Dress Codes Stress Me Out, so I Rely on These 6 Outfit Combinations

I recently went on a first date in a short printed dress and block-heel sandals. It’s a combination I’ve worn quite literally hundreds of times before and, frankly, didn’t realize might be seen as slightly dressed up until I saw my date in jeans, a (not-super-clever) graphic tee, and a baseball cap. On one hand, I felt a momentarily awkward Did I misread the occasion? On the other, it reinforced something I’ve always known: I don’t really do occasional dressing in the first place.

Yes, I’ll abide by the really specific dress codes, such as for weddings or a super-corporate office (which I’ve never worked in, to be honest). However, nothing in my closet is separated by dressed-up or dressed-down, first dates or weekend errands, work or brunch. Instead, the best way I organize what I wear is by using tried-and-true outfit combinations that fit a variety of purposes. They’re all slightly elevated, yet in no way formal, ensembles. They’re also comfortable, put together, and not too serious, which is usually the way I like to feel.

Ahead, I’m sharing the six combinations that I return to time and again. Monday at the office? Sure. Packing for a long weekend getaway? Yep. (Another) last-minute date? You bet.

Casual Jacket + Fancier Heels
cute, casual outfit ideas



I'm quite a fan of outfits that are pretty low-key aside from the footwear.

Bold Trouser + Graphic Tee
cute casual outfit ideas



In case you got the impression I'm not a fan of graphic tees, just know that's not the case. For me personally, I'd wear one with some nice high-waisted trousers.

Flirty Dress + Sensible Heels
cute casual outfit ideas



It's foolproof. For anything. Trust me.

Tonal Dressing (With a Pop)
cute casual outfit ideas



Instead of speaking about specific pieces, I'll say that head-to-toe tonal dressing always looks cool and elevated for any occasion. Add a hint of color with your shoes, a bag, or a subtle print.

Statement Top + Laid-Back Denim
cute casual outfit ideas



Honestly, it's a volume thing: a lot on the top, a little less on the legs.

Of course, I understand some dress codes are much less flexible than others. For instance, here's what to wear to a black-tie wedding.