4 Ways To Dress Up an Outfit

A few weekends ago I had the super fun opportunity to celebrate my friend’s 40th birthday (HBD Donna!!) with a group of friends in a proper ‘going-out’ situation. Needless to say, it was a long time coming in this covid era. We went to a bourbon lounge with a space downstairs reserved just for us, complete with our own bartender. We had food, cake and even some spooky decor. It was super fun.

I don’t think I’d been out like that in almost TWO YEARS, maybe longer. When it came time to pick out something to wear, I struggled with building an outfit that felt different from my day-to-day wear. I was severely out of practice for dressing up, and I totally biffed my outfit. As soon as I got there I wished I’d picked something different (more on that later).

So, in the interest of research and getting better at styling myself for dressier occasions, I spent some time brainstorming and trying on outfits. Below are a few strategies I came up with.

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4 Ways to Dress Up an Outfit:

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1 // Dark Colors

Wearing: Reversible Ribbed Top, c/o; Tapered High Rise Jeans (27); Western Boots, c/o Everlane (old, linked to similar below); Bag; Hollow Hoops

This is probably the most tried-and-true rule for dressing up, in my experience, especially if you prefer simple outfits. Dark tones, when employed head-to-toe, convey a more serious and formal look. You can add visual interest by getting creative with your silhouettes. Here I chose a fitted top and generously cut pants.

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2 // Heeled boots

Wearing: top, c/o Vetta, few seasons old; jeans, TTS; boots, old; Bag, Clare V; Necklace, Monica Vinader

Another great way to elevate an outfit is to elevate your heels, literally! If you don’t wear heels on a regular basis, donning them for a night out is a surefire way to lend a sense of occasion to your outfit. To keep my feet comfortable, I like to opt for lower heeled boots. You can wear a snake print or an architectural boot shape (think pointy or square!) to add some texture or shape to your outfit.

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3 // A Leather (or Vegan Leather) Jacket

Wearing: Jayne Leather Jacket secondhand via Poshmark; Blouse, old; Jeans, no longer available; Mary Janes; Bag, secondhand

I don’t wear this jacket a ton, but whenever I do, it serves its purpose very well. I believe a good leather jacket can be a closet staple for years. I have had some version of one in my closet for the better part of a decade. This particular one I bought secondhand off Poshmark about two years ago. I got it for about 1/3 of the retail price, and it makes anything I pair it with look elevated.

There are so many styles of leather jackets. I prefer a more timeless and classic take, with focus on the moto elements.

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4. A Dress + Tights

Wearing: Coat, older from Aritzia; Dress, c/o; Tights; Boots (these are 20% through Wednesday with my code: ANDREABOOT20)

Wearing a dress and tights is rarely as much of a hassle as I think it’s going to be in my head. Especially when it’s just for a few hours. It’s so fun to shake things up and feel dressy for a bit. And it makes you appreciate your sweats even more when you get home. We missed out on so many opportunities to get dressed up over the last year and a half, and I never want to take that for granted again! Even if it does mean I might teter on the edge of being overdressed. Better that than underdressed, right?

Tip: I almost always size up in tights for more comfort and better fit.

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And, if you’re wondering what I did wear, I’ll fill ya in.

I didn’t get any good pics of my outfit, but I wore a long sleeve knit top with a herringbone wool blazer and some fitted jeans, and lace up boots. As always, I was worried about being cold. It wasn’t cold, and my outfit definitely felt a little lackluster for such a fun occasion. I wish I had followed one of the four tips above instead! Next time!!