I have a fairly small wardrobe, especially if I compare it to my wardrobe when I was in the throes of my shopaholic addiction. I currently have just shy of 100 pieces of clothing spread across 4 seasons, although this doesn’t include jackets and shoes. I have light summer dresses, linen pants, shorts and tank tops for the hot spring/summer seasons and I have a lot of heavier dresses, cozy sweaters and jeans for the cold fall/winter. It’s generally either really hot or really cold where I live. We do get a few months (late September-November and late March-June) where the weather might be idyllic but that’s about it.
A lot of my clothing items are non-seasonal. Depending on what I wear (or don’t wear) with them, I can wear a lot of my items year round. This is especially true for most of my dresses, especially a vintage 90s floral button front one that I found on Etsy 2 years ago.
It’s navy, sleeveless (perfect for layering under sweaters), has tiny tan flowers and a button front. It has a tie detail in the back which I appreciate when my weight shifts. It’s lightweight, but the fabric is heavy enough to give it the perfect drape.
Quintessentially the perfect dress. Which is why I love to wear it through all seasons.
I actually think I prefer to wear it in the colder months more because of how well it plays with the other items in my wardrobe.
outfit 1: dress + denim shirt + converse + large tote
This denim shirt is the most recent addition to my wardrobe. I found it at a local consignment shop while I was waiting for one of my kids to try some things on. It was on a clothing rack in the men’s section, next to the dressing rooms. It’s thick like a denim jacket but with the detailing of a shirt. PSA: check the men’s section when you shop!
I’ve had a denim jacket on my thrift list in the past, but I’ve come to realize that I actually don’t enjoy denim jackets for myself (love them on others!) so this seemed like the perfect piece to add to my wardrobe. I don’t have anything like it and it’ll go with everything.
The denim shirt has a casual feel, and I knew it would be the perfect piece to transition a summer dress to fall. I kept the casual vibe going with my converse sneakers. I added a pair of red trouser socks for a little color accent and my big slate tote bag.
Fun fact…I’ve had this tote for over a decade and it’s one of my favorite items. When we travel, I always take a backpack and this tote. The tote holds all of the things that I need to access while we’re traveling. It’s been through a lot but still looks new…mostly. If I look inside the bag, I can see some light peeking through at the corners so I need to look into a patch kit of some kind.
// levi’s denim shirt
// vintage floral dress
// hansel from basel trouser socks
// chuck taylor converse sneakers
// longchamp tote bag
outfit 2: dress + sweater + slouchy boots + belt
Hands down, this is my favorite way to wear this dress. I love layering cozy sweaters over top and leaving them untucked or front tucked into a belt. The fact that it is sleeveless and that it drapes so nicely makes it perfect for layering under other clothes.
I think I like it so much because it makes it seem like I have more clothes than I do. Once day, it’s a dress; the next, it’s a skirt! I think this is why I only own a couple of skirts as well.
Expect to see these new to me boots with dresses a lot this fall. Every fall for the past few years, I’ve had a pair of slouchy knee high boots on my thrift list. I blame “The Devil Wears Prada” and the outfit with the slouchy Chloe boots in the opening sequence!
So you can’t even imagine how excited I got when I found these brown suede Bedstu boots in a shoe bin at my favorite shop (and I never go through the shoe bins because I find them too overwhelming, but these were sitting on the top!). They were priced at $20 and had never been worn. The suede was a little matted down in some places but it wasn’t that noticeable. I also remembered that I had some suede tools at home and could probably refresh them, which I was able to do.
I added a cozy cashmere sweater in a different shade of brown for a little contrast. I like how it looks hanging freely…
…but I also really like it with this vintage belt. If you read my last blog post, you’ll recognize this as the belt I recently resized.
One of my favorite cold weather styling tips is to use a belt to tuck sweaters into. Simply fold the sweater hem under slightly and tuck it into the belt as if it was a waistband. You might have to play around with how much to fold up under to get it to sit inside the belt just right.
// eileen fisher sweater
// vintage floral dress
// bedstu suede boots
// vintage leather belt
outfit 3: dress + turtleneck + vest + combat boots + belt bag
This outfit is a total surprise for me! For whatever reason, I can’t remember ever styling this dress with black boots. In the past, I’ve always worn it with my converse or with brown boots.
I think the fact that it’s navy and tan has made me shy away from black. A long time ago, I read or heard somewhere that you’re not supposed to wear black with navy (or brown). And as much as I try to ignore those deeply ingrained “rules”, sometimes they still stop me.
But here’s proof to myself to fully let them go because I love this combo!
I was originally just going to style the dress with the turtleneck but it felt a little dull like that. I’m not much for jewelry right now and I remembered this amazing vintage vest and I thought I should just give a try.
And now I have a new favorite outfit combo!
To read more about this vest, check out this post for how I cleaned it and this post for some other ways I’ll be styling it this fall.
In keeping with the rocker chic vibe, I added my platform combat boots. This is the third year for these. They are my most worn pair of boots once the weather cools down and they still look amazing.
I knew I didn’t want a big bag with this outfit so that it wouldn’t distract away from the detailing on the vest. I also feel like there’s quite a bit going on so I opted for my small black circle belt bag.
Added bonus: I can tighten the strap and wear it around my waist if I need (or want) to be hands free.
// vintage leather vest
// vintage floral dress
// vince wool turtleneck
// cuyana belt bag
Did you have a favorite combo? What’s your favorite way to transition a summer dress for fall?
