It’s the first Monday of the Summer! And with that, some fresh outfit inspiration awaits. While the 90 and 100-degree temperatures in Chicago have definitely felt like summer, last week officially marked the Summer Solstice! It feels like summer has been in full swing for the last few weeks since Memorial Day, but now we’re officially changing the page on the seasons.
My What I Wore Last Week posts used to be a weekly series that I hope to return to someday! I’ve bitten off way more than I can chew this year and am trying my best to keep all the different balls in the air. While I wish I could have made the time to share these outfits weekly, here’s a look at all of the outfits I’ve been wearing and repeating over the last few months!
Please bear with me — this post is LENGTHY! But I tried to include lots of sizing details, restaurant recommendations, and even a celeb sighting. 😉
We’ve had a really wonderful spring here in Chicago, which I believe can be attributed to it being an El Niño year. Since it was warmer than usual, I’m hopeful that you can take inspiration from a lot of my spring outfits and apply it to styling your summer looks!
Dressier Outfits
Here’s what I’ve worn for dinner dates, events, and nights out recently!
Sandro Alecia Ribbed Midi Dress
This dress is so not in my normal wheelhouse, but since I’m in my bridal era, I figured I’d take a bit of a risk with a longer white dress. The ribbed material is on the thicker side, so I didn’t necessarily feel like Spanx were an absolute necessity. But the low neckline did encourage me to wear a slip! Since I don’t typically go for a form-fitting silhouette on the bottom, I felt more comfortable in a pair of high-rise shorts underneath, too.
The dress is advertised as a ‘midi’ online, but since I’m 5’5″, it hits right at my ankle.
I wore this out to a fancy dinner at NEXT. (The Bobby Flay menu is unreal – highly recommend it if you’re into prix fixe fine dining!)
- Sandro Ribbed Midi Dress (TTS – I have the size 38!)
- PS: more sizes are available here!
- Loeffler Randall Raffia Clutch
- Mignonne Gavigan Hoop Earrings
- also available in a mini size here!
- Raye Denim Sandals
- I’m a true 8.5 and these only come in whole sizes. I got the size 9 and they’re a bit too big, which I realized *after* I wore them out of the house 🙃. If I were doing it over, I’d probably order this pair instead, especially knowing they’d be a bit easier to walk in with the back strap! Oh, and they’re also cheaper. 🫠
Madewell Floral Dress
This sleeveless floral dress has been on repeat! I styled it with the light blue raffia clutch and coordinating earrings again, but went with my bamboo slides to bring in more brown. (Side note: I also went on a major hunt for chocolate brown strappy sandals — more on that to come!)
I wore this dressier outfit to Le Colonial in Lake Forest for a girlfriend’s birthday and a fun fact for fellow Bears fans — we were a few tables away from Caleb Williams the whole night! 🤩
(And then we saw Ryne Sandberg at the new Once Upon a Bagel in Lake Forest the next morning!)
- Madewell Sleeveless V-Neck Floral Dress (TTS – wearing the 6)
- Schutz Gold Bamboo Buckle Slides (TTS)
- Loeffler Randall Raffia Clutch
- Mignonne Gavigan Hoop Earrings
- also available in a mini size here!
- Madewell Sleeveless V-Neck Floral Dress
- Dolce Vita Mesh Flats (TTS – they felt a little snug initially, but broke in nicely!)
- H&M Chunky Fisherman Cardigan (old)
- Caterina Bertini Bag (from last season)
- Target Sneakers
PS: This blue color is definitely the new ‘it’ color! The red of last season, if you will. (Which bodes very well for brides-to-be — I love it as a ‘something blue’ moment!) If you like this Loeffler Randall clutch, peep this crochet tote and this striped raffia clutch.
Tuckernuck White Lace Dress
While this dress is a more recent addition to my wardrobe, get ready to see it on repeat this summer. I’m obsessed! I’ve already worn it 2-3 times in the two weeks I’ve had it.
- Tuckernuck Lace Dress (TTS – I have the Medium)
- it’s also available in brown or a fun cream/red stripe that would be perfect for the 4th of July!
- Schutz Gold Bamboo Buckle Slides (TTS)
- so comfy! I got these sandals last summer and they’ve never once given me a blister. I’ve walked in them A TON, too. Birkenstocks are just not comfortable on my feet for some reason, but I love how these give the vibe, but in a more elevated way. Plus, no break-in time! Also available in black, white, a chocolate brown woven leather that looks like Bottega, and a neutral fabric.
Everyday Outfits
Endless Rose Green Tweed Vest
This tweed top has been another obsession! No joke, I’ve worn it at least six or seven times and have gotten ENDLESS compliments every time I’ve had it on. I even said “‘Yes’ to the Dress” when I was wearing it!
- Tweed Top (TTS – I have the Medium)
- there’s also a pair of matching shorts
- Abercrombie Jeans (TTS – I have the 6)
- read my full Abercrombie Jeans Sizing Guide here
- Schutz Gold Bamboo Buckle Slides (TTS)
- Levi’s Dad Jeans (below on the left)
- Brown Oval Sunglasses
- Clare V Straw Bag (old)
- LV Neverfull
Levi’s Dad Jeans
I got these Levi’s ‘Dad Jeans’ a few months back and they’ve easily become my most-worn pair this spring/summer. I’m obsessed with the fit! Fitted through the waist and hips, but an on-trend relaxed leg. The length is perfect on me, too — right at my ankle bone. There’s no stretch in the fabric, but it does give a lot. I’d say they’re true to size, but to size down if you’re in between. They might be a bit snug when you first put them on, but they will stretch out a bit.
The best part is that they’re under $100! Can’t beat it.
- Sezane Dita Top (TTS – I have the Medium)
- Levi’s Dad Jeans (TTS – I have the 28)
- Abercrombie Short Sleeve Sweater (it’s SO soft – I have the Medium)
- Levi’s Dad Jeans (TTS – I have the 28)
- Crystal Mesh Mary Jane Ballet Flats
- LV Neverfull
These mesh rhinestone ballet flats are a fantastic Amazon dupe I found for the Loeffler Randall Leonie flats! As you’ve probably noticed, I’ve been wearing them non-stop. There wasn’t any break-in time for me and they’ve never given me any blisters either. Highly recommend!
- Amazon Button-Front Cardigan (I have the Medium – such a great ba&sh Gaspard dupe!)
- Amazon Sunglasses (great dupes for the Celine Triomphe sunnies!)
- Levi’s Dad Jeans (TTS – I have the 28)
- Caterina Bertini Bag (from last season)
- Vintage Chanel Slides (I think 2015 based on the textured CC and gold quilted footbed)
- Revolve Sweater (Runs very oversized… I’d probably size down! I have the Medium.)
- Levi’s Dad Jeans (TTS – I have the 28)
- Adidas Sambas
- Core Black / Wonder White is the exact colorway I have… available here + here
- Amazon Socks
- Amazon Top
- Levi’s Dad Jeans (TTS – I have the 28)
- Gucci Marmont Bag
- Vintage Chanel Slides
Rolla’s Sailor Jeans
I made a Reel with these jeans, but they’re even easier to style in the warmer months. They make your butt look great and have such a flattering, wide-leg ankle-length silhouette. Easy to pair with flats, sandals, and sneakers.
- Rolla’s Sailor Jeans (I have the 28. No stretch at all and a bit snug in the waist — I’d size up if you’re in between two sizes.)
- Trovata Clover Blouse (M – TTS)
- the breeziest lightweight fabric for summer that’s also machine-washable!
- Clare V Straw Bag (old)
- Gold Rolly Bracelet
- Tennis Bracelet (have my eyes on this one, though 🤩)
- Boden Raffia Flats (a few years old, but this is the most similar current silhouette)
- Hill House Paz Nap Top (I have the Medium)
- runs smaller than the Ellie Nap Dress… size up if you’re in between!
- Rolla’s Sailor Jeans
- Caterina Bertini Bag (from last season)
- Raffia Dad Sandals (old by Arezzo)
Everlane A-Line Denim Shorts
I’ve had these denim shorts for quite a few years now, but thankfully Everlane still makes them! The A-line shape is very flattering on the legs, they’ve got a nice high rise, and they feel like they’re the perfect length for us 30-something gals, too.
These Everlane A-line denim shorts don’t have any stretch, but they do give a good amount with wear! I’d say they’re true to size, but if you’re in between two sizes, I’d probably take the smaller one.
I adore my AGOLDE Parker Long shorts, but these feel a bit more tailored and thus, a bit more elevated. Easier to dress up, IMO! The raw hem that I have is from a few years ago — the current shorts have a finished hem. (Although you could easily cut it off if you want the raw hem look.)
- Everlane A-Line Denim Shorts (TTS – I have the 28)
- Target Tank (TTS – I have the Medium)
- I have this $8 tank in so many colors… Such a great staple piece!
- Target Crochet Sweater (I took a Large in this for a more oversized fit!)
- Brown Oval Sunglasses
- Dolce Vita Mesh Flats (TTS)
- Abercrombie Short Sleeve Sweater (SO soft – I have the Medium)
- Everlane A-Line Denim Shorts
- Brown Oval Sunglasses
- Target Summer Sweater (such a perfect weight for summer!)
- New Balance 327 Sneakers (TTS)
More Everyday Outfits
- Target Crochet Sweater (I took a Large in this for a more oversized fit!)
- Levi’s Dad Jeans (TTS – I have the 28)
- Gold Sunglasses
- Caterina Bertini Bag (from last season)
- Raffia Dad Sandals (a couple of years old by Arezzo)
- Trovata Blake Top (TTS – I have a medium)
- Citizens of Humanity Jeans (TTS)
- Crystal Mesh Mary Jane Ballet Flats (TTS)
- Revolve Sweater (Runs very oversized… I’d probably size down! I have the Medium.)
- J.Crew Hair Bow (old)
- Levi’s Dad Jeans (TTS – I have the 28)
- Adidas Sambas
- Core Black / Wonder White is the exact colorway I have… available here + here
- Amazon Socks
- Abercrombie Short Sleeve Sweater (SO soft – I have the Medium)
- Everlane A-Line Denim Shorts (TTS)
- Crystal Mesh Mary Jane Ballet Flats (TTS)
- Brown Oval Sunglasses
- Marine Layer Knit Tank (from last year)
- Levi’s Dad Jeans (TTS – I have the 28)
- Raffia Dad Sandals (a couple of years old by Arezzo)
- Maje Short-Sleeved Striped Cardigan (Wearing the French 2 – fits like a 4/6)
- Abercrombie Jeans (TTS – I have the 6)
- read my full Abercrombie Jeans Sizing Guide here
- Tuckable Baby Tee (TTS – I have a M)
- Everlane Barrel Pants (TTS – I have a 6)
- Madewell Chunky Buckle Belt
- I’m *obsessed* with this belt and have recommended it to many styling clients, too! It looks so much more expensive than it is.
- Tweed Slingback Flats (TTS)
- Hanes Tee (Wearing the Medium)
- Abercrombie Cuffed Jeans
- Crystal Mesh Mary Jane Ballet Flats
- Tweed Top (TTS – I have the Medium)
- there’s also a pair of matching shorts
- Abercrombie Jeans (TTS – I have the 6)
- read my full Abercrombie Jeans Sizing Guide here
- Schutz Gold Bamboo Buckle Slides (TTS)
- Brown Oval Sunglasses
- Bernardo Raincoat
- Amazon Leggings (I wear a Small)
- Striped Crew Socks
- Nike Air Max 90 Sneakers
- Revolve Sweater (Runs very oversized… I’d probably size down! I have the Medium.)
- J.Crew Hair Bow (old)
- Levi’s Dad Jeans (TTS – I have the 28)
- Adidas Sambas
- Core Black / Wonder White is the exact colorway I have… available here + here
- Amazon Socks
- Rolla’s Sailor Jeans (TTS – I have the 28)
- Trovata Clover Blouse (M – TTS)
- Clare V Straw Bag (old)
- Gold Rolly Bracelet
- Tennis Bracelet (have my eyes on this one, though 🤩)
- Boden Raffia Flats (a few years old, but this is the most similar current silhouette)
Concert Outfits
While the concerts we’ve seen have run the gamut from rainy & cold to pleasant & mild, here are a few of the outfits I’ve worn…
- Everlane Boxy Oxford Shirt
- Rolla’s Sailor Jeans (TTS)
- Marc Fisher Sneakers (TTS)
- use code JSTURDY20 to take 20% off!
- Mango Striped Crochet Tie-Front Top (M)
- Levi’s Dad Jeans (TTS – I have the 28)
- Amazon Sunglasses
- Adidas Sambas
- Core Black / Wonder White is the exact colorway I have… available here + here
- Bombas No-Show Socks – they’re the best!
- Veronica Beard Puffer Jacket (old; from fall 2016)
- Tuckable Baby Tee
- AGOLDE Jeans (TTS – I sized up for more of a loose fit.)
- more sizes available here
- Woven Crossbody Bag
- Adidas Sambas
- Core Black / Wonder White is the exact colorway I have… available here + here
Work Outfits
Without trying, my work wardrobe follows a very specific formula: jeans + basic top + blazer. No matter the season, it works. This spring, I just added sneakers, ballet flats, or sandals.
- Everlane Blazer (TTS)
- Sezane Dita Top (TTS – I have the Medium)
- Levi’s Dad Jeans (TTS – I have the 28)
- Tweed Slingback Flats (TTS)
- Everlane Blazer
- (Left) Sezane Top + Everlane Trench
- (Middle) White Asymmetrical Bodysuit (TTS – I have the Medium)
- (Right) Zara Lace High-Neck Top (very old)
- similar lace tank here
- Madewell Chunky Buckle Belt
- Silver Handbag
- Levi’s Dad Jeans (TTS – I have the 28)
- Tweed Slingback Flats (TTS)
- Sezane Blazer (I’d size up if you’re in between, as I find the brand to run narrow!)
- Old Navy V-Neck Top (from last fall, similar here)
- Levi’s Dad Jeans (TTS – I have the 28)
- Nike Dunks in Phantom Gold
- Tuckable Baby Tee (TTS – I have a M)
- Everlane Barrel Pants (TTS – I have a 6)
- Madewell Chunky Buckle Belt
- Tweed Slingback Flats (TTS)