How I Style Comfortable Outfits To Look Cool (Ish? Eh?)

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How I Style Comfortable Outfits To Look Cool (Ish? Eh?)

Today

This whole post is a testament to one of my favorite design principles for the more “risk-averse” (me!). Here it is: Start with something simple and classic (basic, even), then make it fun and interesting with the styling. Now I’m not a fashion stylist, and at times I like to amp it up when I go out, but as a lover of mostly casual, comfortable outfits, I need to dress things up to make sure I don’t look like I’m wearing pajamas in public. Once you see my tricks, you see that it’s actually really formulaic (in a way that makes our life easier, hopefully).

Styling Comfortable Outfits: Curating Accessories Elevates The Baggy

The pre-styled version definitely could be doing the walk of shame, but with some styling, she looks totally respectable! I don’t necessarily try to dress things “up”, because a lot of this really can’t be. But by arranging things a certain way on my body and adding the right other things (shoes, scarves, jewelry, hats), it looks like an outfit, not a schlubby pajama set. I didn’t intend to match the hat, bag, and flats, but I think by doing so, it pulls together all the looseness of the shirt and shorts. It should be noted that I was just told by my sister over the weekend that the French tuck is “out,” but I still like it here. And while that scarf on the bag plays no real functional purpose, the hit of a darker tone and pattern gives it a slight edge – just overall less Martha. A floppy hat and a beaded layered necklace certainly help.

Styling Comfortable Outfits: A Hit OF Black And White, Always

On the left – straight out of the bedroom. On the right, she’s a little coo-koo (that smile, oof!) but certainly a respectable lady who could enter the farmers’ market with no embarrassment. I love a hit of black and white in almost every outfit (and room), and that bag and the Sambas take the “roll out of bed” vibe and make it clear you just care about comfort and style equally.

Styling Comfortable Outfits: Matching Sets – Pajamas Or An Intentional Outfit??

Now, when I first put this extremely comfortable gauzy set on, I said, “I mean, sure, it’s extremely soft and doesn’t cut in, but it’s 100% giving pajamas”. My team disagreed and forced me to try to style it. And then after I did, I was like, “Hey! Team! I can go in public in pajamas!!” By adding a millennial-loving belt bag, the leopard sandals, sunglasses, and layered necklaces (with a half-tuck), it looks comfortable with intention.

Top | Shorts | Sandals | Bag | Necklace

Ok, I returned this set, but that’s because the seersucker was too boxy for me (no drape) and the shorts cut in at the waist, which is intolerable to me. But it is a good reminder that a set can look like an outfit with some styling.

Styling Comfortable Outfits: Elevating Striped Linen Bottoms

I just realized I did the EXACT same formula for this outfit as #1 (without the scarf, but that could have been cute). Different hat, darker shorts, and oddly a different linen shirt (the one with pockets is from J.Crew; this one is from Quince – both very good, with the J.Crew one being 10% better, and twice as much). 100% taking this with me on our family vacation in CA (where I am right now :))

Proof that your favorite cheap shirt and favorite splurgy pants don’t necessarily make a good “outfit” unless you style and accessorize right (both are so breathable, lightweight, comfortable, sit and drape nicely, etc). But add a bandana and hat, sunglasses and sandals, and a tuck, and you can wear anything anywhere.

You get it by now:) Boyfriend pajamas, add cute stuff, then outfit. I honestly didn’t even mean to do this post like this. But once we saw all the pre-styled and post-styled shots, I realized I obviously have a way to style out really basic clothes, and seeing the before and after was fun.

Styling Comfortable Outfits: Adding Structure to Fun Flowy Shorts

These shorts cracked me up – 100% bloomers. And the T-shirt didn’t have great proportions (I know this is in, but doesn’t look good on women with big boobs IMHO – something needs to be smaller or shorter). But once I tucked, wrapped, and rolled, it all worked!! I now love the T-shirt (the graphics and the colorway are awesome), and adding the Vans gave that pop of black and white that I love.

This was an outfit that I copied this weekend. It’s not doing anything special, but it’s 100% comfortable, I feel cute, and I could wear it almost anywhere. The silk shorts are so good (and have more structure than silk; they are thicker in a good way). I’m wearing a medium in the shorts, btw. And I LOVE that hat (going to a dude ranch this summer, so bringing that hat).

These Target shorts are the foundation of the outfit by being a black-and-white pattern, but they still give the “boxer shorts” look. But once I put that mustard linen jacket on (it’s my favorite) and scarf (that is a triangle, not a full square) and a pop of red, it totally looks like a respectable “out of the house” outfit.

Here are a few more that I didn’t take befores for, but the styling felt like me and fell into the same patterns as above:

I mostly want to wear jean shorts and a T-shirt, but I think both of these outfits show that the shoes, belts, scarves, and layers make a difference. If I were one of those weirdos who put photos of your styled-out outfits taped onto your closet door, these would be two summer outfits that I want to wear on repeat when I go out. I feel cute, stylish, comfortable, and like me in these (and very PNW appropriate, no heels and very casual).

Sweater | Jeans | Belt | Bag | Sandals

A reminder that you can style a tonal outfit with a couple of pops – the patterned sandals, a belt, bag, and choker. I’ve worn this outfit a lot on the less hot days since I wore it. Nothing special, but it feels like me and is easy/comfortable.

So I figured I’d round up more of my favorite accessories so you can see them on their own: