The UGGs Boots: A 2023 Winter Trend That Won’t Go Away!

Going from stilettos to sneakers is a pretty accurate statement (if not understatement) in my case. In fact if there’s two words that perfectly describe my style for the past couple of years it’s these: Adam Sandler. Yes. I dress like him, and much like him I go for comfort and dad sneakers and baggy clothes, most of the time. You can laugh all you want but the guy’s a genius. He’s always comfortable. You know, it’s quite liberating not to mention it saves time.

Had you told me decades ago I’d be an adaam sandler,  I would have had a panic attack, now I’m actually proud of it. I’m proud of my newfound confidence, my going for comfort instead of pain, finding fashion pleasure in quality and nice details over trendiness… you know – I dabble a little into the being wiser and older thing even style wise.

Now the funny thing about my current Adam-Sandler-style situation is that it is actually a trend in 2023. Isn’t fashion super weird and unpredictable at times? It began circa 2020… the baggy jeans, the UGGs boots, the oversized tees, boyfriend style, celebrity off duty kinda vibe – and now every. single. instagram. influencer is wearing this relaxed homeless luxe uniform.

The 90s baggy jeans, Uggs boots, oversized tee, oversized sweater/sweatshirt and a boyfriend puffer jacket or if you’re more into the Swedish style aesthetic the oversized long coats, extra long scarves and beanies.

Whatever keeps you cozy, warm and has no beautiful quality to it – is your fashion choice. And the best thing about this new style trend is that overall everything does look better, because women look better when we dress for us, for comfort, for fun.

Shop the Uggs outfit:


What UGGs boots to wear in 2023 winter?

The short styles are more trendy these days and TBH given the rise of the bootcut jeans, and boyfriend jeans styles, 90s cut and so on – it makes more sense. They sit better on our feet, and look better with wider jeans style worn over them, no bulging or creasing at the feet. Any color is great but the classic brown UGGs boots are the IT style.

Back in the 90s when Kim Kadashian was fixing clothes for Paris Hilton every cool chick in pop magazines was wearing UGGs boots in summer. But not like today. Boots were ankle length and worn with kitschy outfits that we so loved back in the day. (Juicy couture tracksuits, low waist denim cutoffs, tons of rhinestones and lipgloss and blonde bleached hair.) Fashion is a funny thing ain’t it?!

How to wear UGGs boots in 2023 winter?

Dress in anything you want. Put a pair of short UGGs boots on. That. Is. It. That is exactly what Adam Sandler would do. This style though is more for those of us who did the circus dressing way back when, and are now just happy to enjoy fashion life on a daily basis without the razzamatz. Chill, laid back, easy and fast to get you out of the door on those crazy mornings.

If however you wanna do this UGGs boots trend as a trend per se then it’s easy but you do need to invest more time and effort.

  • good hair (usually a lob or 90s blowout)
  • good makeup (minimal but it takes double the time)
  • great mani
  • pretty jewellery (layered, not too dainty but not chunky either)
  • clean outfits (leggings with socks and a checkered jacket, 90s denim with a big turtleneck and faux fur coat, tracksuit with a buffer jacket)

Actually it sounds more complicated than it is, truth is we do love fashion so it’s actually a pleasure to dress nice and feel comfy at the same time.

The great thing about this trend is how easy it is to wear, BUT (yes there is a but) if you wanna get the instagram look per se you always need new great quality pieces to create this outfit. Thing about relaxed outfits is they only look expensive and luxe when they are actually expensive and luxe. It is an art to wear relaxed clothes that you haven’t just ripped the label off, AND still look expansive and trendy in them. It takes true style and fashion savviness.

Luckily there’s women out there who are moms, who are so busy and are doing the most, usually in our late 30s let’s say – and for who fashion is no longer a priority but a forever love. It’s these women who birthed this style, and who are wearing these UGGs boots outfits, and are the epitome of Adam Sandler coolness.

Or perhaps I’m feeling nostalgic over my well dressed years, and equally a bit left out in this vastness of instagram outfit reels and constantly upgraded looks that are all meant to be ‘relaxed’.

The street outfits:


Shop for UGGs:



Anyway I’d write a novel on all this (the mirage of instagram outfit reels) but now’s not the time.

Now I want you guys to tell me your side of the story when it comes to relaxed outfits and the UGGs? Do you wear them? Do you like them?

xoxo D.