In honor of this unseasonably warm day, I'm going with a lighter look today. This is obviously an extremely easy outfit comprised of all things most guys have in their closets, but that is all the more reason why fit is everything. The t-shirt isn't yellowing, stained or stretched out and the pants are a nice dark wash and fit the leg well. The highlight of this outfit is the cuff and sock combo. You don't see a cuff and sock very often, and now that ankles are at risk of feeling the chill, it's important to know how to do it well if the cuff is your kind of look. The shoes are a Keds-looking oxford that finishes off this casual and easy look well. It looks like he has a plaid button down in his lap to throw on over, which is even better. Unbuttoned or buttoned, it works easily into this simple look.

This picture of Gwen Stefani is actually really old, but the outfit seems surprisingly modern. I'm on a bit of a dressy kick this week, and shorts with tights deserve a mention because I hate for the seasons to limit what I can or can't wear. Tights make shorts possible in the cold temps, and I think Gwen's mostly black look here is great for the upcoming colder months. The tie, to me, is the only dated/questionable thing about this outfit, and it's an easy accessory to lose. Besides that, the buttoned collar with statement necklace and cool belt really add dressy personality to this look and the heels finish off the formal feel. It's definitely a bold look, but keeping the colors understated except for the shorts and just the accessories bold pull it together and make it appropriate for those upcoming holiday parties or just any winter night out.

Monochrome can be tough, especially with dark winter colors. The key is keeping the silhouette simple and doing what you can with subtle patterns and textures, as well as using a color that actually works with the monochrome look. The blogger behind Eat.Sleep.Wear masters the look well with a textured, slouchy sweater and patterned skinnies of the same color. She finished the look off well with matching black shoes and bag, both with what the mags would call "luxe" details, adding to the rich tones and textures in the outfit without overpowering them. The black was a good choice because it's simple and understated. Black is never a bad choice, but it was particularly good here because it doesn't compete, and more oxblood would have been too much and potentially costume-y. This is a sweater/jeans/flats look that is elevated both by a trend and by being dressed up with details like the captoe and tapestry pattern on the colored jean. This is something that's great to keep in mind during quick mornings, because just because your outfit seems simple or casual on paper, doesn't mean it translates to that in person. Get creative with the traditional!

Few things are better than waking up knowing you can spend the whole day in sweats, especially in the winter. Unfortunately, those days don't come very often, so you have to get creative. Creative options usually don't skew so feminine, but Markus Lupfer had the right idea when designing his spring/summer 2014 collection, which this look comes from. This girl looks effortlessly cute and casual as well as extremely comfortable. The length of the sweatshirt and choice of a-line pleated skirt make it so the little-embellished swing top still flatters. Though it's very plain, it's still a bold look with the satin pink panel and shoulder detailing. Accessorizing is optional, some necklace layering could dress this up, but it doesn't need it, as seen here. Mary Jane style flats keep this look young, tasteful and fun. Who needs to wait until spring for this look?

As it gets colder, I have to motivate myself to really dress up. But one benefit of the cold invites the opportunity for one of my favorite items of clothing that exists: the long sleeved mini dress. Especially for cold weather festivities, it's nice to be able to dress up and look feminine and not want to freeze to death. Another bonus of this item is that you don't have to reach for an awkwardly non-complementary jacket or sweater and you don't have to go on an endless search for one because this dress does the job on its own. And this one is no exception. This outfit was part of The Cut's date night suggestions (more here) for fall, and it's so easy and cute. The winter white works well for the temperature in a heavier, embroidered fabric, and the statement necklace is the perfect addition to the simple high neck. I'm usually not crazy about black shoes with white, but the white on these shoes (which I would donate a kidney for) pull the contrasting colors together in a seasonally appropriate way. The red box clutch is the perfect pop of color to finish it off, and this look can go from date night to holiday party with no changes necessary. For those that are less daring with bare legs in the cold, this look can work just as well with tights.

I'm pretty much in the minority of people who aren't under the Blake Lively spell. She famously doesn't work with a stylist, and I really think she should because her fashion choices, particularly for red carpet events, often underwhelm me. But she's famous and beloved and married to Ryan Reynolds, so what do I know? Anyway this isn't about me (or her, really), it's about the outfit. It has been legitimately cold over the last few days and I've been dreaming of living in thick sweaters that make up half of an automatic outfit (side note: there are some great sweaters in stores right now if you are sharing this sentiment). Blake here is doing this sweater dressing in a more risky way while still keeping it together exceptionally well. She's got the black and white color scheme going in so it's safe to mix the Isabel Marant stripes and houndstooth pants (which are extremely awesome but also look sort of navy in this picture?) and the black Louboutin flats and gray purse are the only necessary accessories and they're remarkably unfussy. Bonus for the matching shades. There's so much potential for there to be a lot going on here, and it all just jives. Next time you're wanting to be lazy and uninspired like me, reach for a more interesting knit and a patterned pant instead of the normal ancient sweater/jegging combo and feel like Blake. Or wish you were her, especially after her recent admission of never working out and eating a lot of chocolate. Something to aspire to.

Happy Monday! Today we're keeping it casual with this easy, cool outfit. It's a little cold to go sockless at this point in the season, but this works with socks just as well. Maybe better if you don't go with a cuff, though. First things first, get jeans that fit with a nice wash that can be taken from day to night, from dinner with her parents to the seventh fireball shot on a Saturday night. This look simply doesn't work without some well fitting grownup jeans. Grab your favorite (also grownup) casual belt to polish it off. Take a t-shirt that you'd wear on its own and throw on a shallow v-neck sweater in a color that works with the t-shirt. To finish it off, throw on a casual jacket and get a little risky with white oxfords. White isn't the only risky but cool option, though. Just go with anything that might make you think twice, or that you might think is a little too out there. But just a little bit. Don't forget your watch and sunglasses, and you're good to go. This outfit is so easy it's almost painful every guy doesn't already dress this well. But now you know.

It's officially November, which means that soon we're going to have to seriously start bundling up. The pleasant transition weather in October begins slipping into almost-winter territory right around now. Enter this amazing sweater (the amazing whole outfit comes later). It's Friday which means 1) it's Friday and 2) almost saturday, so this sweater looks pretty much as welcoming as it gets, and she wears it well. Now that it's actually humanly cool enough to wear leather and not be considered a little crazy, these slouchy leather trousers, which are just a little oversized, pair well with the extremely oversized sweater. It's a possibly dangerous look with so much slouch, but the asymmetrical hem of the sweater, sloppy tuck (which helps define the waist) and cuffed ankles give the silhouette some shape. Simple black pumps with interesting detailing were a great, feminine choice to finish off this outfit and add some structure and a bit of refinement. Now go and consider the many options for this sweater while I go get one for myself.

I've been pretty into dresses over shirts lately because I've seen it done well around the interwebz. I can't help but catch a little of this holiday buzz, even though I try to fend it off until after Thanksgiving (one holiday at a time, please). That's why this sparkly dress caught my eye. It's something I'd probably pick up on my own, and would be perfect for pretty much any holiday party, but it looks so good over this unassuming gray turtleneck, too. Add some tights and biker boots and this look becomes daytime cool. Pair it with some pointy (but not too pointy) black pumps with an oh so skinny heel, and it's a not as dressy but extremely interesting night look. I mean, if you're going to be wearing this between now and spring, why not make yourself more comfortable and add some sleeves?

It's easy to default to tights under dresses all fall, but sometimes it's warm enough (or you're just brave enough) to let the thigh feel the chill and let tall boots go unaccompanied on the leg with a dress. Long sleeved minis are one of my favorite things (in the same arena as shorts with sweaters), and this girl wears the combo well. The big belt defines her waist and adds some interest to the plain black dress, and it's the perfect brown to go with black. The brown boots match the belt perfectl, and because they're accessories and they're simple, it doesn't look matchy matchy. This is a great day look, but with a clutch like above, it's also great for evening drinks or dinner, as well as all those family fun times coming up. I know who I'll be copying in the next few weeks.