Shopping·10 min read

What to Wear on the Weekends When You’re Having Fun

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Design: theSkimm | Photos: Free People, Anthropologie, Quince
September 5, 2025

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Whether you’re headed to a nice dinner and in bed by nine (ideal) or grabbing a coffee and strolling through a farmer’s market (also ideal), these outfits will have you covered. From reliable jeans to dresses for all occasions, we’ve found pieces that’ll make you feel your best — so the fun can start when you’re getting dressed.

Looking for more affordable, stylish clothes? Here’s what to wear when working, traveling, and playing — and picks for your kids, too.

cami
Abercrombie & Fitch

The cami of your youth, but better…

The classic cami is having a moment, and we’re here for it, especially this one you can wear without a bra à la Rachel Green. It’s made of soft seamless fabric and has removable pads for a little support. Pair it with your favorite jeans for an effortless look. ($29, Abercrombie & Fitch)

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high-rise-jeans
Abercrombie & Fitch

A pair of high-rise jeans you’ll wear on repeat…

Speaking of favorite jeans, we found your next pair. These are high-rise, relaxed in all the right places, and made to look vintage but still have some stretch. These are the jeans you can throw on with a tee and kitten heels and feel put together. ($90, Abercrombie & Fitch)

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bracelet
Effy Jewelry

A heart bracelet you’ll never get tired of…

We love wearing hearts in a classic, noncorny way, and this negative space heart bracelet fits the bill. It’s made of 14-karat gold with a dainty curb chain. Clasp this on and you’ll never want to take it off. Use code SKIMM10 to take 10% off through October 31. ($315, Effy Jewelry)

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slip-skirt
Free People

A versatile slip skirt…

One thing fashion people know is how to style a skirt a million ways. Start with this one; it’s a slip skirt with lace at the bottom and a high-low hem. Wear it with loafers and a graphic tee one day, then boots and a romantic top the next. It’ll transition seamlessly from season to season. ($78, Free People)

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investment-dress
Nordstrom

An investment mini you can dress up or down…

The next time you’re invited to an engagement party, birthday dinner, or cocktail attire wedding, you’ll be glad to have this beauty. It has lace at the bust and the hem, and the navy and black color combination is chic. Throw a blazer over it for work or date night. ($495, Nordstrom)

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shirt-dress
Anthropologie

A viral Anthropologie shirt dress…

Chances are you’ve seen this dress on your feed, and we’re here to report it’s worth the hype. It has a pleated waist, large flutter sleeves, and a full skirt that give it an interesting silhouette. It looks just as cute with heels to the office as it does with sneakers for a day of exploring a new city. ($178, Anthropologie)

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hoops
Mejuri

A set of gold hoops that look more expensive than they are…

Ever since we first spotted Mejuri hoops in the wild (they’re objectively perfect), we’ve been Mejuri hoops loyalists. This set comes with three sizes, so you can wear the huggies every day, then swap them out for the large ones when you hit the town. ($184, Mejuri)

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t-shirt-dress
Old Navy

A retro style we’re bringing back…

We’re calling it now: The T-shirt dress is making a comeback. It’s comfy, cool, and pairs well with a light layer and any shoe choice. This one is long enough to not worry when the wind blows. ($8.49+, Old Navy)

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capris
Reformation

A pair of silky capris to get in on the trend…

Yes, the capri pants of the early aughts are back in full force. These are a more sophisticated take on the trend with satin fabric and a slightly longer cut. We’re swooning over how it was styled on the model, but they would also look great with your favorite cashmere sweater. ($198, Reformation)

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slip-dress
Abercrombie & Fitch

A slip dress perfect for girls' night…

When you slip this on, you’ll be ready for two-for-one margs or a nice dinner that turns into going out, whatever the party calls for. It has a deep-V neckline and an open back, but is still generous enough to not feel constricting, even if you’re wearing it for hours. ($130, Abercrombie & Fitch)

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corset-dress
Eloquii

A denim corset dress with pin-up vibes…

From the halter style to the zip-up front, this denim dress is a knockout. Though it has a corset to give it a retro feel, the fabric still has a good amount of stretch so you can move and groove. Wear it with a slick-back hairstyle and big hoops like the model. ($159.95, Eloquii)

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levis
Free People

A pair of jeans we’ve been wearing forever…

Before low-rise jeans came back in style, we were wearing these, and we still maintain they’re the best baggy option. They’re mid-rise, so they’re not low enough to make every shirt a crop top, and the slouchiness of the leg is so perfect that it should be studied. We wear these when we’re going out, then again the next morning when we’re grabbing coffee. ($108+, Free People)

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button-up
Gap

A button-up shirt that comes in many striped options…

Never underestimate the power of a button-up shirt. Unbutton it part of the way and let a bralette peek through to make it sexy, or wear it with bike shorts to the farmer’s market on Sunday morning. This Gap version will never go out of style. ($48, Gap)

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silk-cami
Bloomingdale's

A traditional Going Out Top…

This silk cami has a pretty cowl neck and hits right at the waist of your pants. It’s a wardrobe staple, since you can always count on it to make you feel sexy and sophisticated. Wear it with the pants below for a chic all-black ’fit. ($225, Bloomingdale's)

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leather-pants
Quince

A pair of sleek vegan leather pants…

If you’ve committed to going out out (brave), is there anything better to wear than leather pants? We say no. These are high-waisted with a straight leg that goes well with heels or heeled booties. They’ll fit like a glove, but they also have some stretch so you can power walk from bar to bar. ($59.90, Quince)

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shoulder-bag
Madewell

A statement shoulder bag that screams fall…

We’re seeing cow print emerge as a top trend this fall, and we like what we see. This bag is made of cowhide leather and has a hobo-like silhouette that means it’ll fit way more than you think. Grab the matching ballet flats for a superior accessory combo. ($228, Madewell)

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moto-boots
Anthropologie

A pair of moto boots to wear with everything…

The girlies are wearing moto boots with dresses, skirts, and shorts this fall. These are classic, with a single side buckle and a stacked heel, and will only look better the more you wear them. Pair them with this plaid dress and a head scarf for the perfect fall outfit. ($220, Anthropologie)

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choker
Quince

A pretty choker necklace you’ll never want to take off…

We love how dainty this necklace is, with its delicate chain and perfectly proportioned white sapphires. It’ll layer well with your current necklace stack, and the length is adjustable to make it longer than most chokers. Don’t sleep on Quince’s jewelry section. ($69.90, Quince)

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