Hi Friends! Happy FriYAY! I’m heading down to Roanoke, VA today (where I went to college) for their annual President’s Evening gala, which celebrates the donors to the college. And yes, believe it or not, I’m one of them! I love giving back to Roanoke! They did so much for me and donating a little back to my school is the least I can do!

Today I’m sharing a fun way to style this cute little velvet dress I picked up from Madewell the other day. To be honest, when I grabbed it off the rack I wasn’t in love with it, but after trying it on I’m now a fan! You might be wondering, why I bought it if I didn’t really like it…great question! I’ve learned that you can never really judge something until you try it on. And this is exactly why! This dress looked questionable on the hanger, but once I put it on I fell in love.

Madewell currently has a few fun velvet party dresses that can be dressed up for a night out, or made more casual for a day look, like I did here! I always get so excited when I find a dress that can work both ways. It’s like a 2 for 1 deal (at least that’s what I tell myself to justify buying it!). My preference is finding a nice dress and then dressing it down if need be, which is easier IMO than buying a casual dress and dressing it up.

dress: Madewell • boots: Goodnight Macaroon • jacket: Similar here • necklace: Madewell

There are soooo many ways to style a dress to be more casual or a little more fancy, here are my basic guidelines below!

Outwear:

Perhaps the easiest way to dress up or down a look, throw on a jacket! Or maybe I just think this is the easiest option since I’m always cold, so throwing a jacket on is a no-brainer.

To dress up a look, reach for a blazer, something with structure, maybe a collar, and typically, a nicer material. I have a small obsession with tweed blazers, and a slowly growing collection in my closet! Truth be told, about half of my closet space is currently taken up by blazers and jackets. Step one is admitting you have a problem. I’m still at step 0.

To dress down a look, reach for a jacket, something maybe slouchy or oversized, but not always. My 3 go-to options are: a jean jacket, a suede motto jacket, a leather jacket.

Footwear:

“I don’t want to wear comfy shoes” said no woman ever. Ha! I will take any opportunity to wear comfy shoes (ex. booties, boots, slide-ons) over uncomfy shoes (heels, heels, and more heels). Now, with that being said…footwear is an interesting option that you can really play with here. My OTK (over the knee) boots are currently my favorite boots and I’ve been dressing them up and down nonstop. I mean, the other day I wore them to a soccer game and the next night I wore them into the city for a fancy event! I love how, with a dress, OTK boots can kind of step in and replace tights. They cover most, if not all of your leg and they’re definitely warmer than tights, so for that reason alone I’m finding every excuse to throw my OTK boots on even when I’m getting dressed up.

To dress a look up, I’d grab (almost) anything with a real heel. What do I mean by that? I’ve got these super comfy Lucky Brand and Jack Roger booties, that I adore, but the heel–or lack thereof– just ends up making my outfit look frumpy rather than cute. I went to this event a few weeks ago and was running late so I threw on my beloved Lucky Brand booties, a move I ended up regretting when I arrived as everyone else in attendance was wearing stiletto heels. Typical Helen move!

To dress down a look, I’d grab anything but a stiletto heel! Ha! Boots are a no-brainer in my opinion. An unexpected pairing that I often do is my cowboy boots with a dress, it’s really cute! But really any bootie or boot is an easy way to dress down a dress. Obviously another option is to pair a dress with sneakers, not pictured here, but also a favorite of line!

Accessories:

To dress up a look, opt for daintier, classic jewelry and a nice handbag. If it’s an evening event, swap out your daily purse for an evening bag (something small and formal). You can also always add a nice shawl to your dress if you’re worried about being cold!

To dress down a look, opt for bolder, statement jewelry that’s fun! Maybe something that’s more costume jewelry rather than fine jewelry. You can always add a hat or a scarf to dress down the look too! Just imagine a fun fedora for the fall!