Ladies, it’s time to pull out that ‘little long black dress”- you know the one that accentuates your figure perfectly and goes with everything, specifically when you’re looking for something to wear on a date? Often it’s between that or what you wore to work, which technically leaves you with no real option.

As we all know, weather has become extremely fickle and a closet with staple pieces simplifies the process when combating the cold fashionably and for that special night out. When it feels below zero and you’re in need of the ‘perfect date’ look, here are Five Fall Must Haves: The Dating Edition!

Leather something!

Leather during the cold months is an easy find. Whether it’s a leather jacket, leather boots, or leather pants (for the ladies out there who dare to take fashion risks) leather pieces are a staple, and on date night the perfect statement piece. A leather jacket is always a go to. It can be as simple as a classic black motorcycle jacket, as bold as a colored motto jacket, or as funky as one with embellishments, patches, or graffiti. Leather is transformative; you can rock it with distressed jeans and a cunt pump, dress it down with a simple edgy trainer, or dress it up by simply adding a fur collar. The idea is to play around with it! Consider leather pants, skirt, and tops. They all have a place in your closet if worn well. Don’t be afraid to try other variations of leather either, a nice patent leather trench with a simple body-con turtle neck dress and point toe heels, make for a simple, yet stylish statement!

WARNING: The idea is to accentuate your look, and yes, there is such thing as overkill- Don’t be that girl. While leather can be fun, edgy, and sexy, it can also be a bit much if you’re not careful! For all my fashion beginners, the trick is to PICK ONE. Being cognizant of the other fabrics paired with it and the quality of the leather will also help. Lace, sheer, and denim are easy starting points to build from.

Red hues!

You’re going on a date and you want to wear something other than black, nude is typical, pastel colors have passed, but you still want to pop, right? The color is RED! Red is bold, its sexy and depending on the hue, actually match well with more things than you’d think. We’ve all got different undertones, so don’t worry, I’m not encouraging every girl to wear fire engine red, but trust me, someone can! FIND THE RED THAT SUITS YOU- oxblood, burgundy, crimson, ruby red, etc. This will aid in the pairing process. Swap out that black dress for a red one and pair it with a killer shoe! Keep in mind that the most overlooked aspects of an outfit can transform your entire look. So, if a red dress isn’t your thing, take in to consideration a red lip, red nails, or red pumps.

Tip: Consider the time of day. Dinner after five, definitely warrants a sexy red number, don’t be scared! If you’re brunching or going somewhere casual, consider a tailored oxblood sweat suit with nude suede peep toe bootie or edgy trainers, and a longline nude duster coat.

Invest in stylish coats and accessories!

There is nothing worse than having on the perfect outfit and putting your Columbia wind breaker over it- You just went from “ouuu” to “blah” with the zip of a jacket. A fall must have is clearly the very thing that keeps you from freezing your butt off, trying to look cute- a coat, hat, scarf, and gloves! So, invest in ones that are chic. There are many stylish down feather and longline coats in different fabrics, colors, and prints. If black is your go to color for coats, details will be your best friend! Fur linings, leather or satin trim, removable belts, and modern cuts are great things to look for. A classic fur coat is always appreciated too. As far as accessories go, have fun with it! A really great functional accessory is the fur stole! It’s warm and adds elegance or edge to any outfit. It can be paired with a wool trench or leather jacket, and serve as an evening shawl. A fur stole alone, if styled correctly, will be a statement in itself.


Are the holy grail of warmth and sleek chic. They’re perfect for layering and elongate the neck. It’s a really basic piece that can turn a regular outfit up a notch. Don’t just think cotton twill; expand your variety of turtlenecks with different fabrics from mesh and sheer, to lace, or with other pieces like knitted jumpers and body-con dresses. A sleek black ribbed turtleneck body-con dress with exaggerated sleeves, paired with OTK (over the knee) or thigh high boots, and a long plaid wool coat or cape is perfect for a night out. In the day time, try swapping out that regular scoop-neck tee with a turtleneck, pair with skinny jeans, booties and a camouflage anorak.

Tip: For shorter necklines, swap out that turtleneck with a mock-neck. Mock-necks create the illusion of a longer neckline because they are long enough to cover your neck without excess fabric creating an unflattering cutoff below the chin.

Bold ankle booties!

Booties are indeed a fall necessity and personally a fave of mine! First and foremost, they’re comfortable, so if it’s a date that requires walking, use your better judgment and go with these. The key is to find that statement bootie that could transform an extremely plain outfit, or pair nicely with casual and evening attire. When I say bold, I mean bold! Denim, patent leather, clear or metallic heels, oddly shaped heels, snake print, and suede are pretty standard options. If you’re not as confident in your fashion journey take subtle risks. If you’re comfortable with a black bootie, get it in a point toe patent leather or paisley velvet. Booties are best paired with pants and jeans, so build from there.

Tip: Ankle boots are diverse- they come in different heel heights, widths, and toe shapes. For a sleek look, go with pointed toe or tall skinnier heels. For a more casual look, round or squared toes and chunkier heels are best.

Fashionably yours,


Dey is known for both her melodic voice and setting fashion trends among her peers.  When Dey is not giving out fashion tip, she writes about current events, urban culture, arts.  You can find more of her work here