Jeanne says: I love these boots — they go with almost everything in my wardrobe and they were relatively inexpensive. I like them with a rolled up jean, but I could just as easily see them with leggings or a skirt.
Kate says: I don’t usually wear heeled booties (flat ones are so much more comfortable!), but these are comfortable and I love the taupe color. Here I’ve styled them with this great colorblock sweater and my most style-blogger-worthy fedora. But like Mom says, these would be great with a floaty dress and leather jacket, or leggings and oversized sweater.
Jeanne says: It has been weird this year to stylishly dress up in distressed denim. I have two other VERY distressed versions with patches and holes, but these were my first distressed pair. Once I get over the fact that they are distressed, it is fun to dress them up with dressier shoes, tops and jewelry. These Gap 1969 skinnies are very flattering — if you haven’t, you should try them!
Kate looks more traditionally dressed up in dark skinny jeans. Once again, she combines several different colors on the top and pops on an interesting pump and voila! Kate, of course, in general wears jeans far more often than I do. She finds lots of ways to wear them in her business casual office; I, on the other hand, have to wait for Friday or the weekend!
Kate says: I do indeed wear jeans at least once a week to work, but I usually stick with these darker wash jeans or my black jeans — they feel a little more professional. It also helps to wear a blouse (versus a t-shirt or something more casual) and heels! I love these bright colors together, and I think brights also help make an outfit look more dressy.
Mom goes the other route for dressing up her jeans: popped collar, tucked in shirt, and gold jewelry. This works because she went with one of her less distressed pairs of boyfriend jeans — so they have the looser fit and messy cuff, but aren’t quite so casual. Her combination of pink and red is very chic, of course!
Jeanne says: The highlight of this outfit is my DIY necklace made from old and re-purposed brooches. I do love these jeans with my cage heels and, all in all, I felt pretty groovy and, dare I say it, young in this look. The truth is that I cannot wear these heels for long periods of time, but they sure do look great!
Kate looks pretty spiffy in her dressed-up jeans. I love her top with the red wedges and, once again, she teaches me to simply throw on a great necklace whether it “matches” or not. She looks ready to go out for the evening or to a big work meeting. It’s also interesting to note that we are both cuffing our jeans here — not a boyfriend jeans look — but a slight variation on the norm.
Kate says: This outfit is showcasing one of my go-to formulas: dark jeans, printed top, and bright accessories. I wore this to work, but this outfit could easily transition to happy hour or a dinner date. What I love about a print is that it gives you so many color options to play with — my red wedges do match, but turquoise always goes with anything!
Mom’s outfit follows a similar formula, with some slight twists — her cage heels certainly take the outfit to a new level of dressiness. And her homemade brooch necklace can so easily be thrown on with any outfit to add major bling and attitude. I think she wore this to work on a Friday, but her ensemble is just as versatile as mine!
Kate says: This is a “formula” outfit for me: jeans + blazer + tee + statement necklace. It’s comfortable, quick, and *usually* looks good. These booties are a new-ish addition to my wardrobe, and I wear them all the time. I was looking for a winter version of my Toms – comfortable, easy to throw on, and goes with everything. And they have fit the bill! I can wear them with skinny jeans or flared jeans, dresses, and skirts.
This is a cute casual outfit on Mom that really flatters her figure – you can see exactly how slim she is! The patchwork jacket is not really my style, but Mom has a knack for choosing quirky items that work really well for her. The colors are warm and work nicely with her scarf and boots. I think her boots have a heel, but they are still nice and casual with her cuffed jeans.
Jeanne says: This jacket was one of my favorite purchases this year, but ended up being harder to wear than I thought originally. I actually end up pinning the front closed each time I wear it. Anyway, it can be dressed up or down for Casual Friday as you see here. That mustard color is one of my favorites. The boots have a tiny heel and were an end-of-season find.
Kate and I both had on casual boots and cuffed skinny jeans in these photos. She looks cute and fresh. I like how Kate uses her blazers with her jeans; it looks like she tossed it on so casually, but it really brings just a bit more polish to her outfit. Had I been wearing that outfit, I probably would have thrown in another color with that great top, but that’s just “quirky” me!