How to Get Back into the Game

A man standing in a navy, unbuttoned suit, wearing a white, textured shirt.


Getting back into dating can be quite a daunting task. After a breakup, you might find yourself a little lost, realizing how heavily you relied on your partner for your fashion needs. However, discovering your own preferences and style is the absolute key to dating. Confidence is crucial and is brought out when you're wearing what you're most comfortable in. Of course, finding a balance is important, as you probably shouldn’t show up in sweats and a t-shirt. Begin by investing in some classic pieces that will last you—through the good times and the bad. Take the time to embrace this opportunity to start over and find yourself again. Now is the chance to try those styles you’ve always wanted; those that your ex wouldn’t allow or even made fun of. For some, finding your style may be a little more challenging. Once you consider the setting of your date, I’ll guide you with the appropriate outfits that will get you back into the game. If you are still unsure of your look leading up to your date, just ask her what she thinks. You would be surprised by how effective of an ice-breaker this is, as they would likely love to help.

On a wooden background; A black sweater, over a white shirt. White sneakers, a black belt, and gray chinos

Business Casual

Say you’re taking your date to a nice dinner or you’re trying to meet someone out at a club. The worst thing you can do is show up underdressed. You want to reflect the formality of your location, so a business casual look is fitting. To avoid a messy look, consider the following options. Pair black/navy trousers to a matching sweater, layered over a brighter button-down, such as pink, white, light blue, or anything that pops. Have the collar laid neatly over the sweater's neckline, to add a sophisticated touch. Alternatively, wear a more monotone palette with dark gray, navy, or black. For another business casual look, pair a light-colored pair of jeans or chinos with a white, beige, or gray t-shirt. Complete the outfit by layering with a dark blazer, cardigan, or jacket. This is an ideal look, as it can be easily transitioned after work, simply by swapping out your shirts. Cap it off with a shoe that suits the color of the top (black boots and a black blazer, gray dress shoes to a gray cardigan). Fit is very important, as it can either accent your physique or make it unflattering. In keeping with fashion trends, do try a modern fit when possible, but only if it makes you feel comfortable and confident.


On a wooden background. A beige shirt, black jeans, and white sneakers, along with a brown watch and glasses



You're preparing for a more casual date, such as at a coffee shop or maybe a picnic in the park. You have more room to groove and can try out different variations. If you don't already have a preferred look, try playing it safe by resorting to color binary. Black and white shirts are to a man, what dresses might be to a woman - timeless go-tos. When in doubt, rely on these staples and alternate them into any look, as you’re sure to match whatever she comes in. A black shirt will instantly make your physique slimmer, while the white shirt can provide a flattering contrast. Try pairing a white shirt with light-washed or gray jeans and white shoes. You may be onto me by now and realize that color coordination is at the core of each of these looks … which is exactly right. As long as you match, especially when meeting someone for the first time, you're sure to leave a lasting impression. You can’t go wrong with neutral pieces. Lastly, a few little tricks… if you’d like to make yourself appear taller, opt for a dark pair of pants, which cut off right before perfectly matching shoes, to achieve what is called a “no break.” If the weather permits, opt for a structured jacket, as it’ll obscure your figure and define the attractive V-shape of your silhouette. Now, keep your posture straight, and your chin up, and you’ll find that new special someone in no time!  



Elliot Russ
Stately stylist, writer, and designer based in Los Angeles, CA