Tyler just moved from Phoenix to Portland, Oregon (because hates 70 degree weather and sunshine for November-January, apparently). He’s been feeling out the whole Pacific NW vibe and has noticed not only do they have enormous bookstores and enjoy putting birds on things, but they also have some interesting fashion trends. For instance, they’re kind of into leggings as pants.
Tyler has very strong feelings about leggings. He especially has very strong feelings about leggings as pants.
Because I’m a fan of both strong feelings, and fashion in general, I invited Tyler over to Real Estate Tangent today to educate the world (and by ‘world’ I mean ‘my 5 readers’) about how and how not to wear leggings in a (potential) series we’re gonna call: Hey, Tyler, what do you think of my outfit?
Elizabeth: So… Hey, Tyler, what do you think of this outfit?

Tyler: I’m not sure if you’re going for the seasonal elf look or the timeless Link from The Legend Of Zelda cosplay thing, but that is for you to decide. The ruffled (what do you even call boots that aren’t all that structured?) boots make me think you have a thing for Peter Pan, but they match well.
This would be fantastic maternity wear, no doubt. The look on your face in the second pic is a great “you can’t see the baby bulge, right?” type of thing I’d expect any young mother to have.
The shirt is great, chest up; I can’t get over the bob thing the ‘flowing’ part is doing, though. I’m sure it’s comfy, but why not try something more fitted?
Unless you ARE pregnant, and if so, congrats! I can’t even tell.
Elizabeth: OK, that’s sort of valid. I think I bought this shirt when I was pregnant and decided it could be a crossover top. Although this is a moderately humiliating exercise since I wore this out in public today. Can we focus on the leggings as pants for a second? Is this an acceptable length top to wear over leggings?
Tyler: Yep. Just have to cover the butt when standing. Not that I don’t appreciate a too-short top with leggings, but it’s weird because then I try to figure out the exact shape of the legging-wearer’s ass, and it creeps me out. Leaving something to the imagination is good, like you did here with your “am I or am I not pregnant again” outfit.
Elizabeth: Ok, so what about this one? Should I wear this to the mall tomorrow?

Tyler: Yes, but only if you spray tan yourself orange and chew gum with your mouth open. Oh, and if you were 17 and about to go on a ski trip. Or if your family needed cash and you decided that a ski-bunny-themed prostitute thing would be a big money maker.
Also required for this outfit to work: one LARGE ring and blue eyeshadow.
Oh, and so help me if I can see your butt eating your panty line if I walk behind you in that outfit. I would straight up YELL that your ass crack was hungry.
Elizabeth: You’re against VPL, noted. I will make careful underwear choices if I’m going to be in your presence from now on.
This next one I’m thinking of wearing to a holiday party. It seems OK when I’ve got my arms below shoulder height, but as you can see, when I go to ‘raise the roof’ things get a little sketchy. Should I keep my elbows to my side all night to keep out of whoreville?

Tyler: Yeah, that’s a pretty whorish outfit. You either have to OWN that or accept that your ass hangs out every time you’re not standing still.
This may be okay with you; my wife can’t find pants that don’t show off the top of her ass crack whenever she sits down, and I think she’s accepted it. Though I probably shouldn’t try to toss stuff in there.
Anyway, whorish, so if that’s what you’re going for…oh, the prostitute joke was based on a news story today: some former Olympian was busted for being an escort in Las Vegas.
I have no idea if I’m using semicolons or colons correctly right now.
Elizabeth: YOU ARE THE WORST ADVICE-GIVER EVER. Also I’m pretty sure you’re drunk. You told me if my butt is covered with my arms down I’m fine. AND IT TOTALLY WAS. I’m still wearing it. This is the last time I take pictures of my butt and post them on the internet for you.*
Now I’m afraid to ask, but what about this one?

Tyler: I admit I’m a bit jealous of this outfit. No way I can pull if off, but it’s obviously a running or gym outfit, and is in no way gratuitous — but on me? No way do I wanna look like a stuffed sausage moose knuckle.
Now if you were to go shopping in this, but you weren’t sweaty or anything? I’d think “YEAH WE GET IT. YOU’RE GETTING OLDER AND YOU HAVE SELF ESTEEM ISSUES” and I’d feel bad that you felt that way.
Elizabeth: So I shouldn’t wear it to the grocery store after I go running because I didn’t have time to shower and change like I did last week? (Refrain from referring to me as ‘older’ or so help me I’ll fly to Portland just poke you in the eyeball.)
Tyler: You misunderstood. Basically, the worse you look in them, the more authentic they are.
Oh my god.
I’ve gone Portland.
Elizabeth: Oh I GET IT. If I want to wear leggings I just need to stop bathing. I will remember this for when I come to visit you.
Let’s talk about sequined leggings. If the leggings have a layer of sequins over the top, are they appropriate to wear just as pants? Because I kind of think this is working:

Tyler: Yes, let’s talk about this horrible outfit in the picture. The sequins look like holes from here, so what it really seems like you’re wearing is a dress that’s been ripped half off and runs in your very dark stockings while in some sort of struggle. So…rape survivor? Is that a thing?
Elizabeth: I’ve been having some wine, so I’m thinking what you’re really saying is this outfit is super cute. I mean I think it’s super cute and I just invented it, so it must be true. Orange, sequins, flower necklace and flower shoes, what could possibly be wrong about it? I’m pretty sure that’s what Jason said after he was like So that’s one Tyler’s supposed to hate and think you look terrible in, right? and then I said, Haha, that’s funny because I’m totally wearing it tomorrow night.
(See how I just ignored your gross rape joke because it was gross?)
But I guess the point of all of this is, what do you think I should wear with these leggings? Because I really like them but I can never figure out what I should wear on top:

Tyler: Topless, smoking a bong. Maybe a couple of hemp necklaces.
Wait, are those furry creatures on your legs(not a euphemism!)?
Elizabeth: OK, then, I guess it’s time to wrap this up. I think we’ve all learned so much about how not to wear leggings, old maternity shirts, slouchy boots and rapey sequins. Maybe next time we can learn what Tyler thinks we should wear.
*I told Jason about this blog post idea and I think he was only half listening because later when I asked him if I should actually take pictures from the back to send he said, Well are you and Tyler going to do this publicly or are the pictures just for him? …no, I don’t understand why he thought it would be OK if I was just sending pictures of my outfits to Tyler for his personal use, except that sometimes Jason is like, Babe, you just do what you need to do and let me watch The Cooking Channel, alright?