10 TIMELESS SUMMER OUTFITS TO WEAR YEAR AFTER YEAR

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It’s been so fun to embrace different aspects of my style at our new location. I’ve been leaning into my love of summer dresses on hot days, matching sets in the mornings and lots of elevated loungewear. I’ve found that, as always, 1 part simplicity to 2 parts quality, with a sprinkle of interest, is the style recipe that works best for me.

Here’s a collection of 10 timeless summer outfits I’ve been wearing at the lake this season (and plan to for years to come).

Ps. Enjoy the first outfit shoot in my “new-to-me” studio, aka. the boat house!


This post is not sponsored or produced in partnership with any brands mentioned but does contain affiliate links and some gifted items. If you see something you like and decide to shop through the links included, I may earn commission on a sale at no additional cost to you. All opinions are always my own and I only share items I love and think you might too. Thanks for supporting Style Bee!


1 | SMOCKED DRESS

Bonus points if it has multi-functional straps…and pockets!


Style Bee - 12 Timeless Summer Outfits To Wear Year After Year
  • Style Bee - 12 Timeless Summer Outfits To Wear Year After Year
  • Style Bee - 12 Timeless Summer Outfits To Wear Year After Year
Style Bee - 12 Timeless Summer Outfits To Wear Year After Year

SMOCKED TIERED DRESS | VETTA | gifted | TTS wearing my usual dress size. | Three colour options and a great price-point for the quality.

LEATHER STRAP SANDAL IN SADDLE | Jenni Kayne | gifted | TTS | Use LEE15 for 15% Off anytime. | Similar for less here.

BEADED BAG | ANCÁN | old | Linked to a similar option on sale & try your favourite vintage shop.


This dress is the perfect combination of carefree and comfortable. I really like the breathability of linen, which is blended with Tencel for a silky feel, making it less prone to deep creases. I wear it with my minimal leather sandals and a textural tote bag for a look that’s great for just about any easy-going summer occasion. I love this one for patio lunches in town and visits with friends on the dock. If it gets chilly I just throw a cardigan or denim jacket on top.

I LOVE the smocked bodice because it means no bra needed while still offering support and lots of texture, so my nips aren’t the star of the show lol. The straps are also fully adjustable so you can wear it with them crossed at the back, tied as a halter-top, tucked in for a strapless look or just as a regular shoulder strap. VETTA always incorporates clever details like this into into their pieces.


2 | MATCHING STRIPED PAJAMA SET


Style Bee - 12 Timeless Summer Outfits To Wear Year After Year
  • Style Bee - 12 Timeless Summer Outfits To Wear Year After Year
  • Style Bee - 12 Timeless Summer Outfits To Wear Year After Year
Style Bee - 12 Timeless Summer Outfits To Wear Year After Year

THE STRIPE SET (Top & Bottom) | Soft Focus | gifted | TTS | Canadian brand!

LONGLINE CAMI | Soft Focus | sold out | Linked to similar option. | Canadian brand!

EVA ARIZONA (White) | Birkenstock | TTS ( I wear a US 7 and have the 37)


In the summer months I usually sleep in a matching tank and brief set, so when I have my morning coffee on the dock and walk Dobby around the yard it’s nice to have a set like this to put on.

I also think that this set would make the perfect addition to any travel packing list. Sleep in the nude or in your skivvies then just pop this on for a pastry run or over a swimsuit as you head to the beach!


3 | CUTOFFS, A CROP TOP & A CARDIGAN


Style Bee - 12 Timeless Summer Outfits To Wear Year After Year
Style Bee - 12 Timeless Summer Outfits To Wear Year After Year
Style Bee - 12 Timeless Summer Outfits To Wear Year After Year

CROP TOP | old | Linked to a similar option.

CASHMERE COCOON CARDIGAN | Jenni Kayne | gifted | Full review here. | Use LEE15 for 15% Off | Cotton version here.

DEE HIGH RISE SHORTS (IN CHIMES) | AGOLDE | TTS (I vary between 26/27 and got the 27 in these) | Similar option for less here and here.

RILEY FLIP FLOPS (IN SUNKISSED) | TKEES | TTS I wear my usual 7 | Canadian Brand!


This one has been a regular this summer. I love when it’s warm enough for shorts all day and cool enough for a soft and cozy sweater in the morning or evening. This oatmeal colour is a great way to add warmth and keep the look feeling summery.

Ps. I’ve noticed that this cardigan has been a reader favourite for early fall. If you’re considering it, be sure to check out my full review!


4 | BEACH DAY UNIFORM


Style Bee - 12 Timeless Summer Outfits To Wear Year After Year
  • Style Bee - 12 Timeless Summer Outfits To Wear Year After Year
  • Style Bee - 12 Timeless Summer Outfits To Wear Year After Year

EVA ONE PIECE | YOU SWIM | One suit fits 7 sizes thanks to a super stretchy fabric that feels amazing on.

MESH PANT | sold out | Na Nin | Linked to the shorts version (which I also have a really like).

KLINT BOATER HAT |  Janessa Leoné | TTS but I added padding strips for a snug fit. | I also love this packable option.

RILEY FLIP FLOPS (IN SABLE) | TKEES | TTS I wear my usual 7 | Canadian Brand!


I bought these pants at the end of last summer and I’m so happy I did because they’ve become the perfect companion to a swimsuit on hot days. The light mesh material lets the breeze right in but a touch of coverage keeps me feeling at ease. Paired with a one-piece suit, a simple flip flop, a boater hat, and lots of sunscreen, I’m good to go for boat rides and dock hangs.


5 | T-SHIRT, JEANS & BIRKS



COTTON BASIC TEE (Sage) | Jenni Kayne | gifted | Runs a bit large, I sized down from S to XS. | Use LEE15 for 15% Off

90’s CHEEKY JEANS | EVERLANE | TTS (if between, size down) | Wash is old, linked to similar.

EVA ARIZONA (White) | Birkenstock | TTS ( I wear a US 7 and have the 37)


This combo rarely goes wrong and I’m very into the fresh punch that my white EVA Birkenstocks add to such a simple outfit. I’ve been loving the ultra soft, oversized fit of this cotton tee and find it’s super light but has a lovely drape.


6 | BLACK LINEN SUNDRESS


Style Bee - 12 Timeless Summer Outfits To Wear Year After Year
Style Bee - 12 Timeless Summer Outfits To Wear Year After Year
  • Style Bee - 12 Timeless Summer Outfits To Wear Year After Year
  • Style Bee - 12 Timeless Summer Outfits To Wear Year After Year

MILOS DRESS (Black) | Harly Jae | TTS | Canadian brand!

CIRCULO TOTE | Artisan & Fox | gifted years ago | This option has a similar look in a softer construction.

LEATHER STRAP SANDAL IN SADDLE | Jenni Kayne | gifted | TTS | Use LEE15 for 15% Off anytime. | Similar for less here.


I snapped this beauty up after having it on my list for a couple of summers and it has quickly jumped to the top of my “favourite things to wear” list. It’s just everything you want in a garment on a smokin’ hot day when you mostly want to be naked but also need to be covered. The neckline and covered elastic straps are so beautifully designed and extremely comfortable. Oh and it’s made in Canada! 10/10 would recommend.


7 | STRIPED TEE & JERSEY PANTS


Style Bee - 12 Timeless Summer Outfits To Wear Year After Year
Style Bee - 12 Timeless Summer Outfits To Wear Year After Year
  • Style Bee - 12 Timeless Summer Outfits To Wear Year After Year
  • Style Bee - 12 Timeless Summer Outfits To Wear Year After Year
Style Bee - 12 Timeless Summer Outfits To Wear Year After Year

THE COMFY WIDE LEG PANT (Black) | ENCIRCLED | gifted | TTS | Canadian brand! | Use LEE10 for 10% Off anytime.

THE EVERYDAY BOXY TEE (Golden Yellow Stripe Bamboo) | ENCIRCLED | gifted | TTS for a loose fit and it’s reversible! | Canadian brand! | Use LEE10 for 10% Off anytime.

WOVEN CIRCLE BAG | old

EVA ARIZONA (White) | Birkenstock | TTS ( I wear a US 7 and have the 37)


Isn’t it great when an outfit as comfy as pjs can look entirely legit? This is one of those. Encircled is a Canadian brand I’ve been wearing for many years and I’m just a little bit obsessed with the latest pant and top they kindly sent for me to test out. I love the length of these pants, long but not too long, and the shape of the leg, wide but not too wide. IMHO, they’re a perfect elevated lounge pant. Plus, they’re miraculously resistant to lint and pet fur, something that has long plagued my love of black pants.

I’ve also been reaching for this striped tee on a regular basis because it’s impossibly soft and lightweight, ideal for hot days. Paired with a black pant and some fresh white Birks, I’m all set for a bakery run, a bit of gardening, a walk with Dobby, some computer work, or whatever the day may call for.


8 | FLORAL MINIDRESS


Style Bee - 12 Timeless Summer Outfits To Wear Year After Year
Style Bee - 12 Timeless Summer Outfits To Wear Year After Year
  • Style Bee - 12 Timeless Summer Outfits To Wear Year After Year
  • Style Bee - 12 Timeless Summer Outfits To Wear Year After Year

SUMMER GARDEN WRAP DRESS (On Sale!) | FRANK AND OAK | gifted | TTS | Canadian brand!

LEATHER STRAP SANDAL IN SADDLE | Jenni Kayne | gifted | TTS | Use LEE15 for 15% Off anytime. | Similar for less here.

BEADED BAG | ANCÁN | old | Linked to a similar option on sale & try your favourite vintage shop.


Another fail-safe summer look I keep in my seasonal repertoire is the floral minidress. It’s an easy win whenever I’m feeling like I need a sartorial pick-me-up. This is my favourite sort of dress to bring on trips too because it’s so versatile and easy to pack. I can wear something like this with a pair of minimal slides, espadrilles or a strappy block heeled sandal if I want to take it up a notch.


9 | BLACK TANK & BLACK SHORTS


Style Bee - 10 Timeless Summer Outfits To Wear Year After Year
  • Style Bee - 10 Timeless Summer Outfits To Wear Year After Year
  • Style Bee - 10 Timeless Summer Outfits To Wear Year After Year

BLACK CROP TANK | old | HOI BO (a very cool Canadian brand) | Similar here and here.

LINEN CHINO SHORT | low stock | FRANK & OAK | gifted | TTS | Canadian Brand! | Similar here.

RILEY FLIP FLOPS (IN SABLE) | TKEES | TTS I wear my usual 7 | Canadian Brand!

DENIM JACKET | Everlane | old | Linked to a very similar option.


This is my answer to function-forward chic. A stretchy black fitted tank and comfortable black shorts in a soft fabric and loose shape with black flip flops (or Tevas) and a denim jacket. Works every time!


10 | LIGHT & COZY KNITS



ALPACA COCOON CARDIGAN | Jenni Kayne | giftedUse LEE15 for 15% Off | Cotton version here.

GOOD COTTON ESSENTIAL TEE (Bright White) | FRANK AND OAK | gifted | TTS | Canadian Brand!

COTTON/CASHMERE JOGGERS (Oatmeal) | Jenni Kayne | giftedUse LEE15 for 15% Off | TTS wearing my usual Small, you may want to size up for a slouchier fit.

EVA ARIZONA (White) | Birkenstock | TTS ( I wear a US 7 and have the 37)


Depending on where you live your summer closet may not require any knitwear at all, but here at the lake some cozy layers have been super handy. When the temps dip, I’ve been reaching for these cotton/cashmere joggers a ton and wearing them with an easy-going t-shirt, my Birks and a chunky cardigan. It’s my go-to uniform for outdoor evenings or screened porch dinners when cool air starts making its way across the lake.


& THERE YOU HAVE 10 TIMELESS SUMMER OUTFITS!

Do you have summer looks you return to year after year? If so, let’s hear about them!

I hope this post will inspire you to keep repeating the outfits you love and maybe give you some ideas to keep your closet feeling fresh for the final weeks of the summer season.

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