Andréa Bernholtz, celebrity fashion expert, fashion advisor for Us Weekly's Fashion Police, and founder of Swiminista, says, “I think the easiest most versatile budget friendly item to own is a midi caftan, it’s my go to! You can find a variety of colors on Amazon and they look as good as most high end easy caftans.”

The effortless chic vibes this kaftan dress brings to the party invite you to wear it anywhere you can. It has a basic V-neck and simple detailed trim that give it a clean, polished finish. The batwing sleeves flow freely around your arms and in the breeze, helping you stay cool from poolside to date night.

• Available colors: 10
• Available sizes: One size

The extra-wide legs of these lounge pants give you room to move freely while being active (or lounging). They also have a wide, elastic waistband that fits snugly and securely to you without pinching or chafing your skin. And the silky-soft material keeps them lightweight and breathable so you won’t overheat if you wear them to yoga.

• Available colors: 24
• Available sizes: Small — 3X-Large

For a budget-friendlier version of boyfriend jeans, check out these classics from Levi’s. They’re slim without being tight, are designed to maintain their shape through all-day wear, and are described as “super stretchy.” They come in at mid-rise and look excellent with legs cuffed to show off your shoes.

• Available colors: 8
• Available sizes: 2 — 28 Plus

According to Bernholtz, kaftans really shine when you “[accessorize] with a long statement necklace or an embellished belt.” She continues, “You will look chic and polished.” This pendant necklace adds a delicate elegance to any outfit, from kaftans and beyond. The pendant has an intricate cutout design that resembles lace and is set atop a chic cluster of tassels. The chain measures just over 34 inches and has a 3-inch extender if you want added length.

• Available colors: 26
• Available sizes: One size

This oversize kaftan is an option that gives you a fun way to express yourself through fun prints and vibrant colors. Let your artsy side shine through by finding the one that speaks to you. It has a laid-back and relaxed feel, with just a touch of drama thanks to the striking silhouette. Pair it with flip-flops to hit the beach or strappy sandals for a night out on the town.

• Available colors: 46
• Available sizes: One size

Shapoff adds, “A crisp oversized/boyfriend button down should be a staple wardrobe piece. This can be used for so many purposes and helps elevate any look.” When it comes to styling, she shares, “I also love the idea of wearing with a tank top underneath and having the button down worn open and free flowing.”

She recommends this flowy button-down for the task. Breezy and beautiful, you can wear it open, half-closed, or fully buttoned up depending on the look you want. The sleeves can be kept long with the cuffs buttoned, and look casual-cool when rolled up. Versatility is huge with this one.

• Available colors: 22
• Available sizes: Small — 2X-Large

Celebrity stylist Tracy Shapoff says, “A perfect fitting boyfriend jean is key for every wardrobe. This style has continued throughout seasons for many years now.”

A favorite of hers, these high-rise straight-leg jeans can be styled in so many ways, you could get away with wearing them every day. There’s a single button and zip-up closure and the standard five belt loops. For a dash of edge, there is distressed detailing on one of the legs. You can never go wrong with having a solid pair of jeans that will work all year long.

• Available colors: 1
• Available sizes: 24 — 31

Shapoff informs, “My favorite item for everyone's wardrobe is a boyfriend blazer. Black should be the first color purchase as it can go with just about everything.” This slim, oversize blazer adds understated, casual professionalism to any outfit. Another recommendation of Shapoff’s, it feels nicely retro without going full old school.

• Available colors: 25
• Available sizes: X-Small — 2X-Large

This button-down tunic is one of those workhorse pieces of clothing that gives you outfit options all year long. The bottom hits right around mid-thigh for versatility with leggings. Or, pair it with skinny jeans and embellished flats for chic a day at the office.

• Available colors: 16
• Available sizes: 12 Plus — 44 Plus

This short sleeve blouse is nice and lightweight, made from a breathable material. Its simple but sophisticated style ensures this item will be a timeless classic in your closet. Wear it solo or layer it with a blazer, or even with a cardigan for a casual day out. Shapoff says that styling a button-down “loosely tucked in” with jeans is a win.

• Available colors: 18
• Available sizes: Small — 2X-Large

Shapoff says, “Whether you are going to work, running errands or heading out to dinner, a blazer can be paired with just about every outfit. [...] A blazer looks professional yet trendy all in one.” This oversize blazer emanates casual chic. Designed with a double-breasted opening on the front for more retro feels, the side pockets have a classic fold-over top that looks nice and also protects anything you may put inside them.

If the thought of a statement blazer really sings to you, for a splurge option Shapoff loves this fishbone blazer by Anine Bing.

• Available colors: 11
• Available sizes: Small — 2X-Large

Shapoff continues, “For fall I've always been a big fan of the loafer, and for the last two years the loafer has made a huge appearance. Last year really went heavy into the ‘chunky loafer,’ which we are still seeing through this fall.”

These platform loafers are a fun twist on the classic shoe. Nonslip rubber soles are perfect for all weather and terrains, and they easily slip on and off with no buckles or shoelaces needed. For a fun splurge option, Shapoff likes these crinkle patent loafers by Franco Sarto.

• Available colors: 11
• Available sizes: 5 — 11

Classic loafers are another wardrobe staple for Shapoff, who describes them as “a great shoe to either have fun with when wearing a cute Fall mini skirt (think plaids) and chunky sweater, or I love [them] with a pair of jeans and an oversized ‘boyfriend’ button down.”

Riffing off her tip, these flat loafers are a closet must-have — and they’re a true bargain. The inner lining is a faux suede that cradles your feet like a hug, and their enduring style means they look as good with dress pants and skirts as they do with jeans and leggings.

• Available colors: 10
• Available sizes: 5.5 — 15

Milan-based personal stylist Paolina Farina recommends wrap dresses in “Diane Von Furstenberg’s style” when it comes to pieces that look good on everyone. This darling wrap dress is a fabulous essential item. The short sleeves are sweet and fluttery, with complementing ruffles along the hem of the skirt. Choose from 31 colors and patterns ranging from florals to polka dots, jewel tones, and pretty pastels.

• Available colors: 31
• Available sizes: Small — X-Large

For another option that tends to always look gorgeous, “Empire style dresses are a good choice,” says Farina. This airy sleeveless maxi dress is a pretty piece that’s definitely a good choice. The empire waist drops down to a floor-length maxi skirt with tons of movement, and thick tank sleeves provide great support and are wide enough to hide bra straps. There are also hidden pockets on the side, which are an added bonus.

• Available colors: 25
• Available sizes: Small — 3X-Large

A simple shirt dress is another crowd favorite for Farina, and this one brings breezy, casual vibes. The hemline hits below the knee, making it a nice transition-season item. It pairs well with almost any kind of shoe, as well — heels make it a bit formal, while sandals or sneakers keep it in that casual, cool realm.

• Available colors: 7
• Available sizes: X-Small — 2X-Large

When referring to jogger pants, Farina says, “highly recommended.” These essential jogger pants are pushed up a level with cargo pocket detailing. There’s a drawstring waistband, so you’ll always be able to comfortably adjust them to the right fit. They are fitted down around the ankles for a trendy look. And they are also made from an utterly soft and cushy fabric.

• Available colors: 9
• Available sizes: X-Small — X-Large

There are lots of small fashion features on this pleated cap sleeve blouse to obsess over. The scoop neck and cap sleeves are cute and subtle, and a simple pleated effect across the front and back of the blouse gives it texture. On the back, there is a small button closure that makes a keyhole feature. When it comes to blouses, Farina notes, “They work well on everyone.”

• Available colors: 42
• Available sizes: Small — 2X-Large

Lisa Sanchez, Fashion Editor of the Nines, says, “There is a reason this dress has 4.3 stars with over 14,000 reviews: it’s a winner.” There are tons of colors and patterns, and Sanchez gushes that you can “style them to make them fit myriad occasions, from a casual stroll in the farmers market to work or a cocktail hour when paired with a blazer and jewelry.” Enough said.

• Available colors: 29
• Available sizes: Small — 2X-Large

Of these high-waist pencil pants, Sanchez says, “[These] have an elastic waistband, come in more than a rainbow of colors, and have a fun waist tie. They can be dressed down with a casual pair of sneakers or dressed up with swanky set of heels.” The bow details bring in a fun pop of style and are also adjustable so you can get the perfect fit at the waist and cuffs.

• Available colors: 57
• Available sizes: Small — 2X-Large

Katya Bychkova, style and beauty expert and founder of Style Sprinter, says, “Oversized sweaters and cardigans are always in fashion, but they are particularly in for fall 2022.” She advises going for an option “in neutral hues that looks timeless and helps create that model-off-duty look.”

One of her faves, this chunky cardigan brings relaxed and casual vibes. On the sides, there are two slits that keep the cardigan from getting too clingy even when buttoned all the way.

• Available colors: 4
• Available sizes: 2X-Small — 5X

Playing off Bychkova’s suggestion, this oversize sweater gives you all the effortlessly chic autumn vibes you’ll want to channel as the seasons change. The sleeves are statements for sure with their striking balloon effect. This sweater is long enough that you can tuck it into your jeans or skirt, but it also looks polished left out.

• Available colors: 9
• Available sizes: X-Small — X-Large

Bychkova shares, “[This] is preppy and elegant; this loose-fitted sweater will bring a nautical twist to your neutral look.” The extra wide zip collar brings in a fun fashion detail, while horizontal stripes give a simple but classic look that can be styled in so many ways. Pair it with jeans and boat shoes and head out on the water, or go with leggings and tennis shoes for errands around town.

• Available colors: 2
• Available sizes: X-Small — X-Large

For a budget-friendlier version of the above, this striped sweatshirt is comfy, cozy perfection. It’s so soft you may end up picking up several — especially considering the number of colors and patterns to choose from. Cuffs around the wrists and waist provide a bit of structure for this relaxed-fitting option.

• Available colors: 35
• Available sizes: X-Small — 6X

Bychkova shares that this perfect, double-layer tulle skirt “has been an influencer favorite for years...” And when it comes to its uber-versatile options for styling, she suggests pairing it with “any solid top; the skirt will make the entire look pop.” The mesh material is secured by an elastic waistband.

• Available colors: 18
• Available sizes: X-Small — 2X-Large

“A romantic A-line midi skirt is something to have in your wardrobe for all sorts of last-minute invites,” says Bychkova. This flared midi skirt hits the marks, and its patterns are eye-catching while still being subtle. Short and tall boots alike are excellent style options when wearing this skirt. It’s so versatile and easy to wear that it’s a must-have closet staple.

• Available colors: 14
• Available sizes: Large Plus — 5X-Large Plus

Kiki Baltzi, stylist and fashion blogger at Closs Fashion, says that “[...] you can shamelessly rock any oversized T-shirt, whether it is a graphic tee or just a plain neutral one, and create some fierce looks.” This oversize graphic tee is currently hot on the fashion trends. It looks great with some jeans, a pair of shorts, fashionable leggings, skirts, and more.

• Available colors: 83
• Available sizes: X-Small — 5X-Large Plus

When it comes to rocking the oversize tee look, this version goes all the way. Made of a soft and stretchy cotton blend, it can be worn atop leggings, sweats, or jeans, as a dress, or even as a comfy nightshirt. Reviewers love how well it drapes, and call it “stylish,” “versatile,” and “comfortable.”

• Available colors: 49
• Available sizes: Small — 3X-Large

Baltzi says “a boxy denim jacket” is “literally the most versatile piece of clothing, we all need in our closets.” There is so much to love about this one, which has a solid 4.3-star rating on Amazon. Because it’s designed to fit loosely, it’s great for layering while helping you hold on to your sense of style. “Love this jacket!” one reviewer shared. “Really good quality. Nice and thick denim.”

• Available colors: 4
• Available sizes: X-Small — XX-Large

Caitlyn Parish, founder and CEO of bridesmaid destination Cicinia, recommends this fit and flare dress, describing it as “light and airy,” adding that the “pleats on the skirt add a touch of charm.” It’s versatile too, and she calls it “a great option for everyday wear or for dressing up for a special occasion.”

• Available colors: 11
• Available sizes: X-Small — X-Large

Another gorgeous and versatile dress option, of this chambray pleated wrap dress, Parish says, “I love the print and the fact that it is made from cross-dyed, pre-washed cotton chambray fabric and has a relaxed pleated bodice.” The cottony softness may make it one of your favorites. Loose-fitting short sleeves let your arms move about freely, and two large sash pieces serve as a striking wrap to get the perfect fit around your waist.

• Available colors: 1
• Available sizes: 0 — 36 Plus

Parish calls this floral mini dress “a fun and flirty option.” It makes a statement in more ways than one, starting with the deep plunging Vs on the front and back. The hemline hits just above mid-thigh and is short enough to be cheeky and long enough to be appropriate for many different occasions. Continues Parish, “I love the ... vintage-inspired silhouette ... [It] is sure to make you stand out from the crowd.”

• Available colors: 41
• Available sizes: X-Small — 2X-Large

You get all kinds of funky contrast in this mesh sleeve party dress. Parish calls it “a stunning option for a special occasion.” The bodice looks like a simple flare dress, but those mesh sleeves bring the celebration to wherever you are at the moment. Parish adds, “I love the contrast mesh sleeve and the bow tie neck detail. The dress is made from a soft fabric, so it's very lightweight and comfortable.” Wins all around.

• Available colors: 8
• Available sizes: Large Plus — 4X-Large Plus

Everyone needs to have a cute go-to cocktail dress in their closet. This lacy number wants to be yours. It has a timeless elegance to it and a classic look that you will be able to wear for years to come and throughout any season. Parish says, “I love the lace detailing and [...] silhouette. The dress is made from a nylon blend, so it's very lightweight and comfortable.” Pair it with your favorite seasonal heels and some simple accessories to top it off.

• Available colors: 5
• Available sizes: 0X — 5X