but I’m also very simplistic (think jeans and T-shirt, lol).

Jeans and a tee: What’s the magic that makes it work for you? Does it have to be specific brands, the styling, tailoring? Tell me your secret recipe.

I’m from California, so jeans and a tee are second nature. It is the uniform of Californians! I love (born in SF) more than any other brand because both the men’s and women’s silhouettes work for my curvy figure. That the jeans have a high waist is the only requirement and because I’m short, I love when they hit at my ankle.

Where are your favorite jeans/tees from? 

.

Where would you wear this outfit?

To work, to dinner, to drinks —  so I always dress for any occasion.

Purely because it’s summer: What’s your go-to favorite ice cream/froyo/cold non-dairy order?

I LOVE green tea ice cubes. I also eat about two full watermelons every week in the summer. #WtrmlnSzn.

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Fashion Writer at

How would you describe your style to someone who knows nothing about “fashion,” who has no idea what you look like/who you are/what you’re about?  

This question got existential really fast for me, so after contemplating the cosmos en route to an answer, I asked my husband who quickly said this:

“Your style is like a chef’s tasting at a gourmet restaurant. You have no idea what’s going to come out, but you know how much care and thought and deliberateness went into its preparation, and you know, even before you totally understand what you’re eating, that it’s going to taste amazing.”

(What a guy, right?) I’m not sure about the taste part, but the piece about deliberate inputs and a rotating menu of flavors is spot on.

Jeans and a tee: What’s the magic that makes it work for you? Does it have to be specific brands, the styling, tailoring? Tell us your secret recipe.

My recipe for a good jeans and a tee look has two key ingredients: the tailoring and fit of the jeans, and the styling of the look. The specifications of the tee are secondary; most of the time, any tee will do. To demonstrate the point, I’m wearing my husband’s t-shirt here. Jeans-wise, I prefer a high waist, oversized jean that is not too tight and not too baggy. Styling-wise, I look to infuse a simple outfit like this with my personality. Maybe a scarf or a bandana, layered jewelry or a bright red lip. And fun shoes, of course.

Where are your favorite jeans/tees from?

My favorite jeans, without a doubt, are these button fly Levi’s 501s excavated from the treasure trove known as the vintage jean selection at in SoHo. The first time I went in search of jeans, it took a long time and many rounds of trying jeans on to find the right pair. Subsequently, it’s gotten easier. Now I essentially replace my well-worn (read: tattered) jeans with a similar pair each year.

Where would you wear this outfit?

I’d wear this outfit during the day for a variety of things: running errands or meeting friends for a meal. It’s a good summer travel outfit, too, come to think of it. I wouldn’t wear it in the evening. There’s something too casual about a t-shirt for me to think of putting it on for a .

Purely because it’s summer: What’s your go-to favorite ice cream/fro-yo/cold non-dairy order?

Coffee ice cream!

, Chance tank top — similar , , (I am a shithead and wearing a bag with one daughter’s name on it, but not the other’s).

Founder of

How would you describe your style to someone who knows nothing about “fashion,” who has no idea what you look like/who you are/what you’re about? 

An that is thoughtful enough to consider the possibility that you are craving nourishment from various food groups, which have nothing to do with each other but still want to exist on the same plate. If that doesn’t make sense, the other sentence I would use is: I take fashion very seriously but really enjoy laughing at myself.

Jeans and a tee: What’s the magic that makes it work for you? Does it have to be specific brands, the styling, tailoring? Tell me your secret recipe.

There are two ways I think about styling jeans and a t-shirt. The first: I like to take a (for me this means boxy, crewneck and long enough to be tucked in but short enough, too, to look neat if left out) with (commonly light wash, occasionally ripped at the knees, always high waist) and see how HAM I can go with these two garments as the base — maybe at night it’s through the inclusion of a and and a . To be clear, there would also be and . For the day, particularly over the summer, I’d add a and lots of for my neck, and perhaps a slab of plus but very basic flat sandals, .

The other way I think about styling jeans and a tee is by getting more creative with my definition of jeans and a T-shirt. This outfit in particular was worn on a 90-degree day, so the T-shirt is actually a tank top. It’s not plain white; it’s striped. The jeans aren’t blue; they’re optic white, and the shoes are neither a comfortable flat nor a fancy mule. Instead they’re an in-between wedge that could be worn and interpreted any way that suits your taste. While it might seem like there is not much to this lewk, it actually somewhat perfectly encapsulates a nuance I really like to consider when I want to embody summer: easy dressing that does read careless.

Where are your favorite jeans/tees from?  

for jeans; they are expensive, but I am a sucker for non-stretch denim and they achieve the magic of a pair of vintage Levi’s at scale (in that they are replicable and not one-hit wonders than take hours in a dressing room to land on); tees by . Their crew necks wash well, are boxy and hit me at that perfect length that makes them competent contenders to be tucked in or left out.

Where would you wear this outfit?

Anywhere but the beach or a black tie barbecue. (Not averse to wearing it to a black tie wedding, though.)

Purely because it’s summer: What’s your go-to favorite ice cream/fro-yo/cold non-dairy order?

Juice Press is now making soft serve, which is a much more satisfying way to consume a smoothie IMO, but lately, I am all about the pop-up location in Soho on Spring and Lafayette). They have a campfire marshmallow soft serve flavor that I get topped with chunks of cookie dough and in that moment, I am infinite.

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Fashion Editor

How would you describe your style to someone who knows nothing about “fashion,” who has no idea what you look like/who you are/what you’re about? (Loaded, I know!)

My style has changed so much over the past few years. When I was a plus-size model, I was trying to convey that I was young and feminine (ugh, I know), so I wore a lot of floaty, . Then when I became a fashion editor, I dressed in a more polished, tailored way to come across as sharp and capable. Now that I’m doing my own thing as an entrepreneur, I dress a ton of different ways. If I have an important meeting, I tap into my suiting; if I have a casting, a good wrap dress is in order; and on the days I get to work from home, I live in baggy jeans and soft button-downs or, let’s be real, pajamas.

Jeans and a tee: What’s the magic that makes it work for you? Does it have to be specific brands, the styling, tailoring? Tell me your secret recipe.

Jeans have always been hard for me to get right. Since I’m like a size 16 in the waist and a size 12 in the legs, I’m always compromising on fit somewhere. If I buy to fit the legs, I literally leave the top button undone because the waist is too tight. If I buy to fit the waist, the legs are always too baggy. One brand I do really like the fit of is . And I’ve been getting more into the boyfriend fit — that way, it doesn’t matter if they legs are loose.

Where are your favorite jeans/tees from?

I love Warp and Weft skinnies and Levi’s boyfriend fit.

Where would you wear this outfit?

This is such a cop-out, but I’d wear this outfit almost anywhere — I’d just tweak it a bit. For work, I’d add an elevated handbag. For down time, I’d lose the jacket. For dinner with friends or my fiancé, I’d swap the heels for black slides.

Purely because it’s summer: What’s your go-to favorite ice cream/fro-yo/cold non-dairy order?

Ha! Green tea mochi!

Model

How would you describe your style to someone who knows nothing about “fashion,” who has no idea what you look like/who you are/what you’re about? 

Well, you definitely know about fashion because you’re wearing clothes — maybe it’s the bare minimum of knowing about fashion, but if you know how to dress yourself then you know something…unless you’re nudist, which, then let me describe my style to my best of my ability.

The clothes that I decide to wear everyday sometimes depend on the weather, where I’m going, or a mood I am trying to project. That varies every day, so I definitely don’t stick to one specific style. My most favorite style has always been a mix of punk rock, pin up added with a pinch of spice thanks to my latin roots.

Jeans and a tee: What’s the magic that makes it work for you? Does it have to be specific brands, the styling, tailoring, what? Tell me your secret recipe.

I look for comfort and attitude when it comes to jeans. You have to feel, pardon my language, fucking amazing when you put them on. If that’s not your immediate feeling, the jeans are not meant for you. With a good T-shirt, it’s pretty much the same except for me there has to be some story behind it, whether it’s a statement or a band that I really like. As long as there is a story behind the shirt, you better believe I’ll wear it.

Where are your favorite jeans/tees from? 

My all-time favorite jeans are from  because they have an attitude and fit my personality. As far as tees go, it really depends. They can be from a thrift store ( in LA or in NYC), to hand-me-downs from friends and family, or sometimes I shop on .

Where would you wear this outfit?

Honestly anywhere, from events to casual days . The greatest thing about wearing a T-shirt and a great pair of jeans is that it is acceptable anywhere. It’s an extremely diverse outfit.

Purely because it’s summer: What’s your go-to favorite ice cream/fro-yo/cold non-dairy order?

My all-time favorite ice cream is vanilla with chocolate chips, chocolate chip cookie dough, or 16 Handles’ Euro Tart flavor with frozen yogurt chips and strawberry bites.



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