the best best: outfits to wear this week

Seven looks to get you from Monday to Sunday.

What a week! Take that statement as you wish, because it could apply to a variety of things. This week was giving full-blown simulation in the worst way (can it ever be in a good way?), but the best best is a place for fun, joy, etc. So, per usual, we’re going to leave the headlines to the (other media) professionals and keep things light over here!

What a week, could simply be referring to the whiplash of weather we have been experiencing. And while I hate to always make it about the weather, as I know the forecast is not the same for all of us, it’s hard to ignore. In a world where everything is unprecedented and nothing seems to be consistent, I’d love if the weather could finally step up and commit to summer. In just one week, I have worn outfits that could sit well across three seasons. And while I’m not complaining—because by no means does it compare to the other ‘end of times’ things that have been flooding the news cycle, it does make a round-up of seasonally appropriate outfits a little tricky. So consider this my necessary, weather-related disclaimer!

That said, we have a new season ahead—and it’s a new month (if you recall, these are meant to be monthly), which means it’s time for a fresh batch of the best best: outfits to wear this week. New outfit combinations—and of course, some tried and true, featuring silhouettes that are most likely already hanging in your closet. And remember, it’s not about reinventing the wheel. It’s about pairing your staples with something unexpected. Adding a new piece here, and incorporating a piece you haven’t touched in years there. We want to avoid any unnecessary outfit anxiety before our first cup of coffee, and dare I say, look forward to getting dressed. Because ultimately your outfit is a reflection of you, and something that should make you feel good, confident, and powerful. Which feels important given these “unprecedented times” we’re living in! When it feels like the world is truly out of control, control what you can—and that’s wearing a good outfit.

So with that, I leave you with the best best outfits to wear this week!

Xx, my best best!

Outfit Combo: Full Suit—coordinating Blazer & Trouser (this is exact suit is nearly sold out, but here are a few other options from COS blazer/trouser, Massimo Dutti blazer/trouser, and Mango blazer/trouser), Rib Tank & Sandals

Styling Notes: There really is nothing better than starting your week wearing a full suit! It’s giving businesswomen in the best way, but styling back to your favorite sandals makes it a bit more effortless. If you don’t have a full suit, mixed separates can definitely achieve the same result. However, I can’t recommend adding a full suit to your wardrobe enough; you get SO much mileage on these silhouettes. Work this look into your outfit rotation now, before those temps get too high!

Outfit Combo: Blazer, White Tee, Relaxed Pull Up or Drawstring Trouser (on sale! additional options here, here & here!), Strappy Sandal, and Light Trench

Styling Notes: While the days for this look are numbered, I had to squeeze in one last spring-to-summer transitional fit. There’s truly no better feeling than wearing a trench and sandals at the same time—peak transitional dressing! What makes this outfit work is the balance between tailored and relaxed pieces. It would still look great with just the tee, trousers, and trench, but the blazer really pulls it all together. It’s the same coffee colored blazer from my fully suited look above, and pairing it with the espresso-colored sandals perfectly anchors the outfit. I absolutely adore this color palette—soft, grounded, and effortless. And please button your blazer while you have your trench on, for the perfect layered look!

Bonus Outfit Combo (ft. the same trousers!): Oversized Button Down, Relaxed Pull Up or Drawstring Trouser (on sale! additional options here, here & here!) & Flip Flops

Outfit Combo: Skirt Suit—coordinating Blazer & Skirt (this exact skirt suit is vintage, but options from The Real Real here, here, & here!), Rib Tank & Flip Flops

Styling Notes: The idea of a skirt suit can sometimes feel a bit too serious or mature, but when styled right, it’s effortless and fun! This particular suit originally came in a size 16. I had the skirt tailored down to my size (a US6), but left the blazer as is. The oversized fit, complete with shoulder pads, adds a little drama and keeps the whole look feeling fresh rather than buttoned-up. I styled it with a ribbed tank and flip flops—two casual staples, to tone things down and make this look a little more laid back. It’s all about contrast, and this look does just that!

Outfit Combo: Blazer (another option from Anine Bing here!), Rib Tank, Sequin Skirt (other options from Guizio here, Magda Butrym here & Zara here!) & Kitten Heels (this exact shoe is nearly sold out, but options from Steve Madden here, Larroudé here & Stuart Weitzman here!)

Styling Notes: This look is ALL about the skirt! I purchased this skirt from J.Crew post-holidays on sale. It was such a score, and I have been patiently waiting for warm weather to give it a proper debut! Take this as your reminder to shop off-season. Because the skirt is quite loud (both visually and audibly—it made quite the commotion with every step), I wanted to tone things down for the office. Again, it’s all about balance, so I paired it with soft neutrals. This blazer—beige to me, green to everyone else—ended up being the perfect tonal match. This look is business on top, party on the bottom, and a crowd pleaser!

Outfit Combo: Balloon Top (this exact top is Zara from last summer, but other options Zara here, COS here & MIKOH here!), Printed Trousers (other options from Anthropologie here, Zara here & Sézane here!) & Kitten Heels (this exact shoe is nearly sold out, but options from Aeyde here!)

Styling Notes: And this look is clearly ALL about the pants! As with the skirt above, I paired this bold piece with neutrals to create a more balanced look, but make no mistake, I’ll be pairing these trousers with other stripes, colors, etc. Personally, I see stripes as a neutral—they can go in many directions! I chose to invest in this exact pair from La Veste, because a) I’ve wanted them for over a year, and b) I know I will wear them over and over again. When you know, you know!

Outfit Combo: Short Sleeve Button Down (this exact top is old Staud, but other options Djerf Avenue here, Banana Republic here, & Dôen here!) Silk Midi Skirt, Jellies (these run big, I am a 9.5/10 and I purchased the size 9) & hair pulled back with one of my fav clips!

Styling Notes: The silk midi skirt is a best best closet staple! It’s a piece I reach for all year long and easily tops the list of my most-worn items. It’s versatile, timeless, and always manages to make an outfit feel effortlessly pulled together. For this look, I paired it with a short-sleeved button-down, and the number of buttons buttoned is crucial! I recommend buttoning just the top two buttons to create a relaxed, windswept look. My top is silk, but any lightweight fabric (i.e., cotton, linen, or blends) will do the trick. Finished off with a pair of jellies, this look is easy, breezy, and ready for warm summer weather!

Outfit Combo: Blazer (this style is nearly sold out, other options from Everlane here, Aritzia here, & Mango here), Rib Tank, Cargo Skirt—or pants, or shorts! (This exact skirt is unavailable online, but options from Levi’s here, XX here, & XX here) & sneakers (w/ ribbon laces!)

Styling Notes: I stumbled upon this skirt at an L.L. Bean Japan Collection pop-up and, in the moment, couldn’t decide if it was chic or just…random. The pressure of the limited-time event pushed me to pull the trigger, and I’m happy to report that months later, I love it! I also haven’t seen anything else quite like it, so at $65.37, it feels like a steal. That said, it is one of those pieces that can veer into random territory if not styled thoughtfully. I find that’s often the case with cargo bottoms—they walk a fine line. DONNI was my gateway to cargo pants a few seasons back, and now I’ve got several pairs in rotation and can’t recommend them enough. For this look, the skirt brings that utilitarian edge, while my go-to blazer and tank (which could otherwise feel a bit expected) keep things grounded. I added sneakers for a casual, cool finish, which helps this look feel fresh and fun. You’ll notice there is a clear theme across most of my outfits. Always on a quest to strike the balance between classic and bold. That’s what makes a look feel unique. Same goes for my sneakers—these Sambas are everywhereeeeee, but I swapped out the laces for ribbons to diversify!

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Final note: Happy Father’s Day! Sending big love to all the wonderful dads out there—especially to my incredible dad, Jack Dicapo.

I feel so lucky to have grown up with this amazing man as my father. The lessons I’ve learned from him are truly endless. He’s the reason I love food and cooking (he’s the best chef!), the one who nurtured my interest in politics and history, and who instilled in me a deep curiosity about the world around me. He’s also set the gold standard for punctuality (still working on that one! lol), taught me not to take life too seriously, and of course, passed down a love of martinis.

Grateful every single day that I get to call him Dad. My only wish is that we lived down the street. ❤️